TRESTOLONE ACETATE

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C21H30O3
Molecular Weight	330.4611
Optical Activity	UNSPECIFIED
Defined Stereocenters	7 / 7
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

[H][C@@]12CC[C@H](OC(C)=O)[C@@]1(C)CC[C@]3([H])[C@@]4([H])CCC(=O)C=C4C[C@@H](C)[C@@]23[H]

InChI

InChIKey=IVCRCPJOLWECJU-XQVQQVTHSA-N

InChI=1S/C21H30O3/c1-12-10-14-11-15(23)4-5-16(14)17-8-9-21(3)18(20(12)17)6-7-19(21)24-13(2)22/h11-12,16-20H,4-10H2,1-3H3/t12-,16+,17-,18+,19+,20-,21+/m1/s1

HIDE SMILES / InChI

Molecular Formula	C21H30O3
Molecular Weight	330.4611
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	6 / 7
E/Z Centers	0
Optical Activity	UNSPECIFIED

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/8146434 | https://adisinsight.springer.com/drugs/800016155 | Legato, M.J. (2009) Principles of Gender-Specific Medicine, page 363, retrieved from: https://books.google.ru/books?id=whb9hsUgZtwC

Trestolone is a synthetic androgen that inhibits the release of follicle-stimulating hormone and impairs spermatogenesis. Luteinizing hormone is also suppressed, which cuts production of testosterone. The azoospermia and oligospermia are reversible after discontinuation of trestolone. Trestolone has androgenic and anabolic properties and loss of secondary sex characteristics is not seen. Like testosterone, trestolone undergoes enzymatic aromatization to an estrogen. The use of trestolone instead of testosterone for androgen replacement therapy could have health-promoting effects by reducing the occurrence of prostate disease. Trestolone had been in phase II clinical trial for the andropause control. However, this development was discontinued.

Originator

Approval Year

PubMed

Title	Date	PubMed
Androgen responsiveness of the pituitary gonadotrope cell line LbetaT2.	2001 Sep	11524240
Effect of chronic administration of 7alpha-methyl-19-nortestosterone on serum testosterone, number of spermatozoa and fertility in adult male bonnet monkeys (Macaca radiata).	2002 Aug	12141943
Inhibition of recovery of spermatogenesis in irradiated rats by different androgens.	2002 Sep	12193551
Emerging drugs for hypogonadism.	2006 Nov	17064226
Steroid hormones for contraception in men.	2007 Apr 18	17443545
Dimethandrolone (7alpha,11beta-dimethyl-19-nortestosterone) and 11beta-methyl-19-nortestosterone are not converted to aromatic A-ring products in the presence of recombinant human aromatase.	2008 Jun	18555683
The potent synthetic androgens, dimethandrolone (7α,11β-dimethyl-19-nortestosterone) and 11β-methyl-19-nortestosterone, do not require 5α-reduction to exert their maximal androgenic effects.	2010 Oct	20599615
Effects of synthetic androgens on liver function using the rabbit as a model.	2010 Sep-Oct	20378929

Substance Class	Chemical Created by `admin` on `Fri Dec 15 15:16:09 UTC 2023` Edited by `admin` on `Fri Dec 15 15:16:09 UTC 2023`
Record UNII	52XDF4N1XL
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

TRESTOLONE ACETATE

Official Name

English

U-15,614

Code

English

17β-Hydroxy-7α-methylestr-4-en-3-one acetate

Common Name

English

CDB-903

Code

English

ESTR-4-EN-3-ONE, 17-(ACETYLOXY)-7-METHYL-, (7.ALPHA.,17.BETA.)-

Systematic Name

English

7.ALPHA.-METHYL-19-NORTESTOSTERONE ACETATE

Common Name

English

NSC-69948

Code

English

TRESTOLONE ACETATE [USAN]

Common Name

English

MENT ACETATE

Common Name

English

U-15614

Code

English

Classification Tree Code System Code

NCI_THESAURUS

C243