Clobetasol propionate

Clobetasol propionate
Clinical data

AHFS/Drugs.com	Monograph
Pregnancy category	US: C (Risk not ruled out)
Routes of administration	Topical only
ATC code	D07AD01 (WHO)
Legal status
Legal status	℞ (Prescription only)
Identifiers
IUPAC name [17-(2'-Chloroacetyl)-9-fluoro-11-hydroxy-10,13,16-trimethyl-3-oxo-6,7,8,11,12,14,15,16-octahydrocyclopenta[a]phenanthren-17-yl] propanoate
CAS Number	25122-46-7^Y
PubChem (CID)	32798
IUPHAR/BPS	7062
DrugBank	DB01013^Y
ChemSpider	30399^Y
UNII	779619577M^Y
ChEBI	CHEBI:31414^Y
ChEMBL	CHEMBL1159650^Y
ECHA InfoCard	100.042.380
Chemical and physical data
Formula	C₂₅H₃₂ClFO₅
Molar mass	466.97 g/mol
3D model (Jmol)	Interactive image
SMILES ClCC(=O)[C@]3(OC(=O)CC)[C@]2(C[C@H](O)[C@]4(F)[C@@]/1(\C(=C/C(=O)\C=C\1)CC[C@H]4[C@@H]2C[C@@H]3C)C)C
InChI InChI=1S/C25H32ClFO5/c1-5-21(31)32-25(20(30)13-26)14(2)10-18-17-7-6-15-11-16(28)8-9-22(15,3)24(17,27)19(29)12-23(18,25)4/h8-9,11,14,17-19,29H,5-7,10,12-13H2,1-4H3/t14-,17-,18-,19-,22-,23-,24-,25-/m0/s1^Y Key:CBGUOGMQLZIXBE-XGQKBEPLSA-N^Y
(verify)

Clobetasol propionate /kloʊˈbeɪtəsɒl/^[1] is a corticosteroid of the glucocorticoid class used to treat various skin disorders including eczema and psoriasis. It is also highly effective for contact dermatitis caused by exposure to poison ivy/oak. Clobetasol belongs to US Class I (Europe: class IV) of the corticosteroids, making it one of the most potent available. It comes in shampoo, mousse, ointment and emollient cream presentations. It has very high potency and typically should not be used with occlusive dressings, or for extended continuous use (beyond two weeks). It is also used to treat several autoimmune diseases including alopecia areata, vitiligo, lichen sclerosus, and lichen planus.^[2]

Uses

Clobetasol propionate is used for the treatment of various skin disorders including eczema, herpes labialis,^[3] psoriasis, and lichen sclerosus. It is also used to treat several auto-immune diseases including alopecia areata, vitiligo, lichen planus (auto immune skin nodules), and mycosis fungoides (T-cell skin lymphoma). It is used as first-line treatment for both acute and chronic GVHD of the skin.

Clobetasol proprionate is used cosmetically by dark-skinned women for skin whitening, although this use is controversial. The U.S. Food and Drug Administration has not approved it for that purpose, and sales without a prescription are illegal in the U.S. Nonetheless, it is often sold in U.S. retail beauty supply stores and on the internet. It is also sold internationally, and does not require a prescription in some countries. Whitening creams with clobetasol proprionate, such as Hyprogel, can make skin thin and easily bruised, with visible capillaries, and acne. It can also lead to hypertension, elevated blood sugar, suppression of the body’s natural steroids, and stretch marks, which may be permanent.^[4]

Clobetasol propionate is with mercury and hydroquinone "amongst the most toxic and most used agents in lightening products." Many products sold illegally have higher concentrations of clobetasol propionate than is permitted for prescription drugs.^[5]

Contraindications

According to the California Environmental Protection Agency, clobetasol propionate should not be used by pregnant women, or women expecting to become pregnant soon, as studies with rats shows a risk of birth defects:^[6]

"Studies in the rat following oral administration at dosage levels up to 50 mg/kg per day revealed that the females exhibited an increase in the number of resorbed embryos and a decrease in the number of living fetuses at the highest dose. Pregnancy: Teratogenic Effects (i.e., possibility of causing abnormalities in fetuses): Pregnancy Category C: Clobetasol propionate has not been tested for teratogenicity when applied topically; however, it is absorbed percutaneously, and when administered subcutaneously it was a significant teratogen in both the rabbit and mouse. Clobetasol propionate has greater teratogenic potential than steroids that are less potent.There are no adequate and well-controlled studies of the teratogenic effects of clobetasol propionate in pregnant women. Temovate Cream and Ointment should be used during pregnancy only if the potential benefit justifies the potential risk to the fetus."

Forms

Clobetasol propionate is marketed and sold worldwide under numerous names including Clobex, Clob-x (Colombia), Clovate, Clonovate (T.O. Chemicals, Thailand), Cormax (Watson, US), Pentasol (Colombia), Cosvate, Clop (India), Temovate (US), Dermovate (GlaxoSmithKline, Pakistan, Portugal, Israel), Olux, ClobaDerm, Tenovate, Dermatovate, Butavate, Movate, Novate, and Powercort.^[7]

References

↑ "Clobetasol Propionate Topical Ointment 0.05% Information – Drug Encyclopedia". Kaiser Permanente.
↑ E. Fougera and Co. "CLOBETASOL PROPIONATE CREAM USP, 0.05% CLOBETASOL PROPIONATE OINTMENT USP, 0.05%<". NIH Daily Med.
↑ Hull, C; McKeough, M; Sebastian, K; Kriesel, J; Spruance, S (2009). "Valacyclovir and topical clobetasol gel for the episodic treatment of herpes labialis: A patient-initiated, double-blind, placebo-controlled pilot trial". Journal of the European Academy of Dermatology and Venereology. 23 (3): 263–267. doi:10.1111/j.1468-3083.2008.03047.x. PMID 19143902.
↑ Creams Offering Lighter Skin May Bring Risks By CATHERINE SAINT LOUIS, New York Times, JAN. 15, 2010
↑ Gbetoh MH, Amyot M. (1 July 2016). "Mercury, hydroquinone and clobetasol propionate in skin lightening products in West Africa and Canada.". Environ Res. 150: 403–10. doi:10.1016/j.envres.2016.06.030. PMID 27372064.
↑ Office of Environmental Health Hazard Assessment. "Chemicals Under Consideration For Possible Listing Via The "Formally Required To Be Labeled Or Identified" Mechanism". California Environmental Protection Agency.
↑ "Ulotka Novate / Clobetasoli propionas – leki i suplementy diety, dawkowanie, skład, zastosowanie, opis". DOZ.pl.

Glucocorticoids and antiglucocorticoids (H02)

Glucocorticoids

Pregnene	Cortisone

Pregnenedione	Hydrocortisone (cortisol)^# (Hydrocortisone aceponate Hydrocortisone buteprate Hydrocortisone butyrate) Budesonide Ciclesonide Deflazacort Medrysone Tixocortol Halogenated at 6: Cloprednol Halogenated, with FG at 16: Halcinonide

Pregnadiene	Rimexolone Halogenated, with FG at 16: Flunisolide Triamcinolone Amcinonide Fluocinolone acetonide (Fluocinonide)

Pregnadienediol	Prednisone (Meprednisone) Halogenated at 9: Fluorometholone Halogenated, with FG at 16: Fluocortolone (Clocortolone Diflucortolone Fluocortin) Desoximetasone

Pregnadienetriol	Prednisolone^# (Methylprednisolone Methylprednisolone aceponate Prednicarbate Prednylidene) Desonide Halogenated: Fluprednisolone (Difluprednate Fluperolone) Halogenated, with FG at 16: Dexamethasone^# Betamethasone (Clobetasol Clobetasone Diflorasone Halometasone Ulobetasol) Beclometasone Paramethasone Alclometasone Fluclorolone acetonide Flumetasone Fluprednidene

Pregnatriene	Cortivazol

Androstene	Halogenated, with FG at 16: Fluticasone (Fluticasone propionate Fluticasone furoate)

Others/unsorted	Halogenated: Loteprednol Halogenated, with FG at 16: Fludroxycortide Formocortal Mometasone furoate

Antiglucocorticoids

SGRMs: Dagrocorat^§
Fosdagrocorat^§
Mapracorat^†

Antagonists: Ketoconazole
Mifepristone

Synthesis modifiers

^#WHO-EM
^‡Withdrawn from market
Clinical trials:
- ^†Phase III
- ^§Never to phase III

See also: Androgens and antiandrogens • Estrogens and antiestrogens • Progestogens and antiprogestogens • Mineralocorticoids and antimineralocorticoids

Glucocorticoid receptor modulators

Agonists	5α-Dihydrocorticosterone 11-Deoxycorticosterone (desoxycortone, cortexone) 11-Deoxycortisol (cortodoxone, cortexolone)) 15β-Hydroxycyproterone acetate 17α-Hydroxyprogesterone 21-Deoxycortisol Acrocinonide Alclometasone Algestone acetonide Amcinafal Amcinafide Amcinonide Amebucort Amelometasone Amicinonide Anecortave AZD5423 Beclometasone Beclometasone dipropionate Betamethasone Betamethasone acibutate Betamethasone dipropionate Budesonide Butixocort Chlormadinone acetate Chloroprednisone Ciclesonide Cicortonide Ciprocinonide Clobetasol Clobetasol propionate Clobetasone Clocortolone Cloprednol Cloticasone Cormetasone Corticosterone Cortisone Cortisuzol Cortivazol Cyproterone Cyproterone acetate Deflazacort Deprodone Descinolone Desonide Desoximetasone Dexbudesonide Dexamethasone Dexamethasone acefurate Dexamethasone cipecilate Dexamethasone isonicotinate Dichlorisone Diflorasone Difluocortolone Difluocortolone valerate Difluprednate Domoprednate Doxibetasol Drocinonide Etiprednol dicloacetate Fluazacort Fluclorolone Fluclorolone (flucloronide) Fludrocortisone Fludroxycortide Flumoxonide Flumetasone Flunisolide Fluocinolone Fluocinolone acetonide Fluocinonide Fluocortin Fluocortolone Fluorometholone Fluperolone Fluperolone acetate Fluprednidene Fluprednidene acetate Fluprednisolone Fluticasone Fluticasone furoate Fluticasone propionate Formocortal Gestodene GSK-9027 Halcinonide Halocortolone Halometasone Halopredone Hydrocortamate Hydrocortisone (cortisol) Hydrocortisone aceponate Hydrocortisone buteprate Hydrocortisone-17-butyrate Hydrocortisone-21-butyrate Icometasone enbutate Isoflupredone Isoprednidene Itrocinonide Locicortolone dicibate Loteprednol Mazipredone Meclorisone Medrogestone Medroxyprogesterone acetate Megestrol acetate Medrysone Meprednisone Methylprednisolone Methylprednisolone aceponate Methylprednisolone suleptanate Mometasone Mometasone furoate Naflocort Nicocortonide Nivacortol Osaterone acetate Oxisopred Paramethasone Perdesonide Prednazate Prednazoline Prednicarbate Prednimustine Prednisolamate Prednisolone Prednisolone steaglate Prednisone Prednylidene Procinonide Progesterone Promegestone Quingestrone Resocortol Rimexolone Rofleponide RU-28362 Segesterone acetate (nestorone) Tetrahydrocorticosterone Tetrahydrogestrinone Timobesone Tipredane Tixocortol Tixocortol pivalate Tralonide Triamcinolone Triamcinolone acetonide Triamcinolone benetonide Triamcinolone furetonide Triamcinolone hexacetonide Triclonide Ulobetasol (halobetasol) Vamorolone

Mixed (SEGRAs)	Dagrocorat Fosdagrocorat Mapracorat

Antagonists	3α-Hydroxytibolone 3β-Hydroxytibolone 7α-Hydroxy-DHEA 17α-Methylprogesterone Aglepristone Asoprisnil C108297 C113176 CORT-108297 Cyproterone acetate Formebolone Guggulsterone Ketoconazole Lilopristone LLY-2707 Miconazole Mifepristone Onapristone ORG-34116 ORG-34517 (SCH-900636) ORG-34850 Pregnenolone 16α-carbonitrile Telapristone Tibolone Toripristone Ulipristal acetate

See also: Androgenics • Estrogenics • Mineralocorticoidics • Progestogenics • Steroid hormone metabolism modulators

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