Ethynodiol Diacetate

HCID 9270CAS 297-76-7

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

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
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

Experimental & physicochemical properties

LogP · 2 items

5

5

Solubility3.97e-03 g/L
Melting Point126-127
Physical DescriptionSolid

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

Safety & regulation

GHS classification

GHS Classification · 5 items

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

Other Safety InformationIMAP assessments - 19-Norpregn-4-en-20-yne-3,17-diol, diacetate, (3.beta.,17.alpha.)-: Environment tier I assessment;IMAP assessments - 19-Norpregn-4-en-20-yne-3,17-diol, diacetate, (3.beta.,17.alpha.)-: Human health tier I assessment
Hazard Classes and CategoriesAcute Tox. 4 (95%);Acute Tox. 4 (95%);Acute Tox. 4 (95%);Carc. 2 (100%);Repr. 1B (30%)

Toxicology

Drug Induced Liver Injury · 5 items

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

Chemistry & industry

Pharmacology

Protein Binding50-85%
Pharmacodynamics · 1 item

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 · 1 item

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 · 2 items

Oral contraceptives which owe their effectiveness to hormonal preparations.

Oral contraceptives which owe their effectiveness to synthetic preparations.

Cellular LocationsCytoplasm;Extracellular;Membrane

Uses & manufacturing

Use ClassificationPharmaceuticals
Applications · 4 items

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

国药集团化学试剂有限公司86-21-63210123 · [email protected]
北京华美互利生物化工010-56205725 · [email protected]
阿诺西(上海)生物技术有限公司400-1107768 15058188853 · [email protected]
苏州道澜生物医药科技有限公司15952404857 · [email protected]
上海阿拉丁生化科技股份有限公司400-6206333 13167063860 · [email protected]

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

2 records

Linked notes

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