DES

DIETHYLSTILBESTROL

Created:1999-07-08
Last modified:  2011-06-04

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Chemical Details

Formal Charge0
Atom Count40
Chiral Atom Count0
Bond Count41
Aromatic Bond Count12
2D diagram of DES

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Chemical Component Summary

NameDIETHYLSTILBESTROL
Systematic Name (OpenEye OEToolkits)4-[(E)-4-(4-hydroxyphenyl)hex-3-en-3-yl]phenol
FormulaC18 H20 O2
Molecular Weight268.35
TypeNON-POLYMER

Chemical Descriptors

TypeProgramVersionDescriptor
SMILESACDLabs10.04Oc2ccc(/C(=C(/c1ccc(O)cc1)CC)CC)cc2
SMILESCACTVS3.341CCC(c1ccc(O)cc1)=C(CC)c2ccc(O)cc2
SMILESOpenEye OEToolkits1.5.0CCC(=C(CC)c1ccc(cc1)O)c2ccc(cc2)O
Canonical SMILESCACTVS3.341 CC\C(c1ccc(O)cc1)=C(CC)/c2ccc(O)cc2
Canonical SMILESOpenEye OEToolkits1.5.0 CC/C(=C(/CC)\c1ccc(cc1)O)/c2ccc(cc2)O
InChIInChI1.03 InChI=1S/C18H20O2/c1-3-17(13-5-9-15(19)10-6-13)18(4-2)14-7-11-16(20)12-8-14/h5-12,19-20H,3-4H2,1-2H3/b18-17+
InChIKeyInChI1.03 RGLYKWWBQGJZGM-ISLYRVAYSA-N

Drug Info: DrugBank

DrugBank data are sourced from datasets licensed under a Creative Common's Attribution-NonCommercial 4.0 International License
DrugBank IDDB00255 
NameDiethylstilbestrol
Groups
  • withdrawn
  • approved
  • investigational
DescriptionA synthetic nonsteroidal estrogen used in the treatment of menopausal and postmenopausal disorders. It was also used formerly as a growth promoter in animals. According to the Fourth Annual Report on Carcinogens (NTP 85-002, 1985), diethylstilbestrol has been listed as a known carcinogen. (Merck, 11th ed) The FDA withdrew its approval for the use of all oral and parenteral drug products containing 25 milligrams or more of diethylstilbestrol per unit dose.[L43942]
Synonyms
  • trans-Diethylstilbestrol
  • Diethylstilbestrolum
  • Diethylstilbestrol
  • α,α'-diethyl-(E)-4,4'-stilbenediol
  • trans-Diethylstilboesterol
Brand Names
  • Stilbestrol 0.5mg Tablet
  • Stilbestrol Tablets 0.5 mg
  • Stilbestrol Tablets 1.0 mg
  • Stilbestrol 1.0mg Tablet
  • Stilbestrol Tablets 0.1 mg
IndicationUsed in the treatment of prostate cancer. Previously used in the prevention of miscarriage or premature delivery in pregnant women prone to miscarriage or premature delivery.
Categories
  • Adrenal Cortex Hormones
  • Antineoplastic Agents, Hormonal
  • Antineoplastic and Immunomodulating Agents
  • BCRP/ABCG2 Inhibitors
  • Benzene Derivatives
ATC-Code
  • L02AA04
  • L02AA01
  • G03CC05
  • G03CB02
CAS number56-53-1

Drug Targets

DrugBank data are sourced from datasets licensed under a Creative Common's Attribution-NonCommercial 4.0 International License
NameTarget SequencePharmacological ActionActions
Estrogen receptor betaMDIKNSPSSLNSPSSYNCSQSILPLEHGSIYIPSSYVDSHHEYPAMTFYS...unknownagonist
Estrogen receptorMTMTLHTKASGMALLHQIQGNELEPLNRPQLKIPLERPLGEVYLDSSKPA...unknownagonist
Estrogen-related receptor gammaMDSVELCLPESFSLHYEEELLCRMSNKDRHIDSSCSSFIKTEPSSPASLT...unknownagonist
Steroid hormone receptor ERR1MSSQVVGIEPLYIKAEPASPDSPKGSSETETEPPVALAPGPAPTRCLPGH...unknown
Steroid hormone receptor ERR2MSSDDRHLGSSCGSFIKTEPSSPSSGIDALSHHSPSGSSDASGGFGLALG...unknown
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 CHEMBL411
PubChem 448537
ChEMBL CHEMBL411
ChEBI CHEBI:92795, CHEBI:41922
CCDC/CSD ESTILO03, DESTDM01, XEHNON, XEHPAB, XEHNED, NOCTAD, NOCSUW, NOCSIK, ETSTIL10, NOCTEH, NOCSAC, ESTILO02
COD 2102206, 2102207, 2102209, 2102208, 2102210