CA1326447C - Steroid cream formulation - Google Patents
Steroid cream formulationInfo
- Publication number
- CA1326447C CA1326447C CA000579959A CA579959A CA1326447C CA 1326447 C CA1326447 C CA 1326447C CA 000579959 A CA000579959 A CA 000579959A CA 579959 A CA579959 A CA 579959A CA 1326447 C CA1326447 C CA 1326447C
- Authority
- CA
- Canada
- Prior art keywords
- cream formulation
- tipredane
- weight
- wax
- range
- 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.)
- Expired - Lifetime
Links
- 239000000203 mixture Substances 0.000 title claims abstract description 61
- 239000006071 cream Substances 0.000 title claims abstract description 56
- 238000009472 formulation Methods 0.000 title claims abstract description 49
- 150000003431 steroids Chemical class 0.000 title abstract description 8
- VBICKXHEKHSIBG-UHFFFAOYSA-N 1-monostearoylglycerol Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCC(O)CO VBICKXHEKHSIBG-UHFFFAOYSA-N 0.000 claims abstract description 38
- 229950001669 tipredane Drugs 0.000 claims abstract description 38
- DXEXNWDGDYUITL-FXSSSKFRSA-N Tipredane Chemical compound C1CC2=CC(=O)C=C[C@]2(C)[C@]2(F)[C@@H]1[C@@H]1CC[C@@](SC)(SCC)[C@@]1(C)C[C@@H]2O DXEXNWDGDYUITL-FXSSSKFRSA-N 0.000 claims abstract description 37
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 claims abstract description 36
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 20
- 229940075507 glyceryl monostearate Drugs 0.000 claims abstract description 19
- 239000001788 mono and diglycerides of fatty acids Substances 0.000 claims abstract description 19
- -1 skin conditioners Substances 0.000 claims abstract description 14
- 239000000872 buffer Substances 0.000 claims abstract description 12
- 239000003974 emollient agent Substances 0.000 claims abstract description 12
- 239000002253 acid Substances 0.000 claims abstract description 10
- 230000002378 acidificating effect Effects 0.000 claims abstract description 10
- 239000000314 lubricant Substances 0.000 claims abstract description 9
- 239000001509 sodium citrate Substances 0.000 claims abstract description 9
- NLJMYIDDQXHKNR-UHFFFAOYSA-K sodium citrate Chemical compound O.O.[Na+].[Na+].[Na+].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O NLJMYIDDQXHKNR-UHFFFAOYSA-K 0.000 claims abstract description 9
- 239000000126 substance Substances 0.000 claims abstract description 9
- 239000003963 antioxidant agent Substances 0.000 claims abstract description 7
- 239000003995 emulsifying agent Substances 0.000 claims abstract description 7
- HRZFUMHJMZEROT-UHFFFAOYSA-L sodium disulfite Chemical compound [Na+].[Na+].[O-]S(=O)S([O-])(=O)=O HRZFUMHJMZEROT-UHFFFAOYSA-L 0.000 claims abstract description 7
- 229940001584 sodium metabisulfite Drugs 0.000 claims abstract description 7
- 235000010262 sodium metabisulphite Nutrition 0.000 claims abstract description 7
- 150000004668 long chain fatty acids Chemical class 0.000 claims abstract description 6
- 230000003078 antioxidant effect Effects 0.000 claims abstract description 5
- 239000001508 potassium citrate Substances 0.000 claims abstract description 4
- 229960002635 potassium citrate Drugs 0.000 claims abstract description 4
- QEEAPRPFLLJWCF-UHFFFAOYSA-K potassium citrate (anhydrous) Chemical compound [K+].[K+].[K+].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O QEEAPRPFLLJWCF-UHFFFAOYSA-K 0.000 claims abstract description 4
- 235000011082 potassium citrates Nutrition 0.000 claims abstract description 4
- BXWNKGSJHAJOGX-UHFFFAOYSA-N hexadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCO BXWNKGSJHAJOGX-UHFFFAOYSA-N 0.000 claims description 18
- 239000001993 wax Substances 0.000 claims description 12
- 229960004063 propylene glycol Drugs 0.000 claims description 11
- LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Natural products OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 10
- 229960000541 cetyl alcohol Drugs 0.000 claims description 9
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 8
- 239000000839 emulsion Substances 0.000 claims description 8
- 229920001296 polysiloxane Polymers 0.000 claims description 8
- 239000003381 stabilizer Substances 0.000 claims description 8
- 239000004166 Lanolin Substances 0.000 claims description 7
- 229920001214 Polysorbate 60 Polymers 0.000 claims description 7
- WNROFYMDJYEPJX-UHFFFAOYSA-K aluminium hydroxide Chemical compound [OH-].[OH-].[OH-].[Al+3] WNROFYMDJYEPJX-UHFFFAOYSA-K 0.000 claims description 7
- 239000002738 chelating agent Substances 0.000 claims description 7
- 229940039717 lanolin Drugs 0.000 claims description 7
- 239000002904 solvent Substances 0.000 claims description 7
- 235000006708 antioxidants Nutrition 0.000 claims description 6
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 claims description 6
- 239000012530 fluid Substances 0.000 claims description 6
- 229910052751 metal Inorganic materials 0.000 claims description 6
- 239000002184 metal Substances 0.000 claims description 6
- 239000001818 polyoxyethylene sorbitan monostearate Substances 0.000 claims description 6
- 235000010989 polyoxyethylene sorbitan monostearate Nutrition 0.000 claims description 6
- 229940113124 polysorbate 60 Drugs 0.000 claims description 6
- RMTFNDVZYPHUEF-XZBKPIIZSA-N 3-O-methyl-D-glucose Chemical class O=C[C@H](O)[C@@H](OC)[C@H](O)[C@H](O)CO RMTFNDVZYPHUEF-XZBKPIIZSA-N 0.000 claims description 5
- 229940031722 methyl gluceth-20 Drugs 0.000 claims description 5
- GLDOVTGHNKAZLK-UHFFFAOYSA-N octadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCCCO GLDOVTGHNKAZLK-UHFFFAOYSA-N 0.000 claims description 5
- 239000008213 purified water Substances 0.000 claims description 5
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 claims description 4
- 239000004205 dimethyl polysiloxane Substances 0.000 claims description 4
- 235000013870 dimethyl polysiloxane Nutrition 0.000 claims description 4
- 229910052500 inorganic mineral Inorganic materials 0.000 claims description 4
- 239000011707 mineral Substances 0.000 claims description 4
- 239000002480 mineral oil Substances 0.000 claims description 4
- 235000010446 mineral oil Nutrition 0.000 claims description 4
- 229920000435 poly(dimethylsiloxane) Polymers 0.000 claims description 4
- 239000000843 powder Substances 0.000 claims description 4
- 239000011240 wet gel Substances 0.000 claims description 4
- 235000014113 dietary fatty acids Nutrition 0.000 claims description 3
- 239000000194 fatty acid Substances 0.000 claims description 3
- 229930195729 fatty acid Natural products 0.000 claims description 3
- 150000004665 fatty acids Chemical class 0.000 claims description 3
- 239000003906 humectant Substances 0.000 claims description 3
- 235000019388 lanolin Nutrition 0.000 claims description 3
- BJEPYKJPYRNKOW-REOHCLBHSA-N (S)-malic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O BJEPYKJPYRNKOW-REOHCLBHSA-N 0.000 claims description 2
- 239000004255 Butylated hydroxyanisole Substances 0.000 claims description 2
- 239000004322 Butylated hydroxytoluene Substances 0.000 claims description 2
- 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 claims description 2
- 229920003171 Poly (ethylene oxide) Polymers 0.000 claims description 2
- 229920001213 Polysorbate 20 Polymers 0.000 claims description 2
- 229920002642 Polysorbate 65 Polymers 0.000 claims description 2
- HVUMOYIDDBPOLL-XWVZOOPGSA-N Sorbitan monostearate Chemical compound CCCCCCCCCCCCCCCCCC(=O)OC[C@@H](O)[C@H]1OC[C@H](O)[C@H]1O HVUMOYIDDBPOLL-XWVZOOPGSA-N 0.000 claims description 2
- 235000021355 Stearic acid Nutrition 0.000 claims description 2
- 150000008044 alkali metal hydroxides Chemical class 0.000 claims description 2
- BJEPYKJPYRNKOW-UHFFFAOYSA-N alpha-hydroxysuccinic acid Natural products OC(=O)C(O)CC(O)=O BJEPYKJPYRNKOW-UHFFFAOYSA-N 0.000 claims description 2
- 235000019282 butylated hydroxyanisole Nutrition 0.000 claims description 2
- CZBZUDVBLSSABA-UHFFFAOYSA-N butylated hydroxyanisole Chemical compound COC1=CC=C(O)C(C(C)(C)C)=C1.COC1=CC=C(O)C=C1C(C)(C)C CZBZUDVBLSSABA-UHFFFAOYSA-N 0.000 claims description 2
- 229940043253 butylated hydroxyanisole Drugs 0.000 claims description 2
- 235000010354 butylated hydroxytoluene Nutrition 0.000 claims description 2
- 229940095259 butylated hydroxytoluene Drugs 0.000 claims description 2
- 239000004203 carnauba wax Substances 0.000 claims description 2
- 235000013869 carnauba wax Nutrition 0.000 claims description 2
- 239000012185 ceresin wax Substances 0.000 claims description 2
- 229940073669 ceteareth 20 Drugs 0.000 claims description 2
- 229940008099 dimethicone Drugs 0.000 claims description 2
- 239000001530 fumaric acid Substances 0.000 claims description 2
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 claims description 2
- VTHJTEIRLNZDEV-UHFFFAOYSA-L magnesium dihydroxide Chemical compound [OH-].[OH-].[Mg+2] VTHJTEIRLNZDEV-UHFFFAOYSA-L 0.000 claims description 2
- 239000000347 magnesium hydroxide Substances 0.000 claims description 2
- 229910001862 magnesium hydroxide Inorganic materials 0.000 claims description 2
- 239000001630 malic acid Substances 0.000 claims description 2
- 235000011090 malic acid Nutrition 0.000 claims description 2
- GOQYKNQRPGWPLP-UHFFFAOYSA-N n-heptadecyl alcohol Natural products CCCCCCCCCCCCCCCCCO GOQYKNQRPGWPLP-UHFFFAOYSA-N 0.000 claims description 2
- 230000007935 neutral effect Effects 0.000 claims description 2
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 claims description 2
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 claims description 2
- 239000000256 polyoxyethylene sorbitan monolaurate Substances 0.000 claims description 2
- 235000010486 polyoxyethylene sorbitan monolaurate Nutrition 0.000 claims description 2
- 239000000244 polyoxyethylene sorbitan monooleate Substances 0.000 claims description 2
- 235000010482 polyoxyethylene sorbitan monooleate Nutrition 0.000 claims description 2
- 239000001816 polyoxyethylene sorbitan tristearate Substances 0.000 claims description 2
- 235000010988 polyoxyethylene sorbitan tristearate Nutrition 0.000 claims description 2
- 229940068977 polysorbate 20 Drugs 0.000 claims description 2
- 229940099511 polysorbate 65 Drugs 0.000 claims description 2
- 229920000053 polysorbate 80 Polymers 0.000 claims description 2
- 229940068968 polysorbate 80 Drugs 0.000 claims description 2
- PPASLZSBLFJQEF-RKJRWTFHSA-M sodium ascorbate Substances [Na+].OC[C@@H](O)[C@H]1OC(=O)C(O)=C1[O-] PPASLZSBLFJQEF-RKJRWTFHSA-M 0.000 claims description 2
- 235000010378 sodium ascorbate Nutrition 0.000 claims description 2
- 229960005055 sodium ascorbate Drugs 0.000 claims description 2
- PPASLZSBLFJQEF-RXSVEWSESA-M sodium-L-ascorbate Chemical compound [Na+].OC[C@H](O)[C@H]1OC(=O)C(O)=C1[O-] PPASLZSBLFJQEF-RXSVEWSESA-M 0.000 claims description 2
- 239000001587 sorbitan monostearate Substances 0.000 claims description 2
- 235000011076 sorbitan monostearate Nutrition 0.000 claims description 2
- 229940035048 sorbitan monostearate Drugs 0.000 claims description 2
- 239000008117 stearic acid Substances 0.000 claims description 2
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 claims description 2
- 229940045860 white wax Drugs 0.000 claims description 2
- OVBJJZOQPCKUOR-UHFFFAOYSA-L EDTA disodium salt dihydrate Chemical group O.O.[Na+].[Na+].[O-]C(=O)C[NH+](CC([O-])=O)CC[NH+](CC([O-])=O)CC([O-])=O OVBJJZOQPCKUOR-UHFFFAOYSA-L 0.000 claims 2
- QLBHNVFOQLIYTH-UHFFFAOYSA-L dipotassium;2-[2-[bis(carboxymethyl)amino]ethyl-(carboxylatomethyl)amino]acetate Chemical compound [K+].[K+].OC(=O)CN(CC([O-])=O)CCN(CC(O)=O)CC([O-])=O QLBHNVFOQLIYTH-UHFFFAOYSA-L 0.000 claims 1
- 239000004615 ingredient Substances 0.000 abstract description 3
- 239000012071 phase Substances 0.000 description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- 239000008346 aqueous phase Substances 0.000 description 4
- 238000000265 homogenisation Methods 0.000 description 4
- 238000002156 mixing Methods 0.000 description 4
- WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 3
- ZGTMUACCHSMWAC-UHFFFAOYSA-L EDTA disodium salt (anhydrous) Chemical compound [Na+].[Na+].OC(=O)CN(CC([O-])=O)CCN(CC(O)=O)CC([O-])=O ZGTMUACCHSMWAC-UHFFFAOYSA-L 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 239000013530 defoamer Substances 0.000 description 3
- 229910052736 halogen Inorganic materials 0.000 description 3
- 150000002367 halogens Chemical class 0.000 description 3
- 239000001257 hydrogen Substances 0.000 description 3
- 229910052739 hydrogen Inorganic materials 0.000 description 3
- 235000010755 mineral Nutrition 0.000 description 3
- 239000003921 oil Substances 0.000 description 3
- 239000002562 thickening agent Substances 0.000 description 3
- 239000004743 Polypropylene Substances 0.000 description 2
- 239000004480 active ingredient Substances 0.000 description 2
- 238000013019 agitation Methods 0.000 description 2
- POJWUDADGALRAB-UHFFFAOYSA-N allantoin Chemical compound NC(=O)NC1NC(=O)NC1=O POJWUDADGALRAB-UHFFFAOYSA-N 0.000 description 2
- OGBUMNBNEWYMNJ-UHFFFAOYSA-N batilol Chemical class CCCCCCCCCCCCCCCCCCOCC(O)CO OGBUMNBNEWYMNJ-UHFFFAOYSA-N 0.000 description 2
- 239000000084 colloidal system Substances 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 150000002431 hydrogen Chemical group 0.000 description 2
- 239000008309 hydrophilic cream Substances 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 2
- 125000004356 hydroxy functional group Chemical group O* 0.000 description 2
- 229920001155 polypropylene Polymers 0.000 description 2
- 239000003755 preservative agent Substances 0.000 description 2
- 230000000699 topical effect Effects 0.000 description 2
- IWZNTEPHASCXEA-WTKZELHLSA-N (8R,9S,10R,13S,14S)-13-(hydroxymethyl)-10-methyl-17-methylsulfanyl-6,7,8,9,11,12,14,15,16,17-decahydrocyclopenta[a]phenanthren-3-one Chemical compound OC[C@@]12C(CC[C@H]1[C@@H]1CCC3=CC(C=C[C@]3(C)[C@H]1CC2)=O)SC IWZNTEPHASCXEA-WTKZELHLSA-N 0.000 description 1
- QHZLMUACJMDIAE-SFHVURJKSA-N 1-hexadecanoyl-sn-glycerol Chemical compound CCCCCCCCCCCCCCCC(=O)OC[C@@H](O)CO QHZLMUACJMDIAE-SFHVURJKSA-N 0.000 description 1
- 239000000263 2,3-dihydroxypropyl (Z)-octadec-9-enoate Substances 0.000 description 1
- HXVCOQUDJKMJQY-UHFFFAOYSA-N 2-octyldodecyl octadecanoate Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCC(CCCCCCCC)CCCCCCCCCC HXVCOQUDJKMJQY-UHFFFAOYSA-N 0.000 description 1
- FQCSIUSICFAMDD-UHFFFAOYSA-N 2-oxopyrrolidine-1-carboxylic acid;sodium Chemical compound [Na].OC(=O)N1CCCC1=O FQCSIUSICFAMDD-UHFFFAOYSA-N 0.000 description 1
- RZRNAYUHWVFMIP-GDCKJWNLSA-N 3-oleoyl-sn-glycerol Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OC[C@H](O)CO RZRNAYUHWVFMIP-GDCKJWNLSA-N 0.000 description 1
- HIQIXEFWDLTDED-UHFFFAOYSA-N 4-hydroxy-1-piperidin-4-ylpyrrolidin-2-one Chemical compound O=C1CC(O)CN1C1CCNCC1 HIQIXEFWDLTDED-UHFFFAOYSA-N 0.000 description 1
- POJWUDADGALRAB-PVQJCKRUSA-N Allantoin Natural products NC(=O)N[C@@H]1NC(=O)NC1=O POJWUDADGALRAB-PVQJCKRUSA-N 0.000 description 1
- KRKNYBCHXYNGOX-UHFFFAOYSA-K Citrate Chemical compound [O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O KRKNYBCHXYNGOX-UHFFFAOYSA-K 0.000 description 1
- SNPLKNRPJHDVJA-ZETCQYMHSA-N D-panthenol Chemical compound OCC(C)(C)[C@@H](O)C(=O)NCCCO SNPLKNRPJHDVJA-ZETCQYMHSA-N 0.000 description 1
- QXNVGIXVLWOKEQ-UHFFFAOYSA-N Disodium Chemical compound [Na][Na] QXNVGIXVLWOKEQ-UHFFFAOYSA-N 0.000 description 1
- KCXVZYZYPLLWCC-UHFFFAOYSA-N EDTA Chemical compound OC(=O)CN(CC(O)=O)CCN(CC(O)=O)CC(O)=O KCXVZYZYPLLWCC-UHFFFAOYSA-N 0.000 description 1
- HDIFHQMREAYYJW-XGXNLDPDSA-N Glyceryl Ricinoleate Chemical compound CCCCCC[C@@H](O)C\C=C/CCCCCCCC(=O)OCC(O)CO HDIFHQMREAYYJW-XGXNLDPDSA-N 0.000 description 1
- MUQNGPZZQDCDFT-JNQJZLCISA-N Halcinonide Chemical compound C1CC2=CC(=O)CC[C@]2(C)[C@]2(F)[C@@H]1[C@@H]1C[C@H]3OC(C)(C)O[C@@]3(C(=O)CCl)[C@@]1(C)C[C@@H]2O MUQNGPZZQDCDFT-JNQJZLCISA-N 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
- CIUQSEKGRBULRT-UHFFFAOYSA-N O.O.[K].[K].CC(=O)ON(OC(C)=O)CCN(OC(C)=O)OC(C)=O Chemical compound O.O.[K].[K].CC(=O)ON(OC(C)=O)CCN(OC(C)=O)OC(C)=O CIUQSEKGRBULRT-UHFFFAOYSA-N 0.000 description 1
- QHZLMUACJMDIAE-UHFFFAOYSA-N Palmitic acid monoglyceride Natural products CCCCCCCCCCCCCCCC(=O)OCC(O)CO QHZLMUACJMDIAE-UHFFFAOYSA-N 0.000 description 1
- 239000002202 Polyethylene glycol Substances 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 125000004414 alkyl thio group Chemical group 0.000 description 1
- 229960000458 allantoin Drugs 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 229940121363 anti-inflammatory agent Drugs 0.000 description 1
- 239000002260 anti-inflammatory agent Substances 0.000 description 1
- 230000003110 anti-inflammatory effect Effects 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 125000005110 aryl thio group Chemical group 0.000 description 1
- 125000004104 aryloxy group Chemical group 0.000 description 1
- 235000019445 benzyl alcohol Nutrition 0.000 description 1
- 229960004217 benzyl alcohol Drugs 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 229940081733 cetearyl alcohol Drugs 0.000 description 1
- 108010088172 chelatin Proteins 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 125000000753 cycloalkyl group Chemical group 0.000 description 1
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- WBZKQQHYRPRKNJ-UHFFFAOYSA-L disulfite Chemical compound [O-]S(=O)S([O-])(=O)=O WBZKQQHYRPRKNJ-UHFFFAOYSA-L 0.000 description 1
- SNPLKNRPJHDVJA-UHFFFAOYSA-N dl-panthenol Chemical compound OCC(C)(C)C(O)C(=O)NCCCO SNPLKNRPJHDVJA-UHFFFAOYSA-N 0.000 description 1
- 229940116338 glyceryl ricinoleate Drugs 0.000 description 1
- 229960002383 halcinonide Drugs 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 229940093629 isopropyl isostearate Drugs 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
- 229940075495 isopropyl palmitate Drugs 0.000 description 1
- 150000002646 long chain fatty acid esters Chemical class 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- RZRNAYUHWVFMIP-UHFFFAOYSA-N monoelaidin Natural products CCCCCCCCC=CCCCCCCCC(=O)OCC(O)CO RZRNAYUHWVFMIP-UHFFFAOYSA-N 0.000 description 1
- 150000004682 monohydrates Chemical class 0.000 description 1
- 239000007764 o/w emulsion Substances 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 239000012188 paraffin wax Substances 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 238000005191 phase separation Methods 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- NEOZOXKVMDBOSG-UHFFFAOYSA-N propan-2-yl 16-methylheptadecanoate Chemical compound CC(C)CCCCCCCCCCCCCCC(=O)OC(C)C NEOZOXKVMDBOSG-UHFFFAOYSA-N 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229940083542 sodium Drugs 0.000 description 1
- 235000015424 sodium Nutrition 0.000 description 1
- RBWSWDPRDBEWCR-RKJRWTFHSA-N sodium;(2r)-2-[(2r)-3,4-dihydroxy-5-oxo-2h-furan-2-yl]-2-hydroxyethanolate Chemical compound [Na+].[O-]C[C@@H](O)[C@H]1OC(=O)C(O)=C1O RBWSWDPRDBEWCR-RKJRWTFHSA-N 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 229940012831 stearyl alcohol Drugs 0.000 description 1
Classifications
-
- 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
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/56—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids
- A61K31/565—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids not substituted in position 17 beta by a carbon atom, e.g. estrane, estradiol
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
Landscapes
- Health & Medical Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Veterinary Medicine (AREA)
- Chemical & Material Sciences (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Epidemiology (AREA)
- Dermatology (AREA)
- Organic Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Rheumatology (AREA)
- Pain & Pain Management (AREA)
- Cosmetics (AREA)
- Medicinal Preparation (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US07/120,278 US4868169A (en) | 1987-11-13 | 1987-11-13 | Steroid cream formulation |
| US120,278 | 1987-11-13 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1326447C true CA1326447C (en) | 1994-01-25 |
Family
ID=22389294
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA000579959A Expired - Lifetime CA1326447C (en) | 1987-11-13 | 1988-10-12 | Steroid cream formulation |
Country Status (8)
| Country | Link |
|---|---|
| US (1) | US4868169A (enExample) |
| EP (1) | EP0316834B1 (enExample) |
| JP (1) | JPH01153642A (enExample) |
| AT (1) | ATE77553T1 (enExample) |
| CA (1) | CA1326447C (enExample) |
| DE (1) | DE3872354T2 (enExample) |
| ES (1) | ES2042695T3 (enExample) |
| GR (1) | GR3005747T3 (enExample) |
Families Citing this family (22)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5110809A (en) * | 1988-03-21 | 1992-05-05 | Bristol-Myers Squibb Company | Antifungal gel formulations |
| US5002938A (en) * | 1988-03-21 | 1991-03-26 | Bristol-Myers Squibb Company | Antifungal gel formulations |
| US4883792A (en) * | 1989-01-17 | 1989-11-28 | Peter Timmins | Steroid cream formulation |
| GB9106365D0 (en) * | 1991-03-26 | 1991-05-15 | Bioglan Lab Ltd | An emollient for use with ultraviolet light |
| US5432170A (en) * | 1991-07-16 | 1995-07-11 | Schering Aktiengesellschaft | Process for the production of semisolid preparations containing micronized active ingredients |
| JP2657982B2 (ja) * | 1992-12-24 | 1997-09-30 | ローン−プーラン・ロレ・リミテツド | 新規ステロイド |
| GB9405593D0 (en) * | 1994-03-22 | 1994-05-11 | Zeneca Ltd | Pharmaceutical compositions |
| US20020173547A1 (en) | 1994-03-22 | 2002-11-21 | Jones Christopher Buchan | Pharmaceuticals compositions |
| CZ300146B6 (cs) * | 1995-03-17 | 2009-02-25 | Astrazeneca Uk Limited | Sterilní vodná kompozice obsahující emulzi typu olej ve vode a edetát |
| US6846846B2 (en) * | 2001-10-23 | 2005-01-25 | The Trustees Of Columbia University In The City Of New York | Gentle-acting skin disinfectants |
| AU2003216213B2 (en) * | 2002-02-07 | 2008-10-02 | The Trustees Of Columbia University In The City Of New York | Zinc salt compositions for the prevention of mucosal irritation from spermicides and microbicides |
| US7745425B2 (en) * | 2002-02-07 | 2010-06-29 | The Trustees Of Columbia University In The City Of New York | Non-irritating compositions containing zinc salts |
| US7879365B2 (en) * | 2002-02-07 | 2011-02-01 | The Trustees Of Columbia University In The City Of New York | Zinc salt compositions for the prevention of dermal and mucosal irritation |
| GB0219089D0 (en) * | 2002-08-16 | 2002-09-25 | Dow Corning | Silicone foam control compositions |
| FR2844448B1 (fr) | 2002-09-17 | 2006-06-23 | Lcw Les Colorants Wackherr | Methode de preparation extemporanee de compositions cosmetiques ayant la texture d'une creme, et compositions pour la mise en oeuvre de cette methode |
| CN102319409A (zh) * | 2003-07-17 | 2012-01-18 | 纽约市哥伦比亚大学托管会 | 含有季铵化合物及精油和/或精油成分的协同组合的抗微生物组合物 |
| US7759327B2 (en) * | 2006-01-06 | 2010-07-20 | The Trustees Of Columbia University In The City Of New York | Compositions containing zinc salts for coating medical articles |
| EP1973469A4 (en) * | 2006-01-20 | 2009-12-30 | Wisconsin Alumni Res Found | METHOD AND DEVICE FOR LOW-DOSED COMPUTER TOMOGRAPHY |
| US7801502B2 (en) * | 2006-12-18 | 2010-09-21 | Aai Corporation | Method for implementing continuous radio frequency (RF) alignment in advanced electronic warfare (EW) signal stimulation systems |
| US8361804B2 (en) * | 2008-09-29 | 2013-01-29 | M-I L.L.C. | Method and composition for determining hardness in wellbore fluid filtrate |
| US8409628B2 (en) | 2010-02-04 | 2013-04-02 | Penguin IP Holdings, Inc. | Methods and compositions for oxygenation of skin to treat skin disorders |
| US8900601B2 (en) | 2010-03-31 | 2014-12-02 | Jennifer Bartels | Permeable mixtures, methods and compositions for the skin |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3178345A (en) * | 1964-01-20 | 1965-04-13 | Upjohn Co | Topical steroid composition |
| US3892857A (en) * | 1972-11-24 | 1975-07-01 | Squibb & Sons Inc | Steroid formulation |
| GB1478009A (en) * | 1973-04-02 | 1977-06-29 | Glaxo Lab Ltd | Pharmaceutical compositions |
| US4361559A (en) * | 1981-08-20 | 1982-11-30 | E. R. Squibb & Sons, Inc. | Antiinflammatory 17,17-bis (substituted thio) androstenes |
| US4542129A (en) * | 1982-08-16 | 1985-09-17 | Norman Orentreich | DHEA Formulations and methods for treating dry skin |
-
1987
- 1987-11-13 US US07/120,278 patent/US4868169A/en not_active Expired - Lifetime
-
1988
- 1988-10-12 CA CA000579959A patent/CA1326447C/en not_active Expired - Lifetime
- 1988-11-11 JP JP63286604A patent/JPH01153642A/ja active Pending
- 1988-11-14 ES ES88118920T patent/ES2042695T3/es not_active Expired - Lifetime
- 1988-11-14 AT AT88118920T patent/ATE77553T1/de not_active IP Right Cessation
- 1988-11-14 DE DE8888118920T patent/DE3872354T2/de not_active Expired - Lifetime
- 1988-11-14 EP EP88118920A patent/EP0316834B1/en not_active Expired - Lifetime
-
1992
- 1992-09-22 GR GR920402073T patent/GR3005747T3/el unknown
Also Published As
| Publication number | Publication date |
|---|---|
| DE3872354D1 (de) | 1992-07-30 |
| JPH01153642A (ja) | 1989-06-15 |
| DE3872354T2 (de) | 1992-12-10 |
| EP0316834B1 (en) | 1992-06-24 |
| US4868169A (en) | 1989-09-19 |
| EP0316834A1 (en) | 1989-05-24 |
| GR3005747T3 (enExample) | 1993-06-07 |
| ES2042695T3 (es) | 1993-12-16 |
| ATE77553T1 (de) | 1992-07-15 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKEX | Expiry | ||
| MKEX | Expiry |
Effective date: 20110125 |