Norgestrel

Overview

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. It is taken by mouth.[1–5] WP

Side effects of norgestrel include menstrual irregularities, headaches, nausea, and breast tenderness. 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.[4][6][7] WP

Norgestrel was patented in 1961 and came into medical use, specifically in birth control pills, in 1966. It was subsequently introduced for use in menopausal hormone therapy as well. Norgestrel is sometimes referred to as a "second-generation" progestin. It is marketed widely throughout the world. Norgestrel is available as a generic medication. In 2022, the version with ethinylestradiol was the 264th most commonly prescribed medication in the United States, with more than 1 million prescriptions. In July 2023, the US Food and Drug Administration (FDA) approved norgestrel for over-the-counter sale.[2][5][7–14] WP

Uses, dosage and effects

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.[5][15] WP

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.[4] WP

The ovulation-inhibiting dose of norgestrel appears to be greater than 75 μg/day, as ovulation occurred in 50 to 75% of cycles with this dosage of norgestrel in studies. The ovulation-inhibiting dosage of levonorgestrel, which is twice as potent as norgestrel, is approximately 50 to 60 μg/day. One review lists the ovulation-inhibiting dose of norgestrel as 100 μg/day. The endometrial transformation dose of norgestrel is listed as 12 mg per cycle and the menstrual delay test dose of norgestrel is listed as 0.5 to 2 mg/day.[4][16–19] WP

Pharmacokinetics

The pharmacokinetics of norgestrel have been reviewed.[20] WP

History

History

Norgestrel was first introduced, as a birth control pill in combination with ethinylestradiol, under the brand name Eugynon in Germany in 1966. 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.[5][8][9][21][22] WP

The contraceptive efficacy of norgestrel was established in the U.S. with the original approval for prescription use in 1973.[7] WP

In July 2023, the FDA approved norgestrel for over-the-counter sale. The FDA granted the approval to Laboratoire HRA Pharma which was acquired by Perrigo Company plc.[7][23] WP

Legal status

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. It is also known as dl-norgestrel, DL-norgestrel, or (±)-norgestrel.[1][2][3][5] WP

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, Opill, Ogestrel, Ovral, Ovran, Ovranette, Ovrette, Planovar, Prempak, Progyluton, and Trinordiol among others.[1][2][5][21] WP

Toxicity

Chemistry

Formula

C21H28O2 PC

Molar mass (g/mol)

312.4 PC

IUPAC name (computed by PubChem)

(8R,9S,10R,13S,14S,17R)-13-ethyl-17-ethynyl-17-hydroxy-1,2,6,7,8,9,10,11,12,14,15,16-dodecahydrocyclopenta[a]phenanthren-3-one PC

SMILES

CC[C@]12CC[C@H]3[C@H]([C@@H]1CC[C@]2(C#C)O)CCC4=CC(=O)CC[C@H]34 PC

InChIKey

WWYNJERNGUHSAO-XUDSTZEESA-N PC

PubChem CID

13109

IUPAC name

(8R,9S,10R,13S,14S,17R)-13-ethyl-17-ethynyl-17-hydroxy-1,2,6,7,8,9,10,11,12,14,15,16-dodecahydrocyclopenta[a]phenanthren-3-one WP

Harm reduction information

No harm reduction data is on file for this compound yet. That means no dose, timing or combination data from PsychonautWiki or TripSit. Please don't guess a dose from similar compounds. If you have taken it and feel unwell, contact emergency services or a poison control center.

User reports

Pop culture

No references added yet.

Sources

1. Other Elks J. The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies. 14 November 2014
2. Other Index Nominum 2000: International Drug Directory. 2000
3. Other Morton IK, Hall JM. Concise Dictionary of Pharmacological Agents: Properties and Synonyms. 6 December 2012
4. Journal / agency Kuhl H. Pharmacology of estrogens and progestogens: influence of different routes of administration. Climacteric. 2005. doi:10.1080/13697130500148875 · PMID 16112947
5. Other Norgestrel - brand name list from
6. Journal / agency Learn more about Opill (0.075mg Oral Norgestrel Tablet). 13 July 2023
7. Journal / agency FDA Approves First Nonprescription Daily Oral Contraceptive. 13 July 2023
8. Other Ortiz-Gómez T, Santesmases MJ. Gendered Drugs and Medicine: Historical and Socio-Cultural Perspectives. 22 April 2016
9. Other 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
10. Other Fischer J, Ganellin CR. Analogue-based Drug Discovery. 2006
11. Other Carp HJ. Progestogens in Obstetrics and Gynecology. 9 April 2015
12. Other Generic Lo/Ovral-28 Availability
13. Other The Top 300 of 2022
14. Other Ethinyl Estradiol; Norgestrel Drug Usage Statistics, United States, 2013 - 2022
15. Journal / agency Yuzpe AA, Smith RP, Rademaker AW. A multicenter clinical investigation employing ethinyl estradiol combined with dl-norgestrel as postcoital contraceptive agent. Fertility and Sterility. April 1982. doi:10.1016/s0015-0282(16)46157-1 · PMID 7040117
16. Journal / agency 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. December 2011. doi:10.1016/j.contraception.2011.04.009 · PMID 22078182
17. Journal / agency Schindler AE, Campagnoli C, Druckmann R, Huber J, Pasqualini JR, Schweppe KW, Thijssen JH. Classification and pharmacology of progestins. Maturitas. December 2003. doi:10.1016/j.maturitas.2003.09.014 · PMID 14670641
18. Other Knörr K, Knörr-Gärtner H, Beller FK, Lauritzen C. Geburtshilfe und Gynäkologie: Physiologie und Pathologie der Reproduktion. 8 March 2013
19. Other Leidenberger FA, Strowitzki T, Ortmann O. Klinische Endokrinologie für Frauenärzte. 29 August 2009
20. Other Die Gestagene. 27 November 2013
21. Other William Andrew Publishing. Pharmaceutical Manufacturing Encyclopedia. 22 October 2013
22. Other Marks L. Sexual Chemistry: A History of the Contraceptive Pill. 2010
23. Journal / agency Archived copy

Text and values on this page are quoted from Wikipedia (CC BY-SA 4.0), PubChem (public domain). Each value links to the exact revision it came from.