U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ABSOLUTE
Molecular Formula C20H27NO3
Molecular Weight 329.4333
Optical Activity UNSPECIFIED
Defined Stereocenters 8 / 8
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of TRILOSTANE

SMILES

[H][C@]12O[C@]13CC[C@@]4([H])[C@]5([H])CC[C@H](O)[C@@]5(C)CC[C@]4([H])[C@@]3(C)CC(C#N)=C2O

InChI

InChIKey=KVJXBPDAXMEYOA-CXANFOAXSA-N
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

HIDE SMILES / InChI
Trilostane is a synthetic steroid, which interferes with the formation of both cortisol and aldosterone. It is an inhibitor of 3 beta-hydroxysteroid dehydrogenase. This drug under trade name MODRASTANE was withdrawn from human use in the United States market. But marketed under the trade names Modrenal and is already approved in the United Kingdom for the treatment of advanced post-menopausal breast cancer and Cushing 's disease. In addition, this drug has been successfully developed and marketed for veterinary use in the United Kingdom under the trade name Vetoryl.

Approval Year

PubMed

PubMed

TitleDatePubMed
Treatment of Cushing's syndrome with trilostane (WIN 24,540), an inhibitor of adrenal steroid biosynthesis.
1978 Nov
Inhibition of human placental progesterone synthesis and aromatase activity by synthetic steroidogenic inhibitors in vitro.
1983 Jun
Evidence that the preovulatory rise in intrafollicular progesterone may not be required for ovulation in cattle.
2007 Mar
Effects of a 3beta-hydroxysteroid dehydrogenase inhibitor, trilostane, on the fathead minnow reproductive axis.
2008 Jul
Cushing's disease in dogs and humans.
2009 Jan
The 3beta-hydroxysteroid dehydrogenase inhibitor trilostane shows antidepressant properties in mice.
2009 Jun
Decreased cytochrome c oxidase IV expression reduces steroidogenesis.
2011 Aug
The antidepressant-like effect of the 3β-hydroxysteroid dehydrogenase inhibitor trilostane involves a regulation of β-type estrogen receptors.
2011 Mar
Expression of LH receptor in nonpregnant mouse endometrium: LH induction of 3β-HSD and de novo synthesis of progesterone.
2012 Oct
Effects of fibroblast growth factor 9 (FGF9) on steroidogenesis and gene expression and control of FGF9 mRNA in bovine granulosa cells.
2012 Sep
Temporal changes in biological responses and uncertainty in assessing risks of endocrine-disrupting chemicals: insights from intensive time-course studies with fish.
2015 Apr
17β-trenbolone, an anabolic-androgenic steroid as well as an environmental hormone, contributes to neurodegeneration.
2015 Jan 1

Sample Use Guides

for human: in postmenopausal cancer at a dose of 720 – 960 mg/day
Route of Administration: Oral
In Vitro Use Guide
Curator's Comment: Trilostane may have on cellular cultures of human mammary carcinoma (MCF-7 Evsa-T). Trilostane does not react with any of the main hormonal sex steroid receptors, nor does it interfere with cultures of human mammary cancer cells either containing estrogen receptors and therefore allegedly hormone-dependent (MCF-7 line), or estrogen receptor-negative cells, presumably independent of hormonal manipulations (Evsa-T cell line).
Unknown
Name Type Language
TRILOSTANE
GREEN BOOK   INN   JAN   MART.   MI   ORANGE BOOK   USAN   VANDF   WHO-DD  
INN   USAN  
Official Name English
4α,5-Epoxy-3,17β-dihydroxy-5α-androst-2-ene-2-carbonitrile
Systematic Name English
DESOPAN
Brand Name English
MODRENAL
Brand Name English
TRILOSTANE [GREEN BOOK]
Common Name English
trilostane [INN]
Common Name English
WIN 24,540
Code English
TRILOSTANE [MART.]
Common Name English
TRILOSTANE [JAN]
Common Name English
TRILOSTANE [VANDF]
Common Name English
TRILOSTANE [USAN]
Common Name English
WIN-24540
Code English
ANDROST-2-ENE-2-CARBONITRILE, 4,5-EPOXY-3,17-DIHYDROXY-, (4.ALPHA.,5.ALPHA.,17.BETA.)-
Systematic Name English
NSC-758904
Code English
TRILOSTANE [ORANGE BOOK]
Common Name English
TRILOSTANE [MI]
Common Name English
Trilostane [WHO-DD]
Common Name English
MODRASTANE
Brand Name English
Classification Tree Code System Code
CFR 21 CFR 520.2598
Created by admin on Fri Dec 15 15:18:11 UTC 2023 , Edited by admin on Fri Dec 15 15:18:11 UTC 2023
NCI_THESAURUS C2355
Created by admin on Fri Dec 15 15:18:11 UTC 2023 , Edited by admin on Fri Dec 15 15:18:11 UTC 2023
NCI_THESAURUS C2184
Created by admin on Fri Dec 15 15:18:11 UTC 2023 , Edited by admin on Fri Dec 15 15:18:11 UTC 2023
WHO-ATC H02CA01
Created by admin on Fri Dec 15 15:18:11 UTC 2023 , Edited by admin on Fri Dec 15 15:18:11 UTC 2023
WHO-VATC QH02CA01
Created by admin on Fri Dec 15 15:18:11 UTC 2023 , Edited by admin on Fri Dec 15 15:18:11 UTC 2023
NCI_THESAURUS C2017
Created by admin on Fri Dec 15 15:18:11 UTC 2023 , Edited by admin on Fri Dec 15 15:18:11 UTC 2023
Code System Code Type Description
NSC
758904
Created by admin on Fri Dec 15 15:18:11 UTC 2023 , Edited by admin on Fri Dec 15 15:18:11 UTC 2023
PRIMARY
EVMPD
SUB11297MIG
Created by admin on Fri Dec 15 15:18:11 UTC 2023 , Edited by admin on Fri Dec 15 15:18:11 UTC 2023
PRIMARY
IUPHAR
6850
Created by admin on Fri Dec 15 15:18:11 UTC 2023 , Edited by admin on Fri Dec 15 15:18:11 UTC 2023
PRIMARY
ChEMBL
CHEMBL1200907
Created by admin on Fri Dec 15 15:18:11 UTC 2023 , Edited by admin on Fri Dec 15 15:18:11 UTC 2023
PRIMARY
DAILYMED
L0FPV48Q5R
Created by admin on Fri Dec 15 15:18:11 UTC 2023 , Edited by admin on Fri Dec 15 15:18:11 UTC 2023
PRIMARY
FDA UNII
L0FPV48Q5R
Created by admin on Fri Dec 15 15:18:11 UTC 2023 , Edited by admin on Fri Dec 15 15:18:11 UTC 2023
PRIMARY
PUBCHEM
656583
Created by admin on Fri Dec 15 15:18:11 UTC 2023 , Edited by admin on Fri Dec 15 15:18:11 UTC 2023
PRIMARY
MERCK INDEX
m11137
Created by admin on Fri Dec 15 15:18:11 UTC 2023 , Edited by admin on Fri Dec 15 15:18:11 UTC 2023
PRIMARY Merck Index
RXCUI
38668
Created by admin on Fri Dec 15 15:18:11 UTC 2023 , Edited by admin on Fri Dec 15 15:18:11 UTC 2023
PRIMARY RxNorm
CAS
13647-35-3
Created by admin on Fri Dec 15 15:18:11 UTC 2023 , Edited by admin on Fri Dec 15 15:18:11 UTC 2023
PRIMARY
NCI_THESAURUS
C1263
Created by admin on Fri Dec 15 15:18:11 UTC 2023 , Edited by admin on Fri Dec 15 15:18:11 UTC 2023
PRIMARY
EPA CompTox
DTXSID9023706
Created by admin on Fri Dec 15 15:18:11 UTC 2023 , Edited by admin on Fri Dec 15 15:18:11 UTC 2023
PRIMARY
CHEBI
32260
Created by admin on Fri Dec 15 15:18:11 UTC 2023 , Edited by admin on Fri Dec 15 15:18:11 UTC 2023
PRIMARY
DRUG CENTRAL
2746
Created by admin on Fri Dec 15 15:18:11 UTC 2023 , Edited by admin on Fri Dec 15 15:18:11 UTC 2023
PRIMARY
SMS_ID
100000076938
Created by admin on Fri Dec 15 15:18:11 UTC 2023 , Edited by admin on Fri Dec 15 15:18:11 UTC 2023
PRIMARY
DRUG BANK
DB01108
Created by admin on Fri Dec 15 15:18:11 UTC 2023 , Edited by admin on Fri Dec 15 15:18:11 UTC 2023
PRIMARY
WIKIPEDIA
TRILOSTANE
Created by admin on Fri Dec 15 15:18:11 UTC 2023 , Edited by admin on Fri Dec 15 15:18:11 UTC 2023
PRIMARY
ECHA (EC/EINECS)
237-133-0
Created by admin on Fri Dec 15 15:18:11 UTC 2023 , Edited by admin on Fri Dec 15 15:18:11 UTC 2023
PRIMARY
MESH
C009954
Created by admin on Fri Dec 15 15:18:11 UTC 2023 , Edited by admin on Fri Dec 15 15:18:11 UTC 2023
PRIMARY
INN
3928
Created by admin on Fri Dec 15 15:18:11 UTC 2023 , Edited by admin on Fri Dec 15 15:18:11 UTC 2023
PRIMARY