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

Details

Stereochemistry ABSOLUTE
Molecular Formula C19H30OS
Molecular Weight 306.506
Optical Activity UNSPECIFIED
Defined Stereocenters 9 / 9
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of EPITIOSTANOL

SMILES

[H][C@]12C[C@]3([H])CC[C@@]4([H])[C@]5([H])CC[C@H](O)[C@@]5(C)CC[C@]4([H])[C@@]3(C)C[C@@]1([H])S2

InChI

InChIKey=OBMLHUPNRURLOK-XGRAFVIBSA-N
InChI=1S/C19H30OS/c1-18-8-7-14-12(13(18)5-6-17(18)20)4-3-11-9-15-16(21-15)10-19(11,14)2/h11-17,20H,3-10H2,1-2H3/t11-,12-,13-,14-,15-,16+,17-,18-,19-/m0/s1

HIDE SMILES / InChI

Description
Curator's Comment: description was created based on several sources, including, http://www.ncbi.nlm.nih.gov/pubmed/3023306,

Epitiostanol is androgenic antiestrogen developed for the treatment of breast cancer. The drug inhibits estrogen receptor and activates androgen receptor and was shown to be active in vitro on MCF-7, U-2 and U-3 cells. The current marketing status of Epitiostanol is unknown and is supposed to be "discontimued".

Originator

Approval Year

Unknown
139594
Targets

Targets

Primary TargetPharmacologyConditionPotency
Antagonist
2778
 0.78 µM [Ki]
Androgen receptor
42
Target ID: P10275
Gene ID: 367.0
Gene Symbol: AR
Target Organism: Homo sapiens (Human)
Agonist
2678
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Approved
8429
THIODROL

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
Effects of 2alpha, 3alpha-epithio-5alpha-androstan-17beta-ol (epitiostanol) on hypothalamo-pituitary-gonadal axis in humans.
1975 Jan
Antitumor effect of two oral steroids, mepitiostane and fluoxymesterone, on a pregnancy-dependent mouse mammary tumor (TPDMT-4).
1977 Dec
Differential response of an ovarian-responsive mouse mammary tumor to androgenic and estrogenic agents.
1983 Aug
Human mammary cancer cell mutants with altered hormone receptor activity.
1986 Aug
Absorption and disposition of epithiosteroids in rats (1): Route of administration and plasma levels of epitiostanol.
1991 Jul
Estrogen-depleted condition induces apoptosis of rat mammary cancer cells after entering the S-phase of the cell cycle.
1995 Apr
Patents

Patents

JPH07215878A
2

Sample Use Guides

In Vivo Use Guide
Unknown
Route of Administration: Unknown
In Vitro Use Guide
MCF-7, U-2 and U-3 cell lines were treated with Epitiostanol to test the cells resistance. EC50 values were 3*10(-8), 3*10(-5) and 3*10(-5) M, respectively.
Name Type Language
EPITIOSTANOL
INN   JAN   MART.   MI   WHO-DD  
INN  
Official Name English
EPITHIOANDROSTANOL
Systematic Name English
Epitiostanol [WHO-DD]
Common Name English
EPITIOSTANOL [JAN]
Common Name English
EPITIOSTANOL [MI]
Common Name English
EPITIOSTANOL [MART.]
Common Name English
10275-S
Code English
epitiostanol [INN]
Common Name English
2.ALPHA.,3.ALPHA.-EPITHIO-5.ALPHA.-ANDROSTAN-17.BETA.-OL
Systematic Name English
NSC-194684
Code English
Classification Tree Code System Code
NCI_THESAURUS C2360
Created by admin on Fri Dec 15 15:03:06 GMT 2023 , Edited by admin on Fri Dec 15 15:03:06 GMT 2023
NCI_THESAURUS C243
Created by admin on Fri Dec 15 15:03:06 GMT 2023 , Edited by admin on Fri Dec 15 15:03:06 GMT 2023
Code System Code Type Description
MERCK INDEX
m4950
Created by admin on Fri Dec 15 15:03:06 GMT 2023 , Edited by admin on Fri Dec 15 15:03:06 GMT 2023
PRIMARY Merck Index
CAS
2363-58-8
Created by admin on Fri Dec 15 15:03:06 GMT 2023 , Edited by admin on Fri Dec 15 15:03:06 GMT 2023
PRIMARY
NCI_THESAURUS
C1089
Created by admin on Fri Dec 15 15:03:06 GMT 2023 , Edited by admin on Fri Dec 15 15:03:06 GMT 2023
PRIMARY
INN
3530
Created by admin on Fri Dec 15 15:03:06 GMT 2023 , Edited by admin on Fri Dec 15 15:03:06 GMT 2023
PRIMARY
MESH
C002976
Created by admin on Fri Dec 15 15:03:06 GMT 2023 , Edited by admin on Fri Dec 15 15:03:06 GMT 2023
PRIMARY
FDA UNII
YE7586973L
Created by admin on Fri Dec 15 15:03:06 GMT 2023 , Edited by admin on Fri Dec 15 15:03:06 GMT 2023
PRIMARY
ChEMBL
CHEMBL2106161
Created by admin on Fri Dec 15 15:03:06 GMT 2023 , Edited by admin on Fri Dec 15 15:03:06 GMT 2023
PRIMARY
SMS_ID
100000080494
Created by admin on Fri Dec 15 15:03:06 GMT 2023 , Edited by admin on Fri Dec 15 15:03:06 GMT 2023
PRIMARY
NSC
194684
Created by admin on Fri Dec 15 15:03:06 GMT 2023 , Edited by admin on Fri Dec 15 15:03:06 GMT 2023
PRIMARY
WIKIPEDIA
EPITIOSTANOL
Created by admin on Fri Dec 15 15:03:06 GMT 2023 , Edited by admin on Fri Dec 15 15:03:06 GMT 2023
PRIMARY
DRUG CENTRAL
3181
Created by admin on Fri Dec 15 15:03:06 GMT 2023 , Edited by admin on Fri Dec 15 15:03:06 GMT 2023
PRIMARY
EPA CompTox
DTXSID2045367
Created by admin on Fri Dec 15 15:03:06 GMT 2023 , Edited by admin on Fri Dec 15 15:03:06 GMT 2023
PRIMARY
PUBCHEM
443935
Created by admin on Fri Dec 15 15:03:06 GMT 2023 , Edited by admin on Fri Dec 15 15:03:06 GMT 2023
PRIMARY
EVMPD
SUB06572MIG
Created by admin on Fri Dec 15 15:03:06 GMT 2023 , Edited by admin on Fri Dec 15 15:03:06 GMT 2023
PRIMARY
ACTIVE MOIETY
Structure of EPITIOSTANOL
NIH
NCATS
PRIVACY ACT
ACCESSIBILITY
DISCLAIMER
HHS VULNERABILITY DISCLOSURE
For language access assistance, contact the NCATS Public Information Officer
National Center for Advancing Translational Sciences (NCATS),
6701 Democracy Boulevard, Bethesda MD 20892-4874 • 301-594-8966