Grundinformationen
- Standard-SMILES
C#C[C@]1(OC(C)=O)CC[C@H]2[C@@H]3CCC4=C[C@@H](OC(C)=O)CC[C@@H]4[C@H]3CC[C@@]21C- InChIKey
ONKUMRGIYFNPJW-KIEAKMPYSA-N- Summenformel
- C24H32O4
- Durchschnittliche Molmasse
- 384,5 g/mol
- Monoisotopische Masse
- 384,2300595
Namen und Bezeichner
- Bevorzugter Name
- Ethynodiol Diacetate
- IUPAC
- [(3S,8R,9S,10R,13S,14S,17R)-17-acetyloxy-17-ethynyl-13-methyl-2,3,6,7,8,9,10,11,12,14,15,16-dodecahydro-1H-cyclopenta[a]phenanthren-3-yl] acetate
- Lokaler Name
- Etynodioldi(acetat)
- Englischer Name
- Ethynodiol diacetate
- Summenformel
- C24H32O4
- Molmasse
- 384.51
Namen und Synonyme
Weitere Namen anzeigen
Datenbank-Bezeichner
- CAS
297-76-7- PubChem CID
- 9270
- DTXSID
DTXSID4020614- ChEMBL
CHEMBL1200624- ChEBI
CHEBI:31580- UNII
- 62H10A1236
- EC Number
- 206-044-9
- Nikkaji
- J5.459C
Eigenschaften
Berechnete Struktureigenschaften
- XLogP
- 3,9
- Polarare Oberfläche (TPSA)
- 52,6 Ų
- H-Brücken-Donoren
- 0
- H-Brücken-Akzeptoren
- 4
- Frei drehbare Bindungen
- 5
- Schwere Atome
- 28
- Formalladung
- 0
- Komplexität
- 758
Experimentelle und physikochemische Eigenschaften
LogP
5
5
Physikochemische Eigenschaften
- Schmelzpunkt
- 126 · ~126-127°
- Siedepunkt
- 431.17 °C · 431.17°C (rough estimate)
- Dichte
- 1.0474 · 1.0474 (rough estimate)
- Brechungsindex
- 1.486 · 1.4860 (estimate)
- storage temp.
- 2 · 2-8°C
- Löslichkeit
- Chloroform (Slightly), DMSO (Slightly)
- Aggregatzustand
- Solid
- Farbe
- White
- Wasserlöslichkeit
- 1.4 mg/L · 1.4mg/L(25 ºC)
- CAS Datenbank
- 297 · 297-76-7(CAS DataBase Reference)
- NIST chemische Informationen
- Ethynodiol diacetate(297-76-7)
- EPA chemische Informationen
- Ethynodiol diacetate (297-76-7)
Sicherheit und Regulatorisches
GHS-Klassifizierung
GHS Classification
Danger
H302 (95%): Harmful if swallowed [Warning Acute toxicity, oral];H312 (95%): Harmful in contact with skin [Warning Acute toxicity, dermal];H332 (95%): Harmful if inhaled [Warning Acute toxicity, inhalation];H351 (100%): Suspected of causing cancer [Warning Carcinogenicity];H360 (30%): May damage fertility or the unborn child [Danger Reproductive toxicity]
P203, P261, P264, P270, P271, P280, P301+P317, P302+P352, P304+P340, P317, P318, P321, P330, P362+P364, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 60 reports by companies from 7 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.;Information may vary between notifications depending on impurities, additives, and other factors. The percentage value in parenthesis indicates the notified classification ratio from companies that provide hazard codes. Only hazard codes with percentage values above 10% are shown. For more detailed information, please visit ECHA C&L website.
Gefahrenhinweise
Toxikologische Informationen
Drug Induced Liver Injury
Drug-Induced Liver Injury Severity and Toxicity (DILIst)
ethynodiol diacetate
DILI Positive
Oral
DOI:10.1016/j.drudis.2019.09.022
Sicherheitsdaten
- wgk
- 3
- hs_code
- 2937230000
- RTECS-Nr.
- RC8963000
- risk_code
- 20/21/22-40
- hazard_code
- Xn
- safety_code
- 22-36
Chemie und Industrie
Pharmakologische Informationen
Pharmacodynamics
Ethynodiol Diacetate is used as a female contraceptive. Ethynodiol Diacetate is a progestin or a synthetic form of the naturally occurring female sex hormone, progesterone. In a woman's normal menstrual cycle, an egg matures and is released from the ovaries (ovulation). The ovary then produces progesterone, preventing the release of further eggs and priming the lining of the womb for a possible pregnancy. If pregnancy occurs, progesterone levels in the body remain high, maintaining the womb lining. If pregnancy does not occur, progesterone levels in the body fall, resulting in a menstrual period. Ethynodiol Diacetate tricks the body processes into thinking that ovulation has already occurred, by maintaining high levels of the synthetic progesterone. This prevents the release of eggs from the ovaries.
Mechanism of Action
Binds to the progesterone and estrogen receptors. Target cells include the female reproductive tract, the mammary gland, the hypothalamus, and the pituitary. Once bound to the receptor, progestins like Ethynodiol Diacetate will slow the frequency of release of gonadotropin releasing hormone (GnRH) from the hypothalamus and blunt the pre-ovulatory LH (luteinizing hormone) surge.
MeSH Pharmacological Classification
Oral contraceptives which owe their effectiveness to hormonal preparations.
Oral contraceptives which owe their effectiveness to synthetic preparations.
Verwendung und Herstellung
Anwendungen
BeschreibungEthynodiol diacetate is a synthetic progestogen. It prevents the development of osteoporosis in ovariectomized rats when administered at a dose of 9 μg/animal per day. Ethynodiol diacetate inhibits copulatory ovulation in rabbits. Formulations containing ethynodiol diacetate have been used as oral contraceptives.
VerwendenEthynodiol Diacetate is used as a hormonal contraceptive, birth control.
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