WO1993020796A1 - Procede et composition pour le traitement de l'acne - Google Patents

Procede et composition pour le traitement de l'acne Download PDF

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Publication number
WO1993020796A1
WO1993020796A1 PCT/US1993/003325 US9303325W WO9320796A1 WO 1993020796 A1 WO1993020796 A1 WO 1993020796A1 US 9303325 W US9303325 W US 9303325W WO 9320796 A1 WO9320796 A1 WO 9320796A1
Authority
WO
WIPO (PCT)
Prior art keywords
composition
percent
benzoyl peroxide
weight
clindamycin
Prior art date
Application number
PCT/US1993/003325
Other languages
English (en)
Inventor
Sreekant R. Nadkarni
Paul A. Laskar
Original Assignee
Allergan, 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.)
Filing date
Publication date
Application filed by Allergan, Inc. filed Critical Allergan, Inc.
Publication of WO1993020796A1 publication Critical patent/WO1993020796A1/fr

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Classifications

    • 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
    • A61K31/70—Carbohydrates; Sugars; Derivatives thereof
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
    • A61K8/38—Percompounds, e.g. peracids
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/60—Sugars; Derivatives thereof
    • A61K8/602—Glycosides, e.g. rutin
    • 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
    • A61K9/48—Preparations in capsules, e.g. of gelatin, of chocolate
    • A61K9/50—Microcapsules having a gas, liquid or semi-solid filling; Solid microparticles or pellets surrounded by a distinct coating layer, e.g. coated microspheres, coated drug crystals
    • A61K9/5005—Wall or coating material
    • A61K9/5021—Organic macromolecular compounds
    • A61K9/5052—Proteins, e.g. albumin
    • A61K9/5057—Gelatin
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q19/00—Preparations for care of the skin
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q19/00—Preparations for care of the skin
    • A61Q19/008—Preparations for oily skin

Definitions

  • This invention relates to a method and composition for treating acne vulgaris.
  • Acne vulgaris is an inflammatory disease of the sebaceous glands characterized by an eruption of the skin, often pustular in nature but not suppurative.
  • Acne is a common affliction of the adolescent and affects a small but significant percentage of the adult population. Acne involvement results in unsightly lesions, particularly on the face, and in some cases results in severe scarring.
  • Topical agents are utilized in the treatment of acne and these include sulfur, resorcinol, salicylic acid, benzoyl peroxide, retinoids and topical antibiotics.
  • An effective anti-acne agent (or composition) must exhibit the following activites:
  • Benzoyl peroxide has been suggested for treating acne vulgaris. (See U.S. Patent 4,387,107.) For many years, benzoyl peroxide has been proven to be a particularly powerful keratolytic and anti-seborrhic agent, as well as being endowed with antibacterial properties. Topical benzoyl peroxide compositions, including a vehicle to enhance the efficacy thereof, are known (See U.S. Patent 4, 411,893). Topical compositions of benzoyl peroxide combination with antibiotics are also known. (See U.S. Patents 4,407,794; 4,692,329 and 4,387,107)
  • Peroxides other than benzoyl peroxide, have been suggested for treatment of acne vulgaris, alone, or in combination with other compounds useful in treating acne vulgaris. (See U.S. Patents 4,607,101 and 4,906,617.) These peroxides are suggested as having certain advantages, e.g. stability over benzoyl peroxide.
  • U.S. Patent 4,671,956 identifies the problem of benzoyl peroxide decomposing coingredients in topical formulations to thereby cause itching upon application. It is suggested that this problem may be solved by including a sunscreen in the topical formulation to retard this decomposition effect of benzoyl peroxide.
  • topical compositions for the treatment of acne vulgaris such compositions utilizing as an active ingredient clindamycin or benzoyl peroxide, alone, or in combination with other active ingredients for the treatment of acne vulgaris. Furthermore, it is apparent that there are stability problems associated with topical compositions including benzoyl peroxide,
  • one object of the instant invention is to provide a method of treating acne vulgaris with a topical composition including benzoyl peroxide and clindamycin.
  • Another object of the invention is to provide topical compositions of benzoyl peroxide and clindamycin that are stable to storage over extended periods of time at ambient conditions.
  • the present invention provides a method for treating acne vulgaris by topically applying a composition of benzoyl peroxide and clindamycin in a therapeutically-effective amount.
  • the antibiotic clindamycin (free base), or its pharmaceutically acceptable salts or prodrugs e.g., clindamycin phosphate, clindamycin hydrocholoride
  • Benzoyl peroxide which has keratolytic and antiseborrheic properties, may be present in an amount sufficient to provide from about 0.1 to about 30 percent, and preferably from about 2.5 to about 10 percent, by weight, benzoyl peroxide.
  • the benzoyl peroxide may more preferably be used as hydrous benzoyl peroxide and may be suspended preferably in the
  • the above described topical composition may be in the form of a solution, gel, ointment, cream, a liquid suspension or emulsion or a stick base.
  • the topical composition of this invention may further include a surfactant preferably comprising at least one sulfonic radical, e.g., long-chain alkyl sulfonates or alkyl aryl sulfonates.
  • the surfactant may comprise from about 0.01 to about 5 percent, by weight, and preferably from 0.025 to about 1 percent, of the above topical composition.
  • Surfactants which are useful in the method and composition of this invention include dioctyl sodium sulfosuccinate and sodium dodecylbenzenesulfonate.
  • compositions of this invention are administered topically to treat acne vulgaris. That is, the compositions may be applied as a solution, gel, ointment, cream, a liquid suspension or emulsion or a stick base. Thus, it is preferred that such compositions indude a pharmaceutically acceptable carrier that enhances the efficacy of such topical administration.
  • Pharmaceutically acceptable carriers include conventional emulsifiers, such as fatty alcohols, glycol ethers and esters of fatty adds; conventional emollients, such as isopropyl and butyl esters of fatty adds, e.g. isopropyl myristate; humectants such as glycerin, propylene glycol, polyethylene glycol; and alcohols and acetone; oils such as mineral oil, petroleum oil, oil extracts from animal or vegetable sources; conventional stabilizers including antioxidants and preservatives.
  • the formulation may also indude agents, such as urea, to improve the hydration of the skin.
  • the topical compositions may indude penetration-enhancing agents such as 1-pyrrolidone and N- lower alkyl-2-pyrrolidones, such as N-methyl-2-pyrrolidone; and 1- substituted azacycloaIkan-2-ones such as, for example, 1-n- dodecylazacydoheptan-2-one and other compounds disdosed in U.S. Pat. No. 3,989,816.
  • Longer chain sulfoxides e.g., n-octyl methyl sulfoxide and hexamethylene-lauramide and the other penetration-
  • enhandng agents disdosed in U.S. Patent No. 4,743,588, may also be included in the formulations of this invention.
  • the amount of these compounds which may be used in the present invention ranges from about 0.1 to 25 percent and preferably about 1 to 15 percent by weight of the composition.
  • the amount of the composition to be administered will obviously be an effective amount for the desired result expected therefrom. This, of course, will be ascertained by the ordinary skill of the practitioner. In accordance with the usual prudent formulating practices, a dosage near the lower end of the useful range of the particular agent may be employed initially and the dosage increased as indicated from the observed response, as in the routine procedure of the physidan.
  • the active ingredient(s) formulated, for example, as a gel or lotion or suspension is applied to the affected area of the skin at a rate varying from 0.2 mg per square cm of skin surface per day up to 10 mg per square cm of skin surface per day until the appearance of the affected skin has returned to normal.
  • the gel or lotion or suspension is generally applied for several days.
  • topical compositions of this invention may be applied to the face of a patient with acne 2 to 4 times daily with the result that open and closed comedones are markedly reduced within two weeks
  • the following gel formulations are prepared by dispersing a polyacrylic add, e.g. Carbomer 940, available from B.F. Goodrich, into water. To this dispersion is added a dispersion of hydrous
  • the pH of the resulting dispersion may be buffered with NaOH and a mixture of dtric add monohydrate, and sodium dtrate dihydrate.
  • Hydrous benzoyl peroxide includes about 70% by weight benzoyl peroxide as an active ingredient.
  • Carbopol or carbomer resins are synthetic, high molecular acrylic acid cross- linked to different extents with a polyalkenyl ether (alkyl ethers of either sucrose or pentaerythritol).
  • the topical compositions of the invention are stable to storage. It is believed that this stability is a result of the stabilization of the topical compositions by the sulfonate radical-containing surfactant.
  • Formulations 3 and 4 were also tested for stability to storage as in Example 1 above. The results are reported in Table 2 below.
  • compositions of the invention also showed excellent stability to storage.
  • a cream formulation without dioctyl sodium sulfosucdnate was prepared in the form of an oil-in-water emulsion.
  • This cream formulation had the following composition:
  • Formulation 6 was tested for storage stability. The results are reported in Table 4 below.
  • Glyceryl stearate and polyoxyethylene (100) stearate in combination is an acid- stable, self-emulsifying system available commercially as Arlacel®165 (ICI Americas).
  • Carbomer 934P is a high molecular weight polymer of acrylic acid cross-linked with a polyalkenyl polyether.
  • 5 Brij® 30 is a polyoxyethylene (4) lauryl ether and functions as an emulsifier
  • compositions of further anti-acne gel formulations containing 1.19 percent dindamydn phosphate (equivalent to 1 percent dindamydn) and 5 percent benzoyl peroxide (on an anhydrous basis) are listed below:
  • Microcrystalline cellulose (Avicd RC-591) 2.500
  • a 20 year old male applies 0.5 gms of Formulation to his face 4 times daily. After 10 days, the number of comedones begin to diminish. By the end of four weeks, the number of comedones declines significantly.
  • hydrous benzoyl peroxide i.e., diaryl peroxide, alkyl aryl peroxide, cydoalkyl aryl peroxide may be substituted for hydrous benzoyl peroxide.
  • lauroyl benzoyl peroxide, cydohexyl carbanolyl benzoyl peroxide Various sulfonate radical-containing surfactants may be used in place of diortylsodium sulfosuc ⁇ nate and sodium dodecylbenzene sulfonate.
  • Polyacrylic add commerdally available under the trade name of Carbopols®, may be replaced by various other gelling agents, such as methylcellulose microcrystalline cellulose, hydroxypropyl metiiyl cellulose, colloidal magnesium aluminum silicate.

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  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Veterinary Medicine (AREA)
  • Public Health (AREA)
  • Animal Behavior & Ethology (AREA)
  • Epidemiology (AREA)
  • Birds (AREA)
  • Chemical & Material Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Emergency Medicine (AREA)
  • Engineering & Computer Science (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Molecular Biology (AREA)
  • Dermatology (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Medicinal Preparation (AREA)

Abstract

La présente invention se rapporte à des compositions topiques à base d'un peroxyde d'un acide organique, tel que du peroxyde de benzoyle, et de clindamycine et de ses dérivés, tels que du phosphate de clindamycine, et qui peuvent être utilisés pour traiter l'acné vulgaire. De telles compositions peuvent en outre comprendre un agent tensioactif contenant un radical sulfonique.
PCT/US1993/003325 1992-04-09 1993-04-07 Procede et composition pour le traitement de l'acne WO1993020796A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US86556292A 1992-04-09 1992-04-09
US07/865,562 1992-04-09

Publications (1)

Publication Number Publication Date
WO1993020796A1 true WO1993020796A1 (fr) 1993-10-28

Family

ID=25345786

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/US1993/003325 WO1993020796A1 (fr) 1992-04-09 1993-04-07 Procede et composition pour le traitement de l'acne

Country Status (4)

Country Link
AU (1) AU3975993A (fr)
IL (1) IL105217A0 (fr)
WO (1) WO1993020796A1 (fr)
ZA (1) ZA932483B (fr)

Cited By (12)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6740330B1 (en) * 2001-05-02 2004-05-25 Sirius Laboratories, Inc. Method of treating acne vulgaris and composition
WO2006121429A1 (fr) * 2005-05-06 2006-11-16 Imaginative Research Associates, Inc. Compositions de clindamycin et systeme d'administration pour ces compositions
WO2008006848A1 (fr) * 2006-07-13 2008-01-17 Galderma Research & Development Composition comprenant un rétinoïde et du peroxyde de benzoyle
FR2903604A1 (fr) * 2006-07-13 2008-01-18 Galderma Res & Dev S N C Snc Composition comprenant un retinoide et du peroxyde de benzoyle
FR2910320A1 (fr) * 2006-12-21 2008-06-27 Galderma Res & Dev S N C Snc Emulsion comprenant au moins un retinoide et du peroxyde de benzole
FR2910321A1 (fr) * 2006-12-21 2008-06-27 Galderma Res & Dev S N C Snc Gel creme comprenant au moins un retinoide et du peroxyde de benzole
US8105618B2 (en) 2001-12-21 2012-01-31 Galderma Research & Development Dermatological/cosmetic gels comprising at least one retinoid and/or retinoid salt and benzoyl peroxide
WO2011101868A3 (fr) * 2010-02-18 2012-03-29 Helios Pharmaceuticals Private Limited Préparations pharmaceutiquement stables contenant de la clindamycine et du peroxyde de benzoyle, et méthode associée
KR101253388B1 (ko) * 2009-11-30 2013-04-11 (주)아모레퍼시픽 안정성이 향상된 여드름 개선용 조성물
US8475770B2 (en) 2006-03-31 2013-07-02 Stiefel Research Australia Pty Ltd Foamable suspension gel
WO2014189478A3 (fr) * 2013-05-23 2015-01-15 Kapar Umut Solution d'hygiène auriculaire applicable sous forme de mousse ou de shampoing
US9561208B2 (en) 2008-06-05 2017-02-07 Dow Pharmaceutical Sciences, Inc. Topical pharmaceutical formulations containing a low concentration of benzoyl peroxide in suspension in water and a water-miscible organic solvent

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3969516A (en) * 1974-12-19 1976-07-13 Nelson Research & Development Company Composition and method for treatment of acne
GB2090135A (en) * 1980-12-08 1982-07-07 Rorer Int Overseas A Composition for the Topical Treatment of Acne
US4387107A (en) * 1979-07-25 1983-06-07 Dermik Laboratories, Inc. Stable benzoyl peroxide composition
GB2150436A (en) * 1983-12-01 1985-07-03 Oreal Anti-acne composition based on benzoyl peroxide and solar filter

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3969516A (en) * 1974-12-19 1976-07-13 Nelson Research & Development Company Composition and method for treatment of acne
US4387107A (en) * 1979-07-25 1983-06-07 Dermik Laboratories, Inc. Stable benzoyl peroxide composition
GB2090135A (en) * 1980-12-08 1982-07-07 Rorer Int Overseas A Composition for the Topical Treatment of Acne
GB2150436A (en) * 1983-12-01 1985-07-03 Oreal Anti-acne composition based on benzoyl peroxide and solar filter

Cited By (37)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6740330B1 (en) * 2001-05-02 2004-05-25 Sirius Laboratories, Inc. Method of treating acne vulgaris and composition
US8105618B2 (en) 2001-12-21 2012-01-31 Galderma Research & Development Dermatological/cosmetic gels comprising at least one retinoid and/or retinoid salt and benzoyl peroxide
US9814690B2 (en) 2001-12-21 2017-11-14 Galderma Research & Development Gel composition for treatment of common acne comprising a combination of benzoyl peroxide and adapalene and/or adapalene salt
US8936800B2 (en) 2001-12-21 2015-01-20 Galderma Research & Development Gel composition for treatment of common acne comprising a combination of benzoyl peroxide and adapalene and/or adapalene salt
US8241649B2 (en) 2001-12-21 2012-08-14 Galderma Research & Development Dermatological/cosmetic gels comprising at least one retinoid and/or retinoid salt and benzoyl peroxide
WO2006121429A1 (fr) * 2005-05-06 2006-11-16 Imaginative Research Associates, Inc. Compositions de clindamycin et systeme d'administration pour ces compositions
US9265726B2 (en) 2006-03-31 2016-02-23 Stiefel Research Australia Pty Ltd Foamable suspension gel
US8758728B2 (en) 2006-03-31 2014-06-24 Stiefel Research Australia Pty Ltd Foamable suspension gel
US8475770B2 (en) 2006-03-31 2013-07-02 Stiefel Research Australia Pty Ltd Foamable suspension gel
EP3184108A1 (fr) * 2006-07-13 2017-06-28 Galderma Research & Development Composition comprenant un rétinoïde et du peroxyde de benzoyle
JP2009542773A (ja) * 2006-07-13 2009-12-03 ガルデルマ・リサーチ・アンド・デヴェロップメント レチノイドと過酸化ベンゾイルとを含む組成物
WO2008006848A1 (fr) * 2006-07-13 2008-01-17 Galderma Research & Development Composition comprenant un rétinoïde et du peroxyde de benzoyle
FR2903604A1 (fr) * 2006-07-13 2008-01-18 Galderma Res & Dev S N C Snc Composition comprenant un retinoide et du peroxyde de benzoyle
US9060948B2 (en) 2006-07-13 2015-06-23 Galderma Research & Development Dermatological/cosmetic compositions comprising a retinoid and benzoyl peroxide
US8957112B2 (en) 2006-12-21 2015-02-17 Galderma Research & Development Cream gels comprising at least one retinoid and benzoyl peroxide
US9999577B2 (en) 2006-12-21 2018-06-19 Galderma Research & Development Cream gels comprising at least one retinoid and benzoyl peroxide
WO2008087348A3 (fr) * 2006-12-21 2008-11-06 Galderma Res & Dev Emulsion comprenant au moins un retinoide et du péroxyde de benzoyle
US10925814B2 (en) 2006-12-21 2021-02-23 Galderma Research & Development Cream gels comprising at least one retinoid and benzoyl peroxide
WO2008087348A2 (fr) * 2006-12-21 2008-07-24 Galderma Research & Development Emulsion comprenant au moins un retinoide et du péroxyde de benzoyle
WO2008087354A2 (fr) * 2006-12-21 2008-07-24 Galderma Research & Development Gel creme comprenant au moins un retinoide et du péroxyde de benzoyle
US10702466B2 (en) 2006-12-21 2020-07-07 Galderma Research & Development Emulsions comprising at least one retinoid and benzoyl peroxide
FR2910321A1 (fr) * 2006-12-21 2008-06-27 Galderma Res & Dev S N C Snc Gel creme comprenant au moins un retinoide et du peroxyde de benzole
EP2460562A1 (fr) * 2006-12-21 2012-06-06 Galderma Research & Development Gel creme comprenant au moins un retinoide et du péroxyde de benzoyle
EP2460561A1 (fr) * 2006-12-21 2012-06-06 Galderma Research & Development Emulsion comprenant au moins un retinoide et du péroxyde de benzoyle
FR2910320A1 (fr) * 2006-12-21 2008-06-27 Galderma Res & Dev S N C Snc Emulsion comprenant au moins un retinoide et du peroxyde de benzole
EP3025763A1 (fr) * 2006-12-21 2016-06-01 Galderma Research & Development Gel creme comprenant au moins un retinoide et du peroxyde de benzoyle
CN101631594A (zh) * 2006-12-21 2010-01-20 盖尔德马研究及发展公司 包含至少一种维甲酸类和过氧化苯甲酰的乳液
WO2008087354A3 (fr) * 2006-12-21 2008-11-13 Galderma Res & Dev Gel creme comprenant au moins un retinoide et du péroxyde de benzoyle
US9693988B2 (en) 2008-06-05 2017-07-04 Dow Pharmaceutical Sciences, Inc. Topical pharmaceutical formulations containing a low concentration of benzoyl peroxide in suspension in water and a water-miscible organic solvent
US9561208B2 (en) 2008-06-05 2017-02-07 Dow Pharmaceutical Sciences, Inc. Topical pharmaceutical formulations containing a low concentration of benzoyl peroxide in suspension in water and a water-miscible organic solvent
US10137142B2 (en) 2008-06-05 2018-11-27 Dow Pharmaceutical Sciences, Inc. Topical pharmaceutical formulations containing a low concentration of benzoyl peroxide in suspension in water and a water-miscible organic solvent
US10220049B2 (en) 2008-06-05 2019-03-05 Dow Pharmaceutical Sciences, Inc. Topical pharmaceutical formulations containing a low concentration of benzoyl peroxide in suspension in water and a water-miscible organic solvent
US10624918B2 (en) 2008-06-05 2020-04-21 Dow Pharmaceutical Sciences, Inc. Topical pharmaceutical formulations containing a low concentration of benzoyl peroxide in suspension in water and a water-miscible organic solvent
US11478498B2 (en) 2008-06-05 2022-10-25 Dow Pharmaceutical Sciences, Inc. Topical pharmaceutical formulations containing a low concentration of benzoyl peroxide in suspension in water and a water-miscible organic solvent
KR101253388B1 (ko) * 2009-11-30 2013-04-11 (주)아모레퍼시픽 안정성이 향상된 여드름 개선용 조성물
WO2011101868A3 (fr) * 2010-02-18 2012-03-29 Helios Pharmaceuticals Private Limited Préparations pharmaceutiquement stables contenant de la clindamycine et du peroxyde de benzoyle, et méthode associée
WO2014189478A3 (fr) * 2013-05-23 2015-01-15 Kapar Umut Solution d'hygiène auriculaire applicable sous forme de mousse ou de shampoing

Also Published As

Publication number Publication date
AU3975993A (en) 1993-11-18
IL105217A0 (en) 1993-07-08
ZA932483B (en) 1993-11-03

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