CHEBI:75172 - formestane

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ChEBI Name formestane
ChEBI ID CHEBI:75172
Definition A 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.
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Formula C19H26O3
Net Charge 0
Average Mass 302.40790
Monoisotopic Mass 302.18819
InChI InChI=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
InChIKey OSVMTWJCGUFAOD-KZQROQTASA-N
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]
Roles Classification
Biological Role(s): 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(s): antineoplastic agent
A substance that inhibits or prevents the proliferation of neoplasms.
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ChEBI Ontology
Outgoing 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 Sources
formestane ChemIDplus
formestane WHO MedNet
formestano WHO MedNet
formestanum WHO MedNet
Synonyms Sources
4-hydroxy-4-androstene-3,17-dione ChemIDplus
4-hydroxy-Δ4-androstenedione ChEBI
4-hydroxyandrostenedione ChemIDplus
4-OH-A ChemIDplus
4-OHAD ChEBI
CGP 32349 ChemIDplus
CGP-32349 ChemIDplus
Lentaron KEGG DRUG
Manual Xrefs Databases
1238 DrugCentral
D07260 KEGG DRUG
DB08905 DrugBank
Formestane Wikipedia
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Registry Numbers Types Sources
4198373 Reaxys Registry Number Reaxys
566-48-3 CAS Registry Number ChemIDplus
Citations Waiting for Citations Types Sources
1419285 PubMed citation Europe PMC
1637664 PubMed citation Europe PMC
17207827 PubMed citation Europe PMC
22354842 PubMed citation Europe PMC
23339113 PubMed citation Europe PMC
6665821 PubMed citation Europe PMC
Last Modified
22 February 2017