GESTRINONE

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C21H24O2
Molecular Weight	308.4141
Optical Activity	UNSPECIFIED
Defined Stereocenters	4 / 4
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

[H][C@@]12CC[C@@](O)(C#C)[C@@]1(CC)C=CC3=C4CCC(=O)C=C4CC[C@@]23[H]

InChI

InChIKey=BJJXHLWLUDYTGC-ANULTFPQSA-N

InChI=1S/C21H24O2/c1-3-20-11-9-17-16-8-6-15(22)13-14(16)5-7-18(17)19(20)10-12-21(20,23)4-2/h2,9,11,13,18-19,23H,3,5-8,10,12H2,1H3/t18-,19+,20+,21+/m1/s1

HIDE SMILES / InChI

Description
Sources: https://gp2u.com.au/static/pdf/D/DIMETRIOSE-PI.pdf

Gestrinone is a synthetic trienic 19-norsteroid developed for the treatment of endometriosis. Gestrinone exerts its activity by activating androgen and progesterone receptors. The drug was approved for use in Latin America, Australia and Europe.

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Androgen receptor 42 Target ID: P10275 Gene ID: 367.0 Gene Symbol: AR Target Organism: Homo sapiens (Human) Sources: https://gp2u.com.au/static/pdf/D/DIMETRIOSE-PI.pdf	Agonist 2678		0.59 nM [EC50]
Progesterone receptor 61 Target ID: P06401 Gene ID: 5241.0 Gene Symbol: PGR Target Organism: Homo sapiens (Human) Sources: https://gp2u.com.au/static/pdf/D/DIMETRIOSE-PI.pdf	Agonist 2678		30.0 nM [EC50]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Endometriosis 32 Sources: https://gp2u.com.au/static/pdf/D/DIMETRIOSE-PI.pdf	Primary		Approved 8429	DIMETRIOSE Approved Use Mild to moderate endometriosis with or without accompanying sterility. Treatment is limited to a single course of six months duration per lifetime.

PubMed

Title	Date	PubMed
Long-term follow-up of a controlled trial of laser laparoscopy for pelvic pain.	2001 Apr-Jun	11394422
Gonadotrophin-releasing hormone analogues for endometriosis: bone mineral density.	2003	14583930
Medical therapy of endometriosis.	2003 May	12917790
Athletes' "designer steroid" leads to widening scandal.	2003 Nov 1	14603927
Evaluation of progesterone and estrogen receptor expression in 15 meningiomas of dogs and cats.	2003 Oct	14596471
Anabolic-androgenic steroids and testosterone precursors: ergogenic aids and sport.	2004 Aug	15231229
Potential action of androstenedione on the proliferation and apoptosis of stromal endometrial cells.	2004 Dec 10	15588330
Doping by design.	2004 Feb	14743721
Emerging drugs for endometriosis.	2004 May	15155142
Screening of anabolic steroids in horse urine by liquid chromatography-tandem mass spectrometry.	2005 Apr 29	15862683
Screening for unknown synthetic steroids in human urine by liquid chromatography-tandem mass spectrometry.	2005 Jul	15934041
Detecting doping.	2005 Jun 1	15957228
[Effect of gestrinone on growth and apoptosis in isolated ectopic endometrium cells in vitro].	2005 May	15938784
Cardiovascular toxicities of performance-enhancing substances in sports.	2005 Oct	16212144
Doping control analysis in human urine by liquid chromatography-electrospray ionization ion trap mass spectrometry for the Olympic Games Athens 2004: determination of corticosteroids and quantification of ephedrines, salbutamol and morphine.	2006 Jul 28	17723530
Comparison of crystal structures of human androgen receptor ligand-binding domain complexed with various agonists reveals molecular determinants responsible for binding affinity.	2006 May	16641486
Preoperative treatment for hysteroscopic surgery.	2006 Oct	16926013
Comparative study on the efficacy of Yiweining and Gestrinone for post-operational treatment of stage III endometriosis.	2006 Sep	17005086
Breast pain.	2007 Apr 1	19454068
Endometriosis.	2007 Mar 1	19454060
Mechanism of emergency contraception with gestrinone: a preliminary investigation.	2007 Sep	17707720
Screening of in vitro synthesised metabolites of 4,9,11-trien-3-one steroids by liquid chromatography mass spectrometry.	2008	18708698
Endometriosis: current and future medical therapies.	2008 Apr	18036995
Induction of micronuclei in V79 cells by the anabolic doping steroids tetrahydrogestrinone and trenbolone.	2008 Apr	17764006
Does gestrinone antagonize the effects of estrogen on endometrial implants upon the peritoneum of rats?	2008 Aug	18719766
[Determination of three anabolic steroids by liquid chromatography-mass spectrometry].	2008 Jul	18959243
Structure-activity relationships of synthetic progestins in a yeast-based in vitro androgen bioassay.	2008 May	18395441
Comprehensive screening of acidic and neutral drugs in equine plasma by liquid chromatography-tandem mass spectrometry.	2008 May 2	18054785
Detection of anabolic steroid abuse using a yeast transactivation system.	2008 Oct	18550137
A simple and rapid ESI-LC-MS/MS method for simultaneous screening of doping agents in urine samples.	2009 Apr	20336223
Effect of Yikun Neiyi Wan on the expression of aromatase P450, COX-2, and ER related receptor in endometrial cells in vitro from patients with endometriosis.	2009 Dec	20112494
[Treatment for endometriosis].	2009 Jul-Sep	19994769
Ovulation-stimulation drugs and cancer risks: a long-term follow-up of a British cohort.	2009 Jun 2	19436296
Gestrinone compared with mifepristone for emergency contraception: a randomized controlled trial.	2010 Apr	20308833
Generic sample preparation combined with high-resolution liquid chromatography-time-of-flight mass spectrometry for unification of urine screening in doping-control laboratories.	2010 Apr	20155493
Endometriosis.	2010 Aug 13	21418683
Vaginal adenosarcoma arising from refractory endometriosis: a case report.	2010 Dec	21133871

Patents

Sample Use Guides

In Vivo Use Guide

The recommended dosage is one capsule twice a week. The first dose should be taken on the first day of a menstrual cycle. The second dose should be taken three days later.

Route of Administration: Oral

In Vitro Use Guide

Ectopic endometrium cells were cultured and exposed to gestrinone of different doses of 0, 10(-6) and 10(-4) mol/L respectively. The inhibition of the cells during 48 hours was determined by methylthiazolyl tetrazolium (MTT) assay, and the cell growth curve was made. Gestrinone at different concentrations could inhibit the growth and proliferation of ectopic endometrium cells in a dose- and time-dependent manner. The inhibition rate of cell growth after exposed to gestrinone for 8, 16, 24, 32, 40 and 48 h was 99.6%, 87.3%, 79.8%, 62.3%, 51.7% and 44.2% in the 10(-6) mol/L group, and 99.2%, 77.1%, 69.6%, 51.1%, 33.7% and 23.6% in the 10(-4) mol/L group (P < 0.05), and cell growth curve was changed accordingly. After 24 hour exposure to gestrinone from 10(-6) to 10(-4) mol/l, apoptotic changes of cells were observed under transmission electron microscope.

Name

Type

Language

GESTRINONE

Official Name

English

RU 2323

Code

English

GESTRINONE [MI]

Common Name

English

13-Ethyl-17-hydroxy-18,19-dinor-17α-pregna-4,9,11-trien-20-yn-3-one

Systematic Name

English

RU-2323

Code

English

GESTRINONE [MART.]

Common Name

English

A 46 745

Code

English

R-2323

Code

English

gestrinone [INN]

Common Name

English

Gestrinone [WHO-DD]

Common Name

English

PREGNA-4,9,11-TRIEN-20-YN-3-ONE, 13-ETHYL-17-HYDROXY-18,19-DINOR-, (17.ALPHA.)-

Common Name

English

A-46745

Code

English

R 2323

Code

English

18,19-DINORPREGNA-4,9,11-TRIEN-20-YN-3-ONE, 13-ETHYL-17-HYDROXY-, (17.ALPHA.)-

Systematic Name

English

GESTRINONE [USAN]

Common Name

English

A-46-745

Code

English

GESTRINONE [JAN]

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C776