HCY

(11alpha,14beta)-11,17,21-trihydroxypregn-4-ene-3,20-dione

Created: 2007-10-13
Last modified:  2021-03-01

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Chemical Details

Formal Charge0
Atom Count56
Chiral Atom Count7
Bond Count59
Aromatic Bond Count0
2D diagram of HCY

Chemical Component Summary

Name(11alpha,14beta)-11,17,21-trihydroxypregn-4-ene-3,20-dione
SynonymsCORTISOL
Systematic Name (OpenEye OEToolkits)(8S,9S,10R,11S,13S,14S,17R)-11,17-dihydroxy-17-(2-hydroxyethanoyl)-10,13-dimethyl-2,6,7,8,9,11,12,14,15,16-decahydro-1H-cyclopenta[a]phenanthren-3-one
FormulaC21 H30 O5
Molecular Weight362.46
TypeNON-POLYMER

Chemical Descriptors

TypeProgram Version Descriptor
SMILESACDLabs10.04O=C(CO)C3(O)C2(CC(O)C4C1(C(=CC(=O)CC1)CCC4C2CC3)C)C
SMILESCACTVS3.341C[C]12CCC(=O)C=C1CC[CH]3[CH]4CC[C](O)(C(=O)CO)[C]4(C)C[CH](O)[CH]23
SMILESOpenEye OEToolkits1.5.0CC12CCC(=O)C=C1CCC3C2C(CC4(C3CCC4(C(=O)CO)O)C)O
Canonical SMILESCACTVS3.341 C[C@]12CCC(=O)C=C1CC[C@H]3[C@@H]4CC[C@](O)(C(=O)CO)[C@@]4(C)C[C@H](O)[C@H]23
Canonical SMILESOpenEye OEToolkits1.5.0 C[C@]12CCC(=O)C=C1CC[C@@H]3[C@@H]2[C@H](C[C@]4([C@H]3CC[C@@]4(C(=O)CO)O)C)O
InChIInChI1.03 InChI=1S/C21H30O5/c1-19-7-5-13(23)9-12(19)3-4-14-15-6-8-21(26,17(25)11-22)20(15,2)10-16(24)18(14)19/h9,14-16,18,22,24,26H,3-8,10-11H2,1-2H3/t14-,15-,16-,18+,19-,20-,21-/m0/s1
InChIKeyInChI1.03 JYGXADMDTFJGBT-VWUMJDOOSA-N

Drug Info: DrugBank

DrugBank IDDB00741 
NameHydrocortisone
Groups
  • approved
  • vet_approved
DescriptionHydrocortisone, or cortisol, is a glucocorticoid secreted by the adrenal cortex.[A188387] Hydrocortisone is used to treat immune, inflammatory, and neoplastic conditions.[L10529,L10532,L10535,L10538,L7772,L7321] It was discovered in the 1930s by Edward Kendall and named Compound F, or 17-hydroxycorticosterone.[A188420] Hydrocortisone was granted FDA approval on 5 August 1952.[L10574]
Synonyms
  • Hydrocortisone
  • Hydrocortisonum
  • Cortisol
  • 11β-hydrocortisone
  • (11β)-11,17,21-trihydroxypregn-4-ene-3,20-dione
Brand Names
  • Equaline Anti Itch
  • Hydroxym
  • Welly Human Repair Kit
  • Gelmicin Hydrocortisone with Aloe
  • Topcare Hydrocortisone
IndicationOtic solutions are indicated for infections of the external auditory canal caused by susceptible organisms and with inflammation.[L10529,L10532] Hydrocortisone tablets are indicated for certain endocrine, rheumatic, collagen, allergic, ophthalmic, respiratory, hematologic, neoplastic, edematous, gastrointestinal, and other conditions.[L10535] A hydrocortisone enema is indicated for ulcerative colitis,[L10538] a topical ointment with antibiotics is indicated for corticosteroid responsive dermatoses with infections,[L7772] and a topical cream with [acyclovir] is indicated to treat cold sores.[L7321] Oral granules of hydrocortisone are used as a replacement therapy for Adrenocortical Insufficiency (AI) in children under 17 years of age.[L16533]
Categories
  • 11-Hydroxycorticosteroids
  • 17-Hydroxycorticosteroids
  • Adrenal Cortex Hormones
  • Adrenals
  • Agents for Treatment of Hemorrhoids and Anal Fissures for Topical Use
ATC-Code
  • S01CB03
  • A01AC03
  • S01BA02
  • S01CA03
  • D07AA02
CAS number50-23-7

Drug Targets

NameTarget SequencePharmacological ActionActions
Glucocorticoid receptorMDSKESLTPGREENPSSVLAQERGDVMDFYKTLRGGATVKVSASSPSLAV...unknownagonist
Annexin A1MAMVSEFLKQAWFIENEEQEYVQTVKSSKGGPGSAVSPYPTFNPSSDVAA...unknownagonist
Cytochrome P450 3A4MALIPDLAMETWLLLAVSLVLLYLYGTHSHGLFKKLGIPGPTPLPFLGNI...unknownsubstrate,inducer
Cytochrome P450 3A5MDLIPNLAVETWLLLAVSLVLLYLYGTRTHGLFKRLGIPGPTPLPLLGNV...unknownsubstrate
Cytochrome P450 3A7MDLIPNLAVETWLLLAVSLILLYLYGTRTHGLFKKLGIPGPTPLPFLGNA...unknownsubstrate
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 CHEMBL389621
PubChem 5754
ChEMBL CHEMBL389621
ChEBI CHEBI:17650
CCDC/CSD ZZZPNG01, ZZZPNG03, GOGQEZ, CORTMS01, COWNEI, CORTMS, ZZZPNG02, CORTPY, SACWAY01, SACWAY, ZZZPNG04
COD 1559402