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CHEBI:75172 - formestane

ChEBI IDCHEBI:75172
ChEBI Nameformestane
Stars
DefinitionA 17-oxo steroid that is androst-4-ene-3,17-dione in which the hydrogen at position 4 is replaced by a hydroxy group. Formestane was the first selective, type I steroidal aromatase inhibitor, suppressing oestrogen production from anabolic steroids or prohormones. It was formerly used in the treatment of oestrogen-receptor positive breast cancer in post-meopausal women. As it has poor oral bioavailability, it had to be administered by (fortnightly) intramuscular injection. It fell out of use with the subsequent development of cheaper, orally active aromatase inhibitors. Formestane is listed by the World Anti-Doping Agency as a substance prohibited from use by athletes.
Last Modified22 February 2017
SubmitterGareth Owen
DownloadsMolfile
FormulaC19H26O3
Net Charge0
Average Mass302.414
Monoisotopic Mass302.18819
SMILES[H][C@@]12CCC3=C(O)C(=O)CC[C@]3(C)[C@@]1([H])CC[C@]1(C)C(=O)CC[C@@]21[H]
InChIInChI=1S/C19H26O3/c1-18-10-8-15(20)17(22)14(18)4-3-11-12-5-6-16(21)19(12,2)9-7-13(11)18/h11-13,22H,3-10H2,1-2H3/t11-,12-,13-,18+,19-/m0/s1
InChIKeyOSVMTWJCGUFAOD-KZQROQTASA-N
Wikipedia
Roles Classification
Biological Role:
EC 1.14.14.14 (aromatase) inhibitor  An EC 1.14.14.* (oxidoreductase acting on paired donors, incorporating of 1 atom of oxygen, with reduced flavin or flavoprotein as one donor) inhibitor which interferes with the action of aromatase (EC 1.14.14.14) and so reduces production of estrogenic steroid hormones.
Application:
antineoplastic agent  A substance that inhibits or prevents the proliferation of neoplasms.
ChEBI Ontology
Outgoing Relation(s)
formestane (CHEBI:75172) has parent hydride androstane (CHEBI:35509)
formestane (CHEBI:75172) has role antineoplastic agent (CHEBI:35610)
formestane (CHEBI:75172) has role EC 1.14.14.14 (aromatase) inhibitor (CHEBI:50790)
formestane (CHEBI:75172) is a 17-oxo steroid (CHEBI:19168)
formestane (CHEBI:75172) is a 3-oxo-Δ4 steroid (CHEBI:47909)
formestane (CHEBI:75172) is a enol (CHEBI:33823)
formestane (CHEBI:75172) is a hydroxy steroid (CHEBI:35350)
IUPAC Name 
4-hydroxyandrost-4-ene-3,17-dione
INNs  Source
formestanumWHO MedNet
formestaneChemIDplus
formestanoWHO MedNet
formestaneWHO MedNet
Synonyms  Source
4-hydroxyandrostenedioneChemIDplus
4-hydroxy-Δ4-androstenedioneChEBI
4-OH-AChemIDplus
CGP 32349ChemIDplus
CGP-32349ChemIDplus
4-hydroxy-4-androstene-3,17-dioneChemIDplus
Manual XrefsDatabases
DB08905DrugBank
D07260KEGG DRUG
FormestaneWikipedia
1238DrugCentral
Registry NumbersSources
Reaxys:4198373Reaxys
CAS:566-48-3ChemIDplus
Citations