norgestimate   Click here for help

GtoPdb Ligand ID: 7091

Synonyms: dexnorgestrel | ORF-10131 | RWJ-10131
Approved drug
norgestimate is an approved drug (FDA (1989))
Compound class: Synthetic organic
Comment: Norgestimate is an acetylated progestin (synthelic progesterone-like compound). It is converted to the primary active metabolite norelgestromin (17-deacetylnorgestimate or levonorgestrel 3-oxime) in vivo. 17-deacetylnorgestimate does not cause the androgenic side effects associated with other 19-nortestosterone progestins.
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 2
Hydrogen bond donors 1
Rotatable bonds 3
Topological polar surface area 58.89
Molecular weight 369.23
XLogP 4.8
No. Lipinski's rules broken 0
SMILES / InChI / InChIKey
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Canonical SMILES O/N=C/1\CC[C@H]2C(=C1)CC[C@@H]1[C@@H]2CC[C@]2([C@H]1CC[C@]2(C#C)OC(=O)C)CC
Isomeric SMILES O/N=C/1\CC[C@H]2C(=C1)CC[C@@H]1[C@@H]2CC[C@]2([C@H]1CC[C@]2(C#C)OC(=O)C)CC
InChI InChI=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 Key KIQQMECNKUGGKA-NMYWJIRASA-N
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Summary of Clinical Use Click here for help
Norgestimate is approved along with ethinyl estradiol in combined oral contraceptive formulations.
Mechanism Of Action and Pharmacodynamic Effects Click here for help
Artificial maintainence of high levels of circulating progestin feeds back to reduce the frequency of gonadotrophin-releasing hormone (GnRH) pulses which blunts the pre-ovulatory lutenising hormone (LH) surge, and the ovaries cease cyclic ovulation.