Clobetasol
(8S,9R,10S,11S,13S,14S,16S,17R)-17-(2-chloroacetyl)-9-fluoro-11,17-dihydroxy-10,13,16-trimethyl-6,7,8,11,12,14,15,16-octahydrocyclopenta[a]phenanthren-3-one
Molecular Identity
Clobetasol
(8S,9R,10S,11S,13S,14S,16S,17R)-17-(2-chloroacetyl)-9-fluoro-11,17-dihydroxy-10,13,16-trimethyl-6,7,8,11,12,14,15,16-octahydrocyclopenta[a]phenanthren-3-one
PubChem CID: 5311051
Clobetasol is a 3-oxo-1,4-steroid that is 16beta-methylpregna-1,4-diene-3,20-dione bearing hydroxy groups at the 11beta and 17alpha positions, fluorine at position 9, and a chlorine substituent at position 21. It is used as its 17alpha-propionate ester to treat various skin disorders, including exzema and psoriasis. It has a role as a SMO receptor agonist and an anti-inflammatory drug. It is a tertiary alpha-hydroxy ketone, a glucocorticoid, a 17alpha-hydroxy steroid, an 11beta-hydroxy steroid, a 20-oxo steroid, a fluorinated steroid, a 3-oxo-Delta(1),Delta(4)-steroid and a chlorinated steroid.
2D Structure
Properties
C22H28ClFO4
Molecular Formula
410.90
Molecular Weight
g/mol
410.1660
Exact Mass
Da
2.5
XLogP
Drug-like (Lipinski: < 5)
74.6
TPSA
Good oral absorption (< 140 A²)
2
H-Bond Donors
5
H-Bond Acceptors
808
Complexity
SMILES
Canonical SMILES
SMILES: CC1CC2C3CCC4=CC(=O)C=CC4(C3(C(CC2(C1(C(=O)CCl)O)C)O)F)CIsomeric SMILES
SMILES: C[C@H]1C[C@H]2[C@@H]3CCC4=CC(=O)C=C[C@@]4([C@]3([C@H](C[C@@]2([C@]1(C(=O)CCl)O)C)O)F)CSynonyms(20)
clobetasol25122-41-2ClobetasolumDTXSID2048955Clobecort Amex21-Chloro-9-fluoro-11beta,17-dihydroxy-16beta-methylpregna-1,4-diene-3,20-dioneADN79D536H(11beta,16beta)-21-chloro-9-fluoro-11,17-dihydroxy-16-methylpregna-1,4-diene-3,20-dioneDTXCID9028881CHEBI:205919Pregna-1,4-diene-3,20-dione, 21-chloro-9-fluoro-11,17-dihydroxy-16-methyl-, (11beta,16beta)-clobetasoloClofenazon(1R,2S,10S,11S,13S,14R,15S,17S)-14-(2-chloroacetyl)-1-fluoro-14,17-dihydroxy-2,13,15-trimethyltetracyclo(8.7.0.0^(2,7).0^(11,15))heptadeca-3,6-dien-5-one(1R,2S,10S,11S,13S,14R,15S,17S)-14-(2-chloroacetyl)-1-fluoro-14,17-dihydroxy-2,13,15-trimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-3,6-dien-5-one
Data from PubChem (NCBI)
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