EPITIOSTANOL

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 Search

SMILES

C[C@]12CC[C@H]3[C@@H](CC[C@H]4C[C@@H]5S[C@@H]5C[C@]34C)[C@@H]1CC[C@@H]2O

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

Molecular Formula	C19H30OS
Molecular Weight	306.506
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	9 / 9
E/Z Centers	0
Optical Activity	UNSPECIFIED

Description
Sources: http://www.ncbi.nlm.nih.gov/pubmed/4740596
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

Targets

Primary Target	Pharmacology	Condition	Potency
Estrogen receptor 72 Target ID: CHEMBL2093866 Sources: http://www.ncbi.nlm.nih.gov/pubmed/4740596	Antagonist 2849		0.78 µM [Ki]
Androgen receptor 42 Target ID: P10275 Gene ID: 367.0 Gene Symbol: AR Target Organism: Homo sapiens (Human) Sources: http://www.ncbi.nlm.nih.gov/pubmed/4740596	Agonist 2752

Conditions

Condition	Modality	Targets	Highest Phase	Product
Breast cancer 432 Sources: https://www.jsps.go.jp/j-bilat/semin/gan_report/1978_cancer/breast_report.html	Primary		Approved 8583	THIODROL Approved Use Unknown

Doses

Dose	Population	Adverse events
30 mg 1 times / day multiple, oral Highest studied dose Dose: 30 mg, 1 times / day Route: oral Route: multiple Dose: 30 mg, 1 times / day Sources: https://academic.oup.com/jjco/article-abstract/4/1/65/859994	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: F Food Status: UNKNOWN Sources: https://academic.oup.com/jjco/article-abstract/4/1/65/859994	Other AEs: Hoarseness, Hirsutism... Other AEs: Hoarseness (grade 1-2) Hirsutism (grade 1-2) Sources: https://academic.oup.com/jjco/article-abstract/4/1/65/859994

AEs

AE	Significance	Dose	Population
Hirsutism	grade 1-2	30 mg 1 times / day multiple, oral Highest studied dose Dose: 30 mg, 1 times / day Route: oral Route: multiple Dose: 30 mg, 1 times / day Sources: https://academic.oup.com/jjco/article-abstract/4/1/65/859994	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: F Food Status: UNKNOWN Sources: https://academic.oup.com/jjco/article-abstract/4/1/65/859994
Hoarseness	grade 1-2	30 mg 1 times / day multiple, oral Highest studied dose Dose: 30 mg, 1 times / day Route: oral Route: multiple Dose: 30 mg, 1 times / day Sources: https://academic.oup.com/jjco/article-abstract/4/1/65/859994	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: F Food Status: UNKNOWN Sources: https://academic.oup.com/jjco/article-abstract/4/1/65/859994

PubMed

Title	Date	PubMed
Progesterone receptor membrane component-1 regulates hepcidin biosynthesis.	2016-01	26657863
Estrogen-depleted condition induces apoptosis of rat mammary cancer cells after entering the S-phase of the cell cycle.	1995-04	7641294
Absorption and disposition of epithiosteroids in rats (1): Route of administration and plasma levels of epitiostanol.	1991-07	1776262
Human mammary cancer cell mutants with altered hormone receptor activity.	1986-08	3023306
Differential response of an ovarian-responsive mouse mammary tumor to androgenic and estrogenic agents.	1983-08	6861137
Antitumor effect of two oral steroids, mepitiostane and fluoxymesterone, on a pregnancy-dependent mouse mammary tumor (TPDMT-4).	1977-12	922732
Effects of 2alpha, 3alpha-epithio-5alpha-androstan-17beta-ol (epitiostanol) on hypothalamo-pituitary-gonadal axis in humans.	1975-01	1224948

Patents

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.

Substance Class	Chemical Created by `admin` on `Mon Mar 31 17:36:47 GMT 2025` Edited by `admin` on `Mon Mar 31 17:36:47 GMT 2025`
Record UNII	YE7586973L
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

EPITIOSTANOL

Official Name

English

10275-S

Preferred 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

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