NZ207874A - Topical compositions containing meclofenamic acid - Google Patents

Topical compositions containing meclofenamic acid

Info

Publication number
NZ207874A
NZ207874A NZ20787484A NZ20787484A NZ207874A NZ 207874 A NZ207874 A NZ 207874A NZ 20787484 A NZ20787484 A NZ 20787484A NZ 20787484 A NZ20787484 A NZ 20787484A NZ 207874 A NZ207874 A NZ 207874A
Authority
NZ
New Zealand
Prior art keywords
polyethylene glycol
weight
meclofenamic acid
monostearate
triglyceride
Prior art date
Application number
NZ20787484A
Inventor
S C Belsole
Original Assignee
Warner Lambert Co
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 Warner Lambert Co filed Critical Warner Lambert Co
Publication of NZ207874A publication Critical patent/NZ207874A/en

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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
    • A61K31/185—Acids; Anhydrides, halides or salts thereof, e.g. sulfur acids, imidic, hydrazonic or hydroximic acids
    • A61K31/19—Carboxylic acids, e.g. valproic acid
    • A61K31/195—Carboxylic acids, e.g. valproic acid having an amino group
    • 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
    • A61K47/02—Inorganic compounds
    • 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
    • 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
    • A61K47/10—Alcohols; Phenols; Salts thereof, e.g. glycerol; Polyethylene glycols [PEG]; Poloxamers; PEG/POE alkyl ethers
    • 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
    • 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
    • A61K47/44—Oils, fats or waxes according to two or more groups of A61K47/02-A61K47/42; Natural or modified natural oils, fats or waxes, e.g. castor oil, polyethoxylated castor oil, montan wax, lignite, shellac, rosin, beeswax or lanolin

Landscapes

  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Epidemiology (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Dermatology (AREA)
  • Medicinal Preparation (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)

Description

New Zealand Paient Spedficaiion for Paient Number £07874 2 078 7 4 O Priority Date(s): .. !St. . T. ■?.
Complete Specification Filed: Class: KflC/.4\ $f. $7 Publication Date: P.O. Journal, No: "i'i'MW '/Js/.'Z'Z Patents Form No. 5 NEW ZEALAND PATENTS ACT 1953 COMPLETE SPECIFICATION "MECLOFENAMIC ACID TOPICAL PHARMACEUTICAL COMPOSITION" £,WE WARNER-LAMBERT-COMPANY a corporation organized under the laws of the State of Delaware, U.S.A. of 201 Tabor Road, Morris Plains, New Jersey 07950, U.S.A. hereby declare the invention, for which i-/we pray that a patent may be granted to-ae/us, and the method by which it is to be performed, to be particularly described in and by the following statement 207874 The present invention relates to topically active compositions containing meclofenamic acid in a suitable topical vehicle. Also encompassed within the scope of this invention is the process for production of said topically active compositions and the treatment of inflammation by topical application of said compositions.
Although not completely understood, the effects of nonsteroidal anti-inflammatory drugs (NSAID) is thought to be due to their interference with prostaglandin biosynthesis. This activity is likely to be related to the inhibition of cyclooxygenase and lipoxygenase in arachidonic acid metabolism.
Side effects, mostly associated with gastrointestinal disturbances, have been reported with oral NSAID therapy. Topical application should be considered a valuable alternative mode of administration. Direct application to inflammed joints should result in appreciably lower systemic blood levels and hence better tolerance.
The non-steroidal anti-inflammatory drug, meclofenamic acid, its production and its use in the treatment of arthritis by oral administration is described in New Zealand Patent No. 129559 which is herein incorporated by reference.
-P—s—Cohiantarolli at al,—Arancim For3ch,—Drug Res., 32■(1)■a^4- New Zealand Patent No. 184064 describes the use of combinations containing topically active anti-inflammatory corticosteroid and non-steroidal anti-inflammatory agents for the topical treatment of cutaneous disorders.
Meclofenamic acid is virtually water-insoluble and therefore, a hydroalcoholic gel could not be formulated at the desired concentration of drug. The drug is also insoluble in glycerin, isopropyl myristate and mineral oil. The use of the latter two solvents is described in New Zealand Patent No. 134064. Its solubility in propylene glycol, ethyl alcohol and linoleic acid is somewhat less than 5%. -—-—- *29S 207874 According to the present invention it was found that meclofenamic acid is soluble in the following water-miscible solvents to an extent of at best 5% at room temperature and more with the aid of heating up to 50°C: polyethylene glycol 400 polyethylene glycol -8 monolaurate polyethylene glycol glucose ethers also referred to as [PEG Glucose Ethers (Glucam - E 10, P-20)] polyethylene glycol - 75 Lanolin Oil also referred to as (Lantrol AWS) polypropylene (PPG)-5-Ceteth-10 Phosphate also referred to as (Crodafos SG).
Meclofenamic acid was found to have a highly favourable octanol/water partition coefficient and we have now discovered novel gel and cream formulations which provide maximal topical activity for meclofenamic acid.
Broadly speaking the gel formulation is a clear gel of meclofenamic acid in a co-solvert system of a polyethylene glycol ester, water soluble lanolin oil, an alcohol and a thickening agent.
The polyethylene glycol ester is selected from the group of polyethylene glycol esters consisting of polyethylene glycol mono- and dilaurate and polyethylene glycol mono- and dioleate. The preferred polyethylene glycol esters are polyethylene glycol -8 monolaurate, polyethylene glycol -4 and -8 dilaurate, polyethylene glycol -8 monoleate and polyethylene glycol -8 dioleate. The most preferred polyethylene glycol ester is polyethylene glycol 400 monolaurate.
The preferred water soluble lanolin oil is a polyethylene glycol lanolin oil and the most preferred is polyethylene glycol - 75 lanolin oil.
The preferred thickening agent is silicon dioxide colloidal. 207874 Finally the alcohol is selected from the group of 3 and 4 carbon containing alcohols consisting of propyl, isopropyl, butyl, sec-butyl and tert-butyl. The preferred alcohol is isopropyl alcohol.
The meclofenamic acid is present in the range of about 3 to 10% by weight and preferably about 5% by weight.
The polyethylene glycol ester is present in the range of 30 to 60% by weight and preferably about 50% by weight. The water soluble lanolin is present in the range of up to 2C% by weight and preferably about 10% by weight. The thickening agent is present from 5 to 10% by weight and preferably about 5% by weight. Sufficient alcohol is used to q.s. the formulation.
The gel formulation is prepared by dissolving meclofenamic acid in a heated and stirred solution of polyethylene glycol ester and water soluble lanolin oil. The solution is allowed to cool and an alcohol is added with continued stirring until the solution cools to room temperature. A thickening agent is added with stirring and finally sufficient alcohol to make a clear gel.
The cream formulation is a homogenized emulsion of a polyethylene glycol ester, glyceryl or propylene glycol monostearate, a triglyceride, mineral oil and an aqueous solution of a preservative to which is added meclofenamic acid or the sodium salt thereof.
The polyethylene glycol ester is selected from the group consisting of polyethylene glycol monostearate and polyethylene glycol monolaurate. The preferred polyethylene glycol esters are polyethylene glycol 40, 45, 50, 75 and -6-32 monostearate and polyethylene glycol -75 and -150 monolaurate. The most preferred polyethylene glycol ester is polyethylene glycol -6-32 monostearate.
The triglyceride is selected from the group consisting of caprylic/capric triglyceride, caprylic/ capric/stearic triglyceride and hydrogenated palm oi£j i- 1 Lz triglyceride. The preferred triglyceride is caprylic/ capric triglyceride. [( t&AIti 7 078 74 The preservative is selected from the group consisting of sorbic acid and benzoic acid and a combination of methylparaben and propylparaben. The preferred preservative is sorbic acid.
The meclofenamic acid or the sodium salt thereof is present in the range of about 3 to 10% by weight preferably about 5% by weight. Meclofenamic acid is the preferred form of the active ingredient.
The polyethylene glycol ester and glyceryl or propylene monostearate are present in the range of 5 to 12% by weight and preferably about 9% by weight. The triglyceride is present in the range 3 to 10% by weight and preferably about 5% by weight. The mineral oil is present in the range of 5 to 10% by weight and preferably about 8% by weight.
The preservative is present in sufficient amount to function as a preservative. Usually about 0.1% by weight is sufficient.
The cream formulation is prepared by adding meclofenamic acid or the sodium salt thereof to an emulsion prepared by mixing a warm aqueous solution of preservative with a melt of a polyethylene glycol ester, glyceryl or propylene monostearate, a triglyceride and mineral oil.
The pH is adjusted to the range 4.5 to 5 and the cream homogenized and cooled to room temperature.
In order to further illustrate the practice of this invention, the following examples are included: EXAMPLE 1 A clear gel containing 5% meclofenamic acid was prepared from the following ingredients: % INGREDIENTS 1000.00 g . 0 1.
Meclofenamic Acid 50. 00 9 50. 0 2.
PEG-8 Laurate (PEG 400 monolaurate) q- s. or 500. 00 g . 0 3.
PEG-75 Lanolin Oil (Lantrol AWS) q. s. or 100. 00 g . 0 4 .
Silicon Dioxide Colloidal NF q. s. or 50. 00 g .
Isopropyl Alcohol USP q. s. to 1000. 00 g 2 07874 The PEG-8 laurate (polyethylene glycol 4 00 monolaurate) and PEG-75 lanolin oil (Lantrol AWS) was heated to 90°C. To the resulting solution was added meclofenamic acid with heating to maintain a temperature of 90°C and with stirring until the meclofenamic acid dissolved. The solution was allowed to cool to 40°C and 300 g. of isopropyl alcohol was added. Stirring was continued until the solution cooled to room temperature. Silicon dioxide colloidal NF was added to the solution with high shear mixing for 10 minutes. Sufficient isopropyl alcohol was added to make 1000 g and mixed until a uniform clear, pale yellow gel containing 5% meclofenamic acid was obtained.
EXAMPLE 2 A gel containing 5% sodium meclofenamate is prepared according to the process of EXAMPLE 1 by replacing the meclofenamic acid with 50.00 g. of sodium meclofenamate.
EXAMPLE 3 A cream containing 5% meclofenamic acid is prepared from the following ingredients: . 00 1.
Meclofenamic Acid 50 O O • g 9. 00 2.
Polyethylene Glycol -6-32 Monostearate 90 .00 g 9. 00 3.
Glyceryl Monostearate 90 .00 g . 00 4.
Caprylic/Capric Triglyceride 50 O O • g 8. 00 .
Mineral Oil 80 .00 g 0. 1 6.
Sorbic Acid (preservative) 1 g - 7.
Triethanolamine q.s. to pH 4.5 - - 5.0 - 8.
Water, distilled q.s. to 100 O O g The polyethylene glycol -6-32 monostearate, glyceryl monostearate, caprylic/capric triglyceride and mineral oil are combined in a suitable jacketed tank and melted by heating to 60°C.
An aqueous solution of sorbic acid is prepared in a jacketed tank equipped with a paddle mixer by dissolving 2 078 the sorbic acid with mixing in the minimum amount of water preheated to 60°C. The aqueous solution of sorbic acid is added with agitation to the melted polyethylene glycol -6-32 monostearate, glyceryl monostearate, caprylic/capric triglyceride and mineral oil to form an emulsion. The meclofenamic acid is added to the emulsion with continued agitation and while maintaining the temperature at 60°C.
The pH of the resulting cream is adjusted to 4.5 - 5.0 with the addition of triethanolamine and the cream is circulated through an in-line homogenizer and allowed to cool to room temperature.
EXAMPLE 4 A cream containing 5% sodium meclofenamate is prepared according to the procedure of EXAMPLE 3 by replacing the meclofenamic acid with 50.00 g of sodium meclofenamate.

Claims (12)

WHAT WE CLAIM IS:
1. A stable non-aqueous clear gel composition comprising 3 to 10% by weight meclofenamic acid; 30 to 60% by weight of a polyethylene glycol ester selected from the group consisting of polyethylene glycol mono- and dilaurate and polyethylene glycol mono- and dioleate; up to 20% by weight of a polyethylene glycol lanolin oil; 50 to 10% by weight of silicon dioxide colloidal and sufficient amount of an alcohol containing 3 to 4 carbon atoms to q.s. the formulation.
2. A gel composition according to Claim 1 wherein the polyethylene glycol ester is selected from the group consisting of polyethylene glycol -8 monolaurate, polyethylene glycol -4 and -8 dilaurate, polyethylene glycol -8 monoleate and polyethylene glycol —8 monoloafco and polyethylene glycol -8 dioleate and the alcohol is selected from the group -consisting of propyl, isopropyl, butyl, sec-butyl and tert-butyl.
3. A gel composition according to Claim 1 comprising about 5% by weight meclofenamic acid, about 50% by weight polyethylene glycol -8 monolaurate, about 10% by weight polyethylene glycol-75 lanolin oil, about 5% by weight silicon dioxide colloidal and about 30% by weight isopropyl alcohol. /"V (lag
4. A process for producing a gel according to Claim 1 which comprises the steps: a) dissolving meclofenamic acid in a heated and stirred solution of polyethylene glycol ester and polyethylene alycol lanolin oil, b) ~ adding an alcohol containing 3 to 4 carbon atoms and coolinq to room temperature, and c) adding -a- silicon dioxide colloidal with high shear stirring until a clear gel is obtained.
5. A cream composition comprisina 3 to 10% by weight meclofenamic acid; 5 to 12% by weight of a polyethylene glycol ester selected from polyethylene glycol monostearate and polyethylene glycol monolaurate; 5 to 12% by weight glyceryl or propylene monostearate; 3 to 10% by weight of a 4- 207874 - 9 - triglyceride selected from the group consisting of caprylic/capric triglyceride, caprylic/capric/stearic triglyceride/, and hydrogenated palm oil triglyceride,■about 5 to 10% by weight mineral oil and about 0.1% by weight of ^ a preservative selected from the group consisting of sorbic ^ acid and benzoic acid and a combination of methylparaben and propylparaben.
6. A cream composition according to Claim 5 wherein the polyethylene glycol ester is selected from the group consisting of polyethylene glycol 40, 45, 50, """* 75, and -6-32 monostearate and polyethylene glycol -75;and -150 monolaurate.;
7. A cream composition according to Claim 5 comprising about 5% by weight meclofenamic acid, about 9% by weight polyethylene glycol -6-32 monostearate,;abuul 9% by weight glyceryl monostearate- about 5% by weight caprylic/capric triglyceride, about- 8% by weight mineral oil, and a sorbic acid preservative, the composition being adjusted to a pH of 4.5 to 5.0.;
8. A process for producing a cream according to Claim 5 which comprises the steps:;a) melting a mixture of polyethylene glycol ester, glyceryl or propylene monostearate, a triglyceride and mineral oil,;b) adding an aqueous solution of a preser-vative with mixing to form an emulsion,;c) adding meclofenamic acid to the emulsion with agitation and d) adjusting the pH to 4.5 to 5.0.;
9. A clear gel composition as claimed in Claim 1 and substantially as herein described with reference to any one of the Examples.;
10. A process for preparing a clear gel composition as claimed in Claim 4'substantially as herein described with reference to any one of the Examples.;
11. A cream composition as claimed in Claim 5 substantially as herein described with reference to any one of the Examples.;r* - 10 -
12. A process for producing a cream as claimed in Claim 8 substantially as herein described with reference to any one of the Examples. 207874 A BALDWIN, SON & CAREY (£./$" 0 ATTCriNEYS fOn TIIc A.'rLICANTS W ' < 7
NZ20787484A 1983-04-18 1984-04-17 Topical compositions containing meclofenamic acid NZ207874A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US48597383A 1983-04-18 1983-04-18

Publications (1)

Publication Number Publication Date
NZ207874A true NZ207874A (en) 1987-01-23

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Family Applications (1)

Application Number Title Priority Date Filing Date
NZ20787484A NZ207874A (en) 1983-04-18 1984-04-17 Topical compositions containing meclofenamic acid

Country Status (8)

Country Link
AU (1) AU560035B2 (en)
BE (1) BE899366A (en)
CA (1) CA1229554A (en)
DE (1) DE3414377A1 (en)
FR (1) FR2544198B1 (en)
GB (1) GB2138287B (en)
NL (1) NL8400933A (en)
NZ (1) NZ207874A (en)

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5241925A (en) * 1988-12-27 1993-09-07 Dermamed Apparatus and techniques for administering veterinary medicaments
US5324521A (en) * 1989-12-18 1994-06-28 Dermamed Systems for transdermal administration of medicaments
US5332577A (en) * 1988-12-27 1994-07-26 Dermamed Transdermal administration to humans and animals

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
IT1216233B (en) * 1986-07-02 1990-02-22 Menarini Sas USE OF THE PHARMACEUTICAL FORM 'GEL' CONTAINING N (2,6 DICHLORO M TOLIL) ANTRANILIC ACID (MECLOFENAMIC ACID) APPLICABLE IN THERAPY FOR TOPICAL USE.
WO1988001166A1 (en) * 1986-08-18 1988-02-25 Biota Scientific Management Pty Ltd Stimulation of angiogenesis and promotion of endothelialisation

Family Cites Families (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DD124950A5 (en) * 1975-07-04 1977-03-23
US4185100A (en) * 1976-05-13 1980-01-22 Johnson & Johnson Topical anti-inflammatory drug therapy
NL175882C (en) * 1977-03-28 Procter & Gamble PHARMACEUTICAL PREPARATION CONTAINING AN ANTI-INFLAMMATORY COMPOUND.
JPS5826815A (en) * 1981-08-10 1983-02-17 Ikeda Mohandou:Kk Nonsteroid antiphlogistic ointment and its preparation

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5241925A (en) * 1988-12-27 1993-09-07 Dermamed Apparatus and techniques for administering veterinary medicaments
US5332577A (en) * 1988-12-27 1994-07-26 Dermamed Transdermal administration to humans and animals
US5324521A (en) * 1989-12-18 1994-06-28 Dermamed Systems for transdermal administration of medicaments

Also Published As

Publication number Publication date
AU560035B2 (en) 1987-03-26
FR2544198A1 (en) 1984-10-19
FR2544198B1 (en) 1987-11-20
CA1229554A (en) 1987-11-24
DE3414377A1 (en) 1984-11-15
GB2138287A (en) 1984-10-24
GB2138287B (en) 1986-03-05
AU2514884A (en) 1984-10-25
BE899366A (en) 1984-10-08
NL8400933A (en) 1984-11-16

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