Norgestimate

Norgestimate, sold under the brand names Ortho Tri-Cyclen and Previfem among others, is a progestin medication which is used in birth control pills for women and in menopausal hormone therapy. The medication is available in combination with an estrogen and is not available alone. It is taken by mouth.

Norgestimate
Clinical data
Trade namesCilest, Ortho-Cyclen, Prefest, others
Other namesNGM; ORF-10131; Levonorgestrel acetate oxime; Levonorgestrel 17β-acetate 3-oxime; 17α-Ethynyl-18-methyl-19-nortestosterone 3-oxime 17β-acetate; 17α-Ethynyl-18-methylestr-4-en-17β-ol-3-one 3-oxime 17β-acetate
AHFS/Drugs.comProfessional Drug Facts
Professional Drug Facts
MedlinePlusa601050
Pregnancy
category
  • Use is contraindicated
Routes of
administration
By mouth
Drug classProgestogen; Progestin; Progestogen ester
ATC code
Legal status
Legal status
Pharmacokinetic data
BioavailabilityUnknown
Protein binding• Norelgestromin: 99% (to albumin)
• Levonorgestrel: 98% (to albumin and SHBGTooltip sex hormone-binding globulin)
• Levonorgestrel acetate: ? (to albumin)
MetabolismLiver, intestines (deacetylation, reduction, hydroxylation, conjugation)
MetabolitesNorelgestromin
Levonorgestrel
Levonorgestrel acetate
Elimination half-life• Norgestimate: very short
• Norelgestromin: 17–37 hours
• Levonorgestrel: 24–32 hours
ExcretionUrine: 47%
Feces: 37%
Identifiers
  • [(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
CAS Number
PubChem CID
IUPHAR/BPS
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.167.085
Chemical and physical data
FormulaC23H31NO3
Molar mass369.505 g·mol−1
3D model (JSmol)
Melting point214 to 218 °C (417 to 424 °F)
  • O=C(O[C@@]2(C#C)CC[C@H]1[C@H]4[C@H](CC[C@@]12CC)[C@@H]3/C(=C\C(=N\O)CC3)CC4)C
  • 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 Y
  • Key:KIQQMECNKUGGKA-NMYWJIRASA-N Y
  (verify)

Side effects of the combination of an estrogen and norgestimate include menstrual irregularities, headaches, nausea, abdominal pain, breast tenderness, mood changes, and others. Norgestimate is a progestin, or a synthetic progestogen, and hence is an agonist of the progesterone receptor, the biological target of progestogens like progesterone. It has very weak androgenic activity and no other important hormonal activity. The medication is a prodrug of norelgestromin and to a lesser extent of levonorgestrel in the body.

Norgestimate was patented in 1965 and introduced for medical use, specifically in birth control pills, in 1986. It was introduced for use in menopausal hormone therapy in the United States in 1999. Norgestimate is sometimes referred to as a "third-generation" progestin. It is marketed in birth control pills widely throughout the world, whereas it is available for use in menopausal hormone therapy only in the United States and Brazil. Norgestimate is available as a generic medication. In 2021, the version with ethinylestradiol was the 76th most commonly prescribed medication in the United States, with more than 8 million prescriptions.

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