GB2164254A - Stable topical compositions of anthralin - Google Patents
Stable topical compositions of anthralin Download PDFInfo
- Publication number
- GB2164254A GB2164254A GB08521455A GB8521455A GB2164254A GB 2164254 A GB2164254 A GB 2164254A GB 08521455 A GB08521455 A GB 08521455A GB 8521455 A GB8521455 A GB 8521455A GB 2164254 A GB2164254 A GB 2164254A
- Authority
- GB
- United Kingdom
- Prior art keywords
- anthralin
- composition according
- acid
- composition
- concentration
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
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- 239000000203 mixture Substances 0.000 title claims abstract description 41
- 229960002311 dithranol Drugs 0.000 title claims abstract description 37
- NUZWLKWWNNJHPT-UHFFFAOYSA-N anthralin Chemical group C1C2=CC=CC(O)=C2C(=O)C2=C1C=CC=C2O NUZWLKWWNNJHPT-UHFFFAOYSA-N 0.000 title claims abstract description 8
- 230000000699 topical effect Effects 0.000 title description 3
- 150000004671 saturated fatty acids Chemical class 0.000 claims abstract description 8
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 7
- UFTFJSFQGQCHQW-UHFFFAOYSA-N triformin Chemical compound O=COCC(OC=O)COC=O UFTFJSFQGQCHQW-UHFFFAOYSA-N 0.000 claims abstract description 6
- 208000017520 skin disease Diseases 0.000 claims abstract description 5
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 9
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 claims description 9
- 235000014113 dietary fatty acids Nutrition 0.000 claims description 7
- 239000000194 fatty acid Substances 0.000 claims description 7
- 229930195729 fatty acid Natural products 0.000 claims description 7
- 150000004665 fatty acids Chemical class 0.000 claims description 7
- YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical compound OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 claims description 7
- 239000002562 thickening agent Substances 0.000 claims description 7
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical group O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 6
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 claims description 6
- FJKROLUGYXJWQN-UHFFFAOYSA-N papa-hydroxy-benzoic acid Natural products OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 claims description 5
- 229960004889 salicylic acid Drugs 0.000 claims description 5
- 239000007864 aqueous solution Substances 0.000 claims description 4
- 125000000129 anionic group Chemical group 0.000 claims description 3
- 239000003945 anionic surfactant Substances 0.000 claims description 3
- 239000004310 lactic acid Substances 0.000 claims description 3
- 235000014655 lactic acid Nutrition 0.000 claims description 3
- 239000002736 nonionic surfactant Substances 0.000 claims description 3
- 239000002245 particle Substances 0.000 claims description 2
- 239000000377 silicon dioxide Substances 0.000 claims description 2
- 201000004681 Psoriasis Diseases 0.000 abstract description 10
- 230000003647 oxidation Effects 0.000 abstract description 4
- 238000007254 oxidation reaction Methods 0.000 abstract description 4
- 208000002874 Acne Vulgaris Diseases 0.000 abstract description 2
- 201000004624 Dermatitis Diseases 0.000 abstract description 2
- 206010000496 acne Diseases 0.000 abstract description 2
- 208000010668 atopic eczema Diseases 0.000 abstract description 2
- YUTJCNNFTOIOGT-UHFFFAOYSA-N anthracene-1,8,9-triol Chemical group C1=CC(O)=C2C(O)=C3C(O)=CC=CC3=CC2=C1 YUTJCNNFTOIOGT-UHFFFAOYSA-N 0.000 description 25
- 230000015556 catabolic process Effects 0.000 description 11
- 238000006731 degradation reaction Methods 0.000 description 11
- 239000003981 vehicle Substances 0.000 description 10
- 241000196324 Embryophyta Species 0.000 description 6
- 150000003626 triacylglycerols Chemical class 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- ZCTQGTTXIYCGGC-UHFFFAOYSA-N Benzyl salicylate Chemical compound OC1=CC=CC=C1C(=O)OCC1=CC=CC=C1 ZCTQGTTXIYCGGC-UHFFFAOYSA-N 0.000 description 4
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- 239000002253 acid Substances 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- HIQIXEFWDLTDED-UHFFFAOYSA-N 4-hydroxy-1-piperidin-4-ylpyrrolidin-2-one Chemical compound O=C1CC(O)CN1C1CCNCC1 HIQIXEFWDLTDED-UHFFFAOYSA-N 0.000 description 3
- 239000005632 Capric acid (CAS 334-48-5) Substances 0.000 description 3
- 239000005635 Caprylic acid (CAS 124-07-2) Substances 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
- 239000006210 lotion Substances 0.000 description 3
- FUZZWVXGSFPDMH-UHFFFAOYSA-N n-hexanoic acid Natural products CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 3
- 229960002446 octanoic acid Drugs 0.000 description 3
- 239000002674 ointment Substances 0.000 description 3
- 235000003441 saturated fatty acids Nutrition 0.000 description 3
- 239000003381 stabilizer Substances 0.000 description 3
- VBICKXHEKHSIBG-UHFFFAOYSA-N 1-monostearoylglycerol Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCC(O)CO VBICKXHEKHSIBG-UHFFFAOYSA-N 0.000 description 2
- 229910002016 Aerosil® 200 Inorganic materials 0.000 description 2
- WWZKQHOCKIZLMA-UHFFFAOYSA-N Caprylic acid Natural products CCCCCCCC(O)=O WWZKQHOCKIZLMA-UHFFFAOYSA-N 0.000 description 2
- RGHNJXZEOKUKBD-SQOUGZDYSA-N D-gluconic acid Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C(O)=O RGHNJXZEOKUKBD-SQOUGZDYSA-N 0.000 description 2
- 239000005639 Lauric acid Substances 0.000 description 2
- 238000003556 assay Methods 0.000 description 2
- 235000015165 citric acid Nutrition 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- MMKRHZKQPFCLLS-UHFFFAOYSA-N ethyl myristate Chemical compound CCCCCCCCCCCCCC(=O)OCC MMKRHZKQPFCLLS-UHFFFAOYSA-N 0.000 description 2
- 239000000499 gel Substances 0.000 description 2
- ROBFUDYVXSDBQM-UHFFFAOYSA-N hydroxymalonic acid Chemical compound OC(=O)C(O)C(O)=O ROBFUDYVXSDBQM-UHFFFAOYSA-N 0.000 description 2
- 239000004615 ingredient Substances 0.000 description 2
- POULHZVOKOAJMA-UHFFFAOYSA-N methyl undecanoic acid Natural products CCCCCCCCCCCC(O)=O POULHZVOKOAJMA-UHFFFAOYSA-N 0.000 description 2
- 239000012071 phase Substances 0.000 description 2
- 238000004321 preservation Methods 0.000 description 2
- 238000007127 saponification reaction Methods 0.000 description 2
- 210000004761 scalp Anatomy 0.000 description 2
- 239000002453 shampoo Substances 0.000 description 2
- PRAKJMSDJKAYCZ-UHFFFAOYSA-N squalane Chemical compound CC(C)CCCC(C)CCCC(C)CCCCC(C)CCCC(C)CCCC(C)C PRAKJMSDJKAYCZ-UHFFFAOYSA-N 0.000 description 2
- 229940099259 vaseline Drugs 0.000 description 2
- BJEPYKJPYRNKOW-REOHCLBHSA-N (S)-malic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O BJEPYKJPYRNKOW-REOHCLBHSA-N 0.000 description 1
- RBNPOMFGQQGHHO-UHFFFAOYSA-N -2,3-Dihydroxypropanoic acid Natural products OCC(O)C(O)=O RBNPOMFGQQGHHO-UHFFFAOYSA-N 0.000 description 1
- QMMJWQMCMRUYTG-UHFFFAOYSA-N 1,2,4,5-tetrachloro-3-(trifluoromethyl)benzene Chemical compound FC(F)(F)C1=C(Cl)C(Cl)=CC(Cl)=C1Cl QMMJWQMCMRUYTG-UHFFFAOYSA-N 0.000 description 1
- LGEZTMRIZWCDLW-UHFFFAOYSA-N 14-methylpentadecyl octadecanoate Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCCCCCCCCCCCCCC(C)C LGEZTMRIZWCDLW-UHFFFAOYSA-N 0.000 description 1
- QTDIEDOANJISNP-UHFFFAOYSA-N 2-dodecoxyethyl hydrogen sulfate Chemical compound CCCCCCCCCCCCOCCOS(O)(=O)=O QTDIEDOANJISNP-UHFFFAOYSA-N 0.000 description 1
- KGKQNDQDVZQTAG-UHFFFAOYSA-N 8-methylnonyl 2,2-dimethylpropanoate Chemical compound CC(C)CCCCCCCOC(=O)C(C)(C)C KGKQNDQDVZQTAG-UHFFFAOYSA-N 0.000 description 1
- 229910002012 Aerosil® Inorganic materials 0.000 description 1
- 201000004384 Alopecia Diseases 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- RGHNJXZEOKUKBD-UHFFFAOYSA-N D-gluconic acid Natural products OCC(O)C(O)C(O)C(O)C(O)=O RGHNJXZEOKUKBD-UHFFFAOYSA-N 0.000 description 1
- RBNPOMFGQQGHHO-UWTATZPHSA-N D-glyceric acid Chemical compound OC[C@@H](O)C(O)=O RBNPOMFGQQGHHO-UWTATZPHSA-N 0.000 description 1
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 1
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 1
- IAJILQKETJEXLJ-UHFFFAOYSA-N Galacturonsaeure Natural products O=CC(O)C(O)C(O)C(O)C(O)=O IAJILQKETJEXLJ-UHFFFAOYSA-N 0.000 description 1
- 238000010268 HPLC based assay Methods 0.000 description 1
- 235000019483 Peanut oil Nutrition 0.000 description 1
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 1
- 229920004482 WACKER® Polymers 0.000 description 1
- 208000000260 Warts Diseases 0.000 description 1
- IAJILQKETJEXLJ-RSJOWCBRSA-N aldehydo-D-galacturonic acid Chemical compound O=C[C@H](O)[C@@H](O)[C@@H](O)[C@H](O)C(O)=O IAJILQKETJEXLJ-RSJOWCBRSA-N 0.000 description 1
- 125000005907 alkyl ester group Chemical group 0.000 description 1
- 231100000360 alopecia Toxicity 0.000 description 1
- BJEPYKJPYRNKOW-UHFFFAOYSA-N alpha-hydroxysuccinic acid Natural products OC(=O)C(O)CC(O)=O BJEPYKJPYRNKOW-UHFFFAOYSA-N 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 238000001514 detection method Methods 0.000 description 1
- 230000003203 everyday effect Effects 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 239000000174 gluconic acid Substances 0.000 description 1
- 235000012208 gluconic acid Nutrition 0.000 description 1
- 229940075507 glyceryl monostearate Drugs 0.000 description 1
- IPCSVZSSVZVIGE-UHFFFAOYSA-M hexadecanoate Chemical compound CCCCCCCCCCCCCCCC([O-])=O IPCSVZSSVZVIGE-UHFFFAOYSA-M 0.000 description 1
- 238000004128 high performance liquid chromatography Methods 0.000 description 1
- 238000011835 investigation Methods 0.000 description 1
- 230000007794 irritation Effects 0.000 description 1
- 229940078545 isocetyl stearate Drugs 0.000 description 1
- XUGNVMKQXJXZCD-UHFFFAOYSA-N isopropyl palmitate Chemical compound CCCCCCCCCCCCCCCC(=O)OC(C)C XUGNVMKQXJXZCD-UHFFFAOYSA-N 0.000 description 1
- 229940089456 isopropyl stearate Drugs 0.000 description 1
- 229940057995 liquid paraffin Drugs 0.000 description 1
- 239000001630 malic acid Substances 0.000 description 1
- 235000011090 malic acid Nutrition 0.000 description 1
- 239000001788 mono and diglycerides of fatty acids Substances 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 235000019198 oils Nutrition 0.000 description 1
- 235000006408 oxalic acid Nutrition 0.000 description 1
- 239000012188 paraffin wax Substances 0.000 description 1
- 239000000312 peanut oil Substances 0.000 description 1
- ZPWFUIUNWDIYCJ-UHFFFAOYSA-N propan-2-yl octadecanoate Chemical compound CCCCCCCCCCCCCCCCCC(=O)OC(C)C ZPWFUIUNWDIYCJ-UHFFFAOYSA-N 0.000 description 1
- 150000004053 quinones Chemical class 0.000 description 1
- 239000010499 rapseed oil Substances 0.000 description 1
- 201000010153 skin papilloma Diseases 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000010186 staining Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 239000001993 wax Substances 0.000 description 1
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
- A61K31/12—Ketones
-
- 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
- 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
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Dermatology (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Medicinal Preparation (AREA)
- Cosmetics (AREA)
Abstract
Anthralin-containing compositions which are resistant to oxidation comprise anthralin in a vehicle comprising at least one triglyceride of a saturated fatty acid of plant origin having 6 to 12 carbon atoms. They are useful in the treatment of skin diseases, e.g. acne, eczema and psoriasis.
Description
SPECIFICATION
Stable Compositions of Anthralin in Triglycerides of a Saturated Fatty Acid of Plant Origin having from 6 to 12 Carbon Atoms
The present invention relates to an anhydrous anthralin composition which is resistant to oxidation, containing anthralin in a vehicle comprising at least one triglyceride of a saturated fatty acid of plant origin having from 6 to 12 carbon atoms.
The compositions of the invention are suitable for use in the treatment of skin diseases, and especially in the treatment of acne, warts, alopecia, eczema, and more especially psoriasis.
Anthralin or dithranol (1,8,9-trihydroxyanthracene), is one of the rare substances found to be especially active in the topical treatment of psoriasis.
Its use, however, is not without some major disadvantages. Thus, it is readily degraded by oxidation to quinones or polymeric products which are dark in colour and capable of staining not only the skin but also clothing.
Many investigations have been undertaken for the purpose of finding not only vehicles but also certain agents for preventing excessively vigorous degradation of anthralin, and in this way preserving it in its active form.
US Patent No. 4,287,214 suggests the use of a-hydroxy acids as stabilising agents for compositions based on anthralin, and among these glyceric acid, gluconic acid, galacturonic acid, malic acid, citric acid, tartaric acid or tartronic acid, at a concentration of 0.01 to 1% by weight.
US Patent No. 4,367,224 also proposes, for the purpose of obtaining stable anthralin compositions, the use of oxalic acid at a concentration of 0.01 to 2% by weight.
In US Patent No. 4,316,902, on the other hand, it is proposed, for compositions based on anthralin, to use not only the stabilising agents mentioned above but also a vehicle consisting of isopropyl myristate or palmitate and glyceryl monostearate.
More recently, in French Patents No.81/19952 and No.82/01327, the use has been proposed of alkyl esters of fatty acids as well as aromatic esters as sole vehicles for anthralin, these esters, in the abssnce of any other stabilising agent, having proved to constitute completely acceptable vehicles for the good preservation of anthralin.
Among these esters, isopropyl myristate has been shown to be the most effective for the preservation of anthralin, the degree of degradation after two months not exceeding approximately 15%.
It has been possible, however, to establish that the activity of the compositions based on anthralin was partially dependent on its degree of solubilisation in the vehicle or solvent used.
In other words, in order to obtain good activity, it is appropriate for a relatively large proportion of the anthralin to be soluble.
The majority of vehicles recognised hitherto, and mentioned above, do not dissolve anthralin well while maintaining as small a degree of degradation as possible.
As a result of new research, it has now been observed that the solubility and stability of anthralin is
much improved by using triglycerides of saturated fatty acids of plant origin.
The use of these triglycerides of fatty acids, while increasing the solubility and maintaining the degree of degradation at an acceptable percentage, has also enabled the properties of the compositions to be improved, the latter spreading more readily, being better tolerated and not leaving the skin with an unpleasant greasy feel.
The present invention provides an anhydrous composition of anthralin, resistant to oxidation which is designed for treating skin diseases, especially psoriasis, the vehicle of the said composition comprising at least one triglyceride of a saturated fatty acid of plant origin having from 6 to 12 carbon atoms.
Preferably more than one fatty acid is used and the distribution of the fatty acids in the triglyceride is preferably as follows.
- caproic acid (C6): < 3% - caprylic acid (C8): 50 to 80% -capricacid (C10): 15to45% - lauric acid (C12): < 5%
Triglycerides of saturated fatty acids of plant origin as defined above preferably have a viscosity at 20"C of from 27 to 30 cP.
Among the triglycerides of saturated fatty acids of plant origin having from 6 to 12 carbon atoms, which can be used as vehicles for anthralin, there may be mentioned those sold by DYNAMIT NOBEL under the following names: 1-"MlGLYOL 810", in which the distribution of fatty acids is as follows: - caproic acid (C6): 3% max - caprylic acid (C8): 65--80% -capricacid (C1O) 1530%
w -- lauric acid (C12): 3% max, and the physiochemical characteristics of which are as follows:
-acid value: 0.1 max
- saponification number: 340--360 - cloud point; 0 C max - refractive index (20"C): 1.4490--1.4510 - viscosity at 20 C: 27-30 (cP) and
2--"MIGLYOL 8129, in which the distribution of fatty acids is as follows: - caproic acid (C6): 3% max -caprylicacid (C8): 50--65% -capricacid (C10): 3045% - Iauric acid (C12): 5% max and the physicochemical characteristics of which are as follows:
-acid value: 0.1 max
- saponification number: 325345 - cloud point: 10 C max - refractive index (20 C): 1.44801.4500 - viscosity at 20 C: 2s32 (cP).
The concentration of anthralin in the composition is generally from 0.05 to 3% by weight, and preferably from 0.1 to 0.7%.
The compositions can take the form of lotions, gels or ointments.
These compositions can optionally be thickened with the aid of a thickening agent, and this makes it possible to avoid all flowing and thereby prevent irritation on healthy areas of the skin.
Among thickening agents, it is preferred to use silicas having an average particle diameter less than 30 sum, and in particular the silicas sold under the names "AEROSIL 200" and "AEROSIL R 972" by DEGUSSA, or under the names "HDK", especially "HDK N 20 E" silica, by WACKER. The concentration of thickening agent is generally from 2 to 10% by weight.
Other ingredients can also be introduced in the compositions, for example oils and waxes as well as any other ingredient of the compositions for topical application provided they do not influence the stability of the compositions.
When the composition contains salicylic acid, the latter is generally present in a proportion of from 0.01 to 5%, and preferably from 0.05 to 0.3%.
Table I shows the good stability and small degree of degradation of anthralin in "MIGLYOL 812", relative to other known vehicles for anthralin.
TABLE I
Solubility at 20 C % degradation
after 2 months
Products (HPLC assay) at 40 C Miglyol 812 0.68%+0.04
Isopropyl myristate 0.36%+0.03 1015% Benzyl salicylate 0.65%+0.05 > 40%
Isopropyl palmitate 0.42%+0.03 1520% Isopropyl stearate 0.51%+0.02 1520% Butyl stearate < 0.5% 1520% Ethyl myristate < 0.5% 20%
Isocetyl stearate < 0.5% 1015% Isodecyl neopentanoate < 0.5% 10--15%
Liquid paraffin 0.12%+0.03 410% Rape oil 0.42%+0.03 50-70%
Groundnut oil < 0.5% > 10%
Perhydrosqualene 0.12%+0.03 > 10%
As can be observed, "MIGLYOL 812" combines at the same time good solubility and a small degree of degradation of anthralin, which is not the case, for example, with benzyl salicylate which, although it shows comparable solubilising power, does not however prevent degradation of the anthralin since the degree observed is greater than 40%.
The analytical method for determining the degree of degradation of anthralin is based on assay of the active principle in the product after storage under defined conditions.
This assay in the final product is performed by HPLC on a LiChrosorb RP-18 10-- m column of internal diameter 4 mm, length 25 cm, in reverse phase, the mobile phase consisting of: methanol/water+2% acetic acid in proportions 85:15.
Detection is carried out at 250 nm in UV and the RT is 5.7 min.
The assaying takes place relative to a calibration scale for which anthralin is solubilised extemporaneously in chloroform.
The samples of finished products are treated by solubilisation in chloroform.
The percentage degradation is calculated relative to the content of active principle in the sample at time zero (T.0.): level at T.0--level after 2 months at 40"C
% degradation= x100
level at T.0
The present invention also provides a shampoo composition which takes the form of a two-component pack designed to be mixed at the time of use, the first component consisting of the composition according to the invention and the second component being an aqueous solution containing an anionic or nonionic surfactant and having a pH generally from 2 to 7, but preferably from 3 to 5, by the addition, if necessary, of an acid such as citric acid, lactic acid or acetic acid.
In the aqueous phase, the concentration of the anionic or nonionic surfactant is preferably from 5 to 40%, preferably from 7 to 27%, and can also contain a thickening agent.
At the time of first use, the two parts are mixed in variable proportions, depending on the efficacy sought, generally in a ratio of the anhydrous part to the aqueous part of from 10:90 to 50:50.
The mixture obtained is then applied on the scalp and hair to the extent of approximately 20 to 30 g. The mixture is then left to act for approximately 5 minutes to 1 hour, is then emulsified with water and is rinsed copiously with water. The treatment is then continued every day or every other day using the same composition after it has been stored at a temperature below approximately +4 C.
The two-part pack is produced so as to enable, after mixing, treatment to be performed for approximately one week, with one to two shampooings every other day.
Good results in the treatment of psoriasis are generally obtained after 3 to 5 weeks.
By way of illustration and without any limitative character, several examples of compositions will now be given.
EXAMPLE 1
A shampoo is packed in the form of the following two parts:
1) Anhydrous part - Anthralin 0.60 g - MlGLYOL812 q.s. 100g 2) Aqueous part - Sodium lauryl ether sulphate oxyethylenated
using 2.2 moles of ethylene oxide 12 g lactic acid q.s. pH4
--Water q.s. 100g At the time of use, 25% of the anhydrous part (1) is mixed with 75% of the aqueous part (2).
The resulting composition has a milky appearance, and approximately 30 g of it is applied on the scalp and hair.
After an exposure time of the order of 20 min, it is emulsified with water and rinsed.
After 2 weeks, a decline in the psoriasis is noted and the treatment can be continued with the shampooings spaced one or two days apart.
EXAMPLE 2
Composition in gel form for treating psoriasis: - Anthralin 0.6g - AEROSIL 200 8 9 - MIGLYOL812 q.s. 100 g
EXAMPLE 3
Ointment for treating skin diseases, in particular psoriasis: - Anthralin 0.3g - Salicylic acid 0.2g - Vaseline Codex 40g - MIGLYOL 812 q.s. 100g
EXAMPLE 4
Ointment for treating psoriasis: - Anthralin 0.3g - Salicylic acid 0.2g - Vaseline Codex 30 g -Paraffin Codex 15 g - MIGLYOL812 q.s. 1009
EXAMPLE 5
Lotion for treating psoriasis: :
This lotion has the following composition: -Anthralin 0.60 g - Salicylic acid 1g - MlGLYOL812 q.s. 1009
Claims (15)
1. An an hydrous anthralin composition which is suitable for treating skin diseases which comprises anthralin in a vehicle comprising at least one triglyeride of a saturated fatty acid of plant origin having from 6to 12 carbon atoms.
2. A composition according to claim 1 in which the vehicle comprises at least one triglyceride of a plurality of fatty acids of plant origin having from 6 to 12 carbon atoms.
3. A composition according to claim 1 or 2, in which the triglyceride has a viscosity at 20"C of from 27 to 30 cP.
4. A composition according to claim 1,2 or 3 in which the anthralin is present at a concentration of from 0.05 to 3% by weight.
5. A composition according to claim 4 in which the concentration of anthralin is from 0.1 to 0.7%.
6. A composition according to any one of the preceding claims which contains a thickening agent.
7. A composition according to claim 7, in which the thickening agent is silica having an average particle diameter of less than 30 pom.
8. A composition according to claim 6 or 7, in which the thickening agent is present at a concentration of from 2 to 10% by weight relative to the total weight of the composition.
9. A composition according to any one of the preceding claims which contains salicylic acid at a concentration of from 0.01 to 5% by weight.
10. A composition according to claim 9 in which the concentration is from 0.05 to 3%.
11. A composition according to claim 1 substantially as described in any one of Examples 2 to 5.
12. A two-component pack comprising as a first component a composition as claimed in any one of claims 1 to 11 and as a second component an aqueous solution comprising an anionic or nonionic surfactant and having a pH of from 2 to 7.
13. A pack according to claim 12 in which the aqueous solution has a pH of from 3 to 5.
14. A pack according to claim 12 or 13, characterised in that the aqueous solution contains citric acid, lactic acid or acetic acid to maintain the pH within the desired limits.
15. A pack according to claim 12 substantially as described in Example 1.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR8413431A FR2569561B1 (en) | 1984-08-30 | 1984-08-30 | STABLE ANTHRALIN COMPOSITION IN SATURATED FATTY ACID TRIGLYCERIDES OF PLANT ORIGIN WITH 6 TO 12 CARBON ATOMS |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| GB8521455D0 GB8521455D0 (en) | 1985-10-02 |
| GB2164254A true GB2164254A (en) | 1986-03-19 |
| GB2164254B GB2164254B (en) | 1987-12-31 |
Family
ID=9307318
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB08521455A Expired GB2164254B (en) | 1984-08-30 | 1985-08-29 | Stable topical compositions of anthralin |
Country Status (9)
| Country | Link |
|---|---|
| JP (1) | JPS6165825A (en) |
| BE (1) | BE903150A (en) |
| CA (1) | CA1272449A (en) |
| CH (1) | CH664895A5 (en) |
| DE (1) | DE3530914A1 (en) |
| FR (1) | FR2569561B1 (en) |
| GB (1) | GB2164254B (en) |
| IT (1) | IT1201458B (en) |
| NL (1) | NL8502373A (en) |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0337289A1 (en) * | 1988-04-10 | 1989-10-18 | Konrad Minninger | Pharmaceutical composition containing dithranol for the treatment of the skin exfoliative diseases |
| US4961922A (en) * | 1988-04-14 | 1990-10-09 | Centre International De Recherches Dermatolociques | Complexes based on anthralin and a sterol, a process for obtaining them and their use in therapeutics and cosmetics |
| GR890100035A (en) * | 1989-01-23 | 1991-06-07 | Wolff Chem Pharm Gmbh | Method for preparation of a means that contains salicyloxyd against scaling sick |
| WO1998029136A1 (en) * | 1996-12-27 | 1998-07-09 | Takeda Chemical Industries, Ltd. | Stabilized tricyclic compound |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE19926671A1 (en) * | 1999-06-11 | 2000-12-14 | Wella Ag | Anhydrous composition forming stable, transparent skin-compatible gel for use as cosmetic or dermatological base, containing fatty alcohol or its ester and silicon dioxide |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS4971127A (en) * | 1972-11-18 | 1974-07-10 | ||
| DE2331853A1 (en) * | 1973-06-22 | 1975-01-16 | Greither Salus Haus Dr Otto | Stable camomile formulation - contains a bland oil |
| JPS6020362B2 (en) * | 1974-12-28 | 1985-05-21 | 日清製油株式会社 | cosmetics |
| US4316902A (en) * | 1979-09-21 | 1982-02-23 | Yu Ruey J | Therapeutic compositions and vehicles for topical pharmaceuticals |
| FR2485921A1 (en) * | 1980-07-01 | 1982-01-08 | Oreal | COSMETIC COMPOSITION BASED ON AN AQUEOUS DISPERSION OF LIPID SPHERULES |
| US4367224A (en) * | 1981-05-13 | 1983-01-04 | Scott Eugene J Van | Stable dithranol compositions in anhydrous vehicles |
| IL63336A (en) * | 1981-07-16 | 1984-03-30 | Univ Ramot | Electrochemical cell |
| FR2520233A1 (en) * | 1982-01-28 | 1983-07-29 | Oreal | COMPOSITION OF ANTHRALIN OR ONE OF ITS DERIVATIVES IN AN AROMATIC ESTER AND ITS USE IN THE TREATMENT OF SKIN DISEASES |
-
1984
- 1984-08-30 FR FR8413431A patent/FR2569561B1/en not_active Expired - Fee Related
-
1985
- 1985-08-29 IT IT22014/85A patent/IT1201458B/en active
- 1985-08-29 GB GB08521455A patent/GB2164254B/en not_active Expired
- 1985-08-29 CA CA000489648A patent/CA1272449A/en not_active Expired - Fee Related
- 1985-08-29 BE BE0/215522A patent/BE903150A/en not_active IP Right Cessation
- 1985-08-29 NL NL8502373A patent/NL8502373A/en not_active Application Discontinuation
- 1985-08-29 CH CH3711/85A patent/CH664895A5/en not_active IP Right Cessation
- 1985-08-29 DE DE19853530914 patent/DE3530914A1/en not_active Withdrawn
- 1985-08-29 JP JP60191791A patent/JPS6165825A/en active Pending
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0337289A1 (en) * | 1988-04-10 | 1989-10-18 | Konrad Minninger | Pharmaceutical composition containing dithranol for the treatment of the skin exfoliative diseases |
| WO1989009595A1 (en) * | 1988-04-10 | 1989-10-19 | Konrad Minninger | Dithranol-containing pharmaceutical product for flaking skin diseases |
| US4961922A (en) * | 1988-04-14 | 1990-10-09 | Centre International De Recherches Dermatolociques | Complexes based on anthralin and a sterol, a process for obtaining them and their use in therapeutics and cosmetics |
| GR890100035A (en) * | 1989-01-23 | 1991-06-07 | Wolff Chem Pharm Gmbh | Method for preparation of a means that contains salicyloxyd against scaling sick |
| WO1998029136A1 (en) * | 1996-12-27 | 1998-07-09 | Takeda Chemical Industries, Ltd. | Stabilized tricyclic compound |
Also Published As
| Publication number | Publication date |
|---|---|
| JPS6165825A (en) | 1986-04-04 |
| GB8521455D0 (en) | 1985-10-02 |
| FR2569561A1 (en) | 1986-03-07 |
| DE3530914A1 (en) | 1986-03-13 |
| CH664895A5 (en) | 1988-04-15 |
| BE903150A (en) | 1986-02-28 |
| CA1272449A (en) | 1990-08-07 |
| NL8502373A (en) | 1986-03-17 |
| IT8522014A0 (en) | 1985-08-29 |
| IT1201458B (en) | 1989-02-02 |
| FR2569561B1 (en) | 1990-05-18 |
| GB2164254B (en) | 1987-12-31 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PCNP | Patent ceased through non-payment of renewal fee |
Effective date: 19930829 |