CA1297028C - Formulations du metronidazole topique et leurs utilisations therapeutiques - Google Patents

Formulations du metronidazole topique et leurs utilisations therapeutiques

Info

Publication number: CA1297028C
Authority: CA; Canada
Prior art keywords: composition; weight; polymer; metronidazole; preparation
Prior art date: 1987-03-26
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

Application number

CA000533082A

Other languages

English (en)

Inventor

Robert John Borgman

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Galderma SA

Original Assignee

Curatek Pharmaceuticals Inc

Priority date (The priority date 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 date listed.)

1987-03-26

Filing date

1987-03-26

Publication date

1992-03-10

1987-03-26 Application filed by Curatek Pharmaceuticals Inc filed Critical Curatek Pharmaceuticals Inc

1987-03-26 Priority to CA000533082A priority Critical patent/CA1297028C/fr

1992-03-10 Application granted granted Critical

1992-03-10 Publication of CA1297028C publication Critical patent/CA1297028C/fr

2009-03-10 Anticipated expiration legal-status Critical

Status Expired - Lifetime legal-status Critical Current

Links

239000000203 mixture Substances 0.000 title claims abstract description 127
VAOCPAMSLUNLGC-UHFFFAOYSA-N metronidazole Chemical compound CC1=NC=C([N+]([O-])=O)N1CCO VAOCPAMSLUNLGC-UHFFFAOYSA-N 0.000 title claims abstract description 54
229960000282 metronidazole Drugs 0.000 title claims abstract description 51
230000000699 topical effect Effects 0.000 title claims description 15
230000001225 therapeutic effect Effects 0.000 title claims description 12
238000009472 formulation Methods 0.000 title abstract description 41
201000004700 rosacea Diseases 0.000 claims abstract description 19
241001303601 Rosacea Species 0.000 claims abstract description 14
201000004624 Dermatitis Diseases 0.000 claims abstract description 10
239000004615 ingredient Substances 0.000 claims abstract description 9
238000001035 drying Methods 0.000 claims abstract description 4
229920000642 polymer Polymers 0.000 claims description 33
238000002360 preparation method Methods 0.000 claims description 28
DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 claims description 15
208000017520 skin disease Diseases 0.000 claims description 15
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical group O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 14
239000003755 preservative agent Substances 0.000 claims description 13
LXCFILQKKLGQFO-UHFFFAOYSA-N methylparaben Chemical compound COC(=O)C1=CC=C(O)C=C1 LXCFILQKKLGQFO-UHFFFAOYSA-N 0.000 claims description 12
239000003961 penetration enhancing agent Substances 0.000 claims description 12
230000002335 preservative effect Effects 0.000 claims description 12
QELSKZZBTMNZEB-UHFFFAOYSA-N propylparaben Chemical compound CCCOC(=O)C1=CC=C(O)C=C1 QELSKZZBTMNZEB-UHFFFAOYSA-N 0.000 claims description 12
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical group CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims description 10
206010000496 acne Diseases 0.000 claims description 8
208000002874 Acne Vulgaris Diseases 0.000 claims description 7
229920002125 Sokalan® Polymers 0.000 claims description 7
239000003125 aqueous solvent Substances 0.000 claims description 7
229920002554 vinyl polymer Polymers 0.000 claims description 7
239000012153 distilled water Substances 0.000 claims description 6
235000010270 methyl p-hydroxybenzoate Nutrition 0.000 claims description 6
239000004292 methyl p-hydroxybenzoate Substances 0.000 claims description 6
229960002216 methylparaben Drugs 0.000 claims description 6
235000010232 propyl p-hydroxybenzoate Nutrition 0.000 claims description 6
239000004405 propyl p-hydroxybenzoate Substances 0.000 claims description 6
229960003415 propylparaben Drugs 0.000 claims description 6
208000009675 Perioral Dermatitis Diseases 0.000 claims description 5
230000002378 acidificating effect Effects 0.000 claims description 5
206010039793 Seborrhoeic dermatitis Diseases 0.000 claims description 3
230000000069 prophylactic effect Effects 0.000 claims description 3
208000008742 seborrheic dermatitis Diseases 0.000 claims description 3
206010000501 Acne conglobata Diseases 0.000 claims description 2
239000003623 enhancer Substances 0.000 claims description 2
230000000622 irritating effect Effects 0.000 claims description 2
KCXVZYZYPLLWCC-UHFFFAOYSA-N EDTA Chemical compound OC(=O)CN(CC(O)=O)CCN(CC(O)=O)CC(O)=O KCXVZYZYPLLWCC-UHFFFAOYSA-N 0.000 claims 5
229960001484 edetic acid Drugs 0.000 claims 5
239000004480 active ingredient Substances 0.000 claims 2
FJKROLUGYXJWQN-UHFFFAOYSA-N 4-hydroxybenzoic acid Chemical compound OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 claims 1
229940079593 drug Drugs 0.000 abstract description 56
239000003814 drug Substances 0.000 abstract description 56
239000000499 gel Substances 0.000 abstract description 23
230000000694 effects Effects 0.000 abstract description 12
239000012049 topical pharmaceutical composition Substances 0.000 abstract description 7
239000002085 irritant Substances 0.000 abstract 1
231100000021 irritant Toxicity 0.000 abstract 1
229940068196 placebo Drugs 0.000 description 29
239000000902 placebo Substances 0.000 description 29
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 21
210000003491 skin Anatomy 0.000 description 9
239000007864 aqueous solution Substances 0.000 description 8
206010015150 Erythema Diseases 0.000 description 6
231100000321 erythema Toxicity 0.000 description 6
239000003921 oil Substances 0.000 description 6
230000003902 lesion Effects 0.000 description 5
230000035515 penetration Effects 0.000 description 5
230000009467 reduction Effects 0.000 description 5
208000002193 Pain Diseases 0.000 description 4
239000006071 cream Substances 0.000 description 4
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 4
230000006872 improvement Effects 0.000 description 4
230000002757 inflammatory effect Effects 0.000 description 4
238000000034 method Methods 0.000 description 4
230000002459 sustained effect Effects 0.000 description 4
NIXOWILDQLNWCW-UHFFFAOYSA-N Acrylic acid Chemical compound OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 3
206010033733 Papule Diseases 0.000 description 3
208000004210 Pressure Ulcer Diseases 0.000 description 3
208000003251 Pruritus Diseases 0.000 description 3
206010037888 Rash pustular Diseases 0.000 description 3
239000013011 aqueous formulation Substances 0.000 description 3
210000000170 cell membrane Anatomy 0.000 description 3
208000035475 disorder Diseases 0.000 description 3
230000007803 itching Effects 0.000 description 3
238000011176 pooling Methods 0.000 description 3
208000029561 pustule Diseases 0.000 description 3
210000001519 tissue Anatomy 0.000 description 3
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 2
BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 2
208000025865 Ulcer Diseases 0.000 description 2
210000004027 cell Anatomy 0.000 description 2
230000006870 function Effects 0.000 description 2
208000015181 infectious disease Diseases 0.000 description 2
150000002500 ions Chemical class 0.000 description 2
230000007794 irritation Effects 0.000 description 2
239000012528 membrane Substances 0.000 description 2
229910052751 metal Inorganic materials 0.000 description 2
239000002184 metal Substances 0.000 description 2
231100000344 non-irritating Toxicity 0.000 description 2
229960004063 propylene glycol Drugs 0.000 description 2
235000013772 propylene glycol Nutrition 0.000 description 2
239000000243 solution Substances 0.000 description 2
239000002904 solvent Substances 0.000 description 2
238000012546 transfer Methods 0.000 description 2
231100000397 ulcer Toxicity 0.000 description 2
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 description 1
WLAMNBDJUVNPJU-UHFFFAOYSA-N 2-methylbutyric acid Chemical compound CCC(C)C(O)=O WLAMNBDJUVNPJU-UHFFFAOYSA-N 0.000 description 1
206010067484 Adverse reaction Diseases 0.000 description 1
208000017667 Chronic Disease Diseases 0.000 description 1
206010011985 Decubitus ulcer Diseases 0.000 description 1
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 1
241000224432 Entamoeba histolytica Species 0.000 description 1
208000003493 Rhinophyma Diseases 0.000 description 1
240000004808 Saccharomyces cerevisiae Species 0.000 description 1
206010070834 Sensitisation Diseases 0.000 description 1
206010040047 Sepsis Diseases 0.000 description 1
241000224527 Trichomonas vaginalis Species 0.000 description 1
206010046914 Vaginal infection Diseases 0.000 description 1
201000008100 Vaginitis Diseases 0.000 description 1
208000000558 Varicose Ulcer Diseases 0.000 description 1
239000002253 acid Substances 0.000 description 1
230000002333 acnegenic effect Effects 0.000 description 1
230000002730 additional effect Effects 0.000 description 1
230000002411 adverse Effects 0.000 description 1
230000006838 adverse reaction Effects 0.000 description 1
150000001298 alcohols Chemical class 0.000 description 1
150000003973 alkyl amines Chemical class 0.000 description 1
150000001412 amines Chemical class 0.000 description 1
229910021529 ammonia Inorganic materials 0.000 description 1
238000013459 approach Methods 0.000 description 1
230000003115 biocidal effect Effects 0.000 description 1
239000003795 chemical substances by application Substances 0.000 description 1
230000001684 chronic effect Effects 0.000 description 1
239000003086 colorant Substances 0.000 description 1
238000007796 conventional method Methods 0.000 description 1
238000011161 development Methods 0.000 description 1
206010012601 diabetes mellitus Diseases 0.000 description 1
125000005265 dialkylamine group Chemical group 0.000 description 1
238000009792 diffusion process Methods 0.000 description 1
201000010099 disease Diseases 0.000 description 1
238000012377 drug delivery Methods 0.000 description 1
239000003995 emulsifying agent Substances 0.000 description 1
239000000839 emulsion Substances 0.000 description 1
229940007078 entamoeba histolytica Drugs 0.000 description 1
210000001339 epidermal cell Anatomy 0.000 description 1
230000005713 exacerbation Effects 0.000 description 1
210000000887 face Anatomy 0.000 description 1
230000001815 facial effect Effects 0.000 description 1
210000001061 forehead Anatomy 0.000 description 1
230000002496 gastric effect Effects 0.000 description 1
239000012535 impurity Substances 0.000 description 1
230000002401 inhibitory effect Effects 0.000 description 1
230000005764 inhibitory process Effects 0.000 description 1
150000007529 inorganic bases Chemical class 0.000 description 1
230000007774 longterm Effects 0.000 description 1
238000012423 maintenance Methods 0.000 description 1
150000002739 metals Chemical class 0.000 description 1
230000000813 microbial effect Effects 0.000 description 1
230000000116 mitigating effect Effects 0.000 description 1
239000002674 ointment Substances 0.000 description 1
210000000056 organ Anatomy 0.000 description 1
230000008447 perception Effects 0.000 description 1
235000019271 petrolatum Nutrition 0.000 description 1
230000002980 postoperative effect Effects 0.000 description 1
230000002829 reductive effect Effects 0.000 description 1
150000003839 salts Chemical class 0.000 description 1
230000035807 sensation Effects 0.000 description 1
230000008313 sensitization Effects 0.000 description 1
230000005808 skin problem Effects 0.000 description 1
SQMCFUSVGSBKFK-UHFFFAOYSA-M sodium;5-(cyclohexen-1-yl)-1,5-dimethylpyrimidin-3-ide-2,4,6-trione Chemical compound [Na+].O=C1N(C)C(=O)[N-]C(=O)C1(C)C1=CCCCC1 SQMCFUSVGSBKFK-UHFFFAOYSA-M 0.000 description 1
238000003892 spreading Methods 0.000 description 1
230000007480 spreading Effects 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
239000004094 surface-active agent Substances 0.000 description 1
208000024891 symptom Diseases 0.000 description 1
230000009885 systemic effect Effects 0.000 description 1
238000002560 therapeutic procedure Methods 0.000 description 1
125000005270 trialkylamine group Chemical group 0.000 description 1
230000002963 trichomonacidal effect Effects 0.000 description 1
241001148471 unidentified anaerobic bacterium Species 0.000 description 1
238000009827 uniform distribution Methods 0.000 description 1

Landscapes

Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Medicinal Preparation (AREA)

CA000533082A 1987-03-26 1987-03-26 Formulations du metronidazole topique et leurs utilisations therapeutiques Expired - Lifetime CA1297028C (fr)

Priority Applications (1)

Application Number	Priority Date	Filing Date	Title
CA000533082A CA1297028C (fr)	1987-03-26	1987-03-26	Formulations du metronidazole topique et leurs utilisations therapeutiques

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
CA000533082A CA1297028C (fr)	1987-03-26	1987-03-26	Formulations du metronidazole topique et leurs utilisations therapeutiques

Publications (1)

Publication Number	Publication Date
CA1297028C true CA1297028C (fr)	1992-03-10

Family

ID=4135288

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA000533082A Expired - Lifetime CA1297028C (fr)	1987-03-26	1987-03-26	Formulations du metronidazole topique et leurs utilisations therapeutiques

Country Status (1)

Country	Link
CA (1)	CA1297028C (fr)

1987
- 1987-03-26 CA CA000533082A patent/CA1297028C/fr not_active Expired - Lifetime

Legal Events

Date	Code	Title	Description
2009-03-10	MKEX	Expiry
2023-05-26	MKEX	Expiry	Effective date: 20090310

Publication	Publication Date	Title
US4837378A (en)	1989-06-06	Topical metronidazole formulations and therapeutic uses thereof
EP0305380B1 (fr)	1991-09-25	Nouvelles formations topiques a base de metronidazole
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