3WF

Ethinyl estradiol

Created: 2014-11-26
Last modified:  2015-09-09

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Chemical Details

Formal Charge0
Atom Count46
Chiral Atom Count5
Bond Count49
Aromatic Bond Count6
2D diagram of 3WF
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Chemical Component Summary

NameEthinyl estradiol
Systematic Name (OpenEye OEToolkits)(8R,9S,13S,14S,17R)-17-ethynyl-13-methyl-7,8,9,11,12,14,15,16-octahydro-6H-cyclopenta[a]phenanthrene-3,17-diol
FormulaC20 H24 O2
Molecular Weight296.403
TypeNON-POLYMER

Chemical Descriptors

TypeProgram Version Descriptor
SMILESACDLabs12.01Oc1cc4c(cc1)C3CCC2(C(CCC2(C#C)O)C3CC4)C
SMILESCACTVS3.385C[C]12CC[CH]3[CH](CCc4cc(O)ccc34)[CH]1CC[C]2(O)C#C
SMILESOpenEye OEToolkits1.9.2CC12CCC3c4ccc(cc4CCC3C1CCC2(C#C)O)O
Canonical SMILESCACTVS3.385 C[C@]12CC[C@H]3[C@@H](CCc4cc(O)ccc34)[C@@H]1CC[C@@]2(O)C#C
Canonical SMILESOpenEye OEToolkits1.9.2 C[C@]12CC[C@@H]3c4ccc(cc4CC[C@H]3[C@@H]1CC[C@]2(C#C)O)O
InChIInChI1.03 InChI=1S/C20H24O2/c1-3-20(22)11-9-18-17-6-4-13-12-14(21)5-7-15(13)16(17)8-10-19(18,20)2/h1,5,7,12,16-18,21-22H,4,6,8-11H2,2H3/t16-,17-,18+,19+,20+/m1/s1
InChIKeyInChI1.03 BFPYWIDHMRZLRN-SLHNCBLASA-N

Drug Info: DrugBank

DrugBank IDDB00977 
NameEthinylestradiol
Groups approved
DescriptionEthinylestradiol was first synthesized in 1938 by Hans Herloff Inhoffen and Walter Hohlweg at Schering.[A191107] It was developed in an effort to create an estrogen with greater oral bioavailability.[A191107] These properties were achieved by the substitution of an ethinyl group at carbon 17 of [estradiol].[A191107] Ethinylestradiol soon replaced [mestranol] in contraceptive pills.[A191107] Ethinylestradiol was granted FDA approval on 25 June 1943.[L11884]
Synonyms
  • 17-ethinyl-3,17-estradiol
  • Ethinyloestradiol
  • Ethinyl estradiol
  • Etinilestradiol
  • Ethinylestradiolum
Brand Names
  • Ortho 1/35 Tablets (28 Day)
  • Enpresse
  • Drospirenone and Ethinyl Estradiol Tablets 21
  • Junel 21 Day
  • Tri-cyclen Lo (21 Day)
IndicationEthinylestradiol is combined with other drugs for use as a contraceptive, premenstrual dysphoric disorder, moderate acne, moderate to severe vasomotor symptoms of menopause, prevention of postmenopausal osteoporosis.[L11944,L11965,L11947,L11950,L11845,L9806,L11953,L10304,L11956,L11959,L11962]
Categories
  • Adrenal Cortex Hormones
  • Antineoplastic and Immunomodulating Agents
  • BSEP/ABCB11 inducers
  • BSEP/ABCB11 Inhibitors
  • COMT Substrates
ATC-Code
  • G03AA15
  • G03AA11
  • L02AA03
  • G03AA12
  • G03AA16
CAS number57-63-6

Drug Targets

NameTarget SequencePharmacological ActionActions
Estrogen receptorMTMTLHTKASGMALLHQIQGNELEPLNRPQLKIPLERPLGEVYLDSSKPA...unknownagonist
Nuclear receptor subfamily 1 group I member 2MEVRPKESWNHADFVHCEDTESVPGKPSVNADEEVGGPQICRVCGDKATG...unknownagonist
Cytochrome P450 3A4MALIPDLAMETWLLLAVSLVLLYLYGTHSHGLFKKLGIPGPTPLPFLGNI...unknownsubstrate
Cytochrome P450 2C8MEPFVVLVLCLSFMLLFSLWRQSCRRRKLPPGPTPLPIIGNMLQIDVKDI...unknownsubstrate,inhibitor
Cytochrome P450 2C9MDSLVVLVLCLSCLLLLSLWRQSSGRGKLPPGPTPLPVIGNILQIGIKDI...unknownsubstrate
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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 CHEMBL691
PubChem 5991
ChEMBL CHEMBL691
ChEBI CHEBI:4903
CCDC/CSD MIFPOI, PEPVOY, VOBNEG, NOTBOQ, MIFQID, FISWIN, FISWIN01, VOBMIJ, NOTCAD, VOBMOP, MIFRAW, VOBNIK, MIFPAU, VOBNAC, NOTDOS, VOBMIJ01, VOBNEG01