AP641A - Improved ketoconazole shampoo. - Google Patents
Improved ketoconazole shampoo. Download PDFInfo
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- AP641A AP641A APAP/P/1996/000865A AP9600865A AP641A AP 641 A AP641 A AP 641A AP 9600865 A AP9600865 A AP 9600865A AP 641 A AP641 A AP 641A
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q5/00—Preparations for care of the hair
- A61Q5/02—Preparations for cleaning the hair
-
- 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
- A61K8/49—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
- A61P17/08—Antiseborrheics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q5/00—Preparations for care of the hair
- A61Q5/006—Antidandruff preparations
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K2800/00—Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
- A61K2800/40—Chemical, physico-chemical or functional or structural properties of particular ingredients
- A61K2800/52—Stabilizers
- A61K2800/524—Preservatives
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Abstract
A shampoo that contains ketoconazole or elubiol, a surfactant, a foaming agent, thickener sufficient to give the final formulation a viscosity in the range of about 4,000 to about 9,000 cps mpa.S at room temperature i.E., about 20-25 degrees c, preservative, butylated hydroxytoluene or butylated hydroxyamisole in an amount sufficient to retard degradation of the ketoconazole or elubiol, and acid, base or buffer sufficient to give the final composition a ph in the range of from about 4 to about 10.
Description
IMPROVED ANTI-DANDRUFF SHAMPOO
Cross-Reference to Related Application
This application is a continuation-in-part of copending application Serial No. 08/224,382, filed on April 7, 1994.
The invention relates to an improved anti-dandruff shampoo containing ketoconazole or elubiol.
Background of the Invention
Ketoconazole is the generic name for the compound (±)-cis-lacety 1-4- [4-((2-(2,4-dichlorophenyl) -2- (Iff-imidazol-l-y Imethyl) 15 1,3-dioxolan-4-yl]methoxy]phenyl]piperazine, having the formula:
AP/P/ 9 6 / 0 0 8 6 5
A5
Ketoconazole was originally described by Heeres et al., for instance, in U.S. Patent No. 4,335,125, in which its principal utility was as an antifungal compound. Ketoconazole was also disclosed by Rosenberg et al. in U.S. Patent No. 4,569,935 to be useful in the topical treatment of psoriasis and seborrheic dermatitis.
Elubiol is the generic name for the compound (±)-ethyl cis4-(4 -[ [2-(2,4-dichlorophenyl)-2-(lH-imidazol-l-yImethyl)-1,3-1AP 00641 dioxolan-4-yl]methoxy]phenyl]-l-piperazinecarboxylate, having the formula:
N-CO-O-CH.
-CH
Elubiol was also originally described by Heeres et al., for instance, in U.S. Patent No. 4,335,125, in which its principal utility was as an antifungal compound.
Ketoconazole has been marketed in a 2% shampoo formulation (available in the United States by prescription only) for the treatment of scaling due to dandruff. The components of this shampoo include coconut fatty acid diethanolamide, disodium monolauryl ether sulphosuccinate, colorant such as F.D. & C. Red No. 40, hydrochloric acid and/or sodium hydroxide to control pH, ' imidurea, laurdimonium hydrolyzed animal collagen, macrogol 120 methyl glucose dioleate, perfume bouquet, purified water, sodium lauryl ether sulphate, and ketoconazole (2%).
Although the above-described shampoo is efficacious for dandruff treatment, it was desired to improve its cosmetic attributes such as lathering and conditioning, and to develop an
0 efficacious formulation that, if desired, could contain less than 2% of the active agent, i.e., ketoconazole or elubiol. However, since ketoconazole and elubiol are subject to slow degradation by oxidation and hydrolysis, any formulation that contains significantly less than 2% of the active agent must be effective35 ly stabilized in order to have an acceptable shelf life. The
-2AP 00641 present invention is based on the discovery of a formulation for a ketoconazole-containing or elubiol-containing shampoo that exhibits excellent cosmetic attributes such as lathering and conditioning, and is acceptably stable to degradation so that, if desired, the shampoo can be formulated to contain less than 2% ketoconazole.
Brief Summary of the Invention
The present invention provides an aqueous shampoo that contains ketoconazole or elubiol, a surfactant, a foaming agent, ! thickener sufficient to give the final formulation a viscosity in the range of about 4,000 to about 9,000 cps (mPa.s) at room temperature (i.e., about 20-25’C), preservative, an antioxidant selected from the group consisting of butylated hydroxytoluene and butylated hydroxy anisole in an amount sufficient to retard degradation of the ketoconazole or elubiol, and acid, base or buffer sufficient to give the final composition a pH in the range of from about 4 to about 10, preferably from about 6.5 to about
8, and more preferably from 6.9 to 7.4.
The Prior Art
Butylated hydroxytoluene, whose proper chemical name is 2,6Λ bis (1,1-dimethylethyl) -4-methylphenol, also 2,6-di-tert-butyl-pcresol or 2,6-di-tert-butyl-4-methylphenol, is marketed as an antioxidant for food, animal feed, petroleum products, synthetic rubbers, plastics, animal and vegetable oils, and soaps, and as an antiskinning agent in paints and inks. (Ref. - Page 23 8 of the Merck Index, Eleventh Edition.)
Butylated hydroxyanisole, whose proper chemical name is 2(3)-tert-butyl-4-methoxyphenol, is marketed as an antioxidant, especially for food. (Ref. - Page 1547 of the Merck Index,
Eleventh Edition.)
AP/P/ 9 6 / 0 0 8 6 5
-3AP 00641
u.
Detailed Description of -the Invention
The shampoo of the invention contains ketoconazole or elubiol, at least one surfactant, a foaming agent, thickeners sufficient to give the final formulation a viscosity in the range of about 4,000 to about 9,000 cps (mPa.s) at room temperature, preservatives including butylated hydroxytoluene sufficient to prevent degradation of the final composition, and acid, base or buffer sufficient to give the final composition a pH in the range of from about 4 to about 10. Each class of ingredients will be discussed in turn.
The active agent, i.e., ketoconazole or elubiol, is employed in the shampoo in an amount effective to combat scaling due to dandruff. An effective amount will usually be found within the range of from about 0.3 weight percent up to about 3 weight percent of active agent, based on weight of the entire shampoo formulation. Preferred amounts are usually found within the range of from about 0.4 to 2 weight percent, and more preferably from about 0.5 to about l.l weight percent. At concentrations below the indicated range, the effectiveness begins to diminish to unacceptable levels, and at concentrations higher than about s 3 weight percent, the limited solubility of ketoconazole or elubiol in aqueous media, even with surfactants present, becomes a significant factor.
The shampoo of the invention contains one or more surfactants, which are employed principally as cleansing agents. Specific illustrations of surfactants that have been found to be useful include the following compositions:
Sodium laureth sulfate, a composition having the formula CH3(CH2) i0CH2(OCH2C _OSO3Na, wherein n represents a number having an average value or from 1 to 4; and
AP/P/ 96/00865
-4AP 00641
Sodium cocoyl sarcosinate, which is the sodium salt of cocoyl sarcosine. Cocoyl sarcosine is the coconut oil fatty acid amide of sarcosine (N-methylglycine or methylaminoethanoic acid) . Coconut fatty acid is a mixture of myristic acid, lauric acid, palmitic acid and stearic acid.
Other surfactants that can be employed in the shampoo of the invention include sodium C14_l6 olefin sulfonates, sodium lauryl sulfate, cocamidopropylamine oxide, lauramido DEA (lauramido diethanolamine), cocamidopropyl betaine, disodium oleamido MIPA sulfosuccinate, disodium cocamido MIPA sulfosuccinate, disodium laureth sulfosuccinate, cocoamphocarboxy-glycinate, and disodium J' i oleamido MEA sulfosuccinate. These surfactants are all known in the shampoo and cosmetic arts.
The shampoo of the invention also contains foaming agents such as fatty acid mono- and di-alkanolamides, for instance, cocamide MEA (a mixture of coconut acid monoethanolamides of the formula R-CO-NHCH2CH2OH wherein R represents the residue after removal of the carboxyl group of coconut fatty acid), cocamide DEA [a mixture of diethanolamides of the formula R-CO-N(CH2CH2OH)2 wherein R is as defined above], oleamide MEA and oleamide DEA.
> The shampoo of the invention contains a thickener to impart _ 25 a viscosity to the formulation in the range of from about 4,000 to about 9,000 cps (mPa.s) at room temperature. Such thickeners include Carbopol 1342, which is a copolymer of C10.30alkyl acrylates, acrylic acid and/or. methacrylic acid, cross-linked with an allyl ether of sucrose. Other thickeners that can be used include cellulose derivatives such as hydroxypropyl methylcellulose, hydroxyethyl cellulose, carboxymethyl cellulose, and the like. The addition of a small amount of salt (NaCl) also serves to control the viscosity of the final formulation. Usually, the amount of salt added will be within the range of from about 0.25 to 0.6 weight percent.
AP/P/ 9 6 / 0 0 8 6 5
-5AP 00641
The preservatives that can be used in the shampoo of the invention include tetrasodium EDTA (the tetrasodium salt of ethylenediamine tetraacetic acid - used as a chelating agent to protect against degradation caused by metal ions and also to enhance anti-bacterial activity) and quaternium-15 [l-(3-chloroallyl)-3,5,7-triaza-l-azonia-adamantane chloride - used as an anti-microbial agent]. Other preservatives that can be used include paraben, Kathon CG biocide (a mixture of 5-chloro-2methyl-4-isothiazolin-3-one and 2-methyl-4-isothiazolin-3-one), phenoxyethanol, benzyl alcohol, and the like.
J
The shampoo of the invention may also contain other therapeutically active agents, such as the antiseborrheic agent octopirox, a trade name for piroctone, a compound whose chemical name is l-hydroxy-4-methyl-6-(2,4,4-trimethylpentyl)-2(1H) pyridinone.
An important feature of the present invention is the discovery that a carefully controlled amount of an antioxidant selected from the group consisting of butylated hydroxytoluene (BHT) and butylated hydroxyanisole (BHA) is effective to stabilize the ketoconazole or elubiol present in the shampoo against degradation during accelerated aging for 13 weeks at 50°C, which is considered to be predictive of performance during storage at ambient temperatures for two years. Effective stability is considered to be a loss of active ingredient during storage of not more than about 10 percent. The proportion of BHT or BHA that has been found to be most effective is within the range of from about 0.01 to about 1, and preferably 0.1 ± 0.025,
0 weight percent, based on weight of the entire shampoo formulation (See Table 1, below). Surprisingly, proportions greater than this amount do not stabilize as effectively for the 13-week accelerated aging period, although if one extends the accelerated aging period longer than 13 weeks, greater proportions of BHT or
BHA tend to.be more effective, since the BHT or BHA itself is
ΔΡ/Ρ/ 9 6 / 0 0 8 6 5
-6AP 00641 also subject to degradation (see Table 2, below). However, it is well recognized by government regulatory agencies and in the pharmaceutical and cosmetic industries that stability testing for 13 weeks at 50°C is quite sufficient to predict product stability during normal shelf life storage for two (2) years at room temperature. It is also equally important that, for safety reasons (that is, to minimize the potential for skin sensitization) , it is desired to use as small an amount as possible of BHT or BHA.
The shampoo of the invention can contain other materials . such as fragrances, colorants, opacifiers, conditioners such as polyquaternium-7 [the polymeric quaternary ammonium salt of acrylamide and dimethyl diallyl ammonium chloride], pearlizing agents such as ethylene glycol distearate and ethylene glycol monostearate, etc., that are standard in shampoo formulations.
The shampoo contains acids, bases, and buffers, as needed to maintain a pH of from 4 to 10, and preferably from about 6.5 to 8, and more preferably from 6.9 to 7.4. (A neutral pH is desired in order to minimize the potential for skin sensitization.) The nature and mode of use of such materials are known in the art.
'•4 I.** .25
9 8 0 0 / 9 6 Zd/dV
The components of the shampoo are employed in conventional amounts, for example:
(a) 36% to 45% surfactants, (b) 2% to 6% foaming agent, (c) 0.3% to 3% ketoconazole or elubiol, (d) 0.2% to 1.3% thickener, (e) 0.01% to 1% BHT or BHA;
(f) preservatives sufficient to retard degradation of the final composition in order to give adequate shelf life, (g) acid, base or buffer to yield a pH in the desired range, and (h) water QS ad 100% (that is, sufficient water to make 100%) .
-7AP 00641
Standard Preparation of Shampoo
A vessel was charged with a 1.64% stock solution of Carbopol 1342 (prepared using a Quadro disperser which functions by keeping the powdered polymer evenly divided and pulling the powder by a vacuum into a stream of water) and deionized water, and heated to about 70’C. Both surfactants, i.e. sodium laureth sulfate and sodium cocoyl sarcosinate, were added, followed by the foaming agent, cocamide MEA, and a pearlizing agent (ethylene glycol distearate) and mixed until complete dissolution. Then the BHT was added and the mixture was stirred until complete ’ dissolution thereof. The solution was allowed to cool slightly, whereupon the antifungal ingredient ketoconazole was added while stirring well. (The ketoconazole is added while the pH is slightly acidic, to facilitate dissolution.) The mixture was allowed to cool to about 4O’C, at which temperature there were added the conditioner (polyquaternium-7), the preservatives quaternium-15 and tetrasodium EDTA, the colorants and fragrances, and the NaCl for thickening the solution. The pH of the solution was adjusted to 6.9-7.4 with a 25% aq. solution of NaOH and deionized water was added to the final volume.
» Using the general procedure described above, the following shampoo formulations were made:
Example l: Shampoo formulations for normal hair
AP/P/ 9 6 / 0 0 8 6 5
Ingredients | (a) | (b) | |
30 | sodium laureth sulfate | 30 | 30 |
sodium cocoyl sarcosinate | 10 | 10 | |
cocamide MEA | 4 | 4 | |
ketoconazole USP | 1 | 2 | |
glycol distearate | 1.25 | 1.25 | |
35 | polyquaternium-7 | 1 | 1 |
Carbopol 1342 | 0.6 | 0.6 |
-8AP 00641
tetrasodium EDTA | 0.5 | 0.5 | ||
perfume oil | 0.5 | 0.5 | ||
sodium chloride | 0.3 | 0.3 | ||
sodium hydroxide 25% | 0.92 | 0.9 | ||
5 | butylated hydroxytoluene | 0.1 | 0.1 | |
quaternium-15 | 0.05 | 0.05 | ||
colorants | 0.001 | 0.001 | ||
deionized water QS ad | 100 | 100 | ||
10 | Example 2: Shampoo formulations | for oily hair | ||
Parts. | bv weioht | |||
Ingredients | (a) | (b) | (c) | |
sodium laureth sulfate | 33.33 | 33.33 | 33.33 | |
15 | sodium cocoyl sarcosinate | 11 | 11 | 11 |
cocamide MEA | 4 | 4 | 4 | |
ketoconazole USP | 1 | 1 | 2 | |
glycol distearate | 1.25 | 1.25 | 1.25 | |
polyquaternium-7 | 0.6 | 0.6 | 0.6 | |
20 | Carbopol 1342 | 0.75 | 0.75 | 0.75 |
tetrasodium EDTA | 0.5 | 0.5 | 0.5 | |
perfume oil | 0.5 | 0.5 | 0.5 | |
sodium chloride | 0.3 | 0.3 | 0.3 | |
sodium hydroxide 25% | 1.18 | 1.243 | 1.18 | |
.? 5 | butylated hydroxytoluene | 0.1 | 0.1 | 0.1 |
quaternium-15 | 0.05 | 0.05 | 0.05 | |
colorants | 0.0053 | 0.0053 | 0.0053 | |
deionized water QS ad | 100 | 100 | 100 | |
30 | Example 3: Shampoo formulations | for dry or | damaged | |
Parts. | bv weioht | |||
Ingredients | (a) | (b) | (c) | |
sodium laureth sulfate | 30 | 30 | 30 | |
35 | sodium cocoyl sarcosinate | 10 | 10 | 10 |
cocamide MEA | 4 | 4 | 4 | |
ketoconazole USP | 1 | 1 | 2 |
AP/P/ 9 6 / 00 8 6 5
-9AP 00641
glycol distearate | 1.25 | 1.25 | 1.25 |
polyguaternium-7 | 5 | 5 | 5 |
Carbopol 1342 | 0.5 | 0.5 | 0.5 |
tetrasodium EDTA | 0.5 | 0.5 | 0.5 |
perfume oil | 0.5 | 0.5 | 0.5 |
sodium chloride | 0.4 | 0.4 | 0.3 |
sodium hydroxide 25% | 0.7333 | 0.733 | 1.19 |
butylated hydroxytoluene | 0.1 | 0.1 | 0.1 |
quaternium-15 | 0.05 | 0.05 | 0.05 |
colorants | 0.0018 | 0.0018 | 0.0018 |
deionized water QS ad | 100 | 100 | 100 |
In all the formulations given above in Examples 1-3, the proportion of sodium hydroxide may vary slightly, to arrive at the more preferred pH level of 6.9 to 7.4, and the proportion of salt (NaCl) may vary, to arrive at the desired viscosity.
Example 4: Stability Studies
The formulation described above as Example 1 (a) [Shampoo formulation for normal hair containing 1% ketoconazole] was subjected to stability studies, as follows:
f »
-, Shampoo formulations containing 0, 0.01, 0.1, 0.4, 0.7 and
1.0 weight % BHT were stored at 50°C for 24 weeks. At 0, 4, 8,
12, 16, 20 and 24 weeks, samples were taken from each formulation and analyzed for ketoconazole content. The table below reports the percentage of ketoconazole remaining for each sample after the indicated number of weeks:
ΔΡ/Ρ/ 9 6 / 0 0 8 6 5
-10AP 00641
ΙΑΕ1Ε_1
Percent of original proportion of ketoconazole remaining
Stability analyses at 50eC for the 24 weeks is indicated as 5 follows:
Week | 0.0%1 | 0.01% | 0.1% | 0.4% | 0.7% | 1.0% |
0 | 100 | 100 | 100 | 100 | 100 | 100 |
4 | 97.98 | 99.01 | 101.12 | 102.00 | 101.23 | 101.89 |
8 | 97.18 | 97.75 | 98.84 | 101.07 | 100.78 | 102.77 |
12 | 85.61 | 92.30 | 99.48 | 96.35 | 94.49 | 95.91 |
16 | 88.49 | 88.80 | 95.93 | 93.01 | 93.24 | 93.27 |
20 | 82.22 | 84.75 | 87.17 | 90.29 | 89.91 | 93.27 |
24 | 82.12 | 84.13 | 86.44 | 89.46 | 92.82 | 90.68 |
Note - the relative standard deviation for all but two samples was less than 2%.
The samples were also analyzed for BHT content after storage for 24 weeks at 4°C and at 5O°C. The results are displayed in the following table:
TABLE. 2
BHT analysis
FORMULATED % BHT | 4“C 24 wks. % BHT | 50’C 24 wks. % BHT |
1.0% | 0.940% | 0.277% |
0.7% | 0.583% | 0.218% |
0.4% | 0.352% | 0.107% |
0.1% | 0.084% | 0.023% |
0.01% | 0.009% | 0.005 |
0.0% | 0 | 0 |
PLACEBO2 | 0.0968% | 0.0631% |
AP/P/ 9 6 / 0 0 8 6 5 1 Percent BHT in original sample.
2 Contained 0.1% BHT and no ketoconazole.
SUBSTITUTE SHEET (RULE 26)
-11AP 00641
Example 5 - Elubiol-Containing Shampoo Stability Study
Shampoos were made from the formulations shown below in the Table: Table: Shampoo Formulations with 0.1% and 0.5% BHT
Ingredients/Parts, by weight | A (Normal Hair) | B (Dry Hair) |
sodium laureth sulfate | 30.00 | 30.00 |
sodium cocoyl sarcosinate | 10.00 | 10.00 |
Cocamide MEA | 4.00 | 4.00 |
eiubiol | 0.75 | 0.25 |
glycol distearate | 1.25 | 1.25 |
polyquaternium-7 | 1.00 | 5.00 |
Carbopol 1342 NF (1.64%) | 36.58 | 48.54 |
tetrasodium EDTA | 0.50 | 0.50 |
octopirox | 0.75 | 0.75 |
sodium hydroxide 25% | 0.50 | 1.07 |
butylated hydroxytoluene | 0.10 | 0.50 |
quaternium-15 | 0.05 | 0.05 |
colorants | 1.00 | |
kathon | 0.05 | |
perfume oil | 0.5 | |
sodium chloride | 0-0.6 | 0-0.6 |
deionized water gs ad | 100.00 | 100.00 |
AP/P/ 96/00865 * Formula A: more than 98% eiubiol remained after 10 weeks at
50’C at 0.1% BHT.
* Formula B: more than 95% eiubiol remained after 5 months at
40°C at 0.5% BHT.
Both Formula A&B can be extrapolated to 2 years shelf-life at 30 room temperature. Although 0.5% BHT was added for Formula B, it is believed, based on the results from Formula A, that 0.1% BHT will be sufficient to stabilize the formulation to yield acceptable shelf life.
-12SUBSTITUTE SHEET (RULE 26)
AP 00641
1-0
Example 6 - 0.5% Ketoconazole formulation
The following table presents a formulation for a shampoo containing 0.5% ketoconazole:
Table: 0.5% Ketoconazole Shampoo with 0.1% BHT
Ingredients | Parts, by wt. |
sodium laureth sulfate | 30.00 |
sodium cocoyl sarcosinate | 10.00 |
Cocamide MEA | 4.00 |
ketoconazole | 0.50 |
glycol distearate | 0.60 |
polyguaternium-7 | 1.00 |
Carbopol 1342 NF | 0.50 |
tetrasodium EDTA | 0.50 |
sodium hydroxide 25% | 0.50 |
butylated hydroxytoluene | 0.10 |
guaternium-15 | 0.05 |
colorants | 1.00 |
perfume oil | 0.30 |
deionized water gs ad | 100.00 |
Stability: >92% after 2 months @ 49eC (@ pH 7) >95% after 2 months 0 49°C (@ pH 8)
SUBSTITUTE SHEET (RULE 26)
99800/96 Zd/'dV
Claims (16)
- WHAT IS CLAIMED IS:1. An aqueous shampoo that contains an active agent selected from the group consisting of ketoconazole and elubiol
- 5 in an amount effective to combat scaling due to dandruff, a surfactant, a foaming agent, thickener sufficient to give the final formulation a viscosity in the range of about 4,000 to about 9,000 cps (mPa.s) at room temperature, preservative, an antioxidant selected from the group consisting of butylated10 hydroxytoluene and butylated hydroxyanisole in an amount sufficient to retard degradation of the active agent, and acid,
..7 base or buffer sufficient to give of from about 4 to about 10. i the shampoo a pH in the range 15 2. The shampoo of Claim 1 wherein the pH is in the range of from about 6.5 to about 8. 3 . The shampoo of Claim 2 wherein the pH is in the range of from about 6.9 to 7.4. 20 4. The shampoo of Claim 1 wherein the antioxidant is AP/P/ 96/00865 butylated hydroxytoluene employed in an amount of 0.1 ± 0.025 weight percent, based on weight of the shampoo.5. The shampoo of Claim 2 wherein the antioxidant is butylated hydroxytoluene employed in an amount of 0.1 ± 0.025 weight percent, based on weight of the shampoo. - 6. The shampoo of Claim 3 wherein the antioxidant is 30 butylated hydroxytoluene employed in an amount of 0.1 ± 0.025 weight percent, based on weight of the shampoo.
- 7. The shampoo of Claim 4 wherein the active agent is employed in an amount within the range of from about 0.3 weight-14AP 00641 percent to about 3 weight percent, based on weight of the shampoo.
- 8. The shampoo of Claim 7 wherein the active agent is 5 employed in an amount within the range of from about 0.4 weight percent to about 2.0 weight percent, based on weight of the shampoo.
- 9. The shampoo of Claim 8 wherein the active agent is 10 employed in an amount within the range of from about 0.5 weight percent to about 1.1 weight percent, based on weight of the shampoo.
- 10. A shampoo according to Claim 1 comprising one or more 15 surfactants selected from the group consisting of sodium c14.16 olefin sulfonates, sodium lauryl sulfate, sodium laureth sulfate, cocamidopropylamine oxide, lauramido DEA, cocamidopropyl betaine, sodium cocoyl sarcosinate, disodium oleamido MIPA sulfosuccinate, disodium cocamido MIPA sulfosuccinate, disodium laureth sulfosuc20 cinate, cocoamphocarboxy-glycinate, disodium oleamido MEA sulfosuccinate.
- 11. A shampoo according to Claim 1 wherein the foaming agent is selected from the group of fatty acid mono- and25 di-alkanolamides consisting of cocamide MEA, cocamide DEA, oleamide MEA and oleamide DEA.
- 12. A shampoo according to Claim 1 that additionally contains polyquaternium-7 as a conditioner.
- 13. A shampoo according to Claim 1 further comprising one or more pearlizing agents selected from the group consisting of ethylene glycol distearate and ethylene glycol monostearate.AP/P/ 96/00865-15AP 00641 ·».
- 14. A shampoo according to Claim 1 further comprising one or more fragrances and one or more colorants.
- 15. A shampoo according to Claim 1 comprising by weight based on the total weight of the formulation approximately:(a) 36% to 45% surfactants, (b) 2% to 6% foaming agent, (c) 0.3% to 3% active agent, (d) 0.2% to 1.3% thickener, (e) 0.01% to 1% BHT antioxidant;(f) preservatives sufficient to retard degradation of the final composition, (g) acid, base or buffer to yield a pH in the range of from 6.9 to 7.4, and (h) water QS ad 100%.
- 16. A shampoo according to Claim 13 comprising by weight based on the total weight of the formulation approximately:(a) 36% to 45% surfactants, (b) 2% to 6% foaming agent, (c) 0.3% to 3% active agent, (d) 0.4% to 8% conditioner, (e) 0.2% to 1.3% thickener, (f) 1% to 1.5% pearlizing agent, (g) 0.5% to 1% preservative(s), (h) 0.1 ± 0.025% BHT antioxidant, (i) acid, base or buffer to yield a pH in the range of 6.9 to 7.4, (j) fragrance(s) and colorant(s), and (k) water QS ad 100%.ΔΡ/Ρ/ 9 6 / 0 0 8 6 5
- 17. A process of preparing a shampoo formulation as defined in Claim 1 comprising the steps of:(a) heating a solution of thickener and deionized water,-16AP 00641 (b) mixing the surfactants, the foaming agent and optionally the pearlizing agent with the solution of (a), (c) mixing the BHT or BHA with the solution of (b), (d) mixing the active agent with the solution of (c),5 (e) allowing the solution of (d) to cool somewhat and mixing therewith the preservative(s) and the sodium chloride for thickening, and optionally the conditioner, the fragrance(s) and colorant(s), (f) adding acid, base or buffer to the solution of (e) to yield 10 a pH in the range of 4 to 10, and (g) adding deionized water to the solution of (f) to 100%.
- 18. The shampoo of any of Claims 1 to 16 wherein the active agent is ketoconazole.
- 19. The shampoo of any of Claims 1 to 16 wherein the active agent is elubiol.
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US08/224,382 US5456851A (en) | 1994-04-07 | 1994-04-07 | Ketoconazole shampoo containing butylated hydroxytoluene or butylated hydroxyanisole |
Publications (2)
Publication Number | Publication Date |
---|---|
AP9600865A0 AP9600865A0 (en) | 1996-10-31 |
AP641A true AP641A (en) | 1998-04-14 |
Family
ID=22840433
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
APAP/P/1996/000865A AP641A (en) | 1994-04-07 | 1995-03-22 | Improved ketoconazole shampoo. |
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US (1) | US5456851A (en) |
EP (1) | EP0758879B1 (en) |
JP (1) | JPH09511740A (en) |
KR (1) | KR100333424B1 (en) |
CN (1) | CN1102376C (en) |
AP (1) | AP641A (en) |
AT (1) | ATE187325T1 (en) |
AU (1) | AU685620B2 (en) |
BR (1) | BR9507293A (en) |
CZ (1) | CZ291996A3 (en) |
DE (1) | DE69513817T2 (en) |
DK (1) | DK0758879T3 (en) |
ES (1) | ES2140674T3 (en) |
GE (1) | GEP19991855B (en) |
GR (1) | GR3032815T3 (en) |
HU (1) | HUT76031A (en) |
IL (1) | IL113271A (en) |
NO (1) | NO964213L (en) |
NZ (1) | NZ283529A (en) |
PL (1) | PL316689A1 (en) |
RO (1) | RO113608B1 (en) |
RU (1) | RU2154464C2 (en) |
SK (1) | SK128096A3 (en) |
TW (1) | TW364853B (en) |
WO (1) | WO1995027471A1 (en) |
ZA (1) | ZA952856B (en) |
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KR20010020598A (en) * | 1997-07-02 | 2001-03-15 | 콜비 안드레아 엘 | Methods for using compositions containing dichlorophenyl imidazoldioxolan to treat seborrheic dermatitis, dandruff, psoriasis, and acne, and compositions thereof |
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US6635702B1 (en) * | 2000-04-11 | 2003-10-21 | Noveon Ip Holdings Corp. | Stable aqueous surfactant compositions |
US6939873B2 (en) * | 2000-07-26 | 2005-09-06 | Taro Pharmaceuticals Industries Limited | Non-sedating barbituric acid derivatives |
US7683071B2 (en) * | 2000-07-26 | 2010-03-23 | Taro Pharmaceuticals Industries Ltd. | Composition and method for improved bioavailability and enhanced brain delivery of 5,5-diphenyl barbituric acid |
US6756379B2 (en) | 2001-07-26 | 2004-06-29 | Taro Pharmaceutical Industries Ltd. | Non-sedating barbiturate compounds as neuroprotective agents |
US20030099699A1 (en) | 2001-11-13 | 2003-05-29 | Hanshew Dwight D. | Storage stable thyroxine active drug formulations and methods for their production |
US6645526B2 (en) * | 2001-11-13 | 2003-11-11 | Mylan Pharmaceuticals, Inc. | Storage stable thyroxine active drug formulations and methods for their production |
US20040052748A1 (en) * | 2002-09-06 | 2004-03-18 | Vondruska Brian Jay | Compositions of anionic polymeric rheology modifiers and cationic materials |
US7524807B2 (en) * | 2002-11-01 | 2009-04-28 | The Procter & Gamble Company | Rinse-off personal care compositions comprising anionic and/or nonionic perfume polymeric particles |
KR20040049445A (en) * | 2002-12-06 | 2004-06-12 | 주식회사 엘지생활건강 | Pearl Composition For Cleanser |
DE60324703D1 (en) * | 2002-12-11 | 2008-12-24 | Taro Pharma Ind | BARBITIC ACID DERIVATIVES. |
CN100404016C (en) * | 2003-03-11 | 2008-07-23 | 章华东 | Hair dyeing agent and processing method thereof |
EP1781624A4 (en) * | 2004-07-02 | 2010-06-23 | Taro Pharma Ind | A process for preparing 1-methoxymethyl-5,5-diphenylbarbituric acid |
FR2902326B1 (en) * | 2006-06-20 | 2008-12-05 | Oreal | USE OF COUMARIN, BUTYLATED HYDROXYANISOLE AND ETHOXYQUINE FOR THE TREATMENT OF CANITIA |
WO2008066704A2 (en) * | 2006-11-14 | 2008-06-05 | Taro Pharmaceuticals North America, Inc. | Method of improving bioavailability for non-sedating barbiturates |
FR2902320B1 (en) * | 2007-01-22 | 2008-12-05 | Oreal | USE OF BUTYLATED HYDROXYANISOLE FOR THE TREATMENT OF CANITIA |
US8470753B2 (en) * | 2011-01-28 | 2013-06-25 | Rhodia Operations | Personal cleansing systems exhibiting low eye irritation potential |
KR20140057414A (en) | 2011-06-22 | 2014-05-12 | 바이옴 바이오사이언스 피브이티. 엘티디. | Conjugate-based antifungal and antibacterial prodrugs |
MX2015016675A (en) | 2013-06-04 | 2016-07-15 | Vyome Biosciences Pvt Ltd | Coated particles and compositions comprising same. |
CN104721065A (en) * | 2013-12-18 | 2015-06-24 | 武汉海鹏医药科技有限公司 | Neticonazole shampoo and formula and production method thereof |
KR102623439B1 (en) | 2016-01-29 | 2024-01-11 | (주)아모레퍼시픽 | Anti-fungal composition comprising lactobacillus plantarum |
CN110536720A (en) | 2017-04-26 | 2019-12-03 | 宝洁公司 | Composition with thickening polymer |
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1994
- 1994-04-07 US US08/224,382 patent/US5456851A/en not_active Expired - Lifetime
-
1995
- 1995-03-22 CN CN95193302A patent/CN1102376C/en not_active Expired - Lifetime
- 1995-03-22 RO RO96-01933A patent/RO113608B1/en unknown
- 1995-03-22 HU HU9602720A patent/HUT76031A/en unknown
- 1995-03-22 WO PCT/US1995/003197 patent/WO1995027471A1/en not_active Application Discontinuation
- 1995-03-22 JP JP7526338A patent/JPH09511740A/en not_active Ceased
- 1995-03-22 PL PL95316689A patent/PL316689A1/en unknown
- 1995-03-22 GE GEAP19953444A patent/GEP19991855B/en unknown
- 1995-03-22 DE DE69513817T patent/DE69513817T2/en not_active Expired - Lifetime
- 1995-03-22 AU AU21597/95A patent/AU685620B2/en not_active Ceased
- 1995-03-22 CZ CZ962919A patent/CZ291996A3/en unknown
- 1995-03-22 ES ES95914720T patent/ES2140674T3/en not_active Expired - Lifetime
- 1995-03-22 AT AT95914720T patent/ATE187325T1/en not_active IP Right Cessation
- 1995-03-22 DK DK95914720T patent/DK0758879T3/en active
- 1995-03-22 KR KR1019960705574A patent/KR100333424B1/en not_active IP Right Cessation
- 1995-03-22 RU RU96121915/14A patent/RU2154464C2/en active
- 1995-03-22 SK SK1280-96A patent/SK128096A3/en unknown
- 1995-03-22 EP EP95914720A patent/EP0758879B1/en not_active Expired - Lifetime
- 1995-03-22 BR BR9507293A patent/BR9507293A/en not_active IP Right Cessation
- 1995-03-22 AP APAP/P/1996/000865A patent/AP641A/en active
- 1995-04-06 ZA ZA952856A patent/ZA952856B/en unknown
- 1995-04-06 IL IL11327195A patent/IL113271A/en not_active IP Right Cessation
- 1995-06-08 TW TW084105788A patent/TW364853B/en not_active IP Right Cessation
-
1996
- 1996-10-04 NO NO964213A patent/NO964213L/en not_active Application Discontinuation
- 1996-11-27 NZ NZ283529A patent/NZ283529A/en not_active IP Right Cessation
-
2000
- 2000-02-29 GR GR20000400522T patent/GR3032815T3/en not_active IP Right Cessation
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EP0586106A1 (en) * | 1992-08-06 | 1994-03-09 | JOHNSON & JOHNSON CONSUMER PRODUCTS, INC. | Skin care compositions containing imidazoles and retinoids |
Also Published As
Publication number | Publication date |
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AU2159795A (en) | 1995-10-30 |
NO964213L (en) | 1996-11-14 |
AP9600865A0 (en) | 1996-10-31 |
DK0758879T3 (en) | 2000-04-10 |
ZA952856B (en) | 1996-10-07 |
ATE187325T1 (en) | 1999-12-15 |
GEP19991855B (en) | 1999-12-06 |
BR9507293A (en) | 1997-10-07 |
TW364853B (en) | 1999-07-21 |
AU685620B2 (en) | 1998-01-22 |
HU9602720D0 (en) | 1996-11-28 |
DE69513817D1 (en) | 2000-01-13 |
EP0758879B1 (en) | 1999-12-08 |
PL316689A1 (en) | 1997-02-03 |
NZ283529A (en) | 1998-06-26 |
RO113608B1 (en) | 1998-09-30 |
CN1149250A (en) | 1997-05-07 |
KR100333424B1 (en) | 2002-10-25 |
RU2154464C2 (en) | 2000-08-20 |
HUT76031A (en) | 1997-06-30 |
DE69513817T2 (en) | 2000-05-31 |
WO1995027471A1 (en) | 1995-10-19 |
SK128096A3 (en) | 1997-08-06 |
GR3032815T3 (en) | 2000-06-30 |
MX9604644A (en) | 1997-11-29 |
CZ291996A3 (en) | 1997-03-12 |
US5456851A (en) | 1995-10-10 |
JPH09511740A (en) | 1997-11-25 |
EP0758879A1 (en) | 1997-02-26 |
IL113271A0 (en) | 1995-12-08 |
CN1102376C (en) | 2003-03-05 |
IL113271A (en) | 1999-11-30 |
ES2140674T3 (en) | 2000-03-01 |
NO964213D0 (en) | 1996-10-04 |
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