| Identification | More | [Name]
Gestrinone | [CAS]
16320-04-0 | [Synonyms]
13-ETHYL-17ALPHA-HYDROXY-18,19-DINORPREGNA-4,9,11-TRIEN-20-YN-3-ONE
(8s,13s,14s,17r)-13-ethyl-17-ethynyl-17-hydroxy-1,2,6,7,8,14,15,16-octahydrocyclopenta[a]phenanthren-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-17-hydroxy-18,19-dinor-17-alpha-pregna-4,9,11-trien-20-yn-3-one
19-dinor-17-alpha-pregna-4,9,11-trien-20-yn-3-one,13-ethyl-17-hydroxy-1
9,11-trien-20-yn-3-one,13-ethyl-17-hydroxy-19-dinorpregna-(17-alpha)-1
ethylnorgestrienone
gestrigone
r-2323
ru2323
(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-17α-ethynyl-17-hydroxy-4，9，11-gonatrien-3-one
A-46745
Dimetriose
Dimetrose
Nemestran：Tridomose
13-Ethyl-17-alpha-ethynyl-17-hydroxygon-4,9,11-trien-3-one | [EINECS(EC#)]
685-143-2 | [Molecular Formula]
C21H24O2 | [MDL Number]
MFCD00865561 | [Molecular Weight]
308.41 | [MOL File]
16320-04-0.mol |
| Chemical Properties | Back Directory | [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 Data | Back Directory | [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. |
| Material Safety Data Sheet(MSDS) | Back Directory | [msds information]
(8S,13S,14S,17R)-13-Ethyl-17-ethynyl-17-hydroxy-1,2,6,7,8,14,15,16-octahydrocyclopenta[a]phenanthren-3-one(16320-04-0).msds |
| Hazard Information | Back Directory | [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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