Norgestrel

Not to be confused with Levonorgestrel.

Norgestrel
Top, levonorgestrel (CAS 797-63-7 );
Bottom: dextronorgestrel (CAS 797-64-8 ).
Clinical data
Trade namesOpill, others
Other namesdl-Norgestrel; DL-Norgestrel; (±)-Norgestrel; WY-3707; SH-70850; SH-850; FH 122-A; rac-13-Ethyl-17α-ethynyl-19-nortestosterone; rac-13-Ethyl-17α-ethynylestr-4-en-17β-ol-3-one
AHFS/Drugs.comMicromedex Detailed Consumer Information
MedlinePlusa602008
License data
Routes of
administration		By mouth
Drug classProgestin
ATC code
Legal status
Legal status
Identifiers
IUPAC name
  • (8R,9S,10R,13S,14S)-13-ethyl-17-ethynyl-17-hydroxy-1,2,6,7,8,9,10,11,12,14,15,16-dodecahydrocyclopenta[a]phenanthren-3-one
CAS Number
PubChem CID
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.026.758
Chemical and physical data
FormulaC21H28O2
Molar mass312.453 g·mol−1
3D model (JSmol)
SMILES
  • O=C\1CC[C@H]4C(=C/1)/CC[C@@H]3[C@@H]4CC[C@@]2(CC)[C@H]3CCC2(O)C#C
InChI
  • InChI=1S/C21H28O2/c1-3-20-11-9-17-16-8-6-15(22)13-14(16)5-7-18(17)19(20)10-12-21(20,23)4-2/h2,13,16-19,23H,3,5-12H2,1H3/t16-,17+,18+,19-,20-,21?/m0/s1 Y
  • Key:WWYNJERNGUHSAO-CULCCENASA-N Y
  (verify)

Norgestrel, sold under the brand name Opill among others, is a progestin which is used in birth control pills. It is often combined with the estrogen ethinylestradiol, marketed as Ovral. It is also used in menopausal hormone therapy.[3][4][5][6][7] It is taken by mouth.[5][6]

Side effects of norgestrel include menstrual irregularities, headaches, nausea, and breast tenderness.[8] The most common side effects of the norgestrel include irregular bleeding, headaches, dizziness, nausea, increased appetite, abdominal pain, cramps, or bloating.[2] Norgestrel is a progestin, or a synthetic progestogen, and hence is an agonist of the progesterone receptor, the biological target of progestogens like progesterone.[6] It has weak androgenic activity and no other important hormonal activity.[6]

Norgestrel was patented in 1961 and came into medical use, specifically in birth control pills, in 1966.[9][10][11] It was subsequently introduced for use in menopausal hormone therapy as well.[7] Norgestrel is sometimes referred to as a "second-generation" progestin.[12] It is marketed widely throughout the world.[7][4] Norgestrel is available as a generic medication.[13] In 2022, the version with ethinylestradiol was the 264th most commonly prescribed medication in the United States, with more than 1 million prescriptions.[14][15] In July 2023, the US Food and Drug Administration (FDA) approved norgestrel for over-the-counter sale.[2]

  1. ^ "Opill- norgestrel tablet". DailyMed. 4 March 2024. Archived from the original on 11 March 2024. Retrieved 13 March 2024.
  2. ^ a b c "FDA Approves First Nonprescription Daily Oral Contraceptive". U.S. Food and Drug Administration (FDA) (Press release). 13 July 2023. Archived from the original on 13 July 2023. Retrieved 13 July 2023. This article incorporates text from this source, which is in the public domain.
  3. ^ Cite error: The named reference Elks2014 was invoked but never defined (see the help page).
  4. ^ a b Cite error: The named reference IndexNominum2000 was invoked but never defined (see the help page).
  5. ^ a b Morton IK, Hall JM (6 December 2012). Concise Dictionary of Pharmacological Agents: Properties and Synonyms. Springer Science & Business Media. pp. 202–. ISBN 978-94-011-4439-1. Archived from the original on 10 January 2023. Retrieved 10 March 2018.
  6. ^ a b c d Kuhl H (2005). "Pharmacology of estrogens and progestogens: influence of different routes of administration" (PDF). Climacteric. 8 (Suppl 1): 3–63. doi:10.1080/13697130500148875. PMID 16112947. S2CID 24616324. Archived (PDF) from the original on 22 August 2016. Retrieved 10 March 2018.
  7. ^ a b c Cite error: The named reference Drugs.com was invoked but never defined (see the help page).
  8. ^ "Learn more about Opill (0.075mg Oral Norgestrel Tablet)". U.S. Food and Drug Administration (FDA). 13 July 2023. Archived from the original on 9 October 2023. Retrieved 13 March 2024.
  9. ^ Cite error: The named reference Ortiz-GómezSantesmases2016 was invoked but never defined (see the help page).
  10. ^ Cite error: The named reference Pohl2004 was invoked but never defined (see the help page).
  11. ^ Fischer J, Ganellin CR (2006). Analogue-based Drug Discovery. John Wiley & Sons. p. 479. ISBN 9783527607495.
  12. ^ Carp HJ (9 April 2015). Progestogens in Obstetrics and Gynecology. Springer. p. 112. ISBN 978-3-319-14385-9.
  13. ^ "Generic Lo/Ovral-28 Availability". Archived from the original on 2 March 2019. Retrieved 10 March 2018.
  14. ^ "The Top 300 of 2022". ClinCalc. Archived from the original on 30 August 2024. Retrieved 30 August 2024.
  15. ^ "Ethinyl Estradiol; Norgestrel Drug Usage Statistics, United States, 2013 - 2022". ClinCalc. Retrieved 30 August 2024.
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