OXENDOLONE

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C20H30O2
Molecular Weight	302.451
Optical Activity	UNSPECIFIED
Defined Stereocenters	7 / 7
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

[H][C@@]12C[C@H](CC)[C@H](O)[C@@]1(C)CC[C@]3([H])[C@@]4([H])CCC(=O)C=C4CC[C@@]23[H]

InChI

InChIKey=FCKLFGKATYPJPG-SSTBVEFVSA-N

InChI=1S/C20H30O2/c1-3-12-11-18-17-6-4-13-10-14(21)5-7-15(13)16(17)8-9-20(18,2)19(12)22/h10,12,15-19,22H,3-9,11H2,1-2H3/t12-,15-,16+,17+,18-,19-,20-/m0/s1

HIDE SMILES / InChI

Molecular Formula	C20H30O2
Molecular Weight	302.451
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	7 / 7
E/Z Centers	0
Optical Activity	UNSPECIFIED

Description
Sources: http://www.ncbi.nlm.nih.gov/pubmed/294104
Curator's Comment: Description was created based on several sources, including http://www.ncbi.nlm.nih.gov/pubmed/2430141 and http://www.genome.jp/dbget-bin/www_bget?D01329

Oxendolone (brand name Prostetin; former name TSAA-291 is a steroidal antiandrogen and progestin of the 19-nortestosterone group that has been marketed in Japan by Takeda for the treatment of benign prostatic hyperplasia (BPH) since 1981. It is androgen receptor antagonist and it binds to progesterone receptor. It also acts as a weak but clinically relevant inhibitor of 5α-reductase. Oxendolone is approved for the treatment of BPH in Japan.

Originator

Approval Year

Targets

Primary Target	Pharmacology	Potency
Androgen Receptor 167 Target ID: CHEMBL1871 Sources: http://www.genome.jp/dbget-bin/www_bget?D01329	Antagonist 2778	320.0 nM [Ki]
Progesterone receptor 61 Target ID: CHEMBL208 Sources: http://www.ncbi.nlm.nih.gov/pubmed/2430141	Antagonist 2778	20.0 nM [Ki]
Steroid 5-alpha-reductase 15 Target ID: CHEMBL2096664 Sources: http://www.ncbi.nlm.nih.gov/pubmed/7292540	Inhibitor 8297	1.4 µM [IC50]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Benign prostatic hypertrophy 1 Sources: http://www.ncbi.nlm.nih.gov/pubmed/2451412	Primary		Approved 8429	Prostetin Approved Use Indications: prostatic hyperplasia

PubMed

Title	Date	PubMed
Anti-androgen TSAA-291. VII. On the mechanism of anti-androgenic action of 16 beta-ethyl-17 beta-hydroxy-4-oestren-3-one (TSAA-291).	1979	294104
Anti-androgen TSAA-291. III. Hormonal spectra of anti-androgen TSAA-291 (16 beta-ethyl-17 beta-hydroxy-4-oestren-3-one) and its derivatives.	1979	294106
Effect of 16 beta-ethyl-17 beta-hydroxy-4-estren-3-one (TSAA-291) on the binding of promegestone (R5020) and methyltrienolone (R1881) to hyperplastic and neoplastic human prostate.	1986 Sep	2430141

Patents

Sample Use Guides

In Vivo Use Guide

i.m. injections of 400 mg oxendolone for 12 weeks

Route of Administration: Intramuscular

In Vitro Use Guide

Oxendolone inhibited 5-alpha-reductase activity in rat ventral prostates with IC 1.4uM

Substance Class	Chemical Created by `admin` on `Fri Dec 15 15:47:42 UTC 2023` Edited by `admin` on `Fri Dec 15 15:47:42 UTC 2023`
Record UNII	MN4I850D4P
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

OXENDOLONE

Official Name

English

OXENDOLONE [USAN]

Common Name

English

Oxendolone [WHO-DD]

Common Name

English

OXENDOLONE [MI]

Common Name

English

16β-Ethyl-17β-hydroxyestr-4-en-3-one

Systematic Name

English

oxendolone [INN]

Common Name

English

OXENDOLONE [MART.]

Common Name

English

ESTR-4-EN-3-ONE, 16-ETHYL-17-HYDROXY-, (16.BETA.,17.BETA.)-

Systematic Name

English

TSAA-291

Code

English

OXENDOLONE [JAN]

Common Name

English

Code System Code Type Description

ChEMBL

CHEMBL513856