Gestrinone

HCID 27812CAS 16320-04-0

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Basic information

Standard SMILES: C#C[C@]1(O)CC[C@H]2[C@@H]3CCC4=CC(=O)CCC4=C3C=C[C@@]21CC
InChIKey: BJJXHLWLUDYTGC-ANULTFPQSA-N
Molecular formula: C21H24O2
Average molar mass: 308.421 g/mol
Monoisotopic mass: 308.17763001

Names & identifiers

Preferred name: Gestrinone
IUPAC: (1R,3aS,3bS,11aS)-11a-Ethyl-1-ethynyl-1-hydroxy-1,2,3,3a,3b,4,5,8,9,11a-decahydro-7H-cyclopenta[a]phenanthren-7-one
English name: Gestrinone
Molecular formula: C21H24O2
Molecular weight: 308.41

Names & synonyms

ru2323r-2323A-46745DimetroseNeMestranTridoMosegestrigoneGESTRINONEDimetriosegestinone.

Database identifiers

CAS: 16320-04-0
PubChem CID: 27812
DTXSID: DTXSID4023094
ChEMBL: CHEMBL1868702
ChEBI: CHEBI:89642
UNII: 1421533RCM
EC Number: 685-143-2
Nikkaji: J16.136E

Properties

Physicochemical properties

Melting point: 150 · 150-152°C
alpha: 20 · D20 +84.6° (c = 0.41 in methanol)
Boiling point: 388.8 °C · 388.8°C (rough estimate)
Density: 1.104 · 1.1040 (rough estimate)
refractive index: 1.49 · 1.4900 (estimate)
storage temp.: -20 °C · -20°C Freezer
solubility: 20 · 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 · 12.76±0.40(Predicted)
color: Off-white to light yellow
optical activity: 81 to · [α]/D +81 to +88°, c =0.4 in ethanol
Merck: 14 · 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 · 16320-04-0(CAS DataBase Reference)
FDA UNII: 1421533 RCM · 1421533RCM
ATC code: 3 XA02 · G03XA02
UNSPSC Code: 12352200 · 12352200
NACRES: 77 · NA.77
Symbol(GHS): 8 · GHS08
Signal word: Danger
Hazard statements: 360 · H360-H362
Precautionary statements: 201 · P201-P260-P263-P264-P270-P308+P313
WGK Germany: 3 · WGK 3
RTECS: 7964000 · JF7964000
Storage Class: 11 · 11 - Combustible Solids
Hazard Classifications: 2 · Repr. 2
Toxicity: 1 gm/kg · 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.

Safety & regulation

Safety data

wgk: WGK 3
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.
Signal word: Danger
Symbol(GHS): GHS08
Storage Class: 11 - Combustible Solids
Hazard statements: H360-H362
Hazard Classifications: Repr. 2
Precautionary statements: P201-P260-P263-P264-P270-P308+P313

Chemistry & industry

Applications

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

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

Upstream & downstream products

Upstream raw materials

Suppliers50 total

北京华美互利生物化工010-56205725 · [email protected]

广州佳途科技股份有限公司81960175 18933936954 · [email protected]

江苏艾康生物医药研发有限公司025-025-66113011 15955137747 · [email protected]

Hunan Jibang Biological Technology Co., LTD13776644403 · [email protected]

Shandong Hanjiang Chemical Co., Ltd+86-0533-2066820 +8618369939125 · [email protected]

Additional notes

DefinitionChEBI: Gestrinone is an oxo steroid.

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