Chemical Component Summary

NameClobetasol propionate
Synonyms(8alpha,11beta,14beta,16alpha,17alpha)-21-chloro-9-fluoro-11-hydroxy-16-methyl-3,20-dioxopregna-1,4-dien-17-yl propanoate
Identifiers[(8~{S},9~{R},10~{S},11~{S},13~{S},14~{S},16~{S},17~{R})-17-(2-chloranylethanoyl)-9-fluoranyl-10,13,16-trimethyl-11-oxidanyl-3-oxidanylidene-6,7,8,11,12,14,15,16-octahydrocyclopenta[a]phenanthren-17-yl] propanoate
FormulaC25 H32 Cl F O5
Molecular Weight466.97
TypeNON-POLYMER
Isomeric SMILESCCC(=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
InChIInChI=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
InChIKeyCBGUOGMQLZIXBE-XGQKBEPLSA-N

Chemical Details

Formal Charge0
Atom Count64
Chiral Atom Count8
Bond Count67
Aromatic Bond Count0

Drug Info: DrugBank

DrugBank IDDB01013 
NameClobetasol propionate
Groups approved
DescriptionClobetasol propionate is a prednisolone derivative with higher specificity for glucocorticoid receptors than mineralocorticoid receptors.[L11815] It has demonstrated superior activity compared to [fluocinonide][A190963] and was first described in the literature in 1974.[A190936] Clobetasol Propionate was granted FDA approval on 27 December 1985.[L11809]
Synonyms
  • 21-chloro-9-fluoro-11β,17-dihydroxy-16β-methylpregna-1,4-diene-3,20-dione 17-propionate
  • Clobetasol propionate
  • clobetasol 17-propionate
  • clobetasol 17-propanoate
  • Clobetasol propionate E
Brand Names
  • Clobetasol Scalp Application 0.05%
  • Taro-clobetasol Ointment USP, 0.05%
  • Dermovate Crm 0.05%
  • Tovet Foam (Emollient Formulation)
  • Clobetasol Propionate (Emollient)
IndicationClobetasol propionate is indicated to treat moderate to severe plaque psoriasis[L11818,L11821,L11824] as well as inflammatory and pruritic manifestations of corticosteroid responsive dermatoses.[L11815,L11827]
Categories
  • Adrenal Cortex Hormones
  • Anti-Inflammatory Agents
  • Corticosteroids
  • Cytochrome P-450 CYP3A Inducers
  • Cytochrome P-450 CYP3A Substrates
CAS number25122-46-7

Drug Targets

NameTarget SequencePharmacological ActionActions
Glucocorticoid receptorMDSKESLTPGREENPSSVLAQERGDVMDFYKTLRGGATVKVSASSPSLAV...unknownagonist
Annexin A1MAMVSEFLKQAWFIENEEQEYVQTVKSSKGGPGSAVSPYPTFNPSSDVAA...unknowninducer
Mineralocorticoid receptorMETKGYHSLPEGLDMERRWGQVSQAVERSSLGPTERTDENNYMEIVNVSC...unknownagonist
Cytochrome P450 3A4MALIPDLAMETWLLLAVSLVLLYLYGTHSHGLFKKLGIPGPTPLPFLGNI...unknownsubstrate,inducer
Cytochrome P450 3A5MDLIPNLAVETWLLLAVSLVLLYLYGTRTHGLFKRLGIPGPTPLPLLGNV...unknowninducer
View More
Drug Info/Drug Targets: DrugBank 3.0: a comprehensive resource for 'omics' research on drugs. Knox C, Law V, Jewison T, Liu P, Ly S, Frolkis A, Pon A, Banco K, Mak C, Neveu V, Djoumbou Y, Eisner R, Guo AC, Wishart DS. Nucleic Acids Res. 2011 Jan; 39 (Database issue):D1035-41. | PMID:21059682

Related Resource References

Resource NameReference
Pharos CHEMBL1159650
PubChem 32798
ChEMBL CHEMBL1159650
ChEBI CHEBI:31414
CCDC/CSD AMAVOZ
COD 1100668