CHEBI:32260 - trilostane

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ChEBI Name trilostane
ChEBI ID CHEBI:32260
Definition An epoxy steroid that is 3,17β-dihydroxy-5α-androst-2-ene-2-carbonitrile in which the oxygen of the epoxy group is joined to the 4α and 5 α positions.
Stars This entity has been manually annotated by the ChEBI Team.
Supplier Information ChemicalBook:CB9258118, ZINC000003875484
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Fluoxymesterone, sold under the brand names Halotestin and Ultandren among others, is an androgen and anabolic steroid (AAS) medication which is used in the treatment of low testosterone levels in men, delayed puberty in boys, breast cancer in women, and anemia. It is taken by mouth. Side effects of fluoxymesterone include symptoms of masculinization like acne, increased hair growth, voice changes, and increased sexual desire. It can also cause liver damage and cardiovascular side effects like high blood pressure. The drug is a synthetic androgen and anabolic steroid and hence is an agonist of the androgen receptor (AR), the biological target of androgens like testosterone and dihydrotestosterone (DHT). It has strong androgenic effects and moderate anabolic effects, which make it useful for producing masculinization. Fluoxymesterone was first described in 1956 and was introduced for medical use in 1957. In addition to its medical use, fluoxymesterone is used to improve physique and performance. The drug is a controlled substance in many countries and so non-medical use is generally illicit.
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Formula C20H27NO3
Net Charge 0
Average Mass 329.43332
Monoisotopic Mass 329.19909
InChI InChI=1S/C20H27NO3/c1-18-7-6-14-12(13(18)3-4-15(18)22)5-8-20-17(24-20)16(23)11(10-21)9-19(14,20)2/h12-15,17,22-23H,3-9H2,1-2H3/t12-,13-,14-,15-,17+,18-,19+,20+/m0/s1
InChIKey KVJXBPDAXMEYOA-CXANFOAXSA-N
SMILES [H][C@@]12CC[C@@]34O[C@@H]3C(O)=C(C[C@]4(C)[C@@]1([H])CC[C@]1(C)[C@@H](O)CC[C@@]21[H])C#N
Roles Classification
Biological Role(s): EC 1.1.1.210 [3beta(or 20alpha)-hydroxysteroid dehydrogenase] inhibitor
An EC 1.1.1.* (oxidoreductase acting on donor CH-OH group, NAD+ or NADP+ acceptor) inhibitor which interferes with the action of 3beta-hydroxysteroid dehydrogenase (EC 1.1.1.210), a group of steroidogenic enzymes.
Application(s): antineoplastic agent
A substance that inhibits or prevents the proliferation of neoplasms.
abortifacient
A chemical substance that interrupts pregnancy after implantation.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing trilostane (CHEBI:32260) has role abortifacient (CHEBI:50691)
trilostane (CHEBI:32260) has role antineoplastic agent (CHEBI:35610)
trilostane (CHEBI:32260) has role EC 1.1.1.210 [3β(or 20α)-hydroxysteroid dehydrogenase] inhibitor (CHEBI:50788)
trilostane (CHEBI:32260) is a 17β-hydroxy steroid (CHEBI:35343)
trilostane (CHEBI:32260) is a 3-hydroxy steroid (CHEBI:36834)
trilostane (CHEBI:32260) is a androstanoid (CHEBI:50402)
trilostane (CHEBI:32260) is a epoxy steroid (CHEBI:145217)
trilostane (CHEBI:32260) is a nitrile (CHEBI:18379)
IUPAC Name
3,17β-dihydroxy-4α,5-epoxy-5α-androst-2-ene-2-carbonitrile
INNs Sources
trilostane ChemIDplus
trilostano ChemIDplus
trilostanum ChemIDplus
Manual Xrefs Databases
1891 VSDB
2746 DrugCentral
D01180 KEGG DRUG
DB01108 DrugBank
Trilostane Wikipedia
US3296255 Patent
View more database links
Registry Number Type Source
13647-35-3 CAS Registry Number KEGG DRUG
Last Modified
28 October 2019