TRIMEGESTONE

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C22H30O3
Molecular Weight	342.4718
Optical Activity	UNSPECIFIED
Defined Stereocenters	5 / 5
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

[H][C@@]12CC[C@](C)(C(=O)[C@H](C)O)[C@@]1(C)CCC3=C4CCC(=O)C=C4CC[C@@]23[H]

InChI

InChIKey=JUNDJWOLDSCTFK-MTZCLOFQSA-N

InChI=1S/C22H30O3/c1-13(23)20(25)22(3)11-9-19-18-6-4-14-12-15(24)5-7-16(14)17(18)8-10-21(19,22)2/h12-13,18-19,23H,4-11H2,1-3H3/t13-,18+,19-,21-,22+/m0/s1

HIDE SMILES / InChI

Molecular Formula	C22H30O3
Molecular Weight	342.4718
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	5 / 5
E/Z Centers	0
Optical Activity	UNSPECIFIED

Description
Sources: https://botplusweb.portalfarma.com/documentos/FICHAS%20TECNICAS%20POR%20FECHAS%20DE%20ALTA%20PDF/2001-06%20PDF/f63974%20Ondeva.PDF | https://www.pfizerpro.cl/sites/g/files/g10051801/f/201611/TOTELLE%20CONTINUO%201_0%2C125%20GRAGEAS-Jun%2007.pdf | https://www.ncbi.nlm.nih.gov/pubmed/11772282

Trimegestone is a 19-norpregnane progestin. It has a potent progesterone receptor and very low androgen receptor affinities but no detectable affinity to oestrogen receptor. Trimegestone has been developed for use in conjunction with oestrogen and 17-beta-estradiol for postmenopausal hormone replacement therapy. In vitro studies have shown that trimegestone can inhibit cytochrome P450 2C19 (CYP2C19). Although its clinical importance is unknown, trimegestone can moderately elevate the plasma concentration of drugs metabolized through CYP2C19, such as citalopram, imipramine and diazepam. Trimegestone is an effective and well-tolerated new progestin, which does not negate the beneficial effects of oestrogen on lipids.

Approval Year

PubMed

Title	Date	PubMed
Acceptability and patterns of endometrial bleeding in estradiol-based HRT regimens: a comparative study of cyclical sequential combinations of trimegestone or norethisterone acetate.	2001 Dec	11770191
Assessment of the metabolic tolerance in postmenopausal women over a 1-year period of two hormone replacement therapies containing estradiol in combination with either norgestrel or trimegestone.	2002 Apr	12012627
Increased resistance to activated protein C after short-term oral hormone replacement therapy in healthy post-menopausal women.	2002 Dec	12472583
Classification and pharmacology of progestins.	2003 Dec 10	14670641
Current state of hormone replacement therapy: the case for using trimegestone.	2006 Jul	19803961
Which progestogen is more likely to increase the risk of fatal myocardial infarction: a combination of epidemiological and trial evidence.	2006 May 20	16364575

Sample Use Guides

In Vivo Use Guide

The treatment consists of a 28-day administration cycle starting with a daily estradiol tablet for 2 weeks, from day 1 to 14, then a daily administration of combined estradiol/trimegestone tablet for 2 weeks, from day 15 to the day 28.

Route of Administration: Oral

Substance Class	Chemical Created by `admin` on `Sun Dec 18 21:17:01 UTC 2022` Edited by `admin` on `Sun Dec 18 21:17:01 UTC 2022`
Record UNII	4658K0H08W
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

TRIMEGESTONE

Official Name

English

RU-27987

Code

English

RU 27987

Code

English

17?-(S)-Lactoyl-17-methylestra-4,9-dien-3-one

Systematic Name

English

ESTRA-4,9-DIEN-3-ONE, 17-(2-HYDROXY-1-OXOPROPYL)-17-METHYL-, (17.BETA.(S))-

Common Name

English

trimegestone [INN]

Common Name

English

TRIMEGESTONE [MART.]

Common Name

English

Trimegestone [WHO-DD]

Common Name

English

TRIMEGESTONE [USAN]

Common Name

English

Classification Tree Code System Code

WHO-VATC

QG03FA16