Norgestrel Explained

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Verifiedrevid:456663702
Width:225
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Image3:Norgestrel molecule ball.png
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Tradename:Ovral, Opill, others
Dailymedid:Norgestrel
Routes Of Administration:By mouth
Class:Progestogen
Progestin
Atc Prefix:G03
Atc Suffix:AA06
Atc Supplemental: (only combinations with estrogens)
Legal Us:OTC
Legal Us Comment:[1]
Cas Number:6533-00-2
Pubchem:16051930
Drugbank:DB09389
Chemspiderid:10481953
Unii:3J8Q1747Z2
Kegg:D00954
Chembl:2107797
Chebi:7630
Synonyms:dl-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
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
C:21
H:28
O:2
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
Stdinchi: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
Stdinchikey:WWYNJERNGUHSAO-CULCCENASA-N

Norgestrel is a progestin which is used in birth control pills sold under the brand name Ovral in combination with the estrogen ethinylestradiol and Opill by itself. It is also used in menopausal hormone therapy.[2] [3] It is taken by mouth.

Side effects of norgestrel include menstrual irregularities, headaches, nausea, and breast tenderness.[4] The most common side effects of the norgestrel include irregular bleeding, headaches, dizziness, nausea, increased appetite, abdominal pain, cramps, or bloating. Norgestrel 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 weak androgenic activity and no other important hormonal activity.

Norgestrel was patented in 1961 and came into medical use, specifically in birth control pills, in 1966.[5] It was subsequently introduced for use in menopausal hormone therapy as well. Norgestrel is sometimes referred to as a "second-generation" progestin.[6] It is marketed widely throughout the world. Norgestrel is available as a generic medication.[7] In 2021, the version with ethinylestradiol was the 227th most commonly prescribed medication in the United States, with more than 1million prescriptions.[8] [9] In July 2023, the US Food and Drug Administration (FDA) approved norgestrel for over-the-counter sale.[10]

Medical uses

Norgestrel is used in combination with ethinylestradiol or quinestrol in combined birth control pills, alone in progestogen-only birth control pills, and in combination with estradiol or conjugated estrogens in menopausal hormone therapy. It has also been used as an emergency contraceptive in the Yuzpe regimen.[11]

Pharmacology

Pharmacodynamics

Norgestrel is a progestogen, or an agonist of the progesterone receptor. The biological activity of norgestrel lies in the levo enantiomer, levonorgestrel, whereas the dextro isomer is inactive. As such, norgestrel is identical in its hormonal activity to levonorgestrel except that it is half as potent by weight. Levonorgestrel, and by extension norgestrel, have some androgenic activity, but no estrogenic, antimineralocorticoid, or glucocorticoid activity.

The ovulation-inhibiting dose of norgestrel appears to be greater than 75μg/day, as ovulation occurred in 50 to 75% of cycles with this dosage of norgestrel in studies.[12] The ovulation-inhibiting dosage of levonorgestrel, which is twice as potent as norgestrel, is approximately 50 to 60μg/day.[13] One review lists the ovulation-inhibiting dose of norgestrel as 100μg/day.[14] The endometrial transformation dose of norgestrel is listed as 12mg per cycle and the menstrual delay test dose of norgestrel is listed as 0.5 to 2mg/day.[15]

Pharmacokinetics

The pharmacokinetics of norgestrel have been reviewed.

Chemistry

See also: List of progestogens and List of androgens/anabolic steroids.

Norgestrel, also known as rac-13-ethyl-17α-ethynyl-19-nortestosterone or as rac-13-ethyl-17α-ethynylestr-4-en-17β-ol-3-one, is a synthetic estrane steroid and a derivative of testosterone. It is a racemic mixture of stereoisomers dextronorgestrel (the C13α isomer; l-norgestrel, L-norgestrel, or (+)-norgestrel) and levonorgestrel (the C13β isomer; d-norgestrel, D-norgestrel, or (–)-norgestrel), the former of which is inactive (making norgestrel exactly half as potent as levonorgestrel).[16] [17] Norgestrel is more specifically a derivative of norethisterone (17α-ethynyl-19-nortestosterone) and is a member of the gonane (18-methylestrane) subgroup of the 19-nortestosterone family of progestins.[18]

Synthesis

Chemical syntheses of norgestrel have been published.[19]

History

Norgestrel was first introduced, as a birth control pill in combination with ethinylestradiol, under the brand name Eugynon in Germany in 1966.[20] [21] It was subsequently marketed as a combined birth control pill with ethinylestradiol in the United States under the brand name Ovral in 1968, and was marketed in many other countries as well.[22]

The contraceptive efficacy of norgestrel was established in the US with the original approval for prescription use in 1973.

In July 2023, the FDA approved norgestrel for over-the-counter sale.[23] The FDA granted the approval to Laboratoire HRA Pharma which was acquired by Perrigo Company plc.

Society and culture

Generic names

Norgestrel is the generic name of the drug and its international nonproprietary name, United States Adopted Name, United States Pharmacopeia, British Approved Name, Dénomination Commune Française, Denominazione Comune Italiana, and Japanese Accepted Name.[24] [25] [26] It is also known as dl-norgestrel, DL-norgestrel, or (±)-norgestrel.

Brand names

Norgestrel is marketed under a variety of brand names including Cyclacur, Cryselle, Cyclo-Progynova, Duoluton, Elinest, Eugynon, Microgynon, Lo/Ovral, Low-Ogestrel, Logynon, Microlut, Minicon, Nordette, Neogest, Ogestrel, Ovral, Ovran, Ovranette, Ovrette, Planovar, Prempak, Progyluton, and Trinordiol among others.[27]

Notes and References

  1. Web site: Opill- norgestrel tablet . DailyMed . 4 March 2024 . 13 March 2024 . 11 March 2024 . https://web.archive.org/web/20240311132409/https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=69dfa2ac-6a7e-4587-929c-9acabd97973b . live .
  2. Book: Morton IK, Hall JM. Concise Dictionary of Pharmacological Agents: Properties and Synonyms. 6 December 2012. Springer Science & Business Media. 978-94-011-4439-1. 202–. 10 March 2018. 10 January 2023. https://web.archive.org/web/20230110231919/https://books.google.com/books?id=tsjrCAAAQBAJ&pg=PA202. live.
  3. Kuhl H . Pharmacology of estrogens and progestogens: influence of different routes of administration . Climacteric . 8 . Suppl 1 . 3–63 . 2005 . 16112947 . 10.1080/13697130500148875 . 24616324 . 10 March 2018 . 22 August 2016 . https://web.archive.org/web/20160822055012/http://hormonebalance.org/images/documents/Kuhl%2005%20%20Pharm%20Estro%20Progest%20Climacteric_1313155660.pdf . live .
  4. Web site: Learn more about Opill (0.075mg Oral Norgestrel Tablet) . U.S. Food and Drug Administration (FDA) . 13 July 2023 . 13 March 2024 . 9 October 2023 . https://web.archive.org/web/20231009175334/https://www.fda.gov/drugs/postmarket-drug-safety-information-patients-and-providers/opill-0075mg-oral-norgestrel-tablet-information . live .
  5. Book: Fischer J, Ganellin CR . Analogue-based Drug Discovery . 2006 . John Wiley & Sons . 9783527607495 . 479 .
  6. Book: Carp HJ . Progestogens in Obstetrics and Gynecology. 9 April 2015. Springer. 978-3-319-14385-9. 112.
  7. Web site: Generic Lo/Ovral-28 Availability. 10 March 2018. 2 March 2019. https://web.archive.org/web/20190302024543/https://www.drugs.com/availability/generic-lo-ovral-28.html. live.
  8. Web site: The Top 300 of 2021 . ClinCalc . 14 January 2024 . 15 January 2024 . https://web.archive.org/web/20240115223848/https://clincalc.com/DrugStats/Top300Drugs.aspx . live .
  9. Web site: Ethinyl Estradiol; Norgestrel - Drug Usage Statistics . ClinCalc . 14 January 2024 . 7 October 2021 . https://web.archive.org/web/20211007114348/https://clincalc.com/DrugStats/Drugs/EthinylEstradiolNorgestrel . live .
  10. 13 July 2023 . FDA Approves First Nonprescription Daily Oral Contraceptive . 13 July 2023 . U.S. Food and Drug Administration (FDA) . 13 July 2023 . https://web.archive.org/web/20230713130226/https://www.fda.gov/news-events/press-announcements/fda-approves-first-nonprescription-daily-oral-contraceptive . live .
  11. Yuzpe AA, Smith RP, Rademaker AW . A multicenter clinical investigation employing ethinyl estradiol combined with dl-norgestrel as postcoital contraceptive agent . Fertility and Sterility . 37 . 4 . 508–513 . April 1982 . 7040117 . 10.1016/s0015-0282(16)46157-1 . free .
  12. Endrikat J, Gerlinger C, Richard S, Rosenbaum P, Düsterberg B . Ovulation inhibition doses of progestins: a systematic review of the available literature and of marketed preparations worldwide . Contraception . 84 . 6 . 549–57 . December 2011 . 22078182 . 10.1016/j.contraception.2011.04.009 .
  13. Schindler AE, Campagnoli C, Druckmann R, Huber J, Pasqualini JR, Schweppe KW, Thijssen JH . Classification and pharmacology of progestins . Maturitas . 46 . Suppl 1 . S7–S16 . December 2003 . 14670641 . 10.1016/j.maturitas.2003.09.014 .
  14. Book: Knörr K, Knörr-Gärtner H, Beller FK, Lauritzen C. Geburtshilfe und Gynäkologie: Physiologie und Pathologie der Reproduktion. 8 March 2013. Springer-Verlag. 978-3-642-95583-9. 583–. 13 August 2022. 11 January 2023. https://web.archive.org/web/20230111061914/https://books.google.com/books?id=tpmgBgAAQBAJ&pg=PA583. live.
  15. Book: Leidenberger FA, Strowitzki T, Ortmann O. Klinische Endokrinologie für Frauenärzte. 29 August 2009. Springer-Verlag. 978-3-540-89760-6. 225,227. 13 August 2022. 14 July 2023. https://web.archive.org/web/20230714045652/https://books.google.com/books?id=bqokBAAAQBAJ&pg=PA225. live.
  16. Book: Alldredge BK, Corelli RL, Ernst ME. Koda-Kimble and Young's Applied Therapeutics: The Clinical Use of Drugs. 1 February 2012. Lippincott Williams & Wilkins. 978-1-60913-713-7. 1072–. 3 August 2017. 12 January 2023. https://web.archive.org/web/20230112233115/https://books.google.com/books?id=qcVpuHngXK0C&pg=PA1072. live.
  17. Book: Lavery JP, Sanfilippo JS. Pediatric and Adolescent Obstetrics and Gynecology. 6 December 2012. Springer Science & Business Media. 978-1-4612-5064-7. 248–. 3 August 2017. 12 January 2023. https://web.archive.org/web/20230112233116/https://books.google.com/books?id=l9XTBwAAQBAJ&pg=PA248. live.
  18. Book: Offermanns S, Rosenthal W . Encyclopedia of Molecular Pharmacology. 14 August 2008. Springer Science & Business Media. 978-3-540-38916-3. 390–.
  19. Book: Die Gestagene. 27 November 2013. Springer-Verlag. 978-3-642-99941-3. 16–17,284–. 19 September 2018. 14 July 2023. https://web.archive.org/web/20230714045652/https://books.google.com/books?id=t8GpBgAAQBAJ&pg=PA16. live.
  20. Book: Ortiz-Gómez T, Santesmases MJ . Gendered Drugs and Medicine: Historical and Socio-Cultural Perspectives. 22 April 2016. Taylor & Francis. 978-1-317-12981-3. 175–. The 1966 marketing campaign for Schering's second contraceptive, Eugynon, [...] (Schering AG Berline 1966, 11). [...] In 1970 [Schering] had already conducted an opinion poll among doctors in the run up to the marketing campaign for the newly introduced Neogynon. [...].
  21. Book: Pohl WG. Die wissenschaftliche Welt von gestern: die Preisträger des Ignaz L. Lieben-Preises 1865-1937 und des Richard Lieben-Preises 1912-1928: ein Kapitel österreichischer Wissenschaftsgeschichte in Kurzbiografien. 2004. Böhlau Verlag Wien. 978-3-205-77303-0. 150–. [The contraceptive Eugynon is launched in 1966. Neogynon follows in 1970.]. 18 April 2018. 12 January 2023. https://web.archive.org/web/20230112233119/https://books.google.com/books?id=PtTuOXYBi3IC&pg=PA150. live.
  22. Book: Marks L . Sexual Chemistry: A History of the Contraceptive Pill. 2010. Yale University Press. 978-0-300-16791-7. 73–.
  23. Web site: Archived copy . 13 March 2024 . 9 March 2024 . https://web.archive.org/web/20240309031151/https://www.accessdata.fda.gov/drugsatfda_docs/nda/2023/017031Orig1s041SumR.pdf . live .
  24. Book: Elks J . The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies. 14 November 2014. Springer. 978-1-4757-2085-3. 887–.
  25. Book: Index Nominum 2000: International Drug Directory. 2000. Taylor & Francis. 978-3-88763-075-1. 751–.
  26. Web site: Norgestrel - brand name list from . Drugs.com . 17 September 2022 . 9 January 2021 . https://web.archive.org/web/20210109221538/https://www.drugs.com/international/norgestrel.html . live .
  27. Book: William Andrew Publishing. Pharmaceutical Manufacturing Encyclopedia . 3rd . 22 October 2013. Elsevier. 978-0-8155-1856-3. 2935–.

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