TRILOSTANE

US Previously Marketed

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 Search

SMILES

C[C@]12CC[C@H]3[C@@H](CC[C@@]45O[C@@H]4C(O)=C(C[C@]35C)C#N)[C@@H]1CC[C@@H]2O

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

Molecular Formula	C20H27NO3
Molecular Weight	329.4333
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	8 / 8
E/Z Centers	0
Optical Activity	UNSPECIFIED

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/7067627 | https://www.ncbi.nlm.nih.gov/pubmed/17109615 | https://dailymed.nlm.nih.gov/dailymed/archives/fdaDrugInfo.cfm?archiveid=11916

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 This drug under trade name MODRASTANE was withdrawn from human use in the United States market.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.

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
3-beta-hydroxysteroid dehydrogenase/delta 5-->4-isomerase type II 1 Target ID: CHEMBL3670 Sources: https://www.ncbi.nlm.nih.gov/pubmed/6589100	Inhibitor 8504
3-beta-hydroxysteroid dehydrogenase/delta 5-->4-isomerase type I 1 Target ID: CHEMBL1958 Sources: https://www.ncbi.nlm.nih.gov/pubmed/6589100	Inhibitor 8504

Conditions

Condition	Modality	Highest Phase	Product
Cushing’s disease 13 Sources: https://www.ncbi.nlm.nih.gov/pubmed/7067627	Primary	Approved 8583	modrenal Approved Use Unknown
Pituitary-dependent hyperadrenocorticism 1 Sources: https://dailymed.nlm.nih.gov/dailymed/archives/fdaDrugInfo.cfm?archiveid=11916	Primary	Approved 8583	VETORYL Approved Use Unknown
Conn’s syndrome 1 Sources: https://www.ncbi.nlm.nih.gov/pubmed/7067627	Primary	Approved 8583	modrenal Approved Use Unknown
Post-menopausal breast cancer 1 Sources: https://www.ncbi.nlm.nih.gov/pubmed/17109615	Primary	Approved 8583	modrenal Approved Use Unknown

Sourcing

Vendor/Aggregator	ID	URL
ChEBI	CHEBI:32260	https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:32260
ChemicalBook	CB4768762	https://www.chemicalbook.com/ChemicalProductProperty_EN_CB4768762
eMolecules	2733524	https://www.emolecules.com/cgi-bin/more?vid=2733524
eMolecules	29548589	https://www.emolecules.com/cgi-bin/more?vid=29548589
eMolecules	30487977	https://www.emolecules.com/cgi-bin/more?vid=30487977
MolPort	MolPort-003-850-727	https://www.molport.com/shop/molecule-link/MolPort-003-850-727
Selleck Chemicals	Trilostane	http://www.selleckchem.com/products/Trilostane.html
ZINC	ZINC000100038546	http://zinc15.docking.org/substances/ZINC000100038546

PubMed

Title	Date	PubMed
Temporal changes in biological responses and uncertainty in assessing risks of endocrine-disrupting chemicals: insights from intensive time-course studies with fish.	2015-04	25564424
17β-trenbolone, an anabolic-androgenic steroid as well as an environmental hormone, contributes to neurodegeneration.	2015-01-01	25461682
Expression of LH receptor in nonpregnant mouse endometrium: LH induction of 3β-HSD and de novo synthesis of progesterone.	2012-10	22875961
Effects of fibroblast growth factor 9 (FGF9) on steroidogenesis and gene expression and control of FGF9 mRNA in bovine granulosa cells.	2012-09	22798350
Decreased cytochrome c oxidase IV expression reduces steroidogenesis.	2011-08	21558439
The antidepressant-like effect of the 3β-hydroxysteroid dehydrogenase inhibitor trilostane involves a regulation of β-type estrogen receptors.	2011-03	20981412
The 3beta-hydroxysteroid dehydrogenase inhibitor trilostane shows antidepressant properties in mice.	2009-06	19117688
Cushing's disease in dogs and humans.	2009-01	19153526
Effects of a 3beta-hydroxysteroid dehydrogenase inhibitor, trilostane, on the fathead minnow reproductive axis.	2008-07	18397916
Evidence that the preovulatory rise in intrafollicular progesterone may not be required for ovulation in cattle.	2007-03	17332517
Inhibition of human placental progesterone synthesis and aromatase activity by synthetic steroidogenic inhibitors in vitro.	1983-06	6574022
Treatment of Cushing's syndrome with trilostane (WIN 24,540), an inhibitor of adrenal steroid biosynthesis.	1978-11	233687

Sample Use Guides

In Vivo Use Guide

for human: in postmenopausal cancer at a dose of 720 – 960 mg/day

Route of Administration: Oral

In Vitro Use Guide

Unknown

Substance Class	Chemical Created by `admin` on `Mon Mar 31 17:53:24 GMT 2025` Edited by `admin` on `Mon Mar 31 17:53:24 GMT 2025`
Record UNII	L0FPV48Q5R
Record Status	`Validated (UNII)`
Record Version

Download

Name

Type

Language

DESOPAN

Preferred Name

English

TRILOSTANE

Official Name

English

4?,5-Epoxy-3,17?-dihydroxy-5?-androst-2-ene-2-carbonitrile

Systematic 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