Ethynodiol Diacetate
Basic information
- 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- Molecular formula
- C24H32O4
- Average molar mass
- 384.5 g/mol
- Monoisotopic mass
- 384.2300595
Overview
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.
Names & identifiers
- Preferred 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
- English name
- Ethynodiol diacetate
- Molecular formula
- C24H32O4
- Molecular weight
- 384.51
Names & synonyms
ETHYNODIOL DIACETATE297-76-7FemulenContinuinEtynodiol AcetateEtynodiol diacetateSC 11800SC-11800DTXSID402061419-Nor-17alpha-pregn-4-en-20-yne-3beta,17-diol diacetateCHEBI:31580NSC-759288
Show more names
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
Database identifiers
- CAS
297-76-7- PubChem CID
Properties
Computed structural properties
- XLogP
- 3.9
- Topological polar surface area
- 52.6 Ų
- Hydrogen bond donors
- 0
- Hydrogen bond acceptors
- 4
- Rotatable bonds
- 5
- Heavy atoms
- 28
- Formal charge
- 0
- Complexity
- 758
Experimental & physicochemical properties
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
Physicochemical properties
- Melting point
- 126 · ~126-127°
- alpha
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
GHS classification
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.
Hazard information
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%)
Toxicology
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
Safety data
- wgk
- 3
- rtecs
- RC8963000
- hs_code
- 2937230000
- risk_code
- 20/21/22-40
- Signal word
- Warning
- Symbol(GHS)
- GHS07,GHS08
- hazard_code
- Xn
- safety_code
- 22-36
Chemistry & industry
Pharmacology
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
Uses & manufacturing
Use ClassificationPharmaceuticals
Applications
Ethynodiol 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.
Related reactions
2 records
Compound notes
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