Etynodioldi(acetat)
Ethynodiol Diacetate
Grundinformationen
- CAS
297-76-7- 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
Überblick
Ethynodiol diacetate is a steroid ester and a terminal acetylenic compound. It has a role as a contraceptive drug, a synthetic oral contraceptive and an estrogen receptor modulator. It is functionally related to an ethynodiol.
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
ETHYNODIOL DIACETATE297-76-7FemulenContinuinEtynodiol AcetateEtynodiol diacetateSC 11800SC-11800DTXSID402061419-Nor-17alpha-pregn-4-en-20-yne-3beta,17-diol diacetateCHEBI:31580NSC-759288
Weitere Namen anzeigen
EthynodiolCB-8080ovulen508080c.b.EtynodiolLuteonormMetrodiolOvulen 50
(3-beta,17-alpha)-19-Norpregn-4-en-20-yne-3,17-diol diacetate17-alpha-Ethynyl-19-norandrost-4-ene-3-beta,17-beta-diol diacetate17alpha-Ethynyl-3,17-dihydroxy-4-estrene diacetate17alpha-Ethynylestr-4-ene-3beta,17beta-diol acetate3beta, 17beta-Diacetoxy-17alpha-ethynyl-4-oestrene17alpha-Ethynyl-4-estrene-3beta,17beta-diol diacetateDTXCID00614[(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
Datenbank-Bezeichner
- CAS
297-76-7
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
DrugsPharmaceuticals -> Listed in ZINC15
LipidsLipids -> Sterol Lipids [ST] -> Steroids [ST02] -> C21 steroids (gluco/mineralocorticoids, progestogins) and derivatives [ST0203]
LogP5
Solubility3.97e-03 g/L
Human Drugs
FDA approved drugs -> Active ingredient
FDA approved drugs -> Active ingredient
Pharmaceuticals
Endocrine DisruptorsPotential endocrine disrupting compound
Melting Point126-127
Physical DescriptionSolid
Physikochemische Eigenschaften
- Schmelzpunkt
- 126 · ~126-127°
Sicherheit und Regulatorisches
Sicherheitsangaben dienen nur zur Orientierung und ersetzen weder das Sicherheitsdatenblatt (SDB) des Lieferanten noch geltende Vorschriften oder eine fachliche Bewertung.
GHS-Klassifizierung
GHS Classification
Danger
H302 (95%): Harmful if swallowed [Warning Acute toxicity, oral]
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.
Gefahrenhinweise
Other Safety InformationIMAP assessments - 19-Norpregn-4-en-20-yne-3,17-diol, diacetate, (3.beta.,17.alpha.)-: Environment tier I assessment
Hazard Classes and CategoriesAcute Tox. 4 (95%)
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
Protein Binding50-85%
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.
Cellular LocationsCytoplasm
Verwendung und Herstellung
Use ClassificationPharmaceuticals
Anwendungen
Zugehörige Reaktionen
2
Notizen zur Verbindung
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