PROMEGESTONE

Possibly Marketed Outside US

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C22H30O2
Molecular Weight	326.4724
Optical Activity	UNSPECIFIED
Defined Stereocenters	4 / 4
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

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

InChI

InChIKey=QFFCYTLOTYIJMR-XMGTWHOFSA-N

InChI=1S/C22H30O2/c1-4-20(24)22(3)12-10-19-18-7-5-14-13-15(23)6-8-16(14)17(18)9-11-21(19,22)2/h13,18-19H,4-12H2,1-3H3/t18-,19+,21+,22-/m1/s1

HIDE SMILES / InChI

Molecular Formula	C22H30O2
Molecular Weight	326.4724
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	4 / 4
E/Z Centers	0
Optical Activity	UNSPECIFIED

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/6366037 | https://www.ncbi.nlm.nih.gov/pubmed/9927618 | http://www.doctissimo.fr/medicament-SURGESTONE.htm

Promegestone (R 5020) is a potent progestin devoid of androgenic side-effects and has marked anti-estrogenic activity. Promegestone is an AChR noncompetitive antagonist that may alter AChR function by interactions at the lipid-protein interface. Promegestone is used in the treatment of gynecological disorders due to luteal insufficiency.

Approval Year

PubMed

Title	Date	PubMed
Interactions of methoxyacetic acid with androgen receptor.	2009-07-15	18486176
Expression and regulation of tumor necrosis factor (TNF) and TNF-receptor family members in the macaque corpus luteum during the menstrual cycle.	2009-04	18932199
Effects of drospirenone on cardiovascular markers in human aortic endothelial cells.	2009-02	18979300
A composite intronic element directs dynamic binding of the progesterone receptor and GATA-2.	2009-01	19036901
Progesterone suppresses an oxytocin-stimulated signal pathway in COS-7 cells transfected with the oxytocin receptor.	2008-12-22	18674552
Changes in protein tyrosine phosphatase type IVA member 1 and zinc finger protein 36 C3H type-like 1 expression demonstrate altered estrogen and progestin effect in medroxyprogesterone acetate-resistant and estrogen-independent breast cancer cell models.	2008-10-14	19146866
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
Glucocorticoid receptor phosphorylation differentially affects target gene expression.	2008-08	18483179
Progestin-regulated luminal cell and myoepithelial cell-specific responses in mammary organoid culture.	2008-05	18218689
Parallel assessment of the impact of different hormone replacement therapies on breast density by radiologist- and computer-based analyses of mammograms.	2008-04	18365856
Progesterone receptor rapid signaling mediates serine 345 phosphorylation and tethering to specificity protein 1 transcription factors.	2008-04	18202149
Correlation of estrogen sulfotransferase activity and proliferation in normal and carcinomatous human breast. A hypothesis.	2007-11-01	17970064
Progesterone receptor regulates Bcl-2 gene expression through direct binding to its promoter region in uterine leiomyoma cells.	2007-11	17785366
Progestins and breast cancer.	2007-10	17943537
Regulation of 17-beta hydroxysteroid dehydrogenase type 2 in human placental endothelial cells.	2007-09	17538076
Are steroids obligatory mediators of luteinizing hormone/human chorionic gonadotropin-triggered resumption of meiosis in mammals?	2007-09	17525120
Preclinical and clinical properties of trimegestone: a potent and selective progestin.	2007-06	17616854
Oral progestagens before menopause and breast cancer risk.	2007-03-12	17299388
R5020 and RU486 act as progesterone receptor agonists to enhance Sp1/Sp4-dependent gene transcription by an indirect mechanism.	2007-03	17192405
Regulation of expression of the retinoic acid metabolizing enzyme CYP26A1 in uteri of ovariectomized mice after treatment with ovarian steroid hormones.	2007-02	16955405
Testosterone and progesterone rapidly attenuate plasma membrane Gbetagamma-mediated signaling in Xenopus laevis oocytes by signaling through classical steroid receptors.	2007-01	17021048
[Functional study of progesterone receptor isoforms in endometrial cancer cell lines].	2006-10-18	17068617
Steroid receptor profiling of vinclozolin and its primary metabolites.	2006-10-01	16750840
SP1 and SP3 mediate progesterone-dependent induction of the 17beta hydroxysteroid dehydrogenase type 2 gene in human endometrium.	2006-10	16807381
Androgens, progestins, and glucocorticoids induce follicle-stimulating hormone beta-subunit gene expression at the level of the gonadotrope.	2006-09	16675544
Dimethandrolone undecanoate: a new potent orally active androgen with progestational activity.	2006-06	16497801
Trimegestone differentially modulates the expression of matrix metalloproteinases in the endometrial stromal cell.	2006-03	16556677
Role of nonhuman primate models in the discovery and clinical development of selective progesterone receptor modulators (SPRMs).	2006	17118172
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
Progestin activation of nongenomic pathways via cross talk of progesterone receptor with estrogen receptor beta induces proliferation of endometrial stromal cells.	2005-12	16020483
New progestagens for contraceptive use.	2005-11-18	16291771
Biochemical characterization of the Arctic char (Salvelinus alpinus) ovarian progestin membrane receptor.	2005-11-10	16281974
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
Dynamic expression of caspase-2, -3, -8, and -9 proteins and enzyme activity, but not messenger ribonucleic acid, in the monkey corpus luteum during the menstrual cycle.	2005-04	15671090
Differential effects of estrogens and progestins on the anticoagulant tissue factor pathway inhibitor in the rat.	2005-03	15857755
Recent insight on the control of enzymes involved in estrogen formation and transformation in human breast cancer.	2005-02	15860265
Basis of melengestrol acetate action as a progestin.	2005-02	15713363
Progesterone receptors: their localization, binding activity and expression in the pig oviduct during follicular and luteal phases.	2005-01	15620808
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
Progesterone promotes oocyte maturation, but not ovulation, in nonhuman primate follicles without a gonadotropin surge.	2004-07	14985242
The selective estrogen enzyme modulators in breast cancer: a review.	2004-06-07	15172700
One year comparison between two add-back therapies in patients treated with a GnRH agonist for symptomatic endometriosis: a randomized double-blind trial.	2004-06	15105403
Trimegestone in a low-dose, continuous-combined hormone therapy regimen prevents bone loss in osteopenic postmenopausal women.	2004-05-29	15167314
Short-chain fatty acids enhance nuclear receptor activity through mitogen-activated protein kinase activation and histone deacetylase inhibition.	2004-05-04	15103026
Epidermal growth factor suppresses induction by progestin of the adhesion protein desmoplakin in T47D breast cancer cells.	2004	15084247

Patents

Sample Use Guides

In Vivo Use Guide

The daily dosage in luteal insufficiency is usually 0.125 mg to 0.500 mg daily in a single dose from the 16th to the 25th day of the cycle. In the replacement therapy for menopause, isolated estrogen therapy is not recommended (risk of endometrial hyperplasia). In this case, the promégestone must be prescribed for the last 12 days of each therapeutic sequence, followed by an interruption of any replacement treatment lasting approximately one week, during which it is usual to observe a withdrawal haemorrhage. The effective dosage varies from one subject to another. It is usually 0.250 mg to 0.500 mg / day in a single dose. It should be adjusted individually according to the clinical presentation, the dose of estrogen used and the patient's response.

Route of Administration: Oral

Substance Class	Chemical Created by `admin` on `Wed Apr 02 06:54:11 GMT 2025` Edited by `admin` on `Wed Apr 02 06:54:11 GMT 2025`
Record UNII	9XE0V2SQYX
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

SURGESTONE

Preferred Name

English

PROMEGESTONE

Official Name

English

promegestone [INN]

Common Name

English

PROMEGESTONE [MI]

Common Name

English

Promegestone [WHO-DD]

Common Name

English

PROMEGESTONE [MART.]

Common Name

English

Classification Tree Code System Code

WHO-VATC

QG03DB07