Gestrinone

Bezeichnung:Gestrinone

Englisch Name:Gestrinone

CBNumberCB3121391

SummenformelC21H24O2

Molgewicht308.41

Gestrinone physikalisch-chemischer Eigenschaften

Schmelzpunkt	150-152°C
alpha	D20 +84.6° (c = 0.41 in methanol)
Siedepunkt	388.8°C (rough estimate)
Dichte	1.1040 (rough estimate)
Brechungsindex	1.4900 (estimate)
storage temp.	-20°C Freezer
Löslichkeit	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)
Aggregatzustand	A crystalline solid
pka	12.76±0.40(Predicted)
Farbe	Off-white to light yellow
Optische Aktivität	[α]/D +81 to +88°, c =0.4 in ethanol
Merck	14,4415
Stabilität	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 Datenbank	16320-04-0(CAS DataBase Reference)

Sicherheit

RTECS-Nr.	JF7964000
Toxizität	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.

Gefahreninformationscode (GHS)

Beschreibung
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.
Chemische Eigenschaften
Light Yellow Solid
Originator
Roussel UCLAF (France)
Verwenden
Steroidal antiestrogen, antiprogestogen, analog of Norgestrienone. Antigonadotropin. Controlled substance.
Definition
ChEBI: Gestrinone is an oxo steroid.
Trademarks
DIMETROSE
Nebenwirkungen
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].
Einzelnachweise
[1] Xuefeng Gao, Guian Chen, Erruo Wu . “Mechanism of emergency contraception with gestrinone: a preliminary investigation.” Contraception 76 3 (2007): Pages 221-227.