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

[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

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 75 Target ID: CHEMBL2093866 Sources: http://www.ncbi.nlm.nih.gov/pubmed/4740596	Antagonist 2778		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 2678

Conditions

Condition	Modality	Targets	Highest Phase	Product
Breast cancer 434 Sources: https://www.jsps.go.jp/j-bilat/semin/gan_report/1978_cancer/breast_report.html	Primary		Approved 8429	THIODROL Approved Use Unknown

PubMed

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

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 `Fri Dec 15 15:03:06 GMT 2023` Edited by `admin` on `Fri Dec 15 15:03:06 GMT 2023`
Record UNII	YE7586973L
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

EPITIOSTANOL

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