JP2008543876A5 - - Google Patents
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- JP2008543876A5 JP2008543876A5 JP2008517201A JP2008517201A JP2008543876A5 JP 2008543876 A5 JP2008543876 A5 JP 2008543876A5 JP 2008517201 A JP2008517201 A JP 2008517201A JP 2008517201 A JP2008517201 A JP 2008517201A JP 2008543876 A5 JP2008543876 A5 JP 2008543876A5
- Authority
- JP
- Japan
- Prior art keywords
- vasoconstrictor
- skin
- formulation
- epinephrine
- delivery vehicle
- 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.)
- Granted
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- 239000005526 vasoconstrictor agent Substances 0.000 claims description 45
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 41
- UCTWMZQNUQWSLP-VIFPVBQESA-N (R)-adrenaline Chemical compound CNC[C@H](O)C1=CC=C(O)C(O)=C1 UCTWMZQNUQWSLP-VIFPVBQESA-N 0.000 claims description 28
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 23
- 229930182837 (R)-adrenaline Natural products 0.000 claims description 21
- 229960005139 epinephrine Drugs 0.000 claims description 21
- SFLSHLFXELFNJZ-QMMMGPOBSA-N (-)-norepinephrine Chemical compound NC[C@H](O)C1=CC=C(O)C(O)=C1 SFLSHLFXELFNJZ-QMMMGPOBSA-N 0.000 claims description 20
- 229960002748 norepinephrine Drugs 0.000 claims description 20
- SFLSHLFXELFNJZ-UHFFFAOYSA-N norepinephrine Natural products NCC(O)C1=CC=C(O)C(O)=C1 SFLSHLFXELFNJZ-UHFFFAOYSA-N 0.000 claims description 20
- SONNWYBIRXJNDC-VIFPVBQESA-N phenylephrine Chemical compound CNC[C@H](O)C1=CC=CC(O)=C1 SONNWYBIRXJNDC-VIFPVBQESA-N 0.000 claims description 16
- 229960001802 phenylephrine Drugs 0.000 claims description 15
- 208000024891 symptom Diseases 0.000 claims description 9
- 239000003814 drug Substances 0.000 claims description 8
- CNIIGCLFLJGOGP-UHFFFAOYSA-N 2-(1-naphthalenylmethyl)-4,5-dihydro-1H-imidazole Chemical compound C=1C=CC2=CC=CC=C2C=1CC1=NCCN1 CNIIGCLFLJGOGP-UHFFFAOYSA-N 0.000 claims description 6
- WJAJPNHVVFWKKL-UHFFFAOYSA-N Methoxamine Chemical compound COC1=CC=C(OC)C(C(O)C(C)N)=C1 WJAJPNHVVFWKKL-UHFFFAOYSA-N 0.000 claims description 6
- 229960005192 methoxamine Drugs 0.000 claims description 6
- 229960001360 zolmitriptan Drugs 0.000 claims description 4
- UTAZCRNOSWWEFR-ZDUSSCGKSA-N zolmitriptan Chemical compound C=1[C]2C(CCN(C)C)=CN=C2C=CC=1C[C@H]1COC(=O)N1 UTAZCRNOSWWEFR-ZDUSSCGKSA-N 0.000 claims description 4
- 201000004624 Dermatitis Diseases 0.000 claims description 3
- 208000018522 Gastrointestinal disease Diseases 0.000 claims description 3
- 206010036774 Proctitis Diseases 0.000 claims description 3
- 239000003795 chemical substances by application Substances 0.000 claims description 3
- 208000010643 digestive system disease Diseases 0.000 claims description 3
- 208000018685 gastrointestinal system disease Diseases 0.000 claims description 3
- 229960005016 naphazoline Drugs 0.000 claims description 3
- WKEMJKQOLOHJLZ-UHFFFAOYSA-N Almogran Chemical compound C1=C2C(CCN(C)C)=CNC2=CC=C1CS(=O)(=O)N1CCCC1 WKEMJKQOLOHJLZ-UHFFFAOYSA-N 0.000 claims description 2
- 229960002133 almotriptan Drugs 0.000 claims description 2
- 238000002512 chemotherapy Methods 0.000 claims description 2
- 230000008602 contraction Effects 0.000 claims description 2
- 229960000425 rizatriptan Drugs 0.000 claims description 2
- TXHZXHICDBAVJW-UHFFFAOYSA-N rizatriptan Chemical compound C=1[C]2C(CCN(C)C)=CN=C2C=CC=1CN1C=NC=N1 TXHZXHICDBAVJW-UHFFFAOYSA-N 0.000 claims description 2
- BYJAVTDNIXVSPW-UHFFFAOYSA-N tetryzoline Chemical compound N1CCN=C1C1C2=CC=CC=C2CCC1 BYJAVTDNIXVSPW-UHFFFAOYSA-N 0.000 claims 2
- 206010047139 Vasoconstriction Diseases 0.000 claims 1
- 210000004204 blood vessel Anatomy 0.000 claims 1
- 239000012829 chemotherapy agent Substances 0.000 claims 1
- 229960002284 frovatriptan Drugs 0.000 claims 1
- SIBNYOSJIXCDRI-SECBINFHSA-N frovatriptan Chemical compound C1=C(C(N)=O)[CH]C2=C(C[C@H](NC)CC3)C3=NC2=C1 SIBNYOSJIXCDRI-SECBINFHSA-N 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 229960000337 tetryzoline Drugs 0.000 claims 1
- 230000025033 vasoconstriction Effects 0.000 claims 1
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 46
- 210000003491 skin Anatomy 0.000 description 45
- 239000000203 mixture Substances 0.000 description 44
- 238000000034 method Methods 0.000 description 34
- 238000009472 formulation Methods 0.000 description 33
- 230000000699 topical effect Effects 0.000 description 28
- 230000002087 whitening effect Effects 0.000 description 23
- 239000003981 vehicle Substances 0.000 description 21
- 239000000243 solution Substances 0.000 description 13
- 230000005855 radiation Effects 0.000 description 11
- 241000700159 Rattus Species 0.000 description 9
- 239000000825 pharmaceutical preparation Substances 0.000 description 9
- 210000002200 mouth mucosa Anatomy 0.000 description 8
- 238000002360 preparation method Methods 0.000 description 8
- WNPNNLQNNJQYFA-YIDNRZKSSA-N 4-[(1r)-2-amino-1-hydroxyethyl]benzene-1,2-diol;(2r,3r)-2,3-dihydroxybutanedioic acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O.NC[C@H](O)C1=CC=C(O)C(O)=C1 WNPNNLQNNJQYFA-YIDNRZKSSA-N 0.000 description 7
- 239000000556 agonist Substances 0.000 description 7
- 210000004027 cell Anatomy 0.000 description 7
- 102000030619 alpha-1 Adrenergic Receptor Human genes 0.000 description 6
- 108020004102 alpha-1 Adrenergic Receptor Proteins 0.000 description 6
- 229940079593 drug Drugs 0.000 description 6
- 208000003265 stomatitis Diseases 0.000 description 6
- CMSMOCZEIVJLDB-UHFFFAOYSA-N Cyclophosphamide Chemical compound ClCCN(CCCl)P1(=O)NCCCO1 CMSMOCZEIVJLDB-UHFFFAOYSA-N 0.000 description 5
- 206010028116 Mucosal inflammation Diseases 0.000 description 5
- 201000010927 Mucositis Diseases 0.000 description 5
- 210000005166 vasculature Anatomy 0.000 description 5
- 201000004384 Alopecia Diseases 0.000 description 4
- 102000004305 alpha Adrenergic Receptors Human genes 0.000 description 4
- 108090000861 alpha Adrenergic Receptors Proteins 0.000 description 4
- 239000013583 drug formulation Substances 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 238000002474 experimental method Methods 0.000 description 4
- 239000000796 flavoring agent Substances 0.000 description 4
- 210000003780 hair follicle Anatomy 0.000 description 4
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- 206010028980 Neoplasm Diseases 0.000 description 3
- 239000000674 adrenergic antagonist Substances 0.000 description 3
- 239000012062 aqueous buffer Substances 0.000 description 3
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- 201000011510 cancer Diseases 0.000 description 3
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- 230000035699 permeability Effects 0.000 description 3
- 208000006934 radiodermatitis Diseases 0.000 description 3
- 235000019640 taste Nutrition 0.000 description 3
- 239000012049 topical pharmaceutical composition Substances 0.000 description 3
- 241000699800 Cricetinae Species 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- 241001465754 Metazoa Species 0.000 description 2
- MWUXSHHQAYIFBG-UHFFFAOYSA-N Nitric oxide Chemical compound O=[N] MWUXSHHQAYIFBG-UHFFFAOYSA-N 0.000 description 2
- DRHKJLXJIQTDTD-OAHLLOKOSA-N Tamsulosine Chemical compound CCOC1=CC=CC=C1OCCN[C@H](C)CC1=CC=C(OC)C(S(N)(=O)=O)=C1 DRHKJLXJIQTDTD-OAHLLOKOSA-N 0.000 description 2
- WNPNNLQNNJQYFA-UHFFFAOYSA-N [2-(3,4-dihydroxyphenyl)-2-hydroxyethyl]azanium;2,3,4-trihydroxy-4-oxobutanoate Chemical compound OC(=O)C(O)C(O)C(O)=O.NCC(O)C1=CC=C(O)C(O)=C1 WNPNNLQNNJQYFA-UHFFFAOYSA-N 0.000 description 2
- UCTWMZQNUQWSLP-UHFFFAOYSA-N adrenaline Chemical compound CNCC(O)C1=CC=C(O)C(O)=C1 UCTWMZQNUQWSLP-UHFFFAOYSA-N 0.000 description 2
- 229960004607 alfuzosin Drugs 0.000 description 2
- WNMJYKCGWZFFKR-UHFFFAOYSA-N alfuzosin Chemical compound N=1C(N)=C2C=C(OC)C(OC)=CC2=NC=1N(C)CCCNC(=O)C1CCCO1 WNMJYKCGWZFFKR-UHFFFAOYSA-N 0.000 description 2
- 239000002246 antineoplastic agent Substances 0.000 description 2
- 210000000481 breast Anatomy 0.000 description 2
- 239000011248 coating agent Substances 0.000 description 2
- 238000000576 coating method Methods 0.000 description 2
- 229940127089 cytotoxic agent Drugs 0.000 description 2
- XXJWXESWEXIICW-UHFFFAOYSA-N diethylene glycol monoethyl ether Chemical compound CCOCCOCCO XXJWXESWEXIICW-UHFFFAOYSA-N 0.000 description 2
- 229940075557 diethylene glycol monoethyl ether Drugs 0.000 description 2
- 239000003085 diluting agent Substances 0.000 description 2
- 229960001389 doxazosin Drugs 0.000 description 2
- RUZYUOTYCVRMRZ-UHFFFAOYSA-N doxazosin Chemical compound C1OC2=CC=CC=C2OC1C(=O)N(CC1)CCN1C1=NC(N)=C(C=C(C(OC)=C2)OC)C2=N1 RUZYUOTYCVRMRZ-UHFFFAOYSA-N 0.000 description 2
- 230000002500 effect on skin Effects 0.000 description 2
- 239000000839 emulsion Substances 0.000 description 2
- 210000004209 hair Anatomy 0.000 description 2
- 239000002502 liposome Substances 0.000 description 2
- 230000000873 masking effect Effects 0.000 description 2
- 210000000214 mouth Anatomy 0.000 description 2
- 230000003232 mucoadhesive effect Effects 0.000 description 2
- 230000035515 penetration Effects 0.000 description 2
- 239000008194 pharmaceutical composition Substances 0.000 description 2
- 239000000049 pigment Substances 0.000 description 2
- 229960001289 prazosin Drugs 0.000 description 2
- IENZQIKPVFGBNW-UHFFFAOYSA-N prazosin Chemical group N=1C(N)=C2C=C(OC)C(OC)=CC2=NC=1N(CC1)CCN1C(=O)C1=CC=CO1 IENZQIKPVFGBNW-UHFFFAOYSA-N 0.000 description 2
- 230000001681 protective effect Effects 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 235000019333 sodium laurylsulphate Nutrition 0.000 description 2
- 210000000130 stem cell Anatomy 0.000 description 2
- 210000000434 stratum corneum Anatomy 0.000 description 2
- 230000002459 sustained effect Effects 0.000 description 2
- 229960002613 tamsulosin Drugs 0.000 description 2
- 229960001693 terazosin Drugs 0.000 description 2
- VCKUSRYTPJJLNI-UHFFFAOYSA-N terazosin Chemical compound N=1C(N)=C2C=C(OC)C(OC)=CC2=NC=1N(CC1)CCN1C(=O)C1CCCO1 VCKUSRYTPJJLNI-UHFFFAOYSA-N 0.000 description 2
- -1 tetrahydrozaline Chemical compound 0.000 description 2
- 238000002560 therapeutic procedure Methods 0.000 description 2
- 208000020154 Acnes Diseases 0.000 description 1
- 108010061435 Enalapril Proteins 0.000 description 1
- 206010015150 Erythema Diseases 0.000 description 1
- 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 1
- 229940123457 Free radical scavenger Drugs 0.000 description 1
- 241000282412 Homo Species 0.000 description 1
- 108010007859 Lisinopril Proteins 0.000 description 1
- 241000699673 Mesocricetus auratus Species 0.000 description 1
- DBMJMQXJHONAFJ-UHFFFAOYSA-M Sodium laurylsulphate Chemical compound [Na+].CCCCCCCCCCCCOS([O-])(=O)=O DBMJMQXJHONAFJ-UHFFFAOYSA-M 0.000 description 1
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
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- 231100000360 alopecia Toxicity 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 239000005557 antagonist Substances 0.000 description 1
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- 102000016966 beta-2 Adrenergic Receptors Human genes 0.000 description 1
- 108010014499 beta-2 Adrenergic Receptors Proteins 0.000 description 1
- 230000036770 blood supply Effects 0.000 description 1
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- 239000000872 buffer Substances 0.000 description 1
- 229940097633 capoten Drugs 0.000 description 1
- FAKRSMQSSFJEIM-RQJHMYQMSA-N captopril Chemical compound SC[C@@H](C)C(=O)N1CCC[C@H]1C(O)=O FAKRSMQSSFJEIM-RQJHMYQMSA-N 0.000 description 1
- 230000000747 cardiac effect Effects 0.000 description 1
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- GBXSMTUPTTWBMN-XIRDDKMYSA-N enalapril Chemical compound C([C@@H](C(=O)OCC)N[C@@H](C)C(=O)N1[C@@H](CCC1)C(O)=O)CC1=CC=CC=C1 GBXSMTUPTTWBMN-XIRDDKMYSA-N 0.000 description 1
- 231100000321 erythema Toxicity 0.000 description 1
- 210000003238 esophagus Anatomy 0.000 description 1
- IDGUHHHQCWSQLU-UHFFFAOYSA-N ethanol;hydrate Chemical compound O.CCO IDGUHHHQCWSQLU-UHFFFAOYSA-N 0.000 description 1
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- 235000010979 hydroxypropyl methyl cellulose Nutrition 0.000 description 1
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- 239000007928 intraperitoneal injection Substances 0.000 description 1
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- 230000007794 irritation Effects 0.000 description 1
- 150000002632 lipids Chemical class 0.000 description 1
- 229960002394 lisinopril Drugs 0.000 description 1
- RLAWWYSOJDYHDC-BZSNNMDCSA-N lisinopril Chemical compound C([C@H](N[C@@H](CCCCN)C(=O)N1[C@@H](CCC1)C(O)=O)C(O)=O)CC1=CC=CC=C1 RLAWWYSOJDYHDC-BZSNNMDCSA-N 0.000 description 1
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- VOFUROIFQGPCGE-UHFFFAOYSA-N nile red Chemical compound C1=CC=C2C3=NC4=CC=C(N(CC)CC)C=C4OC3=CC(=O)C2=C1 VOFUROIFQGPCGE-UHFFFAOYSA-N 0.000 description 1
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- 229940051841 polyoxyethylene ether Drugs 0.000 description 1
- 229920000056 polyoxyethylene ether Polymers 0.000 description 1
- 239000002516 radical scavenger Substances 0.000 description 1
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- 102000005962 receptors Human genes 0.000 description 1
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- 231100000004 severe toxicity Toxicity 0.000 description 1
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- 229940095064 tartrate Drugs 0.000 description 1
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- 210000002229 urogenital system Anatomy 0.000 description 1
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Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US69157105P | 2005-06-17 | 2005-06-17 | |
| US60/691,571 | 2005-06-17 | ||
| PCT/US2006/023708 WO2006138691A1 (en) | 2005-06-17 | 2006-06-19 | Topical vasoconstrictor preparations and methods for protecting cells during cancer chemotherapy and radiotherapy |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2015039086A Division JP6348437B2 (ja) | 2005-06-17 | 2015-02-27 | 癌の化学療法および放射線療法の際に細胞を保護するための局所的血管収縮剤および方法 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2008543876A JP2008543876A (ja) | 2008-12-04 |
| JP2008543876A5 true JP2008543876A5 (cg-RX-API-DMAC10.html) | 2015-04-16 |
| JP5756250B2 JP5756250B2 (ja) | 2015-07-29 |
Family
ID=37570784
Family Applications (4)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2008517201A Expired - Lifetime JP5756250B2 (ja) | 2005-06-17 | 2006-06-19 | 癌の化学療法および放射線療法の際に細胞を保護するための局所的血管収縮剤および方法 |
| JP2015039086A Expired - Lifetime JP6348437B2 (ja) | 2005-06-17 | 2015-02-27 | 癌の化学療法および放射線療法の際に細胞を保護するための局所的血管収縮剤および方法 |
| JP2016116373A Expired - Lifetime JP6473103B2 (ja) | 2005-06-17 | 2016-06-10 | 癌の化学療法および放射線療法の際に細胞を保護するための局所的血管収縮剤および方法 |
| JP2018190933A Withdrawn JP2018203788A (ja) | 2005-06-17 | 2018-10-09 | 癌の化学療法および放射線療法の際に細胞を保護するための局所的血管収縮剤および方法 |
Family Applications After (3)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2015039086A Expired - Lifetime JP6348437B2 (ja) | 2005-06-17 | 2015-02-27 | 癌の化学療法および放射線療法の際に細胞を保護するための局所的血管収縮剤および方法 |
| JP2016116373A Expired - Lifetime JP6473103B2 (ja) | 2005-06-17 | 2016-06-10 | 癌の化学療法および放射線療法の際に細胞を保護するための局所的血管収縮剤および方法 |
| JP2018190933A Withdrawn JP2018203788A (ja) | 2005-06-17 | 2018-10-09 | 癌の化学療法および放射線療法の際に細胞を保護するための局所的血管収縮剤および方法 |
Country Status (15)
Families Citing this family (39)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US9006175B2 (en) | 1999-06-29 | 2015-04-14 | Mannkind Corporation | Potentiation of glucose elimination |
| JP4681231B2 (ja) | 2002-03-20 | 2011-05-11 | マンカインド コーポレイション | 吸入装置 |
| ATE486064T1 (de) | 2004-08-20 | 2010-11-15 | Mannkind Corp | Katalyse der diketopiperazinsynthese |
| HUE025151T2 (en) | 2004-08-23 | 2016-01-28 | Mannkind Corp | Diceto-piperazine salts for drug delivery |
| PT2656860T (pt) | 2005-06-17 | 2021-07-28 | Wisconsin Alumni Res Found | Preparações vasoconstritoras tópicas e métodos para proteção de células durante a quimoterapia e a radioterapia do cancro |
| MX373000B (es) | 2005-09-14 | 2020-05-21 | Mannkind Corp | Metodo para formulacion de farmaco basado en el aumento de la afinidad de agentes activos hacia las superficies de microparticulas cristalinas. |
| CN104383546B (zh) | 2006-02-22 | 2021-03-02 | 曼金德公司 | 用于改善包含二酮哌嗪和活性剂的微粒的药物性质的方法 |
| US8785396B2 (en) * | 2007-10-24 | 2014-07-22 | Mannkind Corporation | Method and composition for treating migraines |
| MY155524A (en) | 2008-06-13 | 2015-10-30 | Mannkind Corp | A dry powder inhaler and system for drug delivery |
| US8485180B2 (en) | 2008-06-13 | 2013-07-16 | Mannkind Corporation | Dry powder drug delivery system |
| EP2609954B1 (en) | 2008-06-20 | 2021-12-29 | MannKind Corporation | An interactive apparatus for real-time profiling of inhalation efforts |
| TWI494123B (zh) | 2008-08-11 | 2015-08-01 | Mannkind Corp | 超快起作用胰島素之用途 |
| EP2165706A1 (en) * | 2008-09-18 | 2010-03-24 | BioAlliance Pharma | Treating Inflammatory Pain in Mucosa of the Oral Cavity Using Mucosal Prolonged Release Bioadhesive Therapeutic Carriers. |
| US8314106B2 (en) | 2008-12-29 | 2012-11-20 | Mannkind Corporation | Substituted diketopiperazine analogs for use as drug delivery agents |
| US8538707B2 (en) | 2009-03-11 | 2013-09-17 | Mannkind Corporation | Apparatus, system and method for measuring resistance of an inhaler |
| AU2010259943C1 (en) | 2009-06-12 | 2016-03-03 | Mannkind Corporation | Diketopiperazine microparticles with defined specific surface areas |
| JP5784622B2 (ja) | 2009-11-03 | 2015-09-24 | マンカインド コーポレ−ション | 吸入活動をシミュレートするための装置及び方法 |
| RU2531455C2 (ru) | 2010-06-21 | 2014-10-20 | Маннкайнд Корпорейшн | Системы и способы доставки сухих порошковых лекарств |
| MX353285B (es) | 2011-04-01 | 2018-01-05 | Mannkind Corp | Paquete de blister para cartuchos farmaceuticos. |
| US20140343159A1 (en) * | 2011-06-02 | 2014-11-20 | Procertus Biopharm, Inc. | Formulation of small adrenergic agonist salt forms in organic solvents |
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- 2006-06-19 CN CN200680021549.2A patent/CN101198362B/zh not_active Expired - Lifetime
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- 2006-06-19 CN CN201710850996.9A patent/CN107496925A/zh active Pending
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- 2006-06-19 AU AU2006261358A patent/AU2006261358B2/en not_active Expired
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