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Norgestimate

Not to be confused with Norgestomet.

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[1]
ATC code
Legal status
Legal status
Pharmacokinetic data
BioavailabilityUnknown[2]
Protein binding• Norelgestromin: 99% (to albumin)[1]
• Levonorgestrel: 98% (to albumin and SHBGTooltip sex hormone-binding globulin)[1]
• Levonorgestrel acetate: ? (to albumin)[1]
MetabolismLiver, intestines (deacetylation, reduction, hydroxylation, conjugation)[1][3][4]
Metabolites• Norelgestromin[1]
• Levonorgestrel[1]
• Levonorgestrel acetate[1]
Elimination half-life• Norgestimate: very short[1]
• Norelgestromin: 17–37 hours[3][1]
• Levonorgestrel: 24–32 hours[1]
ExcretionUrine: 47%[4]
Feces: 37%[4]
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 Edit this at Wikidata
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 checkY
  • Key:KIQQMECNKUGGKA-NMYWJIRASA-N checkY
  (verify)

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.[1][3][4][5] The medication is available in combination with an estrogen and is not available alone.[6] It is taken by mouth.[1]

Side effects of the combination of an estrogen and norgestimate include menstrual irregularities, headaches, nausea, abdominal pain, breast tenderness, mood changes, and others.[3][4] Norgestimate is a progestin, or a synthetic progestogen, and hence is an agonist of the progesterone receptor, the biological target of progestogens like progesterone.[1] It has very weak androgenic activity and no other important hormonal activity.[1] The medication is a prodrug of norelgestromin and to a lesser extent of levonorgestrel in the body.[1]

Norgestimate was patented in 1965 and introduced for medical use, specifically in birth control pills, in 1986.[7][8] It was introduced for use in menopausal hormone therapy in the United States in 1999.[9] Norgestimate is sometimes referred to as a "third-generation" progestin.[10] 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.[6] Norgestimate is available as a generic medication.[11] In 2021, the version with ethinylestradiol was the 76th most commonly prescribed medication in the United States, with more than 8 million prescriptions.[12][13]

  1. ^ a b c d e f g h i j k l m n o p Kuhl H (August 2005). "Pharmacology of estrogens and progestogens: influence of different routes of administration". Climacteric. 8 (Suppl 1): 3–63. doi:10.1080/13697130500148875. PMID 16112947. S2CID 24616324.
  2. ^ Fotherby K (August 1996). "Bioavailability of orally administered sex steroids used in oral contraception and hormone replacement therapy". Contraception. 54 (2): 59–69. doi:10.1016/0010-7824(96)00136-9. PMID 8842581.
  3. ^ a b c d "Prefest- estradiol/norgestimate kit". DailyMed. 29 February 2016. Retrieved 9 November 2020.
  4. ^ a b c d e "Ortho Tri Cyclen- norgestimate and ethinyl estradiol kit Ortho Cyclen- norgestimate and ethinyl estradiol kit". DailyMed. 16 May 2019. Retrieved 9 November 2020.
  5. ^ Lemke TL, Williams DA (2008). Foye's Principles of Medicinal Chemistry. Lippincott Williams & Wilkins. pp. 1316–. ISBN 978-0-7817-6879-5.
  6. ^ a b Cite error: The named reference Drugs.com was invoked but never defined (see the help page).
  7. ^ Cite error: The named reference RunnebaumRabe2012 was invoked but never defined (see the help page).
  8. ^ Fischer J, Ganellin CR (2006). Analogue-based Drug Discovery. John Wiley & Sons. p. 479. ISBN 9783527607495.
  9. ^ Cite error: The named reference FDA2013 was invoked but never defined (see the help page).
  10. ^ Carp HJ (9 April 2015). Progestogens in Obstetrics and Gynecology. Springer. p. 112. ISBN 978-3-319-14385-9.
  11. ^ "Generic Ortho Tri-Cyclen Availability". Drugs.com.
  12. ^ "The Top 300 of 2021". ClinCalc. Archived from the original on 15 January 2024. Retrieved 14 January 2024.
  13. ^ "Ethinyl Estradiol; Norgestimate - Drug Usage Statistics". ClinCalc. Retrieved 14 January 2024.

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