GB2260903A - Treatment of alopecia with vitamin D3 derivatives - Google Patents
Treatment of alopecia with vitamin D3 derivatives Download PDFInfo
- Publication number
- GB2260903A GB2260903A GB9226957A GB9226957A GB2260903A GB 2260903 A GB2260903 A GB 2260903A GB 9226957 A GB9226957 A GB 9226957A GB 9226957 A GB9226957 A GB 9226957A GB 2260903 A GB2260903 A GB 2260903A
- Authority
- GB
- United Kingdom
- Prior art keywords
- compound
- dihydroxyvitamin
- alopecia
- treatment
- homo
- 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.)
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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
- A61K31/59—Compounds containing 9, 10- seco- cyclopenta[a]hydrophenanthrene ring systems
-
- 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
- A61K8/67—Vitamins
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q7/00—Preparations for affecting hair growth
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- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Veterinary Medicine (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Epidemiology (AREA)
- Dermatology (AREA)
- Birds (AREA)
- Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Cosmetics (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
The use of vitamin D3 analogues for the treatment or prevention of alopecia wherein the active agent is chosen from the following 1,25-dihydroxy vitamin D3 derivatives: (a) as disclosed in WO-87/00834-A1, (b) as disclosed in WO-89/10351-A1, (c) 24-homo- and 26-homo-1 alpha ,25-dihydroxyvitamin D3 and their 22,23-didehydro-analogues, (d) 20-oxa-21-nor-1 alpha ,25-dihydroxyvitamin D3 and 22-oxa-1 alpha ,25-dihydroxyvitamin D3, (e) 26,27-dimethyl and 26,27-diethyl-1 alpha ,25-dihydroxyvitamin D3 and 24,24-difluoro-24-homo-1 alpha ,25-dihydroxyvitamin D3.
Description
NOVEL TREATMENT
This invention relates to the use of certain Vitamin D analogues in the preparation of a pharmaceutical preparation for the treatment and/or prevention of alopecia.
Alopecia (a partial or complete loss of hair) is due to a deficiency of terminal hair which is the visual coloured hair. If the hair loss is due to atrophy or scarring, no regrowth can be expected. But in other cases, even where there is a noticable absence of terminal hair, the skin of a seemingly bald person may contain the socalled vellus hair which is a very fine colourless hair, the presence of which needs microscopic determination. The vellus hair is a precursor to the terminal hair, and a regrowth may thus be promoted both by influencing the conversion of vellus hair to terminal hair and by stimulating the growth of the latter.
Alopecia may result from genetic factors, from ageing, from local or systemic diseases and as a side effect in connection with cancer chemotherapy. Male-pattern baldness is extremely common, it is familial and requires the presence of androgens, but other etiological factors are unknown. Female-pattern alopecia is not infrequent in women.
It is ordinarily confined to thinning of hair in the frontal and the parietal regions.
It is further known that many patients suffering from the hereditary disorder 'vitamin D-dependent ricketts type
II' have alopecia.
This is a puzzling association between hereditary vitamin D resistance and alopecia since alopecia is not generally associated with other vitamin D deficiency states, and it suggests that la,25-dihydroxyvitamin D3 (1,25-(OH)2D3, the active form of vitamin D3) has a physiological role outside its classic targets tissues and may be required to promote differentiation of the hair follicle during the development, see also Arase, S. et al, J. Derm.
Sci. X, 353-360 (1991).
As alopecia is mainly a cosmetic problem, any therapy should never present risks which are unjustifiable. Topical application of the natural form of active vitamin D, i.e.
1,25-(OH)2D3, represents one possibility for such treatment, but because of its potent calcemic activity there will be a risk that, through transdermal absorption, it will give rise to undesired systemic effects leading to hypercalcemia.
However, by choosing a vitamin D analogue which has only moderate activity on calcium metabolism compared to 1,25-(OH)2D3, but having retained the ability to activate receptors for 1,25(OH)2D3 not associated with calcium absorption or bone calcium mobilization it is possible to treat and/or prevent alopecia successfully without having the risk of inducing hypercalcemia.
Examples of such vitamin D analogues for use in the present pharmaceutical preparations are
1) compounds described in international patent
application No. PCT/DK86/00081, international filing
date 14th July, 1986, International Publication No.
WO 87/00834, in particular the compound designated MC
903 (example 5 in said patent application) (confer
also Calverley, M., Tetrahedron 43, 4609-4619 (1987);
Binderup, L. and Bramm, E., Biochemical Pharmacology 37, 889-895 (1988)),
2) compounds described in international patent
application No. PCT/DK89/00079, international filing
date 7th April, 1989, in particular Compound 35 (Ex
ample 2), Compound 37 (Example 4), Compound 38
(Example 5), Compound 54 (Example 9), Compound 55
(Example 10), and Compound 59 - LEO Code CB 966
(Example 12)
3) 24-homo- and 26-homo-la,25-dihydroxyvitamin
D3 (together with their 22,23-didehydro-analogues)
(Ostrem, V.K. et al, Proc. Natl. Acad. Sci.USA 84, 2610-2614 (1987)),
4) 20-oxa-21-nor-la,25-dihydroxyvitamin D3 and 22-oxa-la,25-dihydroxyvitamin D3 (Abe, J. et al, FEBS
Letters 2k, 58-62 (1987)), and
5) 26,27-dimethyl- and 26,27-diethyl-la,25-di
hydroxyvitamin D3, and 24, 24-difluoro-24-homo-la, 25
dihydroxyvitamin D3 (Ikekawa, N. et al, Chem. Pharm.
Bull. 35, 4362-65 (1987)),
The mentioned compounds shall form part of pharmaceutical preparations, in particular for topical use, which are useful in the treatment of human disorders as described above, such as a liniment, a lotion, a cream or a gel which in addition to the vitamin D analogues in question may contain further active ingredients, such as a socalled potassium channel opener like minoxidil, cromokalim or pinacidil. The concentration of the active ingredients will depend upon the choice of vitamin D analogues but will generally be between 1 and 100 pg/g.
The formulations will be applied once or twice daily for prolonged periods of time.
The formulations prepared according to the present invention comprise an active compound in association with a pharmaceutically acceptable vehicle therefore and optionally other therapeutic ingredient(s). The vehicle(s) must be "acceptable" in the sense of being compatible with the other ingredients of the preparations and not deleterious to the recipient thereof.
Preparations suitable for topical administration include liquid or semi-liquid preparations such as liniments, lotions, applicants, oil-in-water or water-in-oil emulsions such as creams, ointments, pastes or gels; or solutions or suspensions.
In addition to the aforementioned ingredients, the preparations of this invention may include one or more additional ingredients such as diluents, buffers, flavouring agents, binders, surface active agents, thickeners, lubricants, preservatives, e.g. methyl hydroxybenzoate (including anti-oxidants), emulsifying agents and the like.
The preparations may, as mentioned above, contain further therapeutically active compounds usually applied in the above mentioned treatment.
In the topical treatment, ointments, creams, gels, or lotions containing from 1-100 sug/g of the vitamin D analogues or metabolites are administered.
The present invention further concerns a method for treating patients suffering from or in risk of getting alopecia, said method consisting of administering topically to a patient in need of treatment an effective amount of one or more of the above mentioned vitamin D analogues or metabolites, alone or in combination with one or more other therapeutically active compounds usually applied in such treatment. The treatment with the present compounds concomitantly with further therapeutically active compounds may be simultaneous or with intervals.
The invention will now be further described in the following non-limiting Examples:
Example 1 Cream Containing MC 903
In 1 g almond oil was dissolved 1 mg MC 903. To this solution was added 40 g of mineral oil and 20 g of self -emulsifying beeswax. The mixture was heated to liquify.
After the addition of 40 ml hot water, the mixture was mixed well. The resulting cream contains approximately 10 pg of MC 903 per gram of cream.
Example 2 Cream containing 22-oxa-la,25-dihydroxy- vitamin D3
By using the procedure described in Example 1, but replacing MC 903 with 22-oxa-la,25-dihydroxyvitamin D3, the desired cream was obtained.
Example3 Cream containing 50 pg MC 903/g
MC 903 ............................ 50 mg
Cetomacrogol 1000 ..................... 25 g
Cetostearyl alcohol ................... 75 g
Chloroallylhexaminium chloride ........ 0.5 g
Glycerol .............................. 30 g Di sodium hydrogenphosphate ............ 2 g
Sodium dihydrogenphosphate ............ 0.1 g
Liquid paraffin ....................... 60 g
Polyoxyethylene stearylether .......... 12 g
White petrolatum ...................... 160 g
Purified water .................. up to 1000 g
Dissolve MC 903 in a solution of glycerol, disodium hydrogenphosphate, sodium dihydrogenphosphate and polyoxyethylene stearylether dissolved in water. Mix with the melted cetomacrogol 1000, liquid paraffin, cetostearyl alcohol and white petrolatum.Homogenize the emulsion and cool. Dissolve chloroallylhexaminium chloride in part of the water and mix until homogeneous with the emulsion. Fill the cream in aluminium tubes.
Example4 Cream containing 100 pg CB 966/g
CB 966 ......................... 100 mg
Cetomacrogol 1000 ...................... 30 g
Cetostearyl alcohol .................... 60 g
Chloroallylhexaminium chloride ......... 0.5 g
Propylenglycol ......................... 30 g Di sodium hydrogenphosphate ............. 2 g
Sodium dihydrogenphosphate ............. 0.1 g
Liquid paraffin ........................ 50 g
White petrolatum ....................... 170 g
Purified water .................... up to 1000 g
Melt cetomacrogol 1000, cetostearyl alcohol, liquid paraffin and white petrolatum at 75 C. Dissolve propylenglycol in water at 75 C and mix the solution with the fatty phase. Homogenize the emulsion and cool to 30 C.Mill
CB 966 to particle size below 5 pm and suspend in an aqueous solution of disodium hydrogenphosphate, sodium dihydrogenphosphate and chloroallylhexaminium chloride. Add the suspension to the emulsion and fill the cream in tubes.
Example 5 Lotion containing 50 pg MC 903/g
MC 903 .................................. 50 mg
Absolute alcohol ......................... 400 g
Hydroxypropylcellulose ................... 1 g
Menthol 1 g
Sodium citrate ........................... 1 g
Propylenglycol ........................... 40 g
Purified water ..................... up to 1000 ml
Dissolve hydroxypropylcellulose, sodium citrate and propylenglycol in water. Mix with a solution of MC 903 and menthol in absolute alcohol. Fill the lotion in polyethylen plastic bottles.
Example 6 Prevention of cytoxan-induced alopecia by
MC 903
Three groups of each 10 5-day-old Sprague-Dawley rats were treated topically over the head and neck with daily doses of
A. 0.15 ml of absolute ethanol
B. 0.2 pg of 1,25(OH)2D3 (calcitriol) dissolved in
0.15 ml of absolute ethanol
C. 0.2 pg of MC 903 dissolved in 0.15 ml of
absolute ethanol for 5 days.
One day after the last topical treatment all rats were treated with cytoxan 35 ml/kg given intraperitoneally.
All animals in group A became totally alopecic whereas all animals in groups B and C were protected.
Whereas the mean serum level of Ca in group B was markedly increased compared to the control rats (group A) no such increase could be detected in the animals in group
C.
Example 7 Prevention of alopecia induced by a combi
nation of Adriamycin and cytoxan by the
vitamin D-analogue KH 10601
Three groups of each 10 5-day-old Sprague Dawley rats were treated over the head and neck with daily doses of
A. 150 pl of propylene glycol
B. 0.2 lug of 1,25(OH)2D3 (calcitriol) in 150 pl of
propylene glycol
C. 0.02 pg of KH 1060 dissolved in 150 pl of
propylene glycol
At the 11th day of age all animals were treated intraperitoneally with cytoxan 25 mg/kg and adriamycin 2.5 ml/kg. The same adriamycin dose was repeated on the 12th day and 13th day of age.
All 10 rats in the control group (group A) developed alopecia over the head and neck. In contrast all animals in groups B and C were protected - primarily at the side of the drug application.
The animals in group B had a significantly higher serum level of Ca than the animals in group A, whereas the serum level of Ca in group C was similar to that in group
A.
1 l(S),3(R)-Dihydroxy-20(R)-(4'-hydroxy-4'-ethyl-11-hex- yloxy)-9,10-seco-pregna-5(Z),7(E),10(19)-triene
Claims (7)
1) compounds described in international patent
application No. PCT/DK86/00081, international filing
date 14th July, 1986, International Publication No.
WO 87/00834, in particular the compound designated MC
903 (example 5 in said patent application) (confer
also Calverley, M., Tetrahedron 43, 4609-4619 (1987);
Binderup, L. and Bramm, E., Biochemical Pharmacology 37, 889-895 (1988)),
2) compounds described in international patent
application No. PCT/DK89/00079, international filing
date 7th April, 1989, in particular Compound 35 (Ex
ample 2), Compound 37 (Example 4), Compound 38
(Example 5), Compound 54 (Example 9), Compound 55
(Example 10), and Compound 59 (Example 12)
3) 24-homo- and 26-homo-la,25-dihydroxyvitamin
D3 (together with their 22,23-didehydro-analogues)
(Ostrem, V.K. et al, Proc. Natl. Acad. Sci.USA 84,
2610-2614 (1987)),
4) 20-oxa-21-nor-la, 25-dihydroxyvitamin D3 and
22-oxa-la,25-dihydroxyvitamin D3 (Abe, J. et al, FEBS
Letters 226, 58-62 (1987)), and
5) 26,27-dimethyl- and 26,27-diethyl-la,25-di
hydroxyvitamin D3, and 24, 24-difluoro-24-homo-la, 25- dihydroxyvitamin D3 (Ikekawa, N. et al, Chem. Pharm.
Bull. 35, 4362-65 (1987)), in the manufacture of a medicament for the treatment and/or prevention of alopecia.
2. The use according to claim 1, in which the active component is (lS,l'E,3R,5Z,7E,20R)-(9,10)-seco-20-(3'cyclopropyl-3'- -hydroxyprop-1 ' -enyl )-1, 3-dihydroxypregna-5, 7,10(19)- -triene.
3. The use according to claim 1, in which the active component is 1(S),3(R)-dihydroxy-20(R)-(5-ethyl-5-hydroxy-1 heptyl)-9,10-secopregna-5(Z),7(E),10(19)-triene.
4. A topical medicament according to any one of claims 1 to 3, containing the active component in an amount of from 0.01 ppm to 10 ppm of the medicament.
5. The use of a compound as defined in any one of the claims 1 to 3 for the treatment and/or prevention of alopecia.
6. The use according to claim 5 of (1S,1'E,3R,5Z,7E,20R)- -(9,10)-seco-20-(3'cyclopropyl-3'-hydroxyprop-1'-enyl)-1,3 -dihydroxypregna-5,7,10(19)-triene.
7. The use according to claim 5 of 1(S),3(R)-dihydroxy 20(R)-(5-ethyl-5-hydroxy-1-heptyl)-9,10-secopregna-5(Z),- 7(E),10(19)-triene.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB929201920A GB9201920D0 (en) | 1992-01-29 | 1992-01-29 | Novel treatment i |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| GB9226957D0 GB9226957D0 (en) | 1993-02-17 |
| GB2260903A true GB2260903A (en) | 1993-05-05 |
Family
ID=10709486
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB929201920A Pending GB9201920D0 (en) | 1992-01-29 | 1992-01-29 | Novel treatment i |
| GB9226957A Withdrawn GB2260903A (en) | 1992-01-29 | 1992-12-24 | Treatment of alopecia with vitamin D3 derivatives |
Family Applications Before (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB929201920A Pending GB9201920D0 (en) | 1992-01-29 | 1992-01-29 | Novel treatment i |
Country Status (1)
| Country | Link |
|---|---|
| GB (2) | GB9201920D0 (en) |
Cited By (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1999051271A2 (en) * | 1998-04-08 | 1999-10-14 | Abbott Laboratories | Compositions comprising glycol derivatives and alcohols |
| WO2000064583A1 (en) * | 1999-04-27 | 2000-11-02 | The Research Foundation Of State University Of New York | Metal catalysts and methods for making and using same |
| WO2003028674A2 (en) * | 2001-10-02 | 2003-04-10 | Cedars-Sinai Medical Center | Method for stimulating hair growth by administering vitamin d analogs |
| US6962891B2 (en) | 2001-08-27 | 2005-11-08 | The Research Foundation Of State University Of New York | Solid support dirhodium catalyst compositions and methods for making and using same |
| US7030051B2 (en) | 2001-08-27 | 2006-04-18 | The Research Foundation Of State University Of New York | Dirhodium catalyst compositions and methods for using same |
| US7385064B1 (en) | 2005-11-30 | 2008-06-10 | The Research Foundation Of State University Of New York | Catalysts for use in enantioselective synthesis |
| US7700798B1 (en) | 2005-06-08 | 2010-04-20 | The Research Foundation Of State University Of New York | Erogorgiaene congeners and methods and intermediates useful in the preparation of same |
| US7816536B2 (en) | 2005-06-10 | 2010-10-19 | The Research Foundation Of State University Of New York | 4-substituted and 7-substituted indoles, benzofurans, benzothiophenes, benzimidazoles, benzoxazoles, and benzothiazoles and methods for making same |
| JP2013501790A (en) * | 2009-08-14 | 2013-01-17 | バーグ バイオシステムズ，エルエルシー | Vitamin D3 and analogs thereof for treating alopecia |
-
1992
- 1992-01-29 GB GB929201920A patent/GB9201920D0/en active Pending
- 1992-12-24 GB GB9226957A patent/GB2260903A/en not_active Withdrawn
Non-Patent Citations (1)
| Title |
|---|
| Clin. Endocrinol. (Oxford), 25(4). 373-81 (1986) * |
Cited By (21)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2011037860A (en) * | 1998-04-08 | 2011-02-24 | Abbott Lab | Cosolvent formulation |
| WO1999051271A3 (en) * | 1998-04-08 | 1999-11-18 | Abbott Lab | Compositions comprising glycol derivatives and alcohols |
| US6136799A (en) * | 1998-04-08 | 2000-10-24 | Abbott Laboratories | Cosolvent formulations |
| JP4664499B2 (en) * | 1998-04-08 | 2011-04-06 | アボット・ラボラトリーズ | Cosolvent formulation |
| JP2002510652A (en) * | 1998-04-08 | 2002-04-09 | アボット・ラボラトリーズ | Co-solvent formulation |
| WO1999051271A2 (en) * | 1998-04-08 | 1999-10-14 | Abbott Laboratories | Compositions comprising glycol derivatives and alcohols |
| US6410746B1 (en) | 1999-04-27 | 2002-06-25 | Research Foundation Of State University Of New York, The | Metal cataltsts and methods for making and using same |
| US7109343B2 (en) | 1999-04-27 | 2006-09-19 | The Research Foundation Of State University Of New York | Metal catalysts and methods for making and using same |
| US6762304B2 (en) | 1999-04-27 | 2004-07-13 | Research Foundation Of State University Of New York | Metal catalysts and methods for making and using same |
| WO2000064583A1 (en) * | 1999-04-27 | 2000-11-02 | The Research Foundation Of State University Of New York | Metal catalysts and methods for making and using same |
| US7030051B2 (en) | 2001-08-27 | 2006-04-18 | The Research Foundation Of State University Of New York | Dirhodium catalyst compositions and methods for using same |
| US6962891B2 (en) | 2001-08-27 | 2005-11-08 | The Research Foundation Of State University Of New York | Solid support dirhodium catalyst compositions and methods for making and using same |
| WO2003028674A3 (en) * | 2001-10-02 | 2003-12-11 | Cedars Sinai Medical Center | Method for stimulating hair growth by administering vitamin d analogs |
| WO2003028674A2 (en) * | 2001-10-02 | 2003-04-10 | Cedars-Sinai Medical Center | Method for stimulating hair growth by administering vitamin d analogs |
| US7700798B1 (en) | 2005-06-08 | 2010-04-20 | The Research Foundation Of State University Of New York | Erogorgiaene congeners and methods and intermediates useful in the preparation of same |
| US7816536B2 (en) | 2005-06-10 | 2010-10-19 | The Research Foundation Of State University Of New York | 4-substituted and 7-substituted indoles, benzofurans, benzothiophenes, benzimidazoles, benzoxazoles, and benzothiazoles and methods for making same |
| US7385064B1 (en) | 2005-11-30 | 2008-06-10 | The Research Foundation Of State University Of New York | Catalysts for use in enantioselective synthesis |
| JP2013501790A (en) * | 2009-08-14 | 2013-01-17 | バーグ バイオシステムズ，エルエルシー | Vitamin D3 and analogs thereof for treating alopecia |
| JP2017008064A (en) * | 2009-08-14 | 2017-01-12 | バーグ エルエルシー | Vitamin d3 and analogs thereof for treating alopecia |
| US9901637B2 (en) | 2009-08-14 | 2018-02-27 | Berg Llc | Vitamin D3 and analogs thereof for treating alopecia |
| US11305016B2 (en) | 2009-08-14 | 2022-04-19 | Berg Llc | Vitamin D3 and analogs thereof for treating alopecia |
Also Published As
| Publication number | Publication date |
|---|---|
| GB9201920D0 (en) | 1992-03-18 |
| GB9226957D0 (en) | 1993-02-17 |
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| Date | Code | Title | Description |
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| WAP | Application withdrawn, taken to be withdrawn or refused ** after publication under section 16(1) |