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
Rat uterine complement C3 expression as a model for progesterone receptor modulators: characterization of the new progestin trimegestone.	2001 Aug	11566438
Effects of 17 beta-estradiol and trimegestone alone, and in combination, on the bone and uterus of ovariectomized rats.	2001 Aug	11560106
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
Effect of trimegestone alone or in combination with estradiol on bone mass and bone turnover in an adult rat model of osteopenia.	2001 Feb	11293924
A 1-year comparison of the efficacy and clinical tolerance in postmenopausal women of two hormone replacement therapies containing estradiol in combination with either norgestrel or trimegestone.	2001 Oct	11727357
Trimegestone: expanding therapeutic choices for the treatment of the menopause.	2001 Sep	11772282
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
Effects of hormone replacement therapy on blood platelets.	2002 Aug	12190961
Gateways to clinical trials.	2002 Dec	12616965
Increased resistance to activated protein C after short-term oral hormone replacement therapy in healthy post-menopausal women.	2002 Dec	12472583
Progestogens in hormonal replacement therapy: new molecules, risks, and benefits.	2002 Jan-Feb	11791081
[Pharma-Clinics. Medication of the month. Totelle Cycle: new sequential estrogen/progesterone regimen for hormone replacement therapy in menopause].	2002 Jun	12180037
Oral oestradiol/trimegestone replacement reduces procarboxypeptidase U (TAFI): a randomized, placebo- controlled, 12-week study in early postmenopausal women.	2002 Mar	11886484
The effect of a change in the dose of trimegestone on the pattern of bleeding in estrogen-treated post-menopausal women: 6 month extension of a dose-ranging study.	2002 May	11980769
Gateways to clinical trials.	2002 Nov	12616707
Classification and pharmacology of progestins.	2003 Dec 10	14670641
Gateways to clinical trials.	2003 Nov	14685303
Clinical experience with trimegestone as a new progestin in HRT.	2003 Nov	14667984
The preclinical biology of a new potent and selective progestin: trimegestone.	2003 Nov	14667983
Hormone therapy and the cardiovascular system: the critical role of progestins.	2003 Oct	15018245
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
New progestogens: a review of their effects in perimenopausal and postmenopausal women.	2004	15493951
Pharmacological profile of progestins.	2004 Apr 15	15063480
Trimegestone in a low-dose, continuous-combined hormone therapy regimen prevents bone loss in osteopenic postmenopausal women.	2004 May-Jun	15167314
Randomized trial of effects of estradiol in combination with either norethisterone acetate or trimegestone on lipids and lipoproteins in postmenopausal women.	2004 Sep	15669554
Efficacy on climacteric symptoms of a continuous combined regimen of 1 mg 17beta-estradiol and trimegestone versus two regimens combining 1 or 2 mg 17beta-estradiol and norethisterone acetate.	2005 Aug	16294457
Molecular and pharmacological properties of a potent and selective novel nonsteroidal progesterone receptor agonist tanaproget.	2005 Aug 5	15937332
Quantitative analysis of gene regulation by seven clinically relevant progestins suggests a highly similar mechanism of action through progesterone receptors in T47D breast cancer cells.	2005 Dec	16157482
Sleep apnea and hormone replacement therapy: a pilot study and a literature review.	2005 Jan	15603568
Differential effects of estrogens and progestins on the anticoagulant tissue factor pathway inhibitor in the rat.	2005 Mar	15857755
Pharmacology of different progestogens: the special case of drospirenone.	2005 Oct	16203650
Current state of hormone replacement therapy: the case for using trimegestone.	2006 Jul	19803961
New progestagens for contraceptive use.	2006 Mar-Apr	16291771
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
Parallel assessment of the impact of different hormone replacement therapies on breast density by radiologist- and computer-based analyses of mammograms.	2008 Apr	18365856
Inhibitors and activation markers of the haemostatic system during hormone therapy: a comparative study of oral estradiol (2 mg)/ dydrogesterone and estradiol (2 mg)/ trimegestone.	2008 Aug	18690345
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
Cardiovascular risk markers during treatment with estradiol and trimegestone or dydrogesterone.	2009 Mar 20	19268506
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

Substance Class	Chemical Created by `admin` on `Sat Dec 16 18:02:25 GMT 2023` Edited by `admin` on `Sat Dec 16 18:02:25 GMT 2023`
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

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