16320-04-0

Basic information

• Product Name: Gestrinone
• Synonyms: (8s,13s,14s,17r)-13-ethyl-17-ethynyl-17-hydroxy-1,2,6,7,8,14,15,16-octahydrocyclopenta[a]phenanthren-3-one;13-ETHYL-17ALPHA-HYDROXY-18,19-DINORPREGNA-4,9,11-TRIEN-20-YN-3-ONE;D-GESTRINONE;GESTRINONE;13-beta-ethyl-17-alpha-ethinyl-17-hydroxy-gona-4,9,11-triene-3-one;13-ethyl-17-alpha-ethinyl-17-hydroxygon-4,9,11-trien-3-one;13-Ethyl-17α-ethynyl-17-hydroxy-4，9，11-gonatrien-3-one;A-46745
• CAS NO: 16320-04-0
• Molecular Formula: C₂₁H₂₄O₂
• Molecular Weight: 308.41
• EINECS: 685-143-2
• Product Categories: Active Pharmaceutical Ingredients;Hormone;Intermediates & Fine Chemicals;Pharmaceuticals;Steroids
• Mol File: 16320-04-0.mol
• Article Data: 1

Chemical Properties

• Melting Point: 150-152°C
• Boiling Point: 388.8°C (rough estimate)
• Flash Point: 214.913 °C
• Appearance: Light yellow solid
• Density: 1.1040 (rough estimate)
• Refractive Index: 1.4900 (estimate)
• Storage Temp.: -20°C Freezer
• PKA: 12.76±0.40(Predicted)
• Merck: 14,4415
• CAS DataBase Reference: Gestrinone(CAS DataBase Reference)
• NIST Chemistry Reference: Gestrinone(16320-04-0)
• EPA Substance Registry System: Gestrinone(16320-04-0)

Safety Data

• RTECS: JF7964000
• Hazardous Substances Data: 16320-04-0(Hazardous Substances Data)

Usage

Description

Gestrinone is a synthetic steroid with antiprogesterone and antiestrogenic activities. It is reported to be useful in the treatment of endometriosis and uterine leiom yomas.

Chemical Properties

Light Yellow Solid

Originator

Roussel UCLAF (France)

Uses

Steroidal antiestrogen, antiprogestogen, analog of Norgestrienone. Antigonadotropin. Controlled substance.

Brand name

DIMETROSE

InChI:InChI=1/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

Synthetic route

gestrinone (16320-04-0) → tetrahydrogestrinone-d4

Conditions	Yield
With deuterium; platinum(IV) oxide In methanol for 0.916667h;	81%

gestrinone (16320-04-0) → Tetrahydrogestrinone (618903-56-3)

Conditions	Yield
With hydrogen; platinum(IV) oxide In methanol for 0.916667h;	78%
With hydrogen; palladium 10% on activated carbon at 20℃; under 760.051 Torr; for 1h;	60%
With hydrogen; Lindlar's catalyst In ethanol at 20℃; for 0.5h;	30.1 mg
Multi-step reaction with 2 steps 1: H2 / Pd/BaSO4 / dioxane / atmospheric pressure 2: H2 / Pd/BaSO4 / dioxane / atmospheric pressure View Scheme

gestrinone (16320-04-0) → dihydrogestrinone (54322-37-1)

Conditions	Yield
With pyridine; hydrogen; palladium on activated charcoal In methanol	75%
With hydrogen; Pd-BaSO4 In 1,4-dioxane atmospheric pressure;

2-(aminooxy)acetic acid hemihydrochloride + gestrinone (16320-04-0) → C23H27NO4

Conditions	Yield
With potassium hydroxide In ethanol Heating;	75%

gestrinone (16320-04-0) → C23H31NO4

Conditions	Yield
Multi-step reaction with 3 steps 1: H2 / Pd/BaSO4 / dioxane / atmospheric pressure 2: H2 / Pd/BaSO4 / dioxane / atmospheric pressure 3: 55 percent / KOH / ethanol / 1 h / Heating View Scheme

gestrinone (16320-04-0) → C21H32O2

Conditions	Yield
Multi-step reaction with 4 steps 1: H2 / Pd/BaSO4 / dioxane / atmospheric pressure 2: H2 / Pd/BaSO4 / dioxane / atmospheric pressure 3: H2 / Pd/BaSO4 / dioxane / atmospheric pressure 4: H2 / Pd/BaSO4 / dioxane / atmospheric pressure View Scheme

gestrinone (16320-04-0) → 17β-Hydroxy-3-oxo-13β.17α-diaethyl-gonadien-(4.9) (14200-42-1)

Conditions	Yield
Multi-step reaction with 3 steps 1: H2 / Pd/BaSO4 / dioxane / atmospheric pressure 2: H2 / Pd/BaSO4 / dioxane / atmospheric pressure 3: H2 / Pd/BaSO4 / dioxane / atmospheric pressure View Scheme

Downstream Products

• 856893-82-8 tetrahydrogestrinone-d4 
• 618903-56-3 Tetrahydrogestrinone 

Related news

Endometrial patterns during therapy with danazol or Gestrinone (cas 16320-04-0) for endometriosis: Structural and ultrastructural study08/09/2019

We treated 36 women with laparoscopically proven endometriosis with danazol 600 mg/d (n = 17) or gestrinone 5.0 mg/wk (n = 19) for 6 months. Endometrial samples were obtained before and at 3 and 6 months of treatment and were studied by light, scanning, and transmission electron microscopy. At 3...detailed

Individual and combined effects of triptoreline and Gestrinone (cas 16320-04-0) on experimental endometriosis in rats08/08/2019

Objectives: To evaluate the effects of triptoreline, gestrinone, and both, on experimental endometriosis in rats. Study design: Experimental endometriosis was surgically induced in 225 Wistar rats. Of these, 202 rats showed at least one grown implant, 22 of which composed the control group, whil...detailed

Gestrinone (cas 16320-04-0) inhibits macrophage function and mitogen-stimulated lymphocyte proliferation in vitro08/07/2019

Clinical and experimental evidence supports the hypothesis that some steroidal drugs with androgenic effects might influence the immune system. The present study investigated whether gestrinone is able to affect macrophage and lymphocyte activity in vitro. Macrophage function was determined by p...detailed

Gestrinone (cas 16320-04-0) versus a gonadotropin-releasing hormone agonist for the treatment of pelvic pain associated with endometriosis: a multicenter, randomized, double-blind study*08/06/2019

ObjectivesTo evaluate the efficacy of gestrinone versus leuprolide acetate (LA) in improving pelvic pain in women with endometriosis and to compare their effects on bone mineral density and serum lipid profile.detailed

Gestrinone (cas 16320-04-0) versus danazol as preoperative treatment for hysteroscopic surgery: a prospective, randomized evaluation08/05/2019

ObjectiveTo compare danazol and gestrinone treatment as preoperative endometrial preparation for operative hysteroscopy.detailed

Gestrinone (cas 16320-04-0) inhibits growth of human uterine leiomyoma may relate to activity regulation of ERα, Src and P38 MAPK08/04/2019

The study was to investigate the effect of gestrinone on the growth of human uterine leiomyoma cells and on the levels and activity of p38, Src and estrogen receptor alpha (ERα). Human uterine leiomyoma cells were cultured and treated with dimethylsulfoxide (DMSO) or a gestrinone concentration ...detailed

Relevant articles and documents

Intermediates for the preparation of trienic steroids

Novel intermediates for the preparation of trienic steroids which intermediates have the formula SPC1 Wherein R is alkyl of 1 to 4 carbon atoms and X is selected from the group consisting of aliphatic of 1 to 6 carbon atoms optionally substituted and cycloalkyl of 3 to 6 carbon atoms and Y is selected from the group consisting of =O and ethylenedioxy.