Ethynodiol diacetate

A summary of the most common chemical descriptors (InChI Key and SMILES codes) for Ethynodiol diacetate are summarized together with 3D and 2D structures and relevant physico-chemical properties.

What is the Ethynodiol diacetate?

The molecule Ethynodiol diacetate presents a molecular formula of C24H32O4 and its IUPAC name is [(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.

Ethynodiol diacetate is a synthetic, orally active progestin and a derivative of ethynodiol. It was first synthesized in 1960. Ethynodiol diacetate is used as a contraceptive in many countries. It is also used in the treatment of endometriosis and menorrhagia in the United States..

Ethynodiol diacetate has a molecular weight of 336.41 and a molecular formula of C22H28O4. The compound is a white, crystalline solid. It is insoluble in water and has a melting point of 165-167 degrees Celsius..

Ethynodiol diacetate is rapidly absorbed from the gastrointestinal tract and is metabolized in the liver. It is excreted in the urine and feces. The elimination half-life of ethynodiol diacetate is approximately 24 hours..

Ethynodiol diacetate inhibits ovulation and fertilization. It also alters the endometrium, which makes it unsuitable for implantation. Ethynodiol diacetate is a progestin, which means it has anti-estrogenic effects..

The most common side effects of ethynodiol diacetate are nausea, vomiting, bloating, breast tenderness, and weight gain. Less common side effects include acne, hirsutism, and changes in menstrual bleeding. Ethynodiol diacetate can also cause mood changes, headaches, and depression..

Ethynodiol diacetate is a safe and effective contraceptive when used as directed. It is important to follow the instructions of your healthcare provider..

3D structure

Cartesian coordinates

Geometry of Ethynodiol diacetate in x, y and z coordinates (Å units) to copy/paste elsewhere. Generated with Open Babel software.

2D drawing

 

Ethynodiol diacetate ONKUMRGIYFNPJW-KIEAKMPYSA-N chemical compound 2D structure molecule svg
Ethynodiol diacetate

 

Molecule descriptors

 
IUPAC name[(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
InChI codeInChI=1S/C24H32O4/c1-5-24(28-16(3)26)13-11-22-21-8-6-17-14-18(27-15(2)25)7-9-19(17)20(21)10-12-23(22,24)4/h1,14,18-22H,6-13H2,2-4H3/t18-,19-,20+,21+,22-,23-,24-/m0/s1
InChI KeyONKUMRGIYFNPJW-KIEAKMPYSA-N
SMILESC#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

Other names (synonyms)

IUPAC nomenclature provides a standardized method for naming chemical compounds. Although this system is widely used in chemistry, many chemical compounds have also other names commonly used in different contexts. These synonyms can come from a variety of sources and are used for a variety of purposes.

One common source of synonyms for chemical compounds is the common or trivial names, assigned on the basis of appearance, properties, or origin of the molecule.

Another source of synonyms are historical or obsolete names employed in the past, however replaced nowadays by more modern or standardized names.

In addition to common and historical names, chemical compounds may also have synonyms that are specific to a particular field or industry.

  • (3-beta,17-alpha)-19-Norpregn-4-en-20-yne-3,17-diol diacetate
  • (3S,8R,9S,10R,13S,14S,17R)-17-ethynyl-13-methyl-2,3,6,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthrene-3,17-diyl diacetate
  • (3beta,17beta)-17-ethynylestr-4-ene-3,17-diyl diacetate
  • 17-alpha-Ethynyl-19-norandrost-4-ene-3-beta,17-beta-diol diacetate
  • 17-alpha-Ethynyl-3,17-dihydroxy-4-estrene diacetate
  • 17-alpha-Ethynyl-4-estrene-3-beta,17-beta-diol diacetate
  • 17-alpha-Ethynylestr-4-ene-3-beta,17-beta-diol acetate
  • 17a-Ethynyl-4-estren-3b,17-diol diacetate
  • 17alpha-Ethynyl-19-norandrost-4-ene-3beta,17-beta-diol diacetate
  • 17alpha-Ethynyl-3,17-dihydroxy-4-estrene diacetate
  • 17alpha-Ethynyl-4-estrene-3beta,17beta-diol diacetate
  • 17alpha-Ethynylestr-4-ene-3beta,17beta-diol acetate
  • 17alpha-ethynylestr-4-ene-3beta,17beta-diyl diacetate
  • 19-Nor-17-alpha-pregn-4-en-20-yne-3-beta,17-diol diacetate
  • 19-Nor-17alpha-pregn-4-en-20-yne-3beta,17-diol diacetate
  • 19-Norpregn-4-en-20-yne-3,17-diol, diacetate, (3.beta.,17.alpha.)-
  • 19-Norpregn-4-en-20-yne-3,17-diol, diacetate, (3b,17a)-
  • 19-norpregn-4-en-20-yn-3beta,17alpha-diol, diacetate
  • 297-76-7
  • 297E767
  • 3-beta, 17-beta-Diacetoxy-17-alpha-ethynyl-4-oestrene
  • 3-beta,17-beta-Diacetoxy-19-nor-17-alpha-pregn-4-en-20-yne
  • 3beta, 17beta-Diacetoxy-17alpha-ethynyl-4-oestrene
  • 3beta,17beta-Diacetoxy-19-nor-17alpha-pregn-4-en-20-yne
  • 62H10A1236
  • 8080 C. B.
  • 8080 CB
  • A820050
  • AB00513958
  • AB00513958_02
  • AS-13382
  • B1508
  • BCP10923
  • BDBM50237627
  • BPBio1_000832
  • BSPBio_000756
  • CCG-220908
  • CCRIS 305
  • CS-4640
  • Cervicundin
  • Continuin
  • D01294
  • DB00823
  • DSSTox_CID_614
  • DSSTox_GSID_20614
  • DSSTox_RID_75690
  • E1315
  • ETHYNODIOL DIACETATE
  • ETHYNODIOL DIACETATE COMPONENT OF KELNOR
  • ETHYNODIOL DIACETATE COMPONENT OF OVULEN
  • Ethinodiol diacetate
  • Ethynodiol (diacetate)
  • Ethynodiol acetate
  • Ethynodiol diacetate
  • Ethynodiol diacetate (JAN/USP)
  • Etynodiol Acetate
  • Etynodiol di(acetate)
  • Etynodiol diacetate
  • Femulen
  • GTPL7072
  • HMS1570F18
  • HMS2097F18
  • HMS3714F18
  • HY-B1089
  • J-017631
  • KELNOR COMPONENT ETHYNODIOL DIACETATE
  • LMST02030124
  • Luto-metrodiol
  • MFCD00083326
  • MLS000028661
  • Metrodiol
  • Metrodiol diacetate
  • NCGC00166138-01
  • NCGC00166138-02
  • NCGC00166138-03
  • NCGC00166138-04
  • NCGC00166138-05
  • NCGC00186466-01
  • NSC 759288
  • NSC-759288
  • OVULEN COMPONENT ETHYNODIOL DIACETATE
  • Ovulen 50
  • Prestwick0_000908
  • Prestwick1_000908
  • Prestwick2_000908
  • Prestwick3_000908
  • Q5405160
  • SC 11800
  • SC-11800
  • SMR000058858
  • SR-01000872687
  • SR-01000872687-1
  • T72249
  • ZOVIA COMPONENT ETHYNODIOL DIACETATE
  • [(3S,8R,9S,10R,13S,14S,17R)-17-acetoxy-17-ethynyl-13-methyl-2,3,6,7,8,9,10,11,12,14,15,16-dodecahydro-1H-cyclopenta[a]phenanthren-3-yl] acetate;Ethynodiol diacetate
  • [(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
  • ethynodiol-diacetate
  • s3160

Reference codes for other databases

There exist several different chemical codes commonly used in orded to identify molecules:
  • ZINC3876023
  • CAS-297-76-7
  • UNII-62H10A1236
  • AKOS015895252
  • DTXSID4020614
  • CHEMBL1200624
  • CHEBI:31580
  • Tox21_112333
  • Tox21_112924
  • Tox21_112333_1
  • EINECS 206-044-9
  • SPBio_002955
  • SCHEMBL40888

Physico-Chemical properties

IUPAC name[(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
Molecular formulaC24H32O4
Molecular weight384.508
Melting point (ºC)
Boiling point (ºC)
Density (g/cm3)
Molar refractivity109.06
LogP4.4
Topological polar surface area52.6

LogP and topological polar surface area (TPSA) values were estimated using Open Babel software.

The n-octanol/water partition coeficient (Kow) data is applied in toxicology and drug research. Kow values are used, to guess the environmental fate of persistent organic pollutants. High partition coefficients values, tend to accumulate in the fatty tissue of organisms. Molecules with a log(Kow) (or LogP) greater than 5 are considered to bioaccumulate.

TPSA values are the sum of the surface area over all polar atoms or molecules, mainly oxygen and nitrogen, also including hydrogen atoms.

In medicinal chemistry, TPSA is used to assess the ability of a drug to permeabilise cells.

For molecules to penetrate the blood-brain barrier (and act on receptors in the central nervous system), TPSA values below 90 Å2 are required. Thus, molecules with a polar surface area greater than 140 Å2 tend to be poorly permeable to cell membranes.