TRIMEGESTONE

Possibly Marketed Outside US

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

C[C@H](O)C(=O)[C@@]1(C)CC[C@H]2[C@@H]3CCC4=CC(=O)CCC4=C3CC[C@]12C

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
The use of newer progestins for contraception.	2010-11	20933114
The haunting of medical journals: how ghostwriting sold "HRT".	2010-09-07	20838656
Identification of genes influencing skeletal phenotypes in congenic P/NP rats.	2010-06	20200994
Presence of steroid hormones and antibiotics in surface water of agricultural, suburban and mixed-use areas.	2009-07	18568409
Classification and pharmacology of progestins.	2009-05-13	19434889
Pharmacological profile of progestins.	2009-05-13	19434887
Cardiovascular risk markers during treatment with estradiol and trimegestone or dydrogesterone.	2009-03-20	19268506
Evaluation of extended and continuous use oral contraceptives.	2008-10	19209272
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.	2008-08	18690345
Parallel assessment of the impact of different hormone replacement therapies on breast density by radiologist- and computer-based analyses of mammograms.	2008-04	18365856
Free synthetic and natural estrogen hormones in influent and effluent of three municipal wastewater treatment plants.	2007-09	17910365
Preclinical and clinical properties of trimegestone: a potent and selective progestin.	2007-06	17616854
Current state of hormone replacement therapy: the case for using trimegestone.	2006-07	19803961
Which progestogen is more likely to increase the risk of fatal myocardial infarction: a combination of epidemiological and trial evidence.	2006-05-20	16364575
Trimegestone differentially modulates the expression of matrix metalloproteinases in the endometrial stromal cell.	2006-03	16556677
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.	2005-12	16157482
New progestagens for contraceptive use.	2005-11-18	16291771
Pharmacology of different progestogens: the special case of drospirenone.	2005-10	16203650
Bleeding profile and endometrial safety of continuous combined regimens 1 mg 17beta-estradiol/trimegestone versus 1 or 2 mg 17beta-estradiol/norethisterone acetate in postmenopausal women.	2005-09	16353319
Molecular and pharmacological properties of a potent and selective novel nonsteroidal progesterone receptor agonist tanaproget.	2005-08-05	15937332
A comparative 2-year study of the effects of sequential regimens of 1 mg 17beta-estradiol and trimegestone with a regimen containing estradiol valerate and norethisterone on the bleeding profile and endometrial safety in postmenopausal women.	2005-08	16294460
A study of the control of climacteric symptoms in postmenopausal women following sequential regimens of 1 mg 17beta-estradiol and trimegestone compared with a regimen containing 1 mg estradiol valerate and norethisterone over a two-year period.	2005-08	16294458
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.	2005-08	16294457
Differential effects of estrogens and progestins on the anticoagulant tissue factor pathway inhibitor in the rat.	2005-03	15857755
Sleep apnea and hormone replacement therapy: a pilot study and a literature review.	2005-01	15603568
Randomized trial of effects of estradiol in combination with either norethisterone acetate or trimegestone on lipids and lipoproteins in postmenopausal women.	2004-09	15669554
Trimegestone in a low-dose, continuous-combined hormone therapy regimen prevents bone loss in osteopenic postmenopausal women.	2004-05-29	15167314
Pharmacological profile of progestins.	2004-04-15	15063480
New progestogens: a review of their effects in perimenopausal and postmenopausal women.	2004	15493951
Classification and pharmacology of progestins.	2003-12-10	14670641
Gateways to clinical trials.	2003-11	14685303
Clinical experience with trimegestone as a new progestin in HRT.	2003-11	14667984
The preclinical biology of a new potent and selective progestin: trimegestone.	2003-11	14667983
Hormone therapy and the cardiovascular system: the critical role of progestins.	2003-10	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.	2003-09	12970290
Gateways to clinical trials.	2002-12	12616965
Increased resistance to activated protein C after short-term oral hormone replacement therapy in healthy post-menopausal women.	2002-12	12472583
Gateways to clinical trials.	2002-11	12616707
Effects of hormone replacement therapy on blood platelets.	2002-08	12190961
[Pharma-Clinics. Medication of the month. Totelle Cycle: new sequential estrogen/progesterone regimen for hormone replacement therapy in menopause].	2002-06	12180037
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.	2002-05	11980769
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.	2002-04	12012627
Oral oestradiol/trimegestone replacement reduces procarboxypeptidase U (TAFI): a randomized, placebo- controlled, 12-week study in early postmenopausal women.	2002-03	11886484
Progestogens in hormonal replacement therapy: new molecules, risks, and benefits.	2002-01-16	11791081
Acceptability and patterns of endometrial bleeding in estradiol-based HRT regimens: a comparative study of cyclical sequential combinations of trimegestone or norethisterone acetate.	2001-12	11770191
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.	2001-10	11727357
Trimegestone: expanding therapeutic choices for the treatment of the menopause.	2001-09	11772282
Rat uterine complement C3 expression as a model for progesterone receptor modulators: characterization of the new progestin trimegestone.	2001-08	11566438
Effects of 17 beta-estradiol and trimegestone alone, and in combination, on the bone and uterus of ovariectomized rats.	2001-08	11560106
Effect of trimegestone alone or in combination with estradiol on bone mass and bone turnover in an adult rat model of osteopenia.	2001-02	11293924

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

Preferred Name

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