PROMEGESTONE

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

[H][C@@]12CC[C@](C)(C(=O)CC)[C@@]1(C)CCC3=C4CCC(=O)C=C4CC[C@@]23[H]

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
Progesterone receptor contains a proline-rich motif that directly interacts with SH3 domains and activates c-Src family tyrosine kinases.	2001 Aug	11545730
Transactivation of progestin- and estrogen-responsive promoters by 19-nor progestins in African Green Monkey Kidney CV1 cells.	2001 Dec	11954666
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
[Progression of a hepatic hemangioma under progestins].	2001 Jan	11300113
The selective estrogen enzyme modulator (SEEM) in breast cancer.	2001 Jan-Mar	11384867
Trimegestone: expanding therapeutic choices for the treatment of the menopause.	2001 Sep	11772282
Direct interaction of the Krüppel-like family (KLF) member, BTEB1, and PR mediates progesterone-responsive gene expression in endometrial epithelial cells.	2002 Jan	11751593
Expression of the progesterone receptor and progesterone- metabolising enzymes in the female and male human kidney.	2002 Nov	12429033
Regulation of nuclear receptor and cofactor expression in breast cancer cell lines.	2003 Apr	12656669
Mitogen-activated protein kinase regulates nuclear association of human progesterone receptors.	2003 Apr	12554776
Classification and pharmacology of progestins.	2003 Dec 10	14670641
Progestins activate vascular endothelial growth factor gene transcription in endometrial adenocarcinoma cells.	2003 Feb	12568850
Characterization and inhibition of fatty acid synthase in pediatric tumor cell lines.	2003 Mar-Apr	12820377
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
Cutaneous microvascular effects of mid-term hormone replacement therapy in healthy postmenopausal women: a prospective placebo controlled trial.	2003 Oct	14618108
Study of 202 natural, synthetic, and environmental chemicals for binding to the androgen receptor.	2003 Oct	14565775
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
Epidermal growth factor suppresses induction by progestin of the adhesion protein desmoplakin in T47D breast cancer cells.	2004	15084247
Intratumoural mRNA expression of genes from the oestradiol metabolic pathway and clinical and histopathological parameters of breast cancer.	2004	14979917
Nongenomic inhibition of oxytocin binding by progesterone in the ovine uterus.	2004 Jan	12954727
Basis of melengestrol acetate action as a progestin.	2005 Feb	15713363
Progesterone receptors: their localization, binding activity and expression in the pig oviduct during follicular and luteal phases.	2005 Jan	15620808
Biochemical characterization of the Arctic char (Salvelinus alpinus) ovarian progestin membrane receptor.	2005 Nov 10	16281974
Androgens, progestins, and glucocorticoids induce follicle-stimulating hormone beta-subunit gene expression at the level of the gonadotrope.	2006 Sep	16675544
Testosterone and progesterone rapidly attenuate plasma membrane Gbetagamma-mediated signaling in Xenopus laevis oocytes by signaling through classical steroid receptors.	2007 Jan	17021048
Regulation of 17-beta hydroxysteroid dehydrogenase type 2 in human placental endothelial cells.	2007 Sep	17538076
Are steroids obligatory mediators of luteinizing hormone/human chorionic gonadotropin-triggered resumption of meiosis in mammals?	2007 Sep	17525120
Correlation of estrogen sulfotransferase activity and proliferation in normal and carcinomatous human breast. A hypothesis.	2007 Sep-Oct	17970064
Glucocorticoid receptor phosphorylation differentially affects target gene expression.	2008 Aug	18483179

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 `Sat Dec 16 15:54:36 GMT 2023` Edited by `admin` on `Sat Dec 16 15:54:36 GMT 2023`
Record UNII	9XE0V2SQYX
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

PROMEGESTONE

Official Name

English

promegestone [INN]

Common Name

English

PROMEGESTONE [MI]

Common Name

English

SURGESTONE

Brand Name

English

Promegestone [WHO-DD]

Common Name

English

PROMEGESTONE [MART.]

Common Name

English

Classification Tree Code System Code

WHO-VATC

QG03DB07