Clobetasol propionate

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Clobetasol propionate
Systematic (IUPAC) name
[(8S,9R,10S,11S,13S,14S,16S,17R)-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
Identifiers
CAS number 25122-46-7
ATC code  ?
PubChem 123917
DrugBank APRD00876
ChemSpider 30399
Chemical data
Formula C25H32ClFO5
Mol. mass 466.97
SMILES eMolecules & PubChem
Synonyms Enterolactone
Physical data
Melt. point 195.5-197(EXP) °C
Solubility in water 3.86(EST) at 25oC mg/mL
Pharmacokinetic data
Bioavailability  ?
Metabolism  ?
Half life  ?
Excretion  ?
Therapeutic considerations
Pregnancy cat.

?

Legal status
Routes Topical

A derivative of PREDNISOLONE with high glucocorticoid activity and low mineralocorticoid activity. Absorbed through the skin faster than FLUOCINONIDE, it is used topically in treatment of PSORIASIS but may cause marked adrenocortical suppression.

Clobetasol propionate is a corticosteroid used to treat various skin disorders including eczema and psoriasis. It comes in ointment and emollient cream presentations. It has very high potency and typically should not be used with occlusive dressings, or for extended continous use (beyond two weeks). It is also used to treat several auto-immune diseases including alopecia areata and lichen planus (auto immune skin nodules).

Clobetasol propionate is marketed and sold worldwide under numerous names including Clobex, Temovate (US), Tenovate, Dermovate, Dermatovate, Butavate and, Movate.

Contents

[edit] General Properties

*Molecular Weight

466.97

*Molecular Formula

C25H32ClFO5

*IUPAC NAME

[(8S,9R,10S,11S,13S,14S,16S,17R)-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

*Canonical Smiles

CCC(=O)OC1(C(CC2C1(CC(C3(C2CCC4=CC(=O)C=CC43C)F)O)C)C)C(=O)CCl

*Isomeric Smiles

CCC(=O)O[C@@]1([C@H](C[C@@H]2[C@@]1(C[C@@H]([C@]3([C@H]2CCC4=CC(=O)C=C[C@@]43C)F)O)C)C)C(=O)CCl


[edit] PhysioChemical Properties

*Melting Point

195.5-197(EXP)

*LogP

3.5(EXP)

*Water Solubility

3.86(EST) at 25C

[edit] 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 cream 0.05%
  • Clobetasol propionate gel 0.05%
  • Clobestasol propianate spray 0.05%

[edit] Possible side effects

[edit] Risk to pregnant women

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 (http://www.oehha.ca.gov/prop65/CRNR_notices/admin_listing/requests_info/referenced_docs/frpkg5r.html):

"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 abnormailities 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."

[edit] External Links

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