CA2718262A1 - Formulations of vitamin k analogs for topical use - Google Patents
Formulations of vitamin k analogs for topical use Download PDFInfo
- Publication number
- CA2718262A1 CA2718262A1 CA2718262A CA2718262A CA2718262A1 CA 2718262 A1 CA2718262 A1 CA 2718262A1 CA 2718262 A CA2718262 A CA 2718262A CA 2718262 A CA2718262 A CA 2718262A CA 2718262 A1 CA2718262 A1 CA 2718262A1
- Authority
- CA
- Canada
- Prior art keywords
- formulation
- menadione
- pharmaceutical formulation
- lotion
- conforms
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Abandoned
Links
- 239000000203 mixture Substances 0.000 title claims description 149
- 238000009472 formulation Methods 0.000 title claims description 137
- 229940046010 vitamin k Drugs 0.000 title abstract description 40
- 230000000699 topical effect Effects 0.000 title description 14
- MJVAVZPDRWSRRC-UHFFFAOYSA-N Menadione Chemical compound C1=CC=C2C(=O)C(C)=CC(=O)C2=C1 MJVAVZPDRWSRRC-UHFFFAOYSA-N 0.000 claims abstract description 217
- 239000011652 vitamin K3 Substances 0.000 claims abstract description 118
- 229940041603 vitamin k 3 Drugs 0.000 claims abstract description 115
- 235000012711 vitamin K3 Nutrition 0.000 claims abstract description 109
- 238000011282 treatment Methods 0.000 claims abstract description 21
- 238000011123 anti-EGFR therapy Methods 0.000 claims abstract description 8
- 239000006210 lotion Substances 0.000 claims description 115
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 63
- 239000008194 pharmaceutical composition Substances 0.000 claims description 50
- WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 claims description 45
- 229940121647 egfr inhibitor Drugs 0.000 claims description 39
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 34
- 239000003755 preservative agent Substances 0.000 claims description 30
- 230000002335 preservative effect Effects 0.000 claims description 24
- 102000052116 epidermal growth factor receptor activity proteins Human genes 0.000 claims description 22
- 108700015053 epidermal growth factor receptor activity proteins Proteins 0.000 claims description 21
- JVTIXNMXDLQEJE-UHFFFAOYSA-N 2-decanoyloxypropyl decanoate 2-octanoyloxypropyl octanoate Chemical compound C(CCCCCCC)(=O)OCC(C)OC(CCCCCCC)=O.C(=O)(CCCCCCCCC)OCC(C)OC(=O)CCCCCCCCC JVTIXNMXDLQEJE-UHFFFAOYSA-N 0.000 claims description 20
- 239000003795 chemical substances by application Substances 0.000 claims description 20
- YOHYSYJDKVYCJI-UHFFFAOYSA-N n-[3-[[6-[3-(trifluoromethyl)anilino]pyrimidin-4-yl]amino]phenyl]cyclopropanecarboxamide Chemical compound FC(F)(F)C1=CC=CC(NC=2N=CN=C(NC=3C=C(NC(=O)C4CC4)C=CC=3)C=2)=C1 YOHYSYJDKVYCJI-UHFFFAOYSA-N 0.000 claims description 20
- 229940075510 carbopol 981 Drugs 0.000 claims description 19
- 239000003349 gelling agent Substances 0.000 claims description 19
- HIQIXEFWDLTDED-UHFFFAOYSA-N 4-hydroxy-1-piperidin-4-ylpyrrolidin-2-one Chemical compound O=C1CC(O)CN1C1CCNCC1 HIQIXEFWDLTDED-UHFFFAOYSA-N 0.000 claims description 18
- 235000019445 benzyl alcohol Nutrition 0.000 claims description 15
- KSCKTBJJRVPGKM-UHFFFAOYSA-N octan-1-olate;titanium(4+) Chemical compound [Ti+4].CCCCCCCC[O-].CCCCCCCC[O-].CCCCCCCC[O-].CCCCCCCC[O-] KSCKTBJJRVPGKM-UHFFFAOYSA-N 0.000 claims description 14
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims description 13
- QELSKZZBTMNZEB-UHFFFAOYSA-N propylparaben Chemical compound CCCOC(=O)C1=CC=C(O)C=C1 QELSKZZBTMNZEB-UHFFFAOYSA-N 0.000 claims description 13
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 12
- 230000003472 neutralizing effect Effects 0.000 claims description 11
- 229920000642 polymer Polymers 0.000 claims description 11
- 239000008213 purified water Substances 0.000 claims description 11
- 229940031578 diisopropyl adipate Drugs 0.000 claims description 10
- LXCFILQKKLGQFO-UHFFFAOYSA-N methylparaben Chemical compound COC(=O)C1=CC=C(O)C=C1 LXCFILQKKLGQFO-UHFFFAOYSA-N 0.000 claims description 10
- HBTAOSGHCXUEKI-UHFFFAOYSA-N 4-chloro-n,n-dimethyl-3-nitrobenzenesulfonamide Chemical compound CN(C)S(=O)(=O)C1=CC=C(Cl)C([N+]([O-])=O)=C1 HBTAOSGHCXUEKI-UHFFFAOYSA-N 0.000 claims description 9
- 238000002560 therapeutic procedure Methods 0.000 claims description 9
- 239000004405 propyl p-hydroxybenzoate Substances 0.000 claims description 8
- 229960003415 propylparaben Drugs 0.000 claims description 8
- 235000010232 propyl p-hydroxybenzoate Nutrition 0.000 claims description 7
- LADGBHLMCUINGV-UHFFFAOYSA-N tricaprin Chemical compound CCCCCCCCCC(=O)OCC(OC(=O)CCCCCCCCC)COC(=O)CCCCCCCCC LADGBHLMCUINGV-UHFFFAOYSA-N 0.000 claims description 7
- 235000019441 ethanol Nutrition 0.000 claims description 6
- 239000002480 mineral oil Substances 0.000 claims description 6
- WWZKQHOCKIZLMA-UHFFFAOYSA-N octanoic acid Chemical compound CCCCCCCC(O)=O WWZKQHOCKIZLMA-UHFFFAOYSA-N 0.000 claims description 6
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 claims description 5
- XMSXQFUHVRWGNA-UHFFFAOYSA-N Decamethylcyclopentasiloxane Chemical compound C[Si]1(C)O[Si](C)(C)O[Si](C)(C)O[Si](C)(C)O[Si](C)(C)O1 XMSXQFUHVRWGNA-UHFFFAOYSA-N 0.000 claims description 5
- 235000010270 methyl p-hydroxybenzoate Nutrition 0.000 claims description 5
- 239000004292 methyl p-hydroxybenzoate Substances 0.000 claims description 5
- 229960002216 methylparaben Drugs 0.000 claims description 5
- 235000010446 mineral oil Nutrition 0.000 claims description 5
- 229940086555 cyclomethicone Drugs 0.000 claims description 4
- 235000019271 petrolatum Nutrition 0.000 claims description 4
- 239000004264 Petrolatum Substances 0.000 claims description 3
- 239000006071 cream Substances 0.000 claims description 3
- 229940116977 epidermal growth factor Drugs 0.000 claims description 3
- 229940066842 petrolatum Drugs 0.000 claims description 3
- 102000009465 Growth Factor Receptors Human genes 0.000 claims description 2
- 108010009202 Growth Factor Receptors Proteins 0.000 claims description 2
- 229940042472 mineral oil Drugs 0.000 claims description 2
- SHUZOJHMOBOZST-UHFFFAOYSA-N phylloquinone Natural products CC(C)CCCCC(C)CCC(C)CCCC(=CCC1=C(C)C(=O)c2ccccc2C1=O)C SHUZOJHMOBOZST-UHFFFAOYSA-N 0.000 abstract description 43
- 229930003448 Vitamin K Natural products 0.000 abstract description 39
- 235000019168 vitamin K Nutrition 0.000 abstract description 39
- 239000011712 vitamin K Substances 0.000 abstract description 39
- 150000003721 vitamin K derivatives Chemical class 0.000 abstract description 39
- 239000012049 topical pharmaceutical composition Substances 0.000 abstract description 24
- 206010061218 Inflammation Diseases 0.000 abstract description 5
- 230000004054 inflammatory process Effects 0.000 abstract description 5
- 230000002265 prevention Effects 0.000 abstract description 5
- 238000001035 drying Methods 0.000 abstract description 2
- 231100000344 non-irritating Toxicity 0.000 abstract description 2
- 210000003491 skin Anatomy 0.000 description 41
- 239000000243 solution Substances 0.000 description 35
- 239000000126 substance Substances 0.000 description 31
- 208000010201 Exanthema Diseases 0.000 description 18
- 201000005884 exanthem Diseases 0.000 description 18
- 206010037844 rash Diseases 0.000 description 18
- 238000010521 absorption reaction Methods 0.000 description 15
- 229940100617 topical lotion Drugs 0.000 description 15
- 206010028980 Neoplasm Diseases 0.000 description 14
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 14
- 229910052782 aluminium Inorganic materials 0.000 description 14
- 229960004217 benzyl alcohol Drugs 0.000 description 14
- 239000000839 emulsion Substances 0.000 description 14
- 239000012071 phase Substances 0.000 description 13
- 201000011510 cancer Diseases 0.000 description 12
- 210000002615 epidermis Anatomy 0.000 description 12
- 238000003556 assay Methods 0.000 description 11
- 239000004615 ingredient Substances 0.000 description 11
- 238000005191 phase separation Methods 0.000 description 11
- 239000002904 solvent Substances 0.000 description 11
- 238000000034 method Methods 0.000 description 10
- 229940068196 placebo Drugs 0.000 description 10
- 239000000902 placebo Substances 0.000 description 10
- 238000000338 in vitro Methods 0.000 description 9
- 239000000546 pharmaceutical excipient Substances 0.000 description 9
- -1 polypropylene Polymers 0.000 description 9
- 238000011161 development Methods 0.000 description 8
- 102000005962 receptors Human genes 0.000 description 8
- 108020003175 receptors Proteins 0.000 description 8
- 231100000046 skin rash Toxicity 0.000 description 8
- MBWXNTAXLNYFJB-NKFFZRIASA-N phylloquinone Chemical class C1=CC=C2C(=O)C(C/C=C(C)/CCC[C@H](C)CCC[C@H](C)CCCC(C)C)=C(C)C(=O)C2=C1 MBWXNTAXLNYFJB-NKFFZRIASA-N 0.000 description 7
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 6
- 229920002125 Sokalan® Polymers 0.000 description 6
- 239000011248 coating agent Substances 0.000 description 6
- 238000000576 coating method Methods 0.000 description 6
- 229940079593 drug Drugs 0.000 description 6
- 239000003814 drug Substances 0.000 description 6
- 238000000926 separation method Methods 0.000 description 6
- 208000002874 Acne Vulgaris Diseases 0.000 description 5
- 201000004624 Dermatitis Diseases 0.000 description 5
- 239000004743 Polypropylene Substances 0.000 description 5
- 206010000496 acne Diseases 0.000 description 5
- 239000008186 active pharmaceutical agent Substances 0.000 description 5
- 230000004071 biological effect Effects 0.000 description 5
- 229960005395 cetuximab Drugs 0.000 description 5
- 230000008859 change Effects 0.000 description 5
- 239000003112 inhibitor Substances 0.000 description 5
- 239000004922 lacquer Substances 0.000 description 5
- DKHGMERMDICWDU-GHDNBGIDSA-N menaquinone-4 Chemical compound C1=CC=C2C(=O)C(C/C=C(C)/CC/C=C(C)/CC/C=C(C)/CCC=C(C)C)=C(C)C(=O)C2=C1 DKHGMERMDICWDU-GHDNBGIDSA-N 0.000 description 5
- 230000035515 penetration Effects 0.000 description 5
- WVDDGKGOMKODPV-ZQBYOMGUSA-N phenyl(114C)methanol Chemical compound O[14CH2]C1=CC=CC=C1 WVDDGKGOMKODPV-ZQBYOMGUSA-N 0.000 description 5
- 229920001155 polypropylene Polymers 0.000 description 5
- 238000009516 primary packaging Methods 0.000 description 5
- 150000003839 salts Chemical class 0.000 description 5
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
- ABSPRNADVQNDOU-UHFFFAOYSA-N Menaquinone 1 Natural products C1=CC=C2C(=O)C(CC=C(C)C)=C(C)C(=O)C2=C1 ABSPRNADVQNDOU-UHFFFAOYSA-N 0.000 description 4
- 206010059516 Skin toxicity Diseases 0.000 description 4
- 230000004913 activation Effects 0.000 description 4
- 210000004207 dermis Anatomy 0.000 description 4
- XXJWXESWEXIICW-UHFFFAOYSA-N diethylene glycol monoethyl ether Chemical compound CCOCCOCCO XXJWXESWEXIICW-UHFFFAOYSA-N 0.000 description 4
- 239000008387 emulsifying waxe Substances 0.000 description 4
- AAKJLRGGTJKAMG-UHFFFAOYSA-N erlotinib Chemical compound C=12C=C(OCCOC)C(OCCOC)=CC2=NC=NC=1NC1=CC=CC(C#C)=C1 AAKJLRGGTJKAMG-UHFFFAOYSA-N 0.000 description 4
- 238000011156 evaluation Methods 0.000 description 4
- XGALLCVXEZPNRQ-UHFFFAOYSA-N gefitinib Chemical compound C=12C=C(OCCCN3CCOCC3)C(OC)=CC2=NC=NC=1NC1=CC=C(F)C(Cl)=C1 XGALLCVXEZPNRQ-UHFFFAOYSA-N 0.000 description 4
- 239000011521 glass Substances 0.000 description 4
- 239000003446 ligand Substances 0.000 description 4
- 239000003921 oil Substances 0.000 description 4
- 235000019198 oils Nutrition 0.000 description 4
- 238000004806 packaging method and process Methods 0.000 description 4
- 235000019175 phylloquinone Nutrition 0.000 description 4
- 239000011772 phylloquinone Substances 0.000 description 4
- 229960001898 phytomenadione Drugs 0.000 description 4
- 230000008569 process Effects 0.000 description 4
- 231100000438 skin toxicity Toxicity 0.000 description 4
- 208000024891 symptom Diseases 0.000 description 4
- 239000003981 vehicle Substances 0.000 description 4
- MEJYDZQQVZJMPP-ULAWRXDQSA-N (3s,3ar,6r,6ar)-3,6-dimethoxy-2,3,3a,5,6,6a-hexahydrofuro[3,2-b]furan Chemical compound CO[C@H]1CO[C@@H]2[C@H](OC)CO[C@@H]21 MEJYDZQQVZJMPP-ULAWRXDQSA-N 0.000 description 3
- RYWSYCQQUDFMAU-UHFFFAOYSA-N Acetomenaphthone Chemical compound C1=CC=C2C(OC(=O)C)=CC(C)=C(OC(C)=O)C2=C1 RYWSYCQQUDFMAU-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 206010015150 Erythema Diseases 0.000 description 3
- 102000008394 Immunoglobulin Fragments Human genes 0.000 description 3
- 108010021625 Immunoglobulin Fragments Proteins 0.000 description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- 239000005551 L01XE03 - Erlotinib Substances 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- PFRQBZFETXBLTP-UHFFFAOYSA-N Vitamin K2 Natural products C1=CC=C2C(=O)C(CC=C(C)CCC=C(C)CCC=C(C)CCC=C(C)CCC=C(C)CCC=C(C)C)=C(C)C(=O)C2=C1 PFRQBZFETXBLTP-UHFFFAOYSA-N 0.000 description 3
- 229960001631 carbomer Drugs 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- 239000003086 colorant Substances 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 230000006866 deterioration Effects 0.000 description 3
- 239000002270 dispersing agent Substances 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 239000003995 emulsifying agent Substances 0.000 description 3
- 229960001433 erlotinib Drugs 0.000 description 3
- 231100000321 erythema Toxicity 0.000 description 3
- 239000011888 foil Substances 0.000 description 3
- 238000012395 formulation development Methods 0.000 description 3
- 230000006870 function Effects 0.000 description 3
- 229960002584 gefitinib Drugs 0.000 description 3
- 210000003780 hair follicle Anatomy 0.000 description 3
- 229920001903 high density polyethylene Polymers 0.000 description 3
- 239000004700 high-density polyethylene Substances 0.000 description 3
- 239000005414 inactive ingredient Substances 0.000 description 3
- 230000002401 inhibitory effect Effects 0.000 description 3
- 229920001684 low density polyethylene Polymers 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 235000009491 menaquinone-4 Nutrition 0.000 description 3
- 239000011676 menaquinone-4 Substances 0.000 description 3
- 229960005481 menatetrenone Drugs 0.000 description 3
- 230000002906 microbiologic effect Effects 0.000 description 3
- 230000035699 permeability Effects 0.000 description 3
- 239000000825 pharmaceutical preparation Substances 0.000 description 3
- 229940068918 polyethylene glycol 400 Drugs 0.000 description 3
- 239000000565 sealant Substances 0.000 description 3
- 231100000245 skin permeability Toxicity 0.000 description 3
- 230000004083 survival effect Effects 0.000 description 3
- 230000009885 systemic effect Effects 0.000 description 3
- 238000012360 testing method Methods 0.000 description 3
- 231100000419 toxicity Toxicity 0.000 description 3
- 230000001988 toxicity Effects 0.000 description 3
- 229940088594 vitamin Drugs 0.000 description 3
- 229930003231 vitamin Natural products 0.000 description 3
- 235000013343 vitamin Nutrition 0.000 description 3
- 239000011782 vitamin Substances 0.000 description 3
- 235000019143 vitamin K2 Nutrition 0.000 description 3
- 239000011728 vitamin K2 Substances 0.000 description 3
- QFOHBWFCKVYLES-UHFFFAOYSA-N Butylparaben Chemical compound CCCCOC(=O)C1=CC=C(O)C=C1 QFOHBWFCKVYLES-UHFFFAOYSA-N 0.000 description 2
- 206010058314 Dysplasia Diseases 0.000 description 2
- ZZSNKZQZMQGXPY-UHFFFAOYSA-N Ethyl cellulose Chemical compound CCOCC1OC(OC)C(OCC)C(OCC)C1OC1C(O)C(O)C(OC)C(CO)O1 ZZSNKZQZMQGXPY-UHFFFAOYSA-N 0.000 description 2
- 206010016936 Folliculitis Diseases 0.000 description 2
- 229920000663 Hydroxyethyl cellulose Polymers 0.000 description 2
- 239000005411 L01XE02 - Gefitinib Substances 0.000 description 2
- 229920003091 Methocel™ Polymers 0.000 description 2
- 235000019483 Peanut oil Nutrition 0.000 description 2
- 102000004022 Protein-Tyrosine Kinases Human genes 0.000 description 2
- 108090000412 Protein-Tyrosine Kinases Proteins 0.000 description 2
- 201000004681 Psoriasis Diseases 0.000 description 2
- 206010037888 Rash pustular Diseases 0.000 description 2
- 206010040914 Skin reaction Diseases 0.000 description 2
- 206010043189 Telangiectasia Diseases 0.000 description 2
- 206010048222 Xerosis Diseases 0.000 description 2
- 230000005856 abnormality Effects 0.000 description 2
- 239000004480 active ingredient Substances 0.000 description 2
- 230000002411 adverse Effects 0.000 description 2
- 208000010668 atopic eczema Diseases 0.000 description 2
- 230000008901 benefit Effects 0.000 description 2
- BLFLLBZGZJTVJG-UHFFFAOYSA-N benzocaine Chemical compound CCOC(=O)C1=CC=C(N)C=C1 BLFLLBZGZJTVJG-UHFFFAOYSA-N 0.000 description 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
- 210000004369 blood Anatomy 0.000 description 2
- 239000008280 blood Substances 0.000 description 2
- 229940075509 carbomer 1342 Drugs 0.000 description 2
- 210000004027 cell Anatomy 0.000 description 2
- 229920002678 cellulose Polymers 0.000 description 2
- 239000001913 cellulose Substances 0.000 description 2
- 239000002537 cosmetic Substances 0.000 description 2
- 230000006378 damage Effects 0.000 description 2
- 230000003111 delayed effect Effects 0.000 description 2
- 230000002939 deleterious effect Effects 0.000 description 2
- 230000008021 deposition Effects 0.000 description 2
- 238000002845 discoloration Methods 0.000 description 2
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 2
- 229940126534 drug product Drugs 0.000 description 2
- 229940088679 drug related substance Drugs 0.000 description 2
- 238000002283 elective surgery Methods 0.000 description 2
- 230000036566 epidermal hyperplasia Effects 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 210000004209 hair Anatomy 0.000 description 2
- 230000002209 hydrophobic effect Effects 0.000 description 2
- 235000019447 hydroxyethyl cellulose Nutrition 0.000 description 2
- 229920003088 hydroxypropyl methyl cellulose Polymers 0.000 description 2
- 208000000069 hyperpigmentation Diseases 0.000 description 2
- 230000003810 hyperpigmentation Effects 0.000 description 2
- 230000005764 inhibitory process Effects 0.000 description 2
- 238000011835 investigation Methods 0.000 description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
- 210000002510 keratinocyte Anatomy 0.000 description 2
- 229940059904 light mineral oil Drugs 0.000 description 2
- 230000000670 limiting effect Effects 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 239000003589 local anesthetic agent Substances 0.000 description 2
- 239000004702 low-density polyethylene Substances 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 230000001404 mediated effect Effects 0.000 description 2
- 239000002207 metabolite Substances 0.000 description 2
- 230000037311 normal skin Effects 0.000 description 2
- 239000000312 peanut oil Substances 0.000 description 2
- 150000003904 phospholipids Chemical class 0.000 description 2
- 230000000704 physical effect Effects 0.000 description 2
- 229920003023 plastic Polymers 0.000 description 2
- 239000004033 plastic Substances 0.000 description 2
- 229920005862 polyol Polymers 0.000 description 2
- 150000003077 polyols Chemical class 0.000 description 2
- 229960003981 proparacaine Drugs 0.000 description 2
- 238000001959 radiotherapy Methods 0.000 description 2
- 230000009467 reduction Effects 0.000 description 2
- 230000002829 reductive effect Effects 0.000 description 2
- 210000004761 scalp Anatomy 0.000 description 2
- 230000011664 signaling Effects 0.000 description 2
- 231100000430 skin reaction Toxicity 0.000 description 2
- 230000035483 skin reaction Effects 0.000 description 2
- 239000007921 spray Substances 0.000 description 2
- 238000003860 storage Methods 0.000 description 2
- 208000009056 telangiectasis Diseases 0.000 description 2
- QIWDGSYHBCMXSI-UHFFFAOYSA-J tetrasodium;(2-methyl-4-phosphonatooxynaphthalen-1-yl) phosphate;hexahydrate Chemical compound O.O.O.O.O.O.[Na+].[Na+].[Na+].[Na+].C1=CC=CC2=C(OP([O-])([O-])=O)C(C)=CC(OP([O-])([O-])=O)=C21 QIWDGSYHBCMXSI-UHFFFAOYSA-J 0.000 description 2
- VBEQCZHXXJYVRD-GACYYNSASA-N uroanthelone Chemical compound C([C@@H](C(=O)N[C@H](C(=O)N[C@@H](CS)C(=O)N[C@@H](CC(N)=O)C(=O)N[C@@H](CS)C(=O)N[C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)NCC(=O)N[C@@H](CC=1C=CC(O)=CC=1)C(=O)N[C@@H](CO)C(=O)NCC(=O)N[C@@H](CC(O)=O)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](CS)C(=O)N[C@@H](CCC(N)=O)C(=O)N[C@@H]([C@@H](C)O)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](CC(O)=O)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](CC=1C2=CC=CC=C2NC=1)C(=O)N[C@@H](CC=1C2=CC=CC=C2NC=1)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CCCNC(N)=N)C(O)=O)C(C)C)[C@@H](C)O)NC(=O)[C@H](CO)NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CO)NC(=O)[C@H](CCC(O)=O)NC(=O)[C@@H](NC(=O)[C@H](CC=1NC=NC=1)NC(=O)[C@H](CCSC)NC(=O)[C@H](CS)NC(=O)[C@@H](NC(=O)CNC(=O)CNC(=O)[C@H](CC(N)=O)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CS)NC(=O)[C@H](CC=1C=CC(O)=CC=1)NC(=O)CNC(=O)[C@H](CC(O)=O)NC(=O)[C@H](CC=1C=CC(O)=CC=1)NC(=O)[C@H](CO)NC(=O)[C@H](CO)NC(=O)[C@H]1N(CCC1)C(=O)[C@H](CS)NC(=O)CNC(=O)[C@H]1N(CCC1)C(=O)[C@H](CC=1C=CC(O)=CC=1)NC(=O)[C@H](CO)NC(=O)[C@@H](N)CC(N)=O)C(C)C)[C@@H](C)CC)C1=CC=C(O)C=C1 VBEQCZHXXJYVRD-GACYYNSASA-N 0.000 description 2
- 150000003722 vitamin derivatives Chemical class 0.000 description 2
- 239000003871 white petrolatum Substances 0.000 description 2
- HEOCBCNFKCOKBX-RELGSGGGSA-N (1s,2e,4r)-4,7,7-trimethyl-2-[(4-methylphenyl)methylidene]bicyclo[2.2.1]heptan-3-one Chemical compound C1=CC(C)=CC=C1\C=C/1C(=O)[C@]2(C)CC[C@H]\1C2(C)C HEOCBCNFKCOKBX-RELGSGGGSA-N 0.000 description 1
- ALSTYHKOOCGGFT-KTKRTIGZSA-N (9Z)-octadecen-1-ol Chemical compound CCCCCCCC\C=C/CCCCCCCCO ALSTYHKOOCGGFT-KTKRTIGZSA-N 0.000 description 1
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 description 1
- MXOAEAUPQDYUQM-QMMMGPOBSA-N (S)-chlorphenesin Chemical compound OC[C@H](O)COC1=CC=C(Cl)C=C1 MXOAEAUPQDYUQM-QMMMGPOBSA-N 0.000 description 1
- DYLIWHYUXAJDOJ-OWOJBTEDSA-N (e)-4-(6-aminopurin-9-yl)but-2-en-1-ol Chemical compound NC1=NC=NC2=C1N=CN2C\C=C\CO DYLIWHYUXAJDOJ-OWOJBTEDSA-N 0.000 description 1
- ABEXEQSGABRUHS-UHFFFAOYSA-N 16-methylheptadecyl 16-methylheptadecanoate Chemical compound CC(C)CCCCCCCCCCCCCCCOC(=O)CCCCCCCCCCCCCCC(C)C ABEXEQSGABRUHS-UHFFFAOYSA-N 0.000 description 1
- BFUUJUGQJUTPAF-UHFFFAOYSA-N 2-(3-amino-4-propoxybenzoyl)oxyethyl-diethylazanium;chloride Chemical compound [Cl-].CCCOC1=CC=C(C(=O)OCC[NH+](CC)CC)C=C1N BFUUJUGQJUTPAF-UHFFFAOYSA-N 0.000 description 1
- PFRQBZFETXBLTP-RCIYGOBDSA-N 2-[(2e,6e,10e,14e,18e)-3,7,11,15,19,23-hexamethyltetracosa-2,6,10,14,18,22-hexaen-1-yl]-3-methyl-1,4-dihydronaphthalene-1,4-dione Chemical compound C1=CC=C2C(=O)C(C/C=C(C)/CC/C=C(C)/CC/C=C(C)/CC/C=C(C)/CC/C=C(C)/CCC=C(C)C)=C(C)C(=O)C2=C1 PFRQBZFETXBLTP-RCIYGOBDSA-N 0.000 description 1
- JBOOHWBSLUXBQW-KAMYIIQDSA-N 2-[(z)-(3-methyl-4-oxonaphthalen-1-ylidene)amino]oxyacetic acid Chemical compound C1=CC=C2C(=O)C(C)=C\C(=N\OCC(O)=O)C2=C1 JBOOHWBSLUXBQW-KAMYIIQDSA-N 0.000 description 1
- JKXYOQDLERSFPT-UHFFFAOYSA-N 2-[2-[2-[2-[2-[2-[2-[2-[2-[2-[2-[2-[2-[2-[2-[2-[2-[2-[2-(2-octadecoxyethoxy)ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethanol Chemical compound CCCCCCCCCCCCCCCCCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCO JKXYOQDLERSFPT-UHFFFAOYSA-N 0.000 description 1
- TYYHDKOVFSVWON-UHFFFAOYSA-N 2-butyl-2-methoxy-1,3-diphenylpropane-1,3-dione Chemical compound C=1C=CC=CC=1C(=O)C(OC)(CCCC)C(=O)C1=CC=CC=C1 TYYHDKOVFSVWON-UHFFFAOYSA-N 0.000 description 1
- HYPYXGZDOYTYDR-HAJWAVTHSA-N 2-methyl-3-[(2e,6e,10e,14e)-3,7,11,15,19-pentamethylicosa-2,6,10,14,18-pentaenyl]naphthalene-1,4-dione Chemical compound C1=CC=C2C(=O)C(C/C=C(C)/CC/C=C(C)/CC/C=C(C)/CC/C=C(C)/CCC=C(C)C)=C(C)C(=O)C2=C1 HYPYXGZDOYTYDR-HAJWAVTHSA-N 0.000 description 1
- BCKLPBBBFNWJHH-UHFFFAOYSA-N 2-methylnaphthalene-1,4-diamine Chemical compound C1=CC=CC2=C(N)C(C)=CC(N)=C21 BCKLPBBBFNWJHH-UHFFFAOYSA-N 0.000 description 1
- LEACJMVNYZDSKR-UHFFFAOYSA-N 2-octyldodecan-1-ol Chemical compound CCCCCCCCCCC(CO)CCCCCCCC LEACJMVNYZDSKR-UHFFFAOYSA-N 0.000 description 1
- QCDWFXQBSFUVSP-UHFFFAOYSA-N 2-phenoxyethanol Chemical compound OCCOC1=CC=CC=C1 QCDWFXQBSFUVSP-UHFFFAOYSA-N 0.000 description 1
- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 description 1
- XXBAQTDVRLRXEV-UHFFFAOYSA-N 3-tetradecoxypropan-1-ol Chemical compound CCCCCCCCCCCCCCOCCCO XXBAQTDVRLRXEV-UHFFFAOYSA-N 0.000 description 1
- NSXDYOBMGOUYQJ-UHFFFAOYSA-N 4,6-dimethyl-1h-pyrimidin-2-one;2-methyl-1,4-dioxo-3h-naphthalene-2-sulfonic acid Chemical compound CC=1C=C(C)NC(=O)N=1.C1=CC=C2C(=O)C(C)(S(O)(=O)=O)CC(=O)C2=C1 NSXDYOBMGOUYQJ-UHFFFAOYSA-N 0.000 description 1
- UGQFCTZXVAPVCS-UHFFFAOYSA-N 4-amino-2-methyl-1-naphthol Chemical compound C1=CC=CC2=C(O)C(C)=CC(N)=C21 UGQFCTZXVAPVCS-UHFFFAOYSA-N 0.000 description 1
- YJRCNAAPGQBVFS-UHFFFAOYSA-N 4-amino-3-methylnaphthalen-1-ol Chemical compound C1=CC=CC2=C(N)C(C)=CC(O)=C21 YJRCNAAPGQBVFS-UHFFFAOYSA-N 0.000 description 1
- OZIWSTQWWVNPDA-UHFFFAOYSA-N 4-amino-3-methylnaphthalen-1-ol;hydrochloride Chemical compound Cl.C1=CC=CC2=C(N)C(C)=CC(O)=C21 OZIWSTQWWVNPDA-UHFFFAOYSA-N 0.000 description 1
- KDOPAZIWBAHVJB-UHFFFAOYSA-N 5h-pyrrolo[3,2-d]pyrimidine Chemical compound C1=NC=C2NC=CC2=N1 KDOPAZIWBAHVJB-UHFFFAOYSA-N 0.000 description 1
- QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 description 1
- 235000019489 Almond oil Nutrition 0.000 description 1
- 201000004384 Alopecia Diseases 0.000 description 1
- 206010003694 Atrophy Diseases 0.000 description 1
- 241000894006 Bacteria Species 0.000 description 1
- 239000005711 Benzoic acid Substances 0.000 description 1
- 241000283690 Bos taurus Species 0.000 description 1
- 206010006784 Burning sensation Diseases 0.000 description 1
- 239000004322 Butylated hydroxytoluene Substances 0.000 description 1
- NLZUEZXRPGMBCV-UHFFFAOYSA-N Butylhydroxytoluene Chemical compound CC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 NLZUEZXRPGMBCV-UHFFFAOYSA-N 0.000 description 1
- 101100408464 Caenorhabditis elegans plc-1 gene Proteins 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical group [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- 241000282472 Canis lupus familiaris Species 0.000 description 1
- 229920002134 Carboxymethyl cellulose Polymers 0.000 description 1
- 102000053642 Catalytic RNA Human genes 0.000 description 1
- 108090000994 Catalytic RNA Proteins 0.000 description 1
- 208000003322 Coinfection Diseases 0.000 description 1
- 206010009944 Colon cancer Diseases 0.000 description 1
- 208000001333 Colorectal Neoplasms Diseases 0.000 description 1
- 229920002785 Croscarmellose sodium Polymers 0.000 description 1
- 229920008716 Darex Polymers 0.000 description 1
- QXNVGIXVLWOKEQ-UHFFFAOYSA-N Disodium Chemical compound [Na][Na] QXNVGIXVLWOKEQ-UHFFFAOYSA-N 0.000 description 1
- IUMSDRXLFWAGNT-UHFFFAOYSA-N Dodecamethylcyclohexasiloxane Chemical compound C[Si]1(C)O[Si](C)(C)O[Si](C)(C)O[Si](C)(C)O[Si](C)(C)O[Si](C)(C)O1 IUMSDRXLFWAGNT-UHFFFAOYSA-N 0.000 description 1
- 102000001301 EGF receptor Human genes 0.000 description 1
- 108060006698 EGF receptor Proteins 0.000 description 1
- 101150039808 Egfr gene Proteins 0.000 description 1
- 241000196324 Embryophyta Species 0.000 description 1
- 102000009024 Epidermal Growth Factor Human genes 0.000 description 1
- 101800003838 Epidermal growth factor Proteins 0.000 description 1
- 241000283086 Equidae Species 0.000 description 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
- 241000282326 Felis catus Species 0.000 description 1
- 206010018338 Glioma Diseases 0.000 description 1
- 101001046960 Homo sapiens Keratin, type II cytoskeletal 1 Proteins 0.000 description 1
- 229920002153 Hydroxypropyl cellulose Polymers 0.000 description 1
- 206010020649 Hyperkeratosis Diseases 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- 102100022905 Keratin, type II cytoskeletal 1 Human genes 0.000 description 1
- 208000001126 Keratosis Diseases 0.000 description 1
- NNJVILVZKWQKPM-UHFFFAOYSA-N Lidocaine Chemical compound CCN(CC)CC(=O)NC1=C(C)C=CC=C1C NNJVILVZKWQKPM-UHFFFAOYSA-N 0.000 description 1
- 241000124008 Mammalia Species 0.000 description 1
- 201000007224 Myeloproliferative neoplasm Diseases 0.000 description 1
- 229930192627 Naphthoquinone Natural products 0.000 description 1
- PCKPVGOLPKLUHR-UHFFFAOYSA-N OH-Indolxyl Natural products C1=CC=C2C(O)=CNC2=C1 PCKPVGOLPKLUHR-UHFFFAOYSA-N 0.000 description 1
- YBGZDTIWKVFICR-JLHYYAGUSA-N Octyl 4-methoxycinnamic acid Chemical compound CCCCC(CC)COC(=O)\C=C\C1=CC=C(OC)C=C1 YBGZDTIWKVFICR-JLHYYAGUSA-N 0.000 description 1
- 239000005642 Oleic acid Substances 0.000 description 1
- ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 description 1
- 208000012868 Overgrowth Diseases 0.000 description 1
- 241001494479 Pecora Species 0.000 description 1
- 229940122907 Phosphatase inhibitor Drugs 0.000 description 1
- 102000004160 Phosphoric Monoester Hydrolases Human genes 0.000 description 1
- 108090000608 Phosphoric Monoester Hydrolases Proteins 0.000 description 1
- 108091000080 Phosphotransferase Proteins 0.000 description 1
- KCLANYCVBBTKTO-UHFFFAOYSA-N Proparacaine Chemical compound CCCOC1=CC=C(C(=O)OCCN(CC)CC)C=C1N KCLANYCVBBTKTO-UHFFFAOYSA-N 0.000 description 1
- 208000003251 Pruritus Diseases 0.000 description 1
- 206010037876 Rash papular Diseases 0.000 description 1
- 108010017324 STAT3 Transcription Factor Proteins 0.000 description 1
- 206010039793 Seborrhoeic dermatitis Diseases 0.000 description 1
- 102100024040 Signal transducer and activator of transcription 3 Human genes 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 208000000102 Squamous Cell Carcinoma of Head and Neck Diseases 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- 241000282887 Suidae Species 0.000 description 1
- XEFQLINVKFYRCS-UHFFFAOYSA-N Triclosan Chemical compound OC1=CC(Cl)=CC=C1OC1=CC=C(Cl)C=C1Cl XEFQLINVKFYRCS-UHFFFAOYSA-N 0.000 description 1
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 1
- 208000027418 Wounds and injury Diseases 0.000 description 1
- 230000002159 abnormal effect Effects 0.000 description 1
- 238000005299 abrasion Methods 0.000 description 1
- VJHCJDRQFCCTHL-UHFFFAOYSA-N acetic acid 2,3,4,5,6-pentahydroxyhexanal Chemical compound CC(O)=O.OCC(O)C(O)C(O)C(O)C=O VJHCJDRQFCCTHL-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 230000003213 activating effect Effects 0.000 description 1
- WNLRTRBMVRJNCN-UHFFFAOYSA-L adipate(2-) Chemical compound [O-]C(=O)CCCCC([O-])=O WNLRTRBMVRJNCN-UHFFFAOYSA-L 0.000 description 1
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
- 125000005233 alkylalcohol group Chemical group 0.000 description 1
- 239000000956 alloy Substances 0.000 description 1
- 229910045601 alloy Inorganic materials 0.000 description 1
- 239000008168 almond oil Substances 0.000 description 1
- 230000004075 alteration Effects 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 239000000730 antalgic agent Substances 0.000 description 1
- 239000003242 anti bacterial agent Substances 0.000 description 1
- 239000002260 anti-inflammatory agent Substances 0.000 description 1
- 229940121363 anti-inflammatory agent Drugs 0.000 description 1
- 230000003110 anti-inflammatory effect Effects 0.000 description 1
- 230000000845 anti-microbial effect Effects 0.000 description 1
- 230000000692 anti-sense effect Effects 0.000 description 1
- 230000000259 anti-tumor effect Effects 0.000 description 1
- 229940088710 antibiotic agent Drugs 0.000 description 1
- 239000004599 antimicrobial Substances 0.000 description 1
- 239000002246 antineoplastic agent Substances 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 235000006708 antioxidants Nutrition 0.000 description 1
- 239000013011 aqueous formulation Substances 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- BTFJIXJJCSYFAL-UHFFFAOYSA-N arachidyl alcohol Natural products CCCCCCCCCCCCCCCCCCCCO BTFJIXJJCSYFAL-UHFFFAOYSA-N 0.000 description 1
- 230000037444 atrophy Effects 0.000 description 1
- 229960005193 avobenzone Drugs 0.000 description 1
- 229960005274 benzocaine Drugs 0.000 description 1
- 235000010233 benzoic acid Nutrition 0.000 description 1
- XSCHRSMBECNVNS-UHFFFAOYSA-N benzopyrazine Natural products N1=CC=NC2=CC=CC=C21 XSCHRSMBECNVNS-UHFFFAOYSA-N 0.000 description 1
- 230000003115 biocidal effect Effects 0.000 description 1
- 239000000560 biocompatible material Substances 0.000 description 1
- 239000000090 biomarker Substances 0.000 description 1
- 239000005388 borosilicate glass Substances 0.000 description 1
- 239000000872 buffer Substances 0.000 description 1
- 229960000400 butamben Drugs 0.000 description 1
- IUWVALYLNVXWKX-UHFFFAOYSA-N butamben Chemical compound CCCCOC(=O)C1=CC=C(N)C=C1 IUWVALYLNVXWKX-UHFFFAOYSA-N 0.000 description 1
- 235000010354 butylated hydroxytoluene Nutrition 0.000 description 1
- 229940095259 butylated hydroxytoluene Drugs 0.000 description 1
- 229940067596 butylparaben Drugs 0.000 description 1
- 235000010948 carboxy methyl cellulose Nutrition 0.000 description 1
- 239000004359 castor oil Substances 0.000 description 1
- 235000019438 castor oil Nutrition 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 238000012512 characterization method Methods 0.000 description 1
- OGEBRHQLRGFBNV-RZDIXWSQSA-N chembl2036808 Chemical compound C12=NC(NCCCC)=NC=C2C(C=2C=CC(F)=CC=2)=NN1C[C@H]1CC[C@H](N)CC1 OGEBRHQLRGFBNV-RZDIXWSQSA-N 0.000 description 1
- 150000005829 chemical entities Chemical class 0.000 description 1
- 229960003993 chlorphenesin Drugs 0.000 description 1
- 229960001747 cinchocaine Drugs 0.000 description 1
- PUFQVTATUTYEAL-UHFFFAOYSA-N cinchocaine Chemical compound C1=CC=CC2=NC(OCCCC)=CC(C(=O)NCCN(CC)CC)=C21 PUFQVTATUTYEAL-UHFFFAOYSA-N 0.000 description 1
- 239000008119 colloidal silica Substances 0.000 description 1
- 201000010989 colorectal carcinoma Diseases 0.000 description 1
- 238000010961 commercial manufacture process Methods 0.000 description 1
- 239000000306 component Substances 0.000 description 1
- 238000013329 compounding Methods 0.000 description 1
- 230000001010 compromised effect Effects 0.000 description 1
- 238000013270 controlled release Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 229960005168 croscarmellose Drugs 0.000 description 1
- 239000001767 crosslinked sodium carboxy methyl cellulose Substances 0.000 description 1
- SASYSVUEVMOWPL-NXVVXOECSA-N decyl oleate Chemical compound CCCCCCCCCCOC(=O)CCCCCCC\C=C/CCCCCCCC SASYSVUEVMOWPL-NXVVXOECSA-N 0.000 description 1
- 238000006731 degradation reaction Methods 0.000 description 1
- SOROIESOUPGGFO-UHFFFAOYSA-N diazolidinylurea Chemical compound OCNC(=O)N(CO)C1N(CO)C(=O)N(CO)C1=O SOROIESOUPGGFO-UHFFFAOYSA-N 0.000 description 1
- 229960001083 diazolidinylurea Drugs 0.000 description 1
- 229940075557 diethylene glycol monoethyl ether Drugs 0.000 description 1
- 230000004069 differentiation Effects 0.000 description 1
- 238000009792 diffusion process Methods 0.000 description 1
- 229940008099 dimethicone Drugs 0.000 description 1
- 239000004205 dimethyl polysiloxane Substances 0.000 description 1
- 235000013870 dimethyl polysiloxane Nutrition 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000035475 disorder Diseases 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- WSDISUOETYTPRL-UHFFFAOYSA-N dmdm hydantoin Chemical compound CC1(C)N(CO)C(=O)N(CO)C1=O WSDISUOETYTPRL-UHFFFAOYSA-N 0.000 description 1
- HUVYTMDMDZRHBN-UHFFFAOYSA-N drometrizole trisiloxane Chemical compound C[Si](C)(C)O[Si](C)(O[Si](C)(C)C)CC(C)CC1=CC(C)=CC(N2N=C3C=CC=CC3=N2)=C1O HUVYTMDMDZRHBN-UHFFFAOYSA-N 0.000 description 1
- 239000003684 drug solvent Substances 0.000 description 1
- 230000004064 dysfunction Effects 0.000 description 1
- 230000002500 effect on skin Effects 0.000 description 1
- 239000003974 emollient agent Substances 0.000 description 1
- 229960004697 enzacamene Drugs 0.000 description 1
- 210000002919 epithelial cell Anatomy 0.000 description 1
- 210000000981 epithelium Anatomy 0.000 description 1
- 229940082789 erbitux Drugs 0.000 description 1
- BEFDCLMNVWHSGT-UHFFFAOYSA-N ethenylcyclopentane Chemical compound C=CC1CCCC1 BEFDCLMNVWHSGT-UHFFFAOYSA-N 0.000 description 1
- 229920001249 ethyl cellulose Polymers 0.000 description 1
- 235000019325 ethyl cellulose Nutrition 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 210000000720 eyelash Anatomy 0.000 description 1
- 230000001815 facial effect Effects 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 229920002457 flexible plastic Polymers 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 239000006260 foam Substances 0.000 description 1
- 230000003325 follicular Effects 0.000 description 1
- ZEMPKEQAKRGZGQ-XOQCFJPHSA-N glycerol triricinoleate Natural products CCCCCC[C@@H](O)CC=CCCCCCCCC(=O)OC[C@@H](COC(=O)CCCCCCCC=CC[C@@H](O)CCCCCC)OC(=O)CCCCCCCC=CC[C@H](O)CCCCCC ZEMPKEQAKRGZGQ-XOQCFJPHSA-N 0.000 description 1
- 239000003102 growth factor Substances 0.000 description 1
- 230000003779 hair growth Effects 0.000 description 1
- 208000024963 hair loss Diseases 0.000 description 1
- 230000003676 hair loss Effects 0.000 description 1
- 201000010536 head and neck cancer Diseases 0.000 description 1
- 208000014829 head and neck neoplasm Diseases 0.000 description 1
- 201000000459 head and neck squamous cell carcinoma Diseases 0.000 description 1
- 230000035876 healing Effects 0.000 description 1
- 238000004128 high performance liquid chromatography Methods 0.000 description 1
- 239000008311 hydrophilic ointment Substances 0.000 description 1
- 235000010977 hydroxypropyl cellulose Nutrition 0.000 description 1
- 235000010979 hydroxypropyl methyl cellulose Nutrition 0.000 description 1
- ZCTXEAQXZGPWFG-UHFFFAOYSA-N imidurea Chemical compound O=C1NC(=O)N(CO)C1NC(=O)NCNC(=O)NC1C(=O)NC(=O)N1CO ZCTXEAQXZGPWFG-UHFFFAOYSA-N 0.000 description 1
- 238000002991 immunohistochemical analysis Methods 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- JYGFTBXVXVMTGB-UHFFFAOYSA-N indolin-2-one Chemical compound C1=CC=C2NC(=O)CC2=C1 JYGFTBXVXVMTGB-UHFFFAOYSA-N 0.000 description 1
- VVVPGLRKXQSQSZ-UHFFFAOYSA-N indolo[3,2-c]carbazole Chemical compound C1=CC=CC2=NC3=C4C5=CC=CC=C5N=C4C=CC3=C21 VVVPGLRKXQSQSZ-UHFFFAOYSA-N 0.000 description 1
- 229960005544 indolocarbazole Drugs 0.000 description 1
- 208000015181 infectious disease Diseases 0.000 description 1
- 230000008595 infiltration Effects 0.000 description 1
- 238000001764 infiltration Methods 0.000 description 1
- 210000004969 inflammatory cell Anatomy 0.000 description 1
- 230000000977 initiatory effect Effects 0.000 description 1
- 208000014674 injury Diseases 0.000 description 1
- 230000000968 intestinal effect Effects 0.000 description 1
- 230000003834 intracellular effect Effects 0.000 description 1
- GOMNOOKGLZYEJT-UHFFFAOYSA-N isoflavone Chemical compound C=1OC2=CC=CC=C2C(=O)C=1C1=CC=CC=C1 GOMNOOKGLZYEJT-UHFFFAOYSA-N 0.000 description 1
- CJWQYWQDLBZGPD-UHFFFAOYSA-N isoflavone Natural products C1=C(OC)C(OC)=CC(OC)=C1C1=COC2=C(C=CC(C)(C)O3)C3=C(OC)C=C2C1=O CJWQYWQDLBZGPD-UHFFFAOYSA-N 0.000 description 1
- 235000008696 isoflavones Nutrition 0.000 description 1
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 description 1
- 229940074928 isopropyl myristate Drugs 0.000 description 1
- XUGNVMKQXJXZCD-UHFFFAOYSA-N isopropyl palmitate Chemical compound CCCCCCCCCCCCCCCC(=O)OC(C)C XUGNVMKQXJXZCD-UHFFFAOYSA-N 0.000 description 1
- 229940060384 isostearyl isostearate Drugs 0.000 description 1
- 230000007803 itching Effects 0.000 description 1
- 229960004194 lidocaine Drugs 0.000 description 1
- 231100001106 life-threatening toxicity Toxicity 0.000 description 1
- 239000000944 linseed oil Substances 0.000 description 1
- 235000021388 linseed oil Nutrition 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- 238000002483 medication Methods 0.000 description 1
- 229940100434 menadiol Drugs 0.000 description 1
- 229950000960 menadiol sodium diphosphate Drugs 0.000 description 1
- 229960004051 menadione sodium bisulfite Drugs 0.000 description 1
- XDPFHGWVCTXHDX-UHFFFAOYSA-M menadione sodium sulfonate Chemical compound [Na+].C1=CC=C2C(=O)C(C)(S([O-])(=O)=O)CC(=O)C2=C1 XDPFHGWVCTXHDX-UHFFFAOYSA-M 0.000 description 1
- 229950010153 menadoxime Drugs 0.000 description 1
- RAKQPZMEYJZGPI-LJWNYQGCSA-N menaquinone-7 Chemical compound C1=CC=C2C(=O)C(C/C=C(C)/CC/C=C(C)/CC/C=C(C)/CC/C=C(C)/CC/C=C(C)/CC/C=C(C)/CCC=C(C)C)=C(C)C(=O)C2=C1 RAKQPZMEYJZGPI-LJWNYQGCSA-N 0.000 description 1
- 235000009464 menaquinone-7 Nutrition 0.000 description 1
- 239000011700 menaquinone-7 Substances 0.000 description 1
- 229920000609 methyl cellulose Polymers 0.000 description 1
- YLGXILFCIXHCMC-JHGZEJCSSA-N methyl cellulose Chemical compound COC1C(OC)C(OC)C(COC)O[C@H]1O[C@H]1C(OC)C(OC)C(OC)OC1COC YLGXILFCIXHCMC-JHGZEJCSSA-N 0.000 description 1
- 235000010981 methylcellulose Nutrition 0.000 description 1
- 229940009674 methylparaben / propylparaben Drugs 0.000 description 1
- 244000005700 microbiome Species 0.000 description 1
- 230000005012 migration Effects 0.000 description 1
- 238000013508 migration Methods 0.000 description 1
- 239000003226 mitogen Substances 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 230000003020 moisturizing effect Effects 0.000 description 1
- 229940045641 monobasic sodium phosphate Drugs 0.000 description 1
- 229910000403 monosodium phosphate Inorganic materials 0.000 description 1
- 235000019799 monosodium phosphate Nutrition 0.000 description 1
- XGXNTJHZPBRBHJ-UHFFFAOYSA-N n-phenylpyrimidin-2-amine Chemical compound N=1C=CC=NC=1NC1=CC=CC=C1 XGXNTJHZPBRBHJ-UHFFFAOYSA-N 0.000 description 1
- 208000026721 nail disease Diseases 0.000 description 1
- 150000002791 naphthoquinones Chemical class 0.000 description 1
- 230000003448 neutrophilic effect Effects 0.000 description 1
- 208000002154 non-small cell lung carcinoma Diseases 0.000 description 1
- 229960001679 octinoxate Drugs 0.000 description 1
- 229960003921 octisalate Drugs 0.000 description 1
- FMJSMJQBSVNSBF-UHFFFAOYSA-N octocrylene Chemical group C=1C=CC=CC=1C(=C(C#N)C(=O)OCC(CC)CCCC)C1=CC=CC=C1 FMJSMJQBSVNSBF-UHFFFAOYSA-N 0.000 description 1
- 229960000601 octocrylene Drugs 0.000 description 1
- WCJLCOAEJIHPCW-UHFFFAOYSA-N octyl 2-hydroxybenzoate Chemical compound CCCCCCCCOC(=O)C1=CC=CC=C1O WCJLCOAEJIHPCW-UHFFFAOYSA-N 0.000 description 1
- 239000002674 ointment Substances 0.000 description 1
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 1
- 229940055577 oleyl alcohol Drugs 0.000 description 1
- XMLQWXUVTXCDDL-UHFFFAOYSA-N oleyl alcohol Natural products CCCCCCC=CCCCCCCCCCCO XMLQWXUVTXCDDL-UHFFFAOYSA-N 0.000 description 1
- 239000004006 olive oil Substances 0.000 description 1
- 235000008390 olive oil Nutrition 0.000 description 1
- DXGLGDHPHMLXJC-UHFFFAOYSA-N oxybenzone Chemical compound OC1=CC(OC)=CC=C1C(=O)C1=CC=CC=C1 DXGLGDHPHMLXJC-UHFFFAOYSA-N 0.000 description 1
- 229960001173 oxybenzone Drugs 0.000 description 1
- 229960003502 oxybuprocaine Drugs 0.000 description 1
- CMHHMUWAYWTMGS-UHFFFAOYSA-N oxybuprocaine Chemical compound CCCCOC1=CC(C(=O)OCCN(CC)CC)=CC=C1N CMHHMUWAYWTMGS-UHFFFAOYSA-N 0.000 description 1
- 229960001972 panitumumab Drugs 0.000 description 1
- 208000012963 papular rash Diseases 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 239000003961 penetration enhancing agent Substances 0.000 description 1
- 229940127557 pharmaceutical product Drugs 0.000 description 1
- 229960005323 phenoxyethanol Drugs 0.000 description 1
- 239000008363 phosphate buffer Substances 0.000 description 1
- 102000020233 phosphotransferase Human genes 0.000 description 1
- 238000001782 photodegradation Methods 0.000 description 1
- LFSXCDWNBUNEEM-UHFFFAOYSA-N phthalazine Chemical compound C1=NN=CC2=CC=CC=C21 LFSXCDWNBUNEEM-UHFFFAOYSA-N 0.000 description 1
- MBWXNTAXLNYFJB-LKUDQCMESA-N phylloquinone Chemical compound C1=CC=C2C(=O)C(C/C=C(C)/CCCC(C)CCCC(C)CCCC(C)C)=C(C)C(=O)C2=C1 MBWXNTAXLNYFJB-LKUDQCMESA-N 0.000 description 1
- 230000035479 physiological effects, processes and functions Effects 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 229920000435 poly(dimethylsiloxane) Polymers 0.000 description 1
- 229940113115 polyethylene glycol 200 Drugs 0.000 description 1
- 239000013641 positive control Substances 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 229940116987 ppg-3 myristyl ether Drugs 0.000 description 1
- 229960001896 pramocaine Drugs 0.000 description 1
- DQKXQSGTHWVTAD-UHFFFAOYSA-N pramocaine Chemical compound C1=CC(OCCCC)=CC=C1OCCCN1CCOCC1 DQKXQSGTHWVTAD-UHFFFAOYSA-N 0.000 description 1
- 230000002028 premature Effects 0.000 description 1
- 230000035755 proliferation Effects 0.000 description 1
- 239000011253 protective coating Substances 0.000 description 1
- BWESROVQGZSBRX-UHFFFAOYSA-N pyrido[3,2-d]pyrimidine Chemical compound C1=NC=NC2=CC=CN=C21 BWESROVQGZSBRX-UHFFFAOYSA-N 0.000 description 1
- JOZPEVMCAKXSEY-UHFFFAOYSA-N pyrimido[5,4-d]pyrimidine Chemical compound N1=CN=CC2=NC=NC=C21 JOZPEVMCAKXSEY-UHFFFAOYSA-N 0.000 description 1
- 238000011002 quantification Methods 0.000 description 1
- JWVCLYRUEFBMGU-UHFFFAOYSA-N quinazoline Chemical compound N1=CN=CC2=CC=CC=C21 JWVCLYRUEFBMGU-UHFFFAOYSA-N 0.000 description 1
- 230000007115 recruitment Effects 0.000 description 1
- 238000005057 refrigeration Methods 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 230000004043 responsiveness Effects 0.000 description 1
- 230000000717 retained effect Effects 0.000 description 1
- 108091092562 ribozyme Proteins 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 238000012216 screening Methods 0.000 description 1
- 210000001732 sebaceous gland Anatomy 0.000 description 1
- 208000008742 seborrheic dermatitis Diseases 0.000 description 1
- 229920002545 silicone oil Polymers 0.000 description 1
- 238000004088 simulation Methods 0.000 description 1
- 231100000274 skin absorption Toxicity 0.000 description 1
- 230000037384 skin absorption Effects 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000001488 sodium phosphate Substances 0.000 description 1
- 229910000162 sodium phosphate Inorganic materials 0.000 description 1
- 235000011008 sodium phosphates Nutrition 0.000 description 1
- 239000007962 solid dispersion Substances 0.000 description 1
- 239000012453 solvate Substances 0.000 description 1
- 235000010199 sorbic acid Nutrition 0.000 description 1
- 239000004334 sorbic acid Substances 0.000 description 1
- 229940075582 sorbic acid Drugs 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 238000011301 standard therapy Methods 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 210000000434 stratum corneum Anatomy 0.000 description 1
- 230000000475 sunscreen effect Effects 0.000 description 1
- 239000000516 sunscreening agent Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 238000007910 systemic administration Methods 0.000 description 1
- 229960002372 tetracaine Drugs 0.000 description 1
- GKCBAIGFKIBETG-UHFFFAOYSA-N tetracaine Chemical compound CCCCNC1=CC=C(C(=O)OCCN(C)C)C=C1 GKCBAIGFKIBETG-UHFFFAOYSA-N 0.000 description 1
- 210000001519 tissue Anatomy 0.000 description 1
- 238000011200 topical administration Methods 0.000 description 1
- 229960003500 triclosan Drugs 0.000 description 1
- 208000029729 tumor suppressor gene on chromosome 11 Diseases 0.000 description 1
- 239000002383 tung oil Substances 0.000 description 1
- 229940121358 tyrosine kinase inhibitor Drugs 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 150000003718 vitamin K5 derivatives Chemical class 0.000 description 1
- 230000029663 wound healing Effects 0.000 description 1
- 239000000230 xanthan gum Substances 0.000 description 1
- 229920001285 xanthan gum Polymers 0.000 description 1
- 235000010493 xanthan gum Nutrition 0.000 description 1
- 229940082509 xanthan gum Drugs 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
- A61K47/06—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite
- A61K47/08—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite containing oxygen, e.g. ethers, acetals, ketones, quinones, aldehydes, peroxides
- A61K47/14—Esters of carboxylic acids, e.g. fatty acid monoglycerides, medium-chain triglycerides, parabens or PEG fatty acid esters
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/12—Ketones
- A61K31/122—Ketones having the oxygen directly attached to a ring, e.g. quinones, vitamin K1, anthralin
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/0012—Galenical forms characterised by the site of application
- A61K9/0014—Skin, i.e. galenical aspects of topical compositions
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Epidemiology (AREA)
- Dermatology (AREA)
- Engineering & Computer Science (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Organic Chemistry (AREA)
- Medicinal Preparation (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US6921808P | 2008-03-13 | 2008-03-13 | |
| US61/069,218 | 2008-03-13 | ||
| US20493909P | 2009-01-13 | 2009-01-13 | |
| US61/204,939 | 2009-01-13 | ||
| PCT/US2009/037041 WO2009114745A1 (en) | 2008-03-13 | 2009-03-13 | Formulations of vitamin k analogs for topical use |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2718262A1 true CA2718262A1 (en) | 2009-09-17 |
Family
ID=40677542
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA2718262A Abandoned CA2718262A1 (en) | 2008-03-13 | 2009-03-13 | Formulations of vitamin k analogs for topical use |
Country Status (7)
| Country | Link |
|---|---|
| US (2) | US8815953B2 (OSRAM) |
| EP (1) | EP2265255A1 (OSRAM) |
| JP (2) | JP2011513501A (OSRAM) |
| KR (1) | KR20110004382A (OSRAM) |
| AU (1) | AU2009223158B2 (OSRAM) |
| CA (1) | CA2718262A1 (OSRAM) |
| WO (1) | WO2009114745A1 (OSRAM) |
Families Citing this family (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2010005989A1 (en) * | 2008-07-09 | 2010-01-14 | Edison Pharmaceuticals, Inc. | Dermatological compositions with anti-aging and skin even-toning properties |
| US20100029784A1 (en) * | 2008-07-30 | 2010-02-04 | Hinman Andrew W | Naphthoquinone compositions with anti-aging, anti-inflammatory and skin even-toning properties |
| RU2012114832A (ru) | 2009-09-14 | 2013-10-27 | Нестек С.А. | Питательные композиции для модулирования воспаления, содержащие экзогенный витамин к2 |
| ITPD20100090A1 (it) * | 2010-03-22 | 2011-09-23 | Sanitas Farmaceutici S R L | Formulazione topica per il trattamento di eruzioni cutanee, in particolare conseguenti a trattamenti con farmaci anti egfr |
| WO2012019032A1 (en) * | 2010-08-06 | 2012-02-09 | Ampere Life Sciences, Inc. | Treatment of mitochondrial diseases with vitamin k |
| JP5062922B2 (ja) | 2011-02-14 | 2012-10-31 | 株式会社Ｊ−オイルミルズ | 皮膚コラーゲン産生促進剤 |
| US9421297B2 (en) | 2014-04-02 | 2016-08-23 | Adhezion Biomedical, Llc | Sterilized compositions of cyanoacrylate monomers and naphthoquinone 2,3-oxides |
| EP3694491A1 (en) | 2017-10-10 | 2020-08-19 | Capsugel Belgium NV | Gelling multiparticulates |
| CN111601617A (zh) | 2017-12-13 | 2020-08-28 | 上海岸阔医药科技有限公司 | 一种用于预防或治疗与egfr 被抑制相关疾病的方法 |
| CN111989095A (zh) | 2018-04-16 | 2020-11-24 | 上海岸阔医药科技有限公司 | 预防或治疗肿瘤疗法副作用的方法 |
| WO2020067663A1 (ko) * | 2018-09-28 | 2020-04-02 | 주식회사 엘지생활건강 | 피부 턴오버 촉진 및 멜라닌 배출 촉진용 조성물 |
| JP7085073B2 (ja) * | 2019-04-17 | 2022-06-15 | アゾーラ セラピューティクス，インコーポレイテッド | 炎症性皮膚疾患を処置するための局所組成物及び方法 |
| WO2023119230A1 (en) | 2021-12-22 | 2023-06-29 | L'oreal | Coagulation pathway and nicotinamide-adenine dinucleotide pathway modulating compositions and methods of their use |
Family Cites Families (81)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4294852A (en) | 1973-11-01 | 1981-10-13 | Johnson & Johnson | Skin treating compositions |
| EP0015436B1 (de) | 1979-03-08 | 1982-02-03 | F. HOFFMANN-LA ROCHE & CO. Aktiengesellschaft | Verfahren zur stereospezifischen Herstellung von Verbindungen der Vitamin K1- und K2-Reihe sowie neue Ausgangsprodukte in diesem Verfahren |
| JPS6025918A (ja) | 1983-07-25 | 1985-02-08 | Ajinomoto Co Inc | 脂溶性薬物含有水性液 |
| DE3406497A1 (de) | 1984-02-23 | 1985-09-05 | Mueller Bernhard Willi Werner | Hochdisperse pharmazeutische mehrkomponentensysteme und verfahren zu ihrer herstellung |
| DE3514724A1 (de) | 1985-04-24 | 1986-10-30 | Albin F. Dr. 4200 Oberhausen Jereb | Salbe zur verbeugung und behandlung von augen- und hauterkrankungen |
| JPS62294636A (ja) | 1986-05-21 | 1987-12-22 | Eisai Co Ltd | ２−メチル−１，４−ナフトキノンの製造法 |
| US5180747A (en) | 1989-02-28 | 1993-01-19 | Nisshin Flour Milling Co., Ltd. | Stabilized fat-soluble vitamin compositions |
| ZA902066B (en) | 1989-04-14 | 1990-12-28 | Minnesota Mining & Mfg | Solid gel external drug delivery system |
| US4966779A (en) | 1989-12-21 | 1990-10-30 | Basf Corporation | Stable, water miscible emulsion comprising a fat-soluble vitamin |
| US5376645A (en) | 1990-01-23 | 1994-12-27 | University Of Kansas | Derivatives of cyclodextrins exhibiting enhanced aqueous solubility and the use thereof |
| KR0166088B1 (ko) | 1990-01-23 | 1999-01-15 | . | 수용해도가 증가된 시클로덱스트린 유도체 및 이의 용도 |
| US5155031A (en) | 1990-06-07 | 1992-10-13 | Posner Barry I | Use of pervanadate as an inhibitor of phosphotyrosine phosphatase |
| FR2672288B1 (fr) | 1991-02-06 | 1993-04-23 | Oreal | Nouveaux amides dipeptidiques derivant de la glycyl-serine, utilisables, notamment dans des compositions cosmetiques, pharmaceutiques ou alimentaires. |
| DE4141351A1 (de) | 1991-12-14 | 1993-06-17 | Basf Ag | Stabile pulverfoermige vitamin- und/oder carotinoid-praeparate und verfahren zu deren herstellung |
| US5650156A (en) | 1993-02-22 | 1997-07-22 | Vivorx Pharmaceuticals, Inc. | Methods for in vivo delivery of nutriceuticals and compositions useful therefor |
| US6537579B1 (en) | 1993-02-22 | 2003-03-25 | American Bioscience, Inc. | Compositions and methods for administration of pharmacologically active compounds |
| US5785976A (en) | 1993-03-05 | 1998-07-28 | Pharmacia & Upjohn Ab | Solid lipid particles, particles of bioactive agents and methods for the manufacture and use thereof |
| US5885486A (en) | 1993-03-05 | 1999-03-23 | Pharmaciaand Upjohn Ab | Solid lipid particles, particles of bioactive agents and methods for the manufacture and use thereof |
| US5643765A (en) | 1993-04-06 | 1997-07-01 | University Of Rochester | Method for quantitative measurement of gene expression using multiplex competitive reverse transcriptase-polymerase chain reaction |
| US5510391A (en) | 1993-10-22 | 1996-04-23 | Mayapple Holdings, Llc | Method of treating blood vessel disorders of the skin using vitamin K |
| FR2719219B1 (fr) | 1994-05-02 | 1996-06-21 | Rocher Yves Biolog Vegetale | Composition cosmétique ou pharmaceutique à usage topique comprenant des vésicules lipidiques. |
| US5637741A (en) | 1994-09-27 | 1997-06-10 | Kuraray Co., Ltd. | Process for producing 2-methyl-1,4-naphthoquinone |
| AU2804297A (en) | 1996-04-22 | 1997-11-12 | Advanced Polymer Systems Inc. | Method of and composition for treating disorders of the skin using vitamin k |
| KR0178456B1 (ko) | 1996-04-25 | 1999-05-15 | 김흥기 | 2-메틸-1,4-나프토퀴논(비타민 k3)의 제조방법 |
| SE9601665D0 (sv) | 1996-04-30 | 1996-04-30 | Bioglan Ab | Biologically active composition |
| US6110891A (en) | 1996-06-21 | 2000-08-29 | Alizyme Therapeutics Ltd. | Lectin compositions and uses thereof |
| DE19642359A1 (de) | 1996-10-14 | 1998-04-16 | Basf Ag | Stabile Emulsionen und Trockenpulver von Mischungen fettlöslicher Vitamine, deren Herstellung und Verwendung |
| US5916749A (en) | 1996-12-13 | 1999-06-29 | Incyte Pharmaceuticals, Inc. | Human phosphatase inhibitor protein |
| US6426078B1 (en) | 1997-03-17 | 2002-07-30 | Roche Vitamins Inc. | Oil in water microemulsion |
| US6372234B1 (en) | 1997-05-27 | 2002-04-16 | Sembiosys Genetics Inc. | Products for topical applications comprising oil bodies |
| US6599513B2 (en) | 1997-05-27 | 2003-07-29 | Sembiosys Genetics Inc. | Products for topical applications comprising oil bodies |
| US6696484B2 (en) | 1997-10-31 | 2004-02-24 | University Of Chicago Office Of Technology And Intellectual Property | Method and compositions for regulation of 5-alpha reductase activity |
| US6576660B1 (en) | 1997-10-31 | 2003-06-10 | Arch Development Corporation | Methods and compositions for regulation of 5-α-reductase activity |
| US6013665A (en) | 1997-12-16 | 2000-01-11 | Abbott Laboratories | Method for enhancing the absorption and transport of lipid soluble compounds using structured glycerides |
| AU4438399A (en) | 1998-06-11 | 1999-12-30 | University Of Medicine And Dentistry Of New Jersey | Wound treatment through inhibition of adenosine diphosphate ribosyl transferase |
| US6207176B1 (en) | 1998-09-14 | 2001-03-27 | National Starch And Chemical Investment Holding Corporation | Starch based adhesives for skin cleaning tape |
| US6383471B1 (en) | 1999-04-06 | 2002-05-07 | Lipocine, Inc. | Compositions and methods for improved delivery of ionizable hydrophobic therapeutic agents |
| US6187822B1 (en) | 1999-06-11 | 2001-02-13 | University Of Medicine & Dentistry Of Nj | Wound treatment through inhibition of adenosine diphosphate ribosyl transferase |
| US6524594B1 (en) | 1999-06-23 | 2003-02-25 | Johnson & Johnson Consumer Companies, Inc. | Foaming oil gel compositions |
| US7927612B2 (en) | 2000-01-19 | 2011-04-19 | Baofa Yu | Combinations and methods for treating neoplasms |
| DE10003786A1 (de) | 2000-01-28 | 2001-08-02 | Merck Patent Gmbh | Galenische Formulierung |
| DE60135732D1 (de) | 2000-02-28 | 2008-10-23 | Univ British Columbia | Topoisomerasehemmern zur behandlung von chirurgischen verklebungen |
| JP2004500392A (ja) | 2000-03-17 | 2004-01-08 | ビーエーエスエフ アクチェンゲゼルシャフト | 水溶性ビタミンの油性懸濁液の製造方法 |
| US20020061304A1 (en) | 2000-03-20 | 2002-05-23 | Pfizer Products Inc. & Osi Pharmaceuticals, Inc. | Combined treatment with keratinocyte growth factor and epidermal growth factor inhibitor |
| US20040047852A1 (en) | 2001-03-02 | 2004-03-11 | Kennedy Thomas Preston | Method of treating cancer |
| US20020040011A1 (en) | 2000-06-01 | 2002-04-04 | Brown Dennis M. | Naphthoquinone compositions and uses thereof |
| PL342071A1 (en) | 2000-08-18 | 2001-02-12 | Szolomicka Orfinger Irena | Cosmetic cream |
| GB0022079D0 (en) | 2000-09-08 | 2000-10-25 | Inst Of Molecul & Cell Biology | Novel protein tyrosine phosphatase inhibitor |
| US6660306B2 (en) | 2000-10-12 | 2003-12-09 | Mickey L. Peshoff | Wound healing compound |
| US7094431B2 (en) | 2000-10-12 | 2006-08-22 | Mickey L. Peshoff | Method of healing skin wounds in mammals and a composition therefor |
| US6774100B2 (en) | 2000-12-06 | 2004-08-10 | Imaginative Research Associates, Inc. | Anhydrous creams, lotions and gels |
| KR100560092B1 (ko) | 2000-12-15 | 2006-03-10 | 파트릭 프랑케 | 저알레르기성 및 비자극성 피부 보호 제제 |
| TR200401156T4 (tr) | 2000-12-15 | 2004-07-21 | Patrick Franke Dr. | Az alerjik olan ve tahriş edici olmayan cilt bakım formülasyonları. |
| US6780439B2 (en) | 2001-03-06 | 2004-08-24 | J. Ronald Wilk | Wound treatment solution and method for using same |
| US6579994B2 (en) | 2001-03-29 | 2003-06-17 | Council Of Scientific And Industrial Research | Process for preparation of 2-Methyl-1,4-naphthoquinone |
| US20070238697A1 (en) | 2001-08-29 | 2007-10-11 | University Of British Columbia | Pharmaceutical compositions and methods relating to fucans |
| US6812220B2 (en) | 2001-08-29 | 2004-11-02 | University Of British Columbia | Pharmaceutical compositions and methods relating to fucans |
| US8156471B2 (en) * | 2001-11-09 | 2012-04-10 | Oracle International Corporation | Multi-language execution method |
| US7405188B2 (en) | 2001-12-12 | 2008-07-29 | Wsp Chemicals & Technology, Llc | Polymeric gel system and compositions for treating keratin substrates containing same |
| CA2472578A1 (en) | 2002-01-24 | 2003-07-31 | Yissum Research Development Company Of The Hebrew University Of Jerusalem | Anti-cancer combination and use thereof |
| JP2003226639A (ja) * | 2002-01-31 | 2003-08-12 | Hisamitsu Pharmaceut Co Inc | 神経成長因子活性増強剤としてのビタミンｋ類を含む医薬組成物およびその使用 |
| US20030170187A1 (en) | 2002-03-01 | 2003-09-11 | Alfred Marchal | Skin treatments containing nano-sized vitamin K |
| AU2003228974A1 (en) | 2002-05-07 | 2003-11-11 | Memgen Corporation | Method of and apparatus for forming three-dimensional structures |
| GB0212749D0 (en) | 2002-06-01 | 2002-07-10 | Boots Co Plc | Personal care compositions |
| GB0220182D0 (en) | 2002-08-30 | 2002-10-09 | Cardiovascular Res Inst Maastr | Organic compounds |
| US7326690B2 (en) | 2002-10-30 | 2008-02-05 | Bach Pharma, Inc. | Modulation of cell fates and activities by phthalazinediones |
| AU2003230980A1 (en) | 2003-04-18 | 2004-11-26 | Northeastern University | Micelle delivery system loaded with a pharmaceutical agent |
| US7320797B2 (en) | 2003-08-29 | 2008-01-22 | Bioderm Research | Antiaging cosmetic delivery systems |
| CA2533887A1 (en) | 2003-09-30 | 2005-04-14 | Acusphere, Inc. | Injectable, oral, or topical sustained release pharmaceutical formulations |
| US20050092969A1 (en) | 2003-10-08 | 2005-05-05 | Kaneka Corporation | Method of stabilizing compound having quinone skeleton and stabilized composition |
| JP2005206521A (ja) | 2004-01-22 | 2005-08-04 | Nippon Menaade Keshohin Kk | 抗菌剤 |
| KR20060002239A (ko) | 2004-07-01 | 2006-01-09 | 삼성전자주식회사 | 레이저 출력 제어장치 |
| CA2584528A1 (en) | 2004-09-17 | 2006-03-23 | Oystershell Nv | Composition for inhibiting or preventing the formation of a biofilm |
| EP1812033A4 (en) | 2004-10-06 | 2009-11-11 | Tiltan Pharma Ltd | METHOD AND COMPOSITION FOR REINFORCE ANTI-ANGIOGENESIS THERAPY |
| WO2006107827A1 (en) | 2005-04-05 | 2006-10-12 | Creighton University | Skin bonding process |
| ATE492275T1 (de) | 2005-04-15 | 2011-01-15 | Einstein Coll Med | Vitamin k zur vorbeugung und behandlung von hautausschlag infolge einer anti-egfr-therapie |
| US20060275504A1 (en) | 2005-06-07 | 2006-12-07 | Tty Biopharm Company Limited | Methods and compositions for augmenting cancer chemotherapeutic agents |
| US20070025950A1 (en) | 2005-07-28 | 2007-02-01 | Elson Melvin L | Composition and method for treating cellulite |
| US7252816B1 (en) * | 2006-03-29 | 2007-08-07 | Dow Pharmaceutical Sciences | Topical acne vulgairs medication with a sunscreen |
| CA2689717C (en) | 2006-06-16 | 2016-10-18 | Summa Health System | Non-toxic anti-cancer drug combining ascorbate, magnesium and a naphthoquinone |
| ES2414708T3 (es) | 2006-07-07 | 2013-07-22 | Tiltan Pharma Ltd | Tratamiento anticanceroso que comprende un bloqueante de H2, al menos un agente antiinflamatorio y un agente citotóxico |
-
2009
- 2009-03-12 US US12/381,467 patent/US8815953B2/en active Active
- 2009-03-13 WO PCT/US2009/037041 patent/WO2009114745A1/en not_active Ceased
- 2009-03-13 EP EP09718881A patent/EP2265255A1/en not_active Withdrawn
- 2009-03-13 KR KR1020107022900A patent/KR20110004382A/ko not_active Ceased
- 2009-03-13 CA CA2718262A patent/CA2718262A1/en not_active Abandoned
- 2009-03-13 AU AU2009223158A patent/AU2009223158B2/en not_active Ceased
- 2009-03-13 JP JP2010550880A patent/JP2011513501A/ja active Pending
-
2014
- 2014-07-21 US US14/336,876 patent/US20140336268A1/en not_active Abandoned
- 2014-10-27 JP JP2014218037A patent/JP2015042658A/ja active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| US8815953B2 (en) | 2014-08-26 |
| JP2011513501A (ja) | 2011-04-28 |
| US20140336268A1 (en) | 2014-11-13 |
| JP2015042658A (ja) | 2015-03-05 |
| AU2009223158A1 (en) | 2009-09-17 |
| US20090234022A1 (en) | 2009-09-17 |
| KR20110004382A (ko) | 2011-01-13 |
| EP2265255A1 (en) | 2010-12-29 |
| WO2009114745A1 (en) | 2009-09-17 |
| AU2009223158B2 (en) | 2014-08-28 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| AU2009223158B2 (en) | Formulations of vitamin K analogs for topical use | |
| CA3056395C (en) | Topical therapy for the treatment of skin malignancies using nanoparticles of taxanes | |
| US20180263897A1 (en) | Diclofenac formulations | |
| US12447146B2 (en) | Topical composition comprising tacrolimus | |
| RU2703713C2 (ru) | Композиции для местного нанесения, содержащие биматопрост, и способы стимуляции роста волос с их помощью | |
| US20140107081A1 (en) | Salicylic acid topical formulation | |
| US20050137164A1 (en) | Diclofenac compositions for the treatment of skin disorders | |
| JP2008531693A (ja) | 局所用ゲル組成物 | |
| JP5667052B2 (ja) | ダナゾールを含む経真皮医薬組成物 | |
| US20230293543A1 (en) | Fenoldopam topical formulations for treating skin disorders | |
| US12458652B2 (en) | Pharmaceutical compositions of spironolactone for deep dermal drug delivery | |
| CN101541321A (zh) | 局部用组合物 | |
| US20110319811A1 (en) | Combination therapy with cryosurgery and low dosage strength imiquimod to treat actinic keratosis | |
| AU2014386711B2 (en) | Compositions that assist skin healing and/or maintain skin health | |
| CA3211573A1 (en) | Topical cannabinoid compositions and methods for treating skin diseases | |
| HK1242222B (en) | Transdermal pharmaceutical compositions comprising a serm | |
| HK1119058A (en) | Topical gels compositions |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EEER | Examination request |
Effective date: 20140228 |
|
| FZDE | Discontinued |
Effective date: 20170314 |