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

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
Progestogens in hormonal replacement therapy: new molecules, risks, and benefits.	2002 Jan-Feb	11791081
Classification and pharmacology of progestins.	2003 Dec 10	14670641
New progestogens: a review of their effects in perimenopausal and postmenopausal women.	2004	15493951
Pharmacological profile of progestins.	2004 Apr 15	15063480
Current state of hormone replacement therapy: the case for using trimegestone.	2006 Jul	19803961
Trimegestone differentially modulates the expression of matrix metalloproteinases in the endometrial stromal cell.	2006 Mar	16556677
New progestagens for contraceptive use.	2006 Mar-Apr	16291771
Free synthetic and natural estrogen hormones in influent and effluent of three municipal wastewater treatment plants.	2007 Sep	17910365
Evaluation of extended and continuous use oral contraceptives.	2008 Oct	19209272
Classification and pharmacology of progestins.	2008 Sep-Oct	19434889
Pharmacological profile of progestins.	2008 Sep-Oct	19434887
Presence of steroid hormones and antibiotics in surface water of agricultural, suburban and mixed-use areas.	2009 Jul	18568409
Identification of genes influencing skeletal phenotypes in congenic P/NP rats.	2010 Jun	20200994
The use of newer progestins for contraception.	2010 Nov	20933114
The haunting of medical journals: how ghostwriting sold "HRT".	2010 Sep 7	20838656

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

Name

Type

Language

TRIMEGESTONE

Official Name

English

RU-27987

Code

English

RU 27987

Code

English

17β-(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