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
Tibolone is not converted by human aromatase to 7alpha-methyl-17alpha-ethynylestradiol (7alpha-MEE): analyses with sensitive bioassays for estrogens and androgens and with LC-MSMS.	2003 Mar	12628686
Bone and muscle protective potential of the prostate-sparing synthetic androgen 7alpha-methyl-19-nortestosterone: evidence from the aged orchidectomized male rat model.	2005 Apr	15784189
Comparison of the growth-promoting effects of testosterone and 7-alpha-methyl-19-nor-testosterone (MENT) on the prostate and levator ani muscle of LPB-tag transgenic mice.	2006 Mar 1	16302273
Steroid hormones for contraception in men.	2007 Apr 18	17443545
The latest options and future agents for treating male hypogonadism.	2007 Dec	18001258
7alpha-methyl-19-nortestosterone (MENT) vs testosterone in combination with etonogestrel implants for spermatogenic suppression in healthy men.	2007 Sep-Oct	17460095
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 GMT 2023` Edited by `admin` on `Fri Dec 15 15:16:09 GMT 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