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Ethynodiol diacetate

Ethynodiol diacetate structure

CAS No:
297-76-7
Formula:
C24H32O4
Chemical Name:
Ethynodiol diacetate
Synonyms:
19-Norpregn-4-en-20-yne-3,17-diol,3,17-diacetate,(3β,17α)-;19-Norpregn-4-en-20-yne-3,17-diol,diacetate,(3β,17α)-;19-Nor-17α-pregn-4-en-20-yne-3β,17-diol,diacetate;SC 11800;Ethynodiol acetate;17α-Ethynyl-4-estrene-3β,17β-diol diacetate;Ethynodiol diacetate;Metrodiol;Metrodiol,diacetate;17α-Ethynyl-4-estren-3β,17-diol diacetate;Ethinodiol diacetate;3β,17β-Diacetoxy-19-nor-17α-pregn-4-en-20-yne;17-Ethynyl-19-norandrost-4-ene-3β,17β-diol diacetate;Cervicundin;17α-Ethynyl-4-estrene-3β,17β-diacetate;8080CB;Luto-Metrodiol;β-Ethynodiol diacetate;Femulen;Continuin;Luteonorm;Etynodiol acetate
Categories:
Active Pharmaceutical Ingredients > Hormones and the Endocrine System

Description

Ethynodiol diacetate is a steroidal progestin which is used as a hormonal contraceptive, it has relatively little or no potency as an androgen,has significant estrogenic effects.

Solid

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 derives from an ethynodiol.|A synthetic progestational hormone used alone or in combination with estrogens as an oral contraceptive. Although etynodiol or ethynodiol are sometimes used as a synonym for ethynodiol diacetate, what is usually being referred to is actually ethynodiol diacetate and not ethynodiol (which is a separate drug that has never been marketed, see [DB13866]).|Ethynodiol Diacetate is the diacetate salt form of ethynodiol, a semi-synthetic progestational hormone agonist. Ethynodiol diacetate binds to cytoplasmic progesterone receptors in the reproductive system and subsequently activates progesterone receptor mediated gene expression. As a result of the negative feedback mechanism, luteinizing hormone (LH) release is inhibited, which leads to an inhibition of ovulation and an alteration in the cervical mucus and endometrium. In addition, ethynodiol diacetate has weak oestrogenic and androgenic properties.|A synthetic progestational hormone used alone or in combination with estrogens as an oral contraceptive (CONTRACEPTIVES, ORAL).

Ethynodiol diacetate Basic Attributes

Molecular Weight：

384.51

Exact Mass：

384.51

EC Number：

206-044-9

UNII：

62H10A1236

DSSTox ID：

DTXSID4020614

NCI Thesaurus Code：

C47525

HScode：

2937230000

Characteristics

PSA：

52.60000

XLogP3：

5.44

Appearance：

Solid

Density：

1.1±0.1 g/cm3

Melting Point：

142-146 °C

Boiling Point：

461.1±45.0 °C at 760 mmHg

Flash Point：

221.8±27.1 °C

Refractive Index：

1.546

Water Solubility：

1.4mg/L(25 ºC)

Storage Conditions：

Keep in a cool, dry, dark location in a tightly sealed container or cylinder. Keep away from incompatible materials, ignition sources and untrained individuals. Secure and label area. Protect containers/cylinders from physical damage.

Vapor Pressure：

8.11E-09mmHg at 25°C

Specific rotation：

D -72.5° (chloroform)

Safety Information

Transport codes：

NONH for all modes of transport

wgk germany：

hazard class code：

20/21/22-40

safety instructions：

22-36

RTECS Number：

RC8963000

Marks：

Precautionary statement(s)：

P280

Hazard Statements：

H302-H312-H332-H351

Toxicity

Protein Binding：

50-85%

Drug Information

Drug Indication：

For the prevention of pregnancy in women who elect to use this product as a method of contraception.

Pharmacology：

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.

MeSH：

Oral contraceptives which owe their effectiveness to hormonal preparations. (See all compounds classified as Contraceptives, Oral, Hormonal.)|Oral contraceptives which owe their effectiveness to synthetic preparations. (See all compounds classified as Contraceptives, Oral, Synthetic.)

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 Entry Terms：

(3 beta, 17 alpha)-19-Norpregn-4-en-20-yne-3,17 diol Diacetate

Ethynodiol diacetate Use and Manufacturing

Uses

anticonvulsant

Use Classification：

Human Drugs -> FDA Approved Drug Products with Therapeutic Equivalence Evaluations (Orange Book) -> Active Ingredients|Lipids -> Sterol Lipids [ST] -> Steroids [ST02] -> C21 steroids (gluco/mineralocorticoids, progestogins) and derivatives [ST0203]|Pharmaceuticals

Computed Properties

Molecular Weight:384.5
XLogP3:3.9
Hydrogen Bond Acceptor Count:4
Rotatable Bond Count:5
Exact Mass:384.23005950
Monoisotopic Mass:384.23005950
Topological Polar Surface Area:52.6
Heavy Atom Count:28
Complexity:758
Defined Atom Stereocenter Count:7
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

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CAS No.: 297-76-7

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CAS No.: 297-76-7

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