Basic information
- 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
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
Show more names
Database identifiers
- CAS
297-76-7- PubChem CID
- 9270
- DTXSID
DTXSID4020614- ChEMBL
CHEMBL1200624- ChEBI
CHEBI:31580- UNII
- 62H10A1236
- EC Number
- 206-044-9
- Nikkaji
- J5.459C
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
LogP
5
5
Physicochemical properties
- Melting point
- 126 · ~126-127°
- alpha
- -72.5 ° · D -72.5° (chloroform)
- Boiling point
- 431.17 °C · 431.17°C (rough estimate)
- Density
- 1.0474 · 1.0474 (rough estimate)
- refractive index
- 1.486 · 1.4860 (estimate)
- storage temp.
- 2 · 2-8°C
- solubility
- Chloroform (Slightly), DMSO (Slightly)
- form
- Solid
- color
- White
- Water Solubility
- 1.4 mg/L · 1.4mg/L(25 ºC)
- CAS DataBase Reference
- 297 · 297-76-7(CAS DataBase Reference)
- FDA UNII
- 62 H10A1236 · 62H10A1236
- ATC code
- 3 DC06 · G03DC06
- NIST Chemistry Reference
- Ethynodiol diacetate(297-76-7)
- EPA Substance Registry System
- Ethynodiol diacetate (297-76-7)
- Symbol(GHS)
- 7 · GHS07,GHS08
- Signal word
- Warning
- Hazard statements
- 302 · H302+H312+H332-H351
- Precautionary statements
- 201 · P201-P280-P301+P312+P330-P302+P352+P312-P304+P340+P312-P308+P313
- Hazard Codes
- Xn
- Risk Statements
- 20 · 20/21/22-40
- Safety Statements
- 22 · 22-36
- WGK Germany
- 3 · 3
- RTECS
- 8963000 · RC8963000
- HS Code
- 2937230000 · 2937230000
Safety & regulation
GHS classification
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.
Hazard information
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
- Hazard statements
- H302+H312+H332-H351
- Precautionary statements
- P201-P280-P301+P312+P330-P302+P352+P312-P304+P340+P312-P308+P313
Chemistry & industry
Pharmacology
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.
Uses & manufacturing
Applications
DescriptionEthynodiol 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.
Usesanticonvulsant
UsesEthynodiol Diacetate is used as a hormonal contraceptive, birth control.
General DescriptionEthynodiol diacetate, 19-norpregn-4-en-20-yne-3β,17α-diol diacetate, is a prodrug ofnorethindrone. A combination of hydrolysis of both estersand oxidation of the C3 alcohol to the ketone is necessary toprovide the fully active progestin.
Upstream & downstream products
Upstream raw materials
Suppliers50 total
Additional notes
DefinitionChEBI: Ethynodiol diacetate is a steroid ester and a terminal acetylenic compound. It has a role as an estrogen receptor modulator, a contraceptive drug and a synthetic oral contraceptive. It is functionally related to an ethynodiol.
Related reactions
Linked notes
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