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
Effects of 17 beta-estradiol and trimegestone alone, and in combination, on the bone and uterus of ovariectomized rats.	2001 Aug	11560106
Increased resistance to activated protein C after short-term oral hormone replacement therapy in healthy post-menopausal women.	2002 Dec	12472583
Gateways to clinical trials.	2003 Nov	14685303
Effect of hormone replacement therapy on plasma levels of the cardiovascular risk factor asymmetric dimethylarginine: a randomized, placebo-controlled 12-week study in healthy early postmenopausal women.	2003 Sep	12970290
Pharmacological profile of progestins.	2004 Apr 15	15063480
Preclinical and clinical properties of trimegestone: a potent and selective progestin.	2007 Jun	17616854
Free synthetic and natural estrogen hormones in influent and effluent of three municipal wastewater treatment plants.	2007 Sep	17910365
Pharmacological profile of progestins.	2008 Sep-Oct	19434887
The use of newer progestins for contraception.	2010 Nov	20933114

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