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

[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

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 This drug under trade name MODRASTANE was withdrawn from human use in the United States market.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 8297
3-beta-hydroxysteroid dehydrogenase/delta 5-->4-isomerase type I 1 Target ID: CHEMBL1958 Sources: https://www.ncbi.nlm.nih.gov/pubmed/6589100	Inhibitor 8297

Conditions

Condition	Modality	Highest Phase	Product
Cushing’s disease 13 Sources: https://www.ncbi.nlm.nih.gov/pubmed/7067627	Primary	Approved 8429	modrenal Approved Use Unknown
Pituitary-dependent hyperadrenocorticism 1 Sources: https://dailymed.nlm.nih.gov/dailymed/archives/fdaDrugInfo.cfm?archiveid=11916	Primary	Approved 8429	VETORYL Approved Use Unknown
Conn’s syndrome 1 Sources: https://www.ncbi.nlm.nih.gov/pubmed/7067627	Primary	Approved 8429	modrenal Approved Use Unknown
Post-menopausal breast cancer 1 Sources: https://www.ncbi.nlm.nih.gov/pubmed/17109615	Primary	Approved 8429	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
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
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

PubMed

Title	Date	PubMed
Inhibition of human placental progesterone synthesis and aromatase activity by synthetic steroidogenic inhibitors in vitro.	1983 Jun	6574022
Expression of LH receptor in nonpregnant mouse endometrium: LH induction of 3β-HSD and de novo synthesis of progesterone.	2012 Oct	22875961
Effects of fibroblast growth factor 9 (FGF9) on steroidogenesis and gene expression and control of FGF9 mRNA in bovine granulosa cells.	2012 Sep	22798350
Temporal changes in biological responses and uncertainty in assessing risks of endocrine-disrupting chemicals: insights from intensive time-course studies with fish.	2015 Apr	25564424
17β-trenbolone, an anabolic-androgenic steroid as well as an environmental hormone, contributes to neurodegeneration.	2015 Jan 1	25461682

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

Name

Type

Language

TRILOSTANE

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