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{{Short description|Progestin medication used for birth control}}
{{Unreferenced stub|auto=yes|date=December 2009}}
{{Distinguish|Levonorgestrel}}
{{Drugbox
{{Use dmy dates|date=March 2024}}
| verifiedrevid = 408343718
{{cs1 config |name-list-style=vanc |display-authors=6}}
| IUPAC_name = (8''R'',9''S'',10''R'',13''S'',14''S'',17''S'')- 13-ethyl-17-ethynyl-17-hydroxy- 1,2,6,7,8,9,10,11,12,14,15, 16- dodecahydrocyclopentaphenanthren-3-one
{{Infobox drug
| Verifiedfields = verified
| Watchedfields = verified
| verifiedrevid = 456663702
| image = Levonorgestrel.svg | image = Levonorgestrel.svg
| width = 225
| alt =
| image2 = Dextronorgestrel.svg
| width2 = 225
| alt2 =
| caption = Top, '''levonorgestrel''' (CAS {{CAS|797-63-7}}); <br />Bottom: '''dextronorgestrel''' (CAS {{CAS|797-64-8}}).
<!-- | image3 = Norgestrel molecule ball.png
| width3 = 225
| alt3 = -->


<!--Clinical data--> <!-- Clinical data -->| pronounce =
| tradename = | tradename = Opill, others
| Drugs.com = {{drugs.com|CONS|norgestrel}} | Drugs.com = {{drugs.com|CONS|norgestrel}}
| MedlinePlus = a602008 | MedlinePlus = a602008
| DailyMedID = Norgestrel
| pregnancy_AU = <!-- A / B1 / B2 / B3 / C / D / X --> | pregnancy_AU = <!-- A / B1 / B2 / B3 / C / D / X -->
| pregnancy_AU_comment =
| pregnancy_US = <!-- A / B / C / D / X -->
| pregnancy_category = | pregnancy_category =
| routes_of_administration = ]
| legal_AU = <!-- Unscheduled / S2 / S4 / S8 -->
| class = ]
| legal_UK = <!-- GSL / P / POM / CD -->
| ATC_prefix = G03
| legal_US = <!-- OTC / Rx-only -->
| legal_status = | ATC_suffix = AA06
| ATC_supplemental = {{ATC|G03|FA10}} {{ATC|G03|FB01}} (only combinations with ]s)
| routes_of_administration =


<!-- Legal status -->| legal_AU = <!-- S2, S3, S4, S5, S6, S7, S8, S9 or Unscheduled -->
<!--Pharmacokinetic data-->
| bioavailability = | legal_AU_comment =
| legal_BR = <!-- OTC, A1, A2, A3, B1, B2, C1, C2, C3, C4, C5, D1, D2, E, F -->
| protein_bound =
| metabolism = | legal_BR_comment =
| legal_CA = <!-- OTC, Rx-only, Schedule I, II, III, IV, V, VI, VII, VIII -->
| elimination_half-life = 5-14 hours
| excretion = | legal_CA_comment =
| legal_DE = <!-- Anlage I, II, III or Unscheduled -->
| legal_DE_comment =
| legal_NZ = <!-- Class A, B, C -->
| legal_NZ_comment =
| legal_UK = <!-- GSL, P, POM, CD, CD Lic, CD POM, CD No Reg POM, CD (Benz) POM, CD (Anab) POM or CD Inv POM / Class A, B, C -->
| legal_UK_comment =
| legal_US = OTC
| legal_US_comment = <ref name="Opill FDA label">{{cite web | title=Opill- norgestrel tablet | website=DailyMed | date=4 March 2024 | url=https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=69dfa2ac-6a7e-4587-929c-9acabd97973b | access-date=13 March 2024 | archive-date=11 March 2024 | archive-url=https://web.archive.org/web/20240311132409/https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=69dfa2ac-6a7e-4587-929c-9acabd97973b | url-status=live }}</ref><ref name="FDA PR 20230713" />
| legal_EU =
| legal_EU_comment =
| legal_UN = <!-- N I, II, III, IV / P I, II, III, IV -->
| legal_UN_comment =
| legal_status = <!-- For countries not listed above -->


<!-- Pharmacokinetic data -->| bioavailability =
<!--Identifiers-->
| protein_bound =
| CASNo_Ref = {{cascite|correct|CAS}}
| metabolism =
| CAS_number_Ref = {{cascite|correct|??}}
| metabolites =
| onset =
| elimination_half-life =
| duration_of_action =
| excretion = <!-- Identifiers -->
| CAS_number_Ref = {{cascite|correct|CAS}}
| CAS_number = 6533-00-2 | CAS_number = 6533-00-2
| ATC_prefix = G03 | CAS_supplemental =
| ATC_suffix = AC03
| ATC_supplemental =
| PubChem = 16051930 | PubChem = 16051930
| IUPHAR_ligand =
| DrugBank_Ref = {{drugbankcite|correct|drugbank}} | DrugBank_Ref = {{drugbankcite|correct|drugbank}}
| DrugBank = DB00506 | DrugBank = DB09389
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} | ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 10481953 | ChemSpiderID = 10481953
Line 41: Line 73:
| KEGG_Ref = {{keggcite|correct|kegg}} | KEGG_Ref = {{keggcite|correct|kegg}}
| KEGG = D00954 | KEGG = D00954
| ChEMBL_Ref = {{ebicite|correct|EBI}}
| ChEMBL = 2107797
| ChEBI_Ref = {{ebicite|correct|EBI}}
| ChEBI = 7630
| NIAID_ChemDB =
| PDB_ligand =
| 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


<!-- Chemical and physical data -->| IUPAC_name = (8''R'',9''S'',10''R'',13''S'',14''S'')-13-ethyl-17-ethynyl-17-hydroxy-1,2,6,7,8,9,10,11,12,14,15,16-dodecahydrocyclopentaphenanthren-3-one
<!--Chemical data-->
| C=21 | H=28 | O=2 | C = 21
| H = 28
| molecular_weight = 312.446 g/mol
| O = 2
| smiles = O=C\1CC4C(=C/1)/CC34CC2(CC)3CCC2(O)C#C
| SMILES = O=C\1CC4C(=C/1)/CC34CC2(CC)3CCC2(O)C#C
| InChI = 1/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
| InChIKey = WWYNJERNGUHSAO-CULCCENABJ
| StdInChI_Ref = {{stdinchicite|correct|chemspider}} | StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| 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 | 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_Ref = {{stdinchicite|correct|chemspider}} | StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = WWYNJERNGUHSAO-CULCCENASA-N | StdInChIKey = WWYNJERNGUHSAO-CULCCENASA-N
| density =
| density_notes =
| melting_point =
| melting_high =
| melting_notes =
| boiling_point =
| boiling_notes =
| solubility =
| sol_units =
| specific_rotation =
}} }}
'''Norgestrel''' is a ] used in ]. Norgestrel is a mixture of two ], dextro-norgestrel (CAS# 797-64-8) and levo-norgestrel (CAS# 797-63-7). Only ] is biologically active. Therefore, while some medications may contain dextronorgestrel, they are often labeled in terms of their levonorgestrel content only, ignoring the inert isomer.
It is used in the hormonal contraceptive Microgynon 30, among others.


<!-- Definition and medical uses -->
==See also==
'''Norgestrel''', sold under the brand name ''']''' among others, is a ] which is used in ]s. It is often combined with the ] ], marketed as Ovral. It is also used in ].<ref name="Elks2014" /><ref name="IndexNominum2000" /><ref name="MortonHall2012">{{cite book|vauthors=Morton IK, Hall JM|title=Concise Dictionary of Pharmacological Agents: Properties and Synonyms|url=https://books.google.com/books?id=tsjrCAAAQBAJ&pg=PA202|date=6 December 2012|publisher=Springer Science & Business Media|isbn=978-94-011-4439-1|pages=202–|access-date=10 March 2018|archive-date=10 January 2023|archive-url=https://web.archive.org/web/20230110231919/https://books.google.com/books?id=tsjrCAAAQBAJ&pg=PA202|url-status=live}}</ref><ref name="pmid16112947">{{cite journal | vauthors = Kuhl H | title = Pharmacology of estrogens and progestogens: influence of different routes of administration | journal = Climacteric | volume = 8 | issue = Suppl 1 | pages = 3–63 | year = 2005 | pmid = 16112947 | doi = 10.1080/13697130500148875 | s2cid = 24616324 | url = http://hormonebalance.org/images/documents/Kuhl%2005%20%20Pharm%20Estro%20Progest%20Climacteric_1313155660.pdf | access-date = 10 March 2018 | archive-date = 22 August 2016 | archive-url = https://web.archive.org/web/20160822055012/http://hormonebalance.org/images/documents/Kuhl%2005%20%20Pharm%20Estro%20Progest%20Climacteric_1313155660.pdf | url-status = live }}</ref><ref name="Drugs.com" /> It is taken ].<ref name="MortonHall2012" /><ref name="pmid16112947" />
* ]

* ]
<!-- Side effects and mechanism -->
* ]
]s of norgestrel include ], ]s, ], and ].<ref>{{cite web | title=Learn more about Opill (0.075mg Oral Norgestrel Tablet) | website=U.S. ] (FDA) | date=13 July 2023 | url=https://www.fda.gov/drugs/postmarket-drug-safety-information-patients-and-providers/opill-0075mg-oral-norgestrel-tablet-information | access-date=13 March 2024 | archive-date=9 October 2023 | archive-url=https://web.archive.org/web/20231009175334/https://www.fda.gov/drugs/postmarket-drug-safety-information-patients-and-providers/opill-0075mg-oral-norgestrel-tablet-information | url-status=live }}</ref> The most common side effects of the norgestrel include irregular bleeding, headaches, dizziness, nausea, increased appetite, abdominal pain, cramps, or bloating.<ref name="FDA PR 20230713" /> Norgestrel is a ], or a ] ], and hence is an ] of the ], the ] of progestogens like ].<ref name="pmid16112947" /> It has weak ]ic activity and no other important hormonal activity.<ref name="pmid16112947" />
{{Sex hormones}}

<!-- History, society and culture -->
Norgestrel was patented in 1961 and came into medical use, specifically in birth control pills, in 1966.<ref name="Ortiz-GómezSantesmases2016" /><ref name="Pohl2004" /><ref name="Fis2006">{{cite book | vauthors = Fischer J, Ganellin CR |title=Analogue-based Drug Discovery |date=2006 |publisher=John Wiley & Sons |isbn=9783527607495 |page=479 |url=https://books.google.com/books?id=FjKfqkaKkAAC&pg=PA479 }}</ref> It was subsequently introduced for use in menopausal hormone therapy as well.<ref name="Drugs.com" /> Norgestrel is sometimes referred to as a "second-generation" progestin.<ref name="Carp2015">{{cite book | vauthors = Carp HJ |title=Progestogens in Obstetrics and Gynecology|url=https://books.google.com/books?id=Ik8SCAAAQBAJ&pg=PA112|date=9 April 2015|publisher=Springer|isbn=978-3-319-14385-9|page=112}}</ref> It is marketed widely throughout the world.<ref name="Drugs.com" /><ref name="IndexNominum2000" /> Norgestrel is available as a ].<ref name="Drugs.com-Generic">{{cite web|url=https://www.drugs.com/availability/generic-lo-ovral-28.html|title=Generic Lo/Ovral-28 Availability|access-date=10 March 2018|archive-date=2 March 2019|archive-url=https://web.archive.org/web/20190302024543/https://www.drugs.com/availability/generic-lo-ovral-28.html|url-status=live}}</ref> In 2022, the version with ] was the 264th most commonly prescribed medication in the United States, with more than 1{{nbsp}}million prescriptions.<ref>{{cite web | title=The Top 300 of 2022 | url=https://clincalc.com/DrugStats/Top300Drugs.aspx | website=ClinCalc | access-date=30 August 2024 | archive-date=30 August 2024 | archive-url=https://web.archive.org/web/20240830202410/https://clincalc.com/DrugStats/Top300Drugs.aspx | url-status=live }}</ref><ref>{{cite web | title = Ethinyl Estradiol; Norgestrel Drug Usage Statistics, United States, 2013 - 2022 | website = ClinCalc | url = https://clincalc.com/DrugStats/Drugs/EthinylEstradiolNorgestrel | access-date = 30 August 2024 }}</ref> In July 2023, the US ] (FDA) approved norgestrel for ] sale.<ref name="FDA PR 20230713">{{Cite press release |date=13 July 2023 |title=FDA Approves First Nonprescription Daily Oral Contraceptive |url=https://www.fda.gov/news-events/press-announcements/fda-approves-first-nonprescription-daily-oral-contraceptive |access-date=13 July 2023 |website=U.S. ] (FDA) |archive-date=13 July 2023 |archive-url=https://web.archive.org/web/20230713130226/https://www.fda.gov/news-events/press-announcements/fda-approves-first-nonprescription-daily-oral-contraceptive |url-status=live }} {{PD-notice}}</ref>
{{TOC limit|3}}

==Medical uses==
Norgestrel is used in combination with ] or ] in ]s, alone in ]s, and in combination with ] or ] in ].<ref name="Drugs.com" /> It has also been used as an ] in the ].<ref name="pmid7040117">{{cite journal | vauthors = Yuzpe AA, Smith RP, Rademaker AW | title = A multicenter clinical investigation employing ethinyl estradiol combined with dl-norgestrel as postcoital contraceptive agent | journal = Fertility and Sterility | volume = 37 | issue = 4 | pages = 508–513 | date = April 1982 | pmid = 7040117 | doi = 10.1016/s0015-0282(16)46157-1 | doi-access = free }}</ref>

==Side effects==
{{See also|Levonorgestrel#Side effects|Progestin#Side effects}}

==Pharmacology==

===Pharmacodynamics===
{{See also|Levonorgestrel#Pharmacodynamics}}

Norgestrel is a ], or an ] of the ].<ref name="pmid16112947" /> The ] of norgestrel lies in the ''levo'' ], ], whereas the ''dextro'' isomer is inactive.<ref name="pmid16112947" /> As such, norgestrel is identical in its hormonal activity to levonorgestrel except that it is half as ] by weight.<ref name="pmid16112947" /> Levonorgestrel, and by extension norgestrel, have some ]ic activity, but no ]ic, ], or ] activity.<ref name="pmid16112947" />

{{Relative affinities of levonorgestrel and metabolites}}

The ]-inhibiting dose of norgestrel appears to be greater than 75{{nbsp}}μg/day, as ovulation occurred in 50 to 75% of cycles with this dosage of norgestrel in studies.<ref name="pmid22078182">{{cite journal | vauthors = Endrikat J, Gerlinger C, Richard S, Rosenbaum P, Düsterberg B | title = Ovulation inhibition doses of progestins: a systematic review of the available literature and of marketed preparations worldwide | journal = Contraception | volume = 84 | issue = 6 | pages = 549–57 | date = December 2011 | pmid = 22078182 | doi = 10.1016/j.contraception.2011.04.009 | url = }}</ref> The ovulation-inhibiting dosage of levonorgestrel, which is twice as potent as norgestrel, is approximately 50 to 60{{nbsp}}μg/day.<ref name="pmid16112947" /><ref name="pmid14670641">{{cite journal | vauthors = Schindler AE, Campagnoli C, Druckmann R, Huber J, Pasqualini JR, Schweppe KW, Thijssen JH | title = Classification and pharmacology of progestins | journal = Maturitas | volume = 46 | issue = Suppl 1 | pages = S7–S16 | date = December 2003 | pmid = 14670641 | doi = 10.1016/j.maturitas.2003.09.014 | url = }}</ref><ref name="pmid22078182" /> One review lists the ovulation-inhibiting dose of norgestrel as 100{{nbsp}}μg/day.<ref name="KnörrKnörr-Gärtner2013">{{cite book|vauthors=Knörr K, Knörr-Gärtner H, Beller FK, Lauritzen C|title=Geburtshilfe und Gynäkologie: Physiologie und Pathologie der Reproduktion|url=https://books.google.com/books?id=tpmgBgAAQBAJ&pg=PA583|date=8 March 2013|publisher=Springer-Verlag|isbn=978-3-642-95583-9|pages=583–|access-date=13 August 2022|archive-date=11 January 2023|archive-url=https://web.archive.org/web/20230111061914/https://books.google.com/books?id=tpmgBgAAQBAJ&pg=PA583|url-status=live}}</ref> The ] of norgestrel is listed as 12{{nbsp}}mg per cycle and the ] dose of norgestrel is listed as 0.5 to 2{{nbsp}}mg/day.<ref name="KnörrKnörr-Gärtner2013" /><ref name="LeidenbergerStrowitzki2009">{{cite book|vauthors=Leidenberger FA, Strowitzki T, Ortmann O|title=Klinische Endokrinologie für Frauenärzte|url=https://books.google.com/books?id=bqokBAAAQBAJ&pg=PA225|date=29 August 2009|publisher=Springer-Verlag|isbn=978-3-540-89760-6|pages=225,227|access-date=13 August 2022|archive-date=14 July 2023|archive-url=https://web.archive.org/web/20230714045652/https://books.google.com/books?id=bqokBAAAQBAJ&pg=PA225|url-status=live}}</ref>

===Pharmacokinetics===
{{See also|Levonorgestrel#Pharmacokinetics}}

The ] of norgestrel have been reviewed.<ref name="Springer2013" />

==Chemistry==
{{See also|List of progestogens|List of androgens/anabolic steroids|Levonorgestrel}}

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 ] ] ] and a ] of ].<ref name="Elks2014" /><ref name="IndexNominum2000" /> It is a ] of ]s dextronorgestrel (the C13α isomer; l-norgestrel, L-norgestrel, or (+)-norgestrel) and ] (the C13β isomer; d-norgestrel, D-norgestrel, or (–)-norgestrel), the former of which is inactive (making norgestrel exactly half as ] as levonorgestrel).<ref name="AlldredgeCorelli2012">{{cite book|vauthors=Alldredge BK, Corelli RL, Ernst ME|title=Koda-Kimble and Young's Applied Therapeutics: The Clinical Use of Drugs|url=https://books.google.com/books?id=qcVpuHngXK0C&pg=PA1072|date=1 February 2012|publisher=Lippincott Williams & Wilkins|isbn=978-1-60913-713-7|pages=1072–|access-date=3 August 2017|archive-date=12 January 2023|archive-url=https://web.archive.org/web/20230112233115/https://books.google.com/books?id=qcVpuHngXK0C&pg=PA1072|url-status=live}}</ref><ref name="LaverySanfilippo2012">{{cite book|vauthors=Lavery JP, Sanfilippo JS|title=Pediatric and Adolescent Obstetrics and Gynecology|url=https://books.google.com/books?id=l9XTBwAAQBAJ&pg=PA248|date=6 December 2012|publisher=Springer Science & Business Media|isbn=978-1-4612-5064-7|pages=248–|access-date=3 August 2017|archive-date=12 January 2023|archive-url=https://web.archive.org/web/20230112233116/https://books.google.com/books?id=l9XTBwAAQBAJ&pg=PA248|url-status=live}}</ref> Norgestrel is more specifically a derivative of ] (17α-ethynyl-19-nortestosterone) and is a member of the ] (18-methylestrane) subgroup of the ] family of progestins.<ref name="OffermannsRosenthal2008">{{cite book| vauthors = Offermanns S, Rosenthal W |title=Encyclopedia of Molecular Pharmacology|url=https://books.google.com/books?id=iwwo5gx8aX8C&pg=PA390|date=14 August 2008|publisher=Springer Science & Business Media|isbn=978-3-540-38916-3|pages=390–}}</ref>

===Synthesis===
] of norgestrel have been published.<ref name="Springer2013">{{cite book|title=Die Gestagene|url=https://books.google.com/books?id=t8GpBgAAQBAJ&pg=PA16|date=27 November 2013|publisher=Springer-Verlag|isbn=978-3-642-99941-3|pages=16–17,284–|access-date=19 September 2018|archive-date=14 July 2023|archive-url=https://web.archive.org/web/20230714045652/https://books.google.com/books?id=t8GpBgAAQBAJ&pg=PA16|url-status=live}}</ref>

==History==
Norgestrel was first introduced, as a birth control pill in combination with ], under the brand name Eugynon in Germany in 1966.<ref name="Ortiz-GómezSantesmases2016">{{cite book| vauthors = Ortiz-Gómez T, Santesmases MJ |title=Gendered Drugs and Medicine: Historical and Socio-Cultural Perspectives|url=https://books.google.com/books?id=snUGDAAAQBAJ&pg=PT175|date=22 April 2016|publisher=Taylor & Francis|isbn=978-1-317-12981-3|pages=175–|quote=The 1966 marketing campaign for Schering's second contraceptive, Eugynon, (Schering AG Berline 1966, 11). In 1970 had already conducted an opinion poll among doctors in the run up to the marketing campaign for the newly introduced Neogynon. }}</ref><ref name="Pohl2004">{{cite book|vauthors=Pohl WG|title=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|url=https://books.google.com/books?id=PtTuOXYBi3IC&pg=PA150|year=2004|publisher=Böhlau Verlag Wien|isbn=978-3-205-77303-0|pages=150–|quote=|access-date=18 April 2018|archive-date=12 January 2023|archive-url=https://web.archive.org/web/20230112233119/https://books.google.com/books?id=PtTuOXYBi3IC&pg=PA150|url-status=live}}</ref> 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.<ref name="Publishing2013" /><ref name="Marks2010">{{cite book| vauthors = Marks L |title=Sexual Chemistry: A History of the Contraceptive Pill|url=https://books.google.com/books?id=_i-s4biQs7MC&pg=PA73|year=2010|publisher=Yale University Press|isbn=978-0-300-16791-7|pages=73–}}</ref><ref name="Drugs.com" />

The contraceptive efficacy of norgestrel was established in the U.S. with the original approval for prescription use in 1973.<ref name="FDA PR 20230713" />

In July 2023, the ] approved norgestrel for ] sale.<ref name="FDA PR 20230713" /><ref>{{Cite web |url=https://www.accessdata.fda.gov/drugsatfda_docs/nda/2023/017031Orig1s041SumR.pdf |title=Archived copy |access-date=13 March 2024 |archive-date=9 March 2024 |archive-url=https://web.archive.org/web/20240309031151/https://www.accessdata.fda.gov/drugsatfda_docs/nda/2023/017031Orig1s041SumR.pdf |url-status=live }}</ref> The FDA granted the approval to Laboratoire HRA Pharma which was acquired by ].<ref name="FDA PR 20230713" />

==Society and culture==

===Generic names===
Norgestrel is the ] of the drug and its ], ], ], ], ], ], and ].<ref name="Elks2014">{{cite book| vauthors = Elks J |title=The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies|url=https://books.google.com/books?id=0vXTBwAAQBAJ&pg=PA887|date=14 November 2014|publisher=Springer|isbn=978-1-4757-2085-3|pages=887–}}</ref><ref name="IndexNominum2000">{{cite book|title=Index Nominum 2000: International Drug Directory|url=https://books.google.com/books?id=5GpcTQD_L2oC&pg=PA751|year=2000|publisher=Taylor & Francis|isbn=978-3-88763-075-1|pages=751–}}</ref><ref name="MortonHall2012" /><ref name="Drugs.com">{{cite web |url=https://www.drugs.com/international/norgestrel.html |title=Norgestrel - brand name list from |publisher=Drugs.com |date= |accessdate=17 September 2022 |archive-date=9 January 2021 |archive-url=https://web.archive.org/web/20210109221538/https://www.drugs.com/international/norgestrel.html |url-status=live }}</ref> It is also known as dl-norgestrel, DL-norgestrel, or (±)-norgestrel.<ref name="Elks2014" /><ref name="IndexNominum2000" /><ref name="MortonHall2012" /><ref name="Drugs.com" />

===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.<ref name="Elks2014" /><ref name="IndexNominum2000" /><ref name="Drugs.com" /><ref name="Publishing2013">{{cite book|author=William Andrew Publishing|title=Pharmaceutical Manufacturing Encyclopedia | edition = 3rd |url=https://books.google.com/books?id=_J2ti4EkYpkC&pg=PA2935-IA56|date=22 October 2013|publisher=Elsevier|isbn=978-0-8155-1856-3|pages=2935–}}</ref>


==References==
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