Clobetasol propionate

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Clobetasol propionate
Clobetasol propionate structure.png
Systematic (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
Clinical data
AHFS/Drugs.com monograph
Pregnancy
category
  • US: C (Risk not ruled out)
Legal status
  • ℞ (Prescription only)
Routes of
administration		 Topical
Identifiers
CAS Number 25122-46-7 YesY
ATC code D07AD01 (WHO)
PubChem CID: 32798
IUPHAR/BPS 7062
DrugBank DB01013 YesY
ChemSpider 30399 YesY
UNII 779619577M YesY
ChEBI CHEBI:31414 YesY
ChEMBL CHEMBL1159650 YesY
Chemical data
Formula C25H32ClFO5
Molecular mass 466.97 g/mol
  • 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=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 YesY
  • Key:CBGUOGMQLZIXBE-XGQKBEPLSA-N YesY
  (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]

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 (India), Temovate (US), Dermovate (GlaxoSmithKline, Pakistan, Portugal, Israel), Olux, Tenovate, Dermatovate, Butavate, Movate, Novate, and Powercort.[3]

Uses

Clobetasol propionate is used for the treatment of various skin disorders including eczema, herpes labialis,[4] 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.

Possible side effects

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 ointment USP 0.05%, supplied in Olux 15 g, 30 g, 45 g, and 60 g tubes.
  • Temovate & emollient 0.05%, supplied in 15 g (NDC 0173-0454-01), 30 g (NDC 0173-0454-02) and 60 g (NDC 0173-0454-03) tubes.
  • Clobetasol propionate foam 0.05%
  • Clobetasol propionate foam 0.10%
  • Clobetasol propionate cream 0.05%
  • Clobetasol propionate gel 0.05%
  • Clobetasol propionate scalp application 0.05%
  • Clobetasol propionate spray 0.05%
  • Dermovate cream and ointment, containing clobetasol propionate 0.05% (UK)
  • Dermol cream and ointment (NZ)

See also

References

  1. ↑ Clobetasol Propionate Topical Ointment 0.05% Information - Drug Encyclopedia
  2. ↑ CLOBETASOL PROPIONATE CREAM USP, 0.05% CLOBETASOL PROPIONATE OINTMENT USP, 0.05%
  3. ↑ • Ulotka Novate / Clobetasoli propionas - leki i suplementy diety, dawkowanie, skład, zastosowanie, opis - DOZ.pl
  4. ↑ Hull C, McKeough M, Sebastian K, Kriesel J, Spruance S. Valacyclovir and topical clobetasol gel for the episodic treatment of herpes labialis: a patient-initiated, double- blind, placebo-controlled pilot trial. J Eur Acad Derma- tol Venereol. 2009;23(3):263-267
  5. ↑ Temovate E Top Precautions and Side Effects
  6. ↑ Chemicals Under Consideration For Possible Listing Via The "Formally Required To Be Labeled Or Identified" Mechanism, Office of Environmental Health Hazard Assessment, California Environmental Protection Agency

External links

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