Gestrinone Chemical Properties

Melting point:

150-152°C

alpha 

D20 +84.6° (c = 0.41 in methanol)

Boiling point:

388.8°C (rough estimate)

Density 

1.1040 (rough estimate)

refractive index 

1.4900 (estimate)

storage temp. 

-20°C Freezer

solubility 

DMF:20.0(Max Conc. mg/mL);64.85(Max Conc. mM)
DMSO:35.0(Max Conc. mg/mL);113.48(Max Conc. mM)
Ethanol:20.0(Max Conc. mg/mL);64.85(Max Conc. mM)
Ethanol:PBS (pH 7.2) (1:5):0.25(Max Conc. mg/mL);81.06(Max Conc. mM)
Water:1.0(Max Conc. mg/mL);3.24(Max Conc. mM)

form 

A crystalline solid

pka

12.76±0.40(Predicted)

color 

Off-white to light yellow

Merck 

14,4415

Stability:

Hygroscopic

InChI

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

InChIKey

BJJXHLWLUDYTGC-ANULTFPQSA-N

SMILES

C1C2C(CC[C@]3([H])C=2C=C[C@@]2(CC)[C@@]3([H])CC[C@]2(C#C)O)=CC(=O)C1

CAS DataBase Reference

16320-04-0(CAS DataBase Reference)

Safety Information

RTECS 

JF7964000

Toxicity

mouse,LDLo,intraperitoneal,1gm/kg (1000mg/kg),BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLDBEHAVIORAL: ALTERED SLEEP TIME (INCLUDING CHANGE IN RIGHTING REFLEX)GASTROINTESTINAL: OTHER CHANGES,Yakuri to Chiryo. Pharmacology and Therapeutics. Vol. 16, Pg. 701, 1988.

MSDS

• Language:English Provider:(8S,13S,14S,17R)-13-Ethyl-17-ethynyl-17-hydroxy-1,2,6,7,8,14,15,16-octahydrocyclopenta[a]phenanthren-3-one

Gestrinone Usage And Synthesis

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.

Definition

ChEBI: Gestrinone is an oxo steroid.

brand name

DIMETROSE

Side effects

Gestrinone, like danazol, inhibits the synthesis of estrogens and progestogens and has been used mainly to prepare patients with an endometrial disorder for hysterectomy. Its most common adverse effects are nausea, headache, mood changes, rash, hot flushes, weight gain, and discomfort in the joints and muscles. In some cases, there is evidence of masculinization.

Mode of action

The primary action of gestrinone is on the hypothalamic-pituitary axis, where it inhibits gonadotrophin release with a weak inhibitory effect on its synthesis. It also possesses anti-estrogen activity. The mode of action of gestrinone used for EC is probably inhibition of implantation by acting on the endometrium rather than inhibiting ovulation[1].

References

[1] Xuefeng Gao, Guian Chen, Erruo Wu . “Mechanism of emergency contraception with gestrinone: a preliminary investigation.” Contraception 76 3 (2007): Pages 221-227.

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