Norelgestromin (USAN:INN:BAN)
Basic information
- CAS
74183-55-4- Standard SMILES
C#C[C@]1(O)CC[C@H]2[C@@H]3CCC4=C/C(=N/O)CC[C@@H]4[C@H]3CC[C@@]21CC- InChIKey
ISHXLNHNDMZNMC-VTKCIJPMSA-N- Molecular formula
- C21H29NO2
- Average molar mass
- 327.5 g/mol
- Monoisotopic mass
- 327.21982917
Overview
Norelgestromin is a steroid. It derives from a hydride of an estrane.
Names & identifiers
- Preferred name
- Norelgestromin (USAN:INN:BAN)
- IUPAC
- (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-ol
- English name
- (3E)-17-Deacetylnorgestimate
- Molecular formula
- C21H29NO2
- Molecular weight
- 327.46
Names & synonyms
Norelgestromin (USAN:INN:BAN)RefChem:1092581anti-Norelgestromin74183-55-4(E)-17-Deacetylnorgestimate((E)-Norelgestromin)17-Desacetyl NorgestimateNorelgestromin, (E)-UM2XKY25DH17-Deacetylnorgestimate, (E)-(3Z)-17-Desacetyl NorgestimateUNII-UM2XKY25DH
Show more names
(3E)-17-Deacetylnorgestimate18,19-Dinorpregn-4-en-20-yn-3-one, 13-ethyl-17-hydroxy-, oxime, (3E,17α)-
Norgestimate impurity C [EP]Ortho EvraNorgestimate metabolite Norelgestromin(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-ol(3E)-13beta-Ethyl-3-(hydroxyimino)-18,19-dinor-17alpha-pregn-4-en-20-yn-17-ol18,19-Dinorpregn-4-en-20-yn-3-one, 13-ethyl-17-hydroxy-, oxime, (3E,17alpha)-(8R,9S,10R,13S,14S,17R,E)-13-ethyl-17-ethynyl-17-hydroxy-6,7,8,9,10,11,12,13,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3(2H)-one oximeNorgestimate EP Impurity C
Database identifiers
- CAS
74183-55-4
Properties
Computed structural properties
- XLogP
- 3.6
- Topological polar surface area
- 52.8 Ų
- Hydrogen bond donors
- 2
- Hydrogen bond acceptors
- 3
- Rotatable bonds
- 2
- Heavy atoms
- 24
- Formal charge
- 0
- Complexity
- 641
Physicochemical properties
- Melting point
- 199 · 199-200 °C(Solv: acetonitrile (75-05-8); ethyl acetate (141-78-6))
- Boiling point
- 491.9 · 491.9±45.0 °C(Predicted)
- Density
- 1.23 · 1.23±0.1 g/cm3(Predicted)
- storage temp.
- -20 °C · -20°C Freezer
- solubility
- Chloroform (Slightly), DMSO (Slightly), Methanol (Slightly)
- pka
- 12.22 · 12.22±0.60(Predicted)
- form
- Solid
- color
- White to Off-White
- FDA UNII
- 2 XKY25DH · UM2XKY25DH
Chemistry & industry
Pharmacology
ATC CodeG03AA13
Applications
UsesE-17-Deacetylnorgestimate is a metabolite of Norgestimate. A contraceptive for birth control used by women.Note- The oxime isomerizes when: 1) Heated in any solvent or heating the crystalline form 2) Dissolved in MeOH at room temperature very quickly 3) Dissolved in acetone or CHCl3 at room temperature in a couple of hours at room temperature4) In EtOAc or EtOAc/isooctane over a couple of days at RT. It is stable in the crystalline form.
Additional notes
DefinitionChEBI: Norelgestromin is a steroid. It derives from a hydride of an estrane.
Related reactions
1 records
Compound notes
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