Norgestimate

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

What is the Norgestimate?

The molecule Norgestimate presents a molecular formula of C23H31NO3 and its IUPAC name is [(3E,8R,9S,10R,13S,14S,17R)-13-ethyl-17-ethynyl-3-hydroxyimino-1,2,6,7,8,9,10,11,12,14,15,16-dodecahydrocyclopenta[a]phenanthren-17-yl] acetate.

Norgestimate is a progestin, or a synthetic progestogen, which is used in birth control pills and in the treatment of secondary amenorrhea. It is also used in the treatment of endometriosis. Norgestimate is the ethinyl estradiol ester of desogestrel, and is more commonly known as desogestrel 3-methyl ether. Norgestimate is a prodrug of desogestrel, meaning that it is metabolized into desogestrel in the body..

Norgestimate is a third-generation progestin, and was first approved for use in the United States in 1993. Norgestimate is used in a variety of birth control pills, including Ortho-Cyclen, Ortho Tri-Cyclen, and Previfem. Norgestimate is also used in the treatment of secondary amenorrhea, and has been shown to be effective in the treatment of endometriosis..

Norgestimate is a safe and effective progestin, and has a low risk of side effects. The most common side effects of norgestimate are nausea, vomiting, headache, and breast tenderness. Norgestimate is a very effective progestin, and is an important part of many birth control pills..

3D structure

Cartesian coordinates

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

2D drawing

 

Norgestimate KIQQMECNKUGGKA-NMYWJIRASA-N chemical compound 2D structure molecule svg
Norgestimate

 

Molecule descriptors

 
IUPAC name[(3E,8R,9S,10R,13S,14S,17R)-13-ethyl-17-ethynyl-3-hydroxyimino-1,2,6,7,8,9,10,11,12,14,15,16-dodecahydrocyclopenta[a]phenanthren-17-yl] acetate
InChI codeInChI=1S/C23H31NO3/c1-4-22-12-10-19-18-9-7-17(24-26)14-16(18)6-8-20(19)21(22)11-13-23(22,5-2)27-15(3)25/h2,14,18-21,26H,4,6-13H2,1,3H3/b24-17+/t18-,19+,20+,21-,22-,23-/m0/s1
InChI KeyKIQQMECNKUGGKA-NMYWJIRASA-N
SMILESC#C[C@]1(OC(C)=O)CC[C@H]2[C@@H]3CCC4=C/C(=N/O)CC[C@@H]4[C@H]3CC[C@@]21CC

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.

  • (+)-13-Ethyl-17-hydroxy-18,19-dinor-17alpha-pregn-4-en-20-yn-3-one oxime acetate (ester)
  • (17alpha)-17-(Acetyloxy)-13-ethyl-18,19-dinorpregn-4-en-20-yn-3-one 3-oxime
  • (1S,2R,5E,10R,11S,14R,15S)-15-ethyl-14-ethynyl-5-(hydroxyimino)tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-6-en-14-yl acetate
  • (3E)-17alpha-ethynyl-3-(hydroxyimino)-18a-homoestr-4-en-17beta-yl acetate
  • 107382-52-5
  • 18,19-DINORPREGN-4-EN-20-YN-3-ONE, 17-(ACETYLOXY)-13-ETHYL-, 3-OXIME, (3E,17.ALPHA.)-
  • 18,19-Dinorpregn-4-en-20-yn-3-one, 17-(acetyloxy)-13-ethyl-, 3-oxime, (3E,17alpha)-
  • 20799-27-3
  • 35189-28-7
  • 351N287
  • A822635
  • AC-655
  • AS-12305
  • D05209
  • DB00957
  • DSSTox_CID_26922
  • DSSTox_GSID_46922
  • DSSTox_RID_82018
  • Dexnorgestrel acetime
  • J-019983
  • NCGC00181353-01
  • NCGC00344561-01
  • NKX8DN6TY9
  • NORGESTIMATE
  • NSC-759159
  • Norgestimate
  • Norgestimate (USP/INN)
  • Norgestimate, E-
  • Norgestimato
  • Norgestimatum
  • ORF 10131
  • ORF-10131
  • RWJ 10131
  • RWJ-10131
  • [(3E,8R,9S,10R,13S,14S,17R)-13-ethyl-17-ethynyl-3-hydroxyimino-1,2,6,7,8,9,10,11,12,14,15,16-dodecahydrocyclopenta[a]phenanthren-17-yl] acetate
  • [(3E,8R,9S,10R,13S,14S,17R)-13-ethyl-17-ethynyl-3-hydroxyimino-1,2,6,7,8,9,10,11,12,14,15,16-dodecahydrocyclopenta[a]phenanthren-17-yl] acetate;Norgestimate
  • anti-Norgestimate
  • d-13beta-Ethyl-17alpha-ethynyl-17beta-acetoxygon-4-en-3-one oxime

Reference codes for other databases

There exist several different chemical codes commonly used in orded to identify molecules:
  • CAS-35189-28-7
  • UNII-NKX8DN6TY9
  • AKOS015917555
  • DTXSID1046922
  • CHEMBL1200934
  • CHEBI:50815
  • Tox21_112811
  • Tox21_112811_1
  • SCHEMBL38317
  • SCHEMBL38318

Physico-Chemical properties

IUPAC name[(3E,8R,9S,10R,13S,14S,17R)-13-ethyl-17-ethynyl-3-hydroxyimino-1,2,6,7,8,9,10,11,12,14,15,16-dodecahydrocyclopenta[a]phenanthren-17-yl] acetate
Molecular formulaC23H31NO3
Molecular weight369.497
Melting point (ºC)
Boiling point (ºC)
Density (g/cm3)
Molar refractivity107.39
LogP4.7
Topological polar surface area58.9

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.