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Norgestrel

April 18, 2024

Not to be confused with Levonorgestrel.

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.[3][4][5][6][7] It is taken by mouth.[5][6]

Norgestrel
Top, levonorgestrel (CAS 797-63-7 );
Bottom: dextronorgestrel (CAS 797-64-8 ).
Clinical data
Trade namesOvral, Opill, 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 classProgestogen; Progestin
ATC code
Legal status
Legal status
Identifiers
  • (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
  • 6533-00-2 Y
PubChem CID
  • 16051930
DrugBank
  • DB09389 Y
ChemSpider
  • 10481953 Y
UNII
  • 3J8Q1747Z2
KEGG
  • D00954 Y
ChEBI
  • CHEBI:7630 Y
ChEMBL
  • ChEMBL2107797 Y
CompTox Dashboard (EPA)
  • DTXSID3047477
ECHA InfoCard100.026.758
Chemical and physical data
FormulaC21H28O2
Molar mass312.453 g·mol−1
3D model (JSmol)
  • Interactive image
  • 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=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)

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 2021, the version with ethinylestradiol was the 227th 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]

Medical uses edit

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.[7] It has also been used as an emergency contraceptive in the Yuzpe regimen.[16]

Side effects edit

See also: Levonorgestrel § Side effects, and Progestin § Side effects

Pharmacology edit

Pharmacodynamics edit

See also: Levonorgestrel § Pharmacodynamics

Norgestrel is a progestogen, or an agonist of the progesterone receptor.[6] The biological activity of norgestrel lies in the levo enantiomer, levonorgestrel, whereas the dextro isomer is inactive.[6] As such, norgestrel is identical in its hormonal activity to levonorgestrel except that it is half as potent by weight.[6] Levonorgestrel, and by extension norgestrel, have some androgenic activity, but no estrogenic, antimineralocorticoid, or glucocorticoid activity.[6]

Relative affinities (%) of levonorgestrel and metabolites
Compound PRTooltip Progesterone receptor ARTooltip Androgen receptor ERTooltip Estrogen receptor GRTooltip Glucocorticoid receptor MRTooltip Mineralocorticoid receptor SHBGTooltip Sex hormone-binding globulin CBGTooltip Corticosteroid binding globulin
Levonorgestrel 150–162 34a, 45 0 1–8 17–75 50 0
5α-Dihydrolevonorgestrel 50 38a 0 ? ? ? ?
3α,5α-Tetrahydrolevonorgestrel ? ? 0.4 ? ? ? ?
3β,5α-Tetrahydrolevonorgestrel ? ? 2.4 ? ? ? ?
Notes: Values are percentages (%). Reference ligands (100%) were promegestone for the PRTooltip progesterone receptor, metribolone (a = mibolerone) for the ARTooltip androgen receptor, E2 for the ERTooltip estrogen receptor, DEXATooltip dexamethasone for the GRTooltip glucocorticoid receptor, aldosterone for the MRTooltip mineralocorticoid receptor, DHTTooltip dihydrotestosterone for SHBGTooltip sex hormone-binding globulin, and cortisol for CBGTooltip Corticosteroid-binding globulin. Sources: See template.

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.[17] The ovulation-inhibiting dosage of levonorgestrel, which is twice as potent as norgestrel, is approximately 50 to 60 μg/day.[6][18][17] One review lists the ovulation-inhibiting dose of norgestrel as 100 μg/day.[19] 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.[19][20]

Pharmacokinetics edit

See also: Levonorgestrel § Pharmacokinetics

The pharmacokinetics of norgestrel have been reviewed.[21]

Chemistry edit

See also: List of progestogens, List of androgens/anabolic steroids, and 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 synthetic estrane steroid and a derivative of testosterone.[3][4] 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).[22][23] 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.[24]

Synthesis edit

Chemical syntheses of norgestrel have been published.[21]

History edit

Norgestrel was first introduced, as a birth control pill in combination with ethinylestradiol, under the brand name Eugynon in Germany in 1966.[9][10] 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.[25][26][7]

The contraceptive efficacy of norgestrel was established in the US with the original approval for prescription use in 1973.[2]

In July 2023, the FDA approved norgestrel for over-the-counter sale.[2][27] The FDA granted the approval to Laboratoire HRA Pharma which was acquired by Perrigo Company plc.[2]

Society and culture edit

Generic names edit

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.[3][4][5][7] It is also known as dl-norgestrel, DL-norgestrel, or (±)-norgestrel.[3][4][5][7]

Brand names edit

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.[3][4][7][25]

References edit

  1. ^ "Opill- norgestrel tablet". DailyMed. 4 March 2024. from the original on 11 March 2024. Retrieved 13 March 2024.
  2. ^ a b c d e f "FDA Approves First Nonprescription Daily Oral Contraceptive". U.S. Food and Drug Administration (FDA) (Press release). 13 July 2023. 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. ^ a b c d e Elks J (14 November 2014). The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies. Springer. pp. 887–. ISBN 978-1-4757-2085-3.
  4. ^ a b c d e f Index Nominum 2000: International Drug Directory. Taylor & Francis. 2000. pp. 751–. ISBN 978-3-88763-075-1.
  5. ^ a b c d 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. from the original on 10 January 2023. Retrieved 10 March 2018.
  6. ^ a b c d e f g h i 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. (PDF) from the original on 22 August 2016. Retrieved 10 March 2018.
  7. ^ a b c d e f g h "Norgestrel - brand name list from". Drugs.com. from the original on 9 January 2021. Retrieved 17 September 2022.
  8. ^ "Learn more about Opill (0.075mg Oral Norgestrel Tablet)". U.S. Food and Drug Administration (FDA). 13 July 2023. from the original on 9 October 2023. Retrieved 13 March 2024.
  9. ^ a b Ortiz-Gómez T, Santesmases MJ (22 April 2016). Gendered Drugs and Medicine: Historical and Socio-Cultural Perspectives. Taylor & Francis. pp. 175–. ISBN 978-1-317-12981-3. 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. [...]
  10. ^ a b Pohl WG (2004). 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. Böhlau Verlag Wien. pp. 150–. ISBN 978-3-205-77303-0. from the original on 12 January 2023. Retrieved 18 April 2018. [The contraceptive Eugynon is launched in 1966. Neogynon follows in 1970.]
  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". from the original on 2 March 2019. Retrieved 10 March 2018.
  14. ^ "The Top 300 of 2021". ClinCalc. from the original on 15 January 2024. Retrieved 14 January 2024.
  15. ^ "Ethinyl Estradiol; Norgestrel - Drug Usage Statistics". ClinCalc. from the original on 7 October 2021. Retrieved 14 January 2024.
  16. ^ Yuzpe AA, Smith RP, Rademaker AW (April 1982). "A multicenter clinical investigation employing ethinyl estradiol combined with dl-norgestrel as postcoital contraceptive agent". Fertility and Sterility. 37 (4): 508–513. doi:10.1016/s0015-0282(16)46157-1. PMID 7040117.
  17. ^ a b Endrikat J, Gerlinger C, Richard S, Rosenbaum P, Düsterberg B (December 2011). "Ovulation inhibition doses of progestins: a systematic review of the available literature and of marketed preparations worldwide". Contraception. 84 (6): 549–57. doi:10.1016/j.contraception.2011.04.009. PMID 22078182.
  18. ^ Schindler AE, Campagnoli C, Druckmann R, Huber J, Pasqualini JR, Schweppe KW, et al. (December 2003). "Classification and pharmacology of progestins". Maturitas. 46 (Suppl 1): S7–S16. doi:10.1016/j.maturitas.2003.09.014. PMID 14670641.
  19. ^ a b Knörr K, Knörr-Gärtner H, Beller FK, Lauritzen C (8 March 2013). Geburtshilfe und Gynäkologie: Physiologie und Pathologie der Reproduktion. Springer-Verlag. pp. 583–. ISBN 978-3-642-95583-9. from the original on 11 January 2023. Retrieved 13 August 2022.
  20. ^ Leidenberger FA, Strowitzki T, Ortmann O (29 August 2009). Klinische Endokrinologie für Frauenärzte. Springer-Verlag. pp. 225, 227. ISBN 978-3-540-89760-6. from the original on 14 July 2023. Retrieved 13 August 2022.
  21. ^ a b Die Gestagene. Springer-Verlag. 27 November 2013. pp. 16–17, 284–. ISBN 978-3-642-99941-3. from the original on 14 July 2023. Retrieved 19 September 2018.
  22. ^ Alldredge BK, Corelli RL, Ernst ME (1 February 2012). Koda-Kimble and Young's Applied Therapeutics: The Clinical Use of Drugs. Lippincott Williams & Wilkins. pp. 1072–. ISBN 978-1-60913-713-7. from the original on 12 January 2023. Retrieved 3 August 2017.
  23. ^ Lavery JP, Sanfilippo JS (6 December 2012). Pediatric and Adolescent Obstetrics and Gynecology. Springer Science & Business Media. pp. 248–. ISBN 978-1-4612-5064-7. from the original on 12 January 2023. Retrieved 3 August 2017.
  24. ^ Offermanns S, Rosenthal W (14 August 2008). Encyclopedia of Molecular Pharmacology. Springer Science & Business Media. pp. 390–. ISBN 978-3-540-38916-3.
  25. ^ a b William Andrew Publishing (22 October 2013). Pharmaceutical Manufacturing Encyclopedia (3rd ed.). Elsevier. pp. 2935–. ISBN 978-0-8155-1856-3.
  26. ^ Marks L (2010). Sexual Chemistry: A History of the Contraceptive Pill. Yale University Press. pp. 73–. ISBN 978-0-300-16791-7.
  27. ^ "Archived copy" (PDF). (PDF) from the original on 9 March 2024. Retrieved 13 March 2024.{{cite web}}: CS1 maint: archived copy as title (link)

April 18, 2024
norgestrel, confused, with, levonorgestrel, progestin, which, used, birth, control, pills, sold, under, brand, name, ovral, combination, with, estrogen, ethinylestradiol, opill, itself, also, used, menopausal, hormone, therapy, taken, mouth, levonorgestrel, bo. Not to be confused with Levonorgestrel 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 3 4 5 6 7 It is taken by mouth 5 6 NorgestrelTop levonorgestrel CAS 797 63 7 Bottom dextronorgestrel CAS 797 64 8 Clinical dataTrade namesOvral Opill othersOther namesdl Norgestrel DL Norgestrel Norgestrel WY 3707 SH 70850 SH 850 FH 122 A rac 13 Ethyl 17a ethynyl 19 nortestosterone rac 13 Ethyl 17a ethynylestr 4 en 17b ol 3 oneAHFS Drugs comMicromedex Detailed Consumer InformationMedlinePlusa602008License dataUS DailyMed NorgestrelRoutes ofadministrationBy mouthDrug classProgestogen ProgestinATC codeG03AA06 WHO G03FA10 WHO G03FB01 WHO only combinations with estrogens Legal statusLegal statusUS OTC 1 2 IdentifiersIUPAC 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 oneCAS Number6533 00 2 YPubChem CID16051930DrugBankDB09389 YChemSpider10481953 YUNII3J8Q1747Z2KEGGD00954 YChEBICHEBI 7630 YChEMBLChEMBL2107797 YCompTox Dashboard EPA DTXSID3047477ECHA InfoCard100 026 758Chemical and physical dataFormulaC 21H 28O 2Molar mass312 453 g mol 13D model JSmol Interactive imageSMILES O C 1CC C H 4C C 1 CC C H 3 C H 4CC C 2 CC C H 3CCC2 O C CInChI 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 YKey WWYNJERNGUHSAO CULCCENASA N Y verify 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 2021 the version with ethinylestradiol was the 227th 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 Contents 1 Medical uses 2 Side effects 3 Pharmacology 3 1 Pharmacodynamics 3 2 Pharmacokinetics 4 Chemistry 4 1 Synthesis 5 History 6 Society and culture 6 1 Generic names 6 2 Brand names 7 ReferencesMedical uses editNorgestrel 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 7 It has also been used as an emergency contraceptive in the Yuzpe regimen 16 Side effects editSee also Levonorgestrel Side effects and Progestin Side effectsPharmacology editPharmacodynamics edit See also Levonorgestrel Pharmacodynamics Norgestrel is a progestogen or an agonist of the progesterone receptor 6 The biological activity of norgestrel lies in the levo enantiomer levonorgestrel whereas the dextro isomer is inactive 6 As such norgestrel is identical in its hormonal activity to levonorgestrel except that it is half as potent by weight 6 Levonorgestrel and by extension norgestrel have some androgenic activity but no estrogenic antimineralocorticoid or glucocorticoid activity 6 vte Relative affinities of levonorgestrel and metabolites Compound PRTooltip Progesterone receptor ARTooltip Androgen receptor ERTooltip Estrogen receptor GRTooltip Glucocorticoid receptor MRTooltip Mineralocorticoid receptor SHBGTooltip Sex hormone binding globulin CBGTooltip Corticosteroid binding globulinLevonorgestrel 150 162 34a 45 0 1 8 17 75 50 05a Dihydrolevonorgestrel 50 38a 0 3a 5a Tetrahydrolevonorgestrel 0 4 3b 5a Tetrahydrolevonorgestrel 2 4 Notes Values are percentages Reference ligands 100 were promegestone for the PRTooltip progesterone receptor metribolone a mibolerone for the ARTooltip androgen receptor E2 for the ERTooltip estrogen receptor DEXATooltip dexamethasone for the GRTooltip glucocorticoid receptor aldosterone for the MRTooltip mineralocorticoid receptor DHTTooltip dihydrotestosterone for SHBGTooltip sex hormone binding globulin and cortisol for CBGTooltip Corticosteroid binding globulin Sources See template The ovulation inhibiting dose of norgestrel appears to be greater than 75 mg day as ovulation occurred in 50 to 75 of cycles with this dosage of norgestrel in studies 17 The ovulation inhibiting dosage of levonorgestrel which is twice as potent as norgestrel is approximately 50 to 60 mg day 6 18 17 One review lists the ovulation inhibiting dose of norgestrel as 100 mg day 19 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 19 20 Pharmacokinetics edit See also Levonorgestrel Pharmacokinetics The pharmacokinetics of norgestrel have been reviewed 21 Chemistry editSee also List of progestogens List of androgens anabolic steroids and Levonorgestrel Norgestrel also known as rac 13 ethyl 17a ethynyl 19 nortestosterone or as rac 13 ethyl 17a ethynylestr 4 en 17b ol 3 one is a synthetic estrane steroid and a derivative of testosterone 3 4 It is a racemic mixture of stereoisomers dextronorgestrel the C13a isomer l norgestrel L norgestrel or norgestrel and levonorgestrel the C13b isomer d norgestrel D norgestrel or norgestrel the former of which is inactive making norgestrel exactly half as potent as levonorgestrel 22 23 Norgestrel is more specifically a derivative of norethisterone 17a ethynyl 19 nortestosterone and is a member of the gonane 18 methylestrane subgroup of the 19 nortestosterone family of progestins 24 Synthesis edit Chemical syntheses of norgestrel have been published 21 History editNorgestrel was first introduced as a birth control pill in combination with ethinylestradiol under the brand name Eugynon in Germany in 1966 9 10 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 25 26 7 The contraceptive efficacy of norgestrel was established in the US with the original approval for prescription use in 1973 2 In July 2023 the FDA approved norgestrel for over the counter sale 2 27 The FDA granted the approval to Laboratoire HRA Pharma which was acquired by Perrigo Company plc 2 Society and culture editGeneric names edit Norgestrel is the generic name of the drug and its international nonproprietary name United States Adopted Name United States Pharmacopeia British Approved Name Denomination Commune Francaise Denominazione Comune Italiana and Japanese Accepted Name 3 4 5 7 It is also known as dl norgestrel DL norgestrel or norgestrel 3 4 5 7 Brand names edit 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 3 4 7 25 References edit Opill norgestrel tablet DailyMed 4 March 2024 Archived from the original on 11 March 2024 Retrieved 13 March 2024 a b c d e f 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 nbsp This article incorporates text from this source which is in the public domain a b c d e Elks J 14 November 2014 The Dictionary of Drugs Chemical Data Chemical Data Structures and Bibliographies Springer pp 887 ISBN 978 1 4757 2085 3 a b c d e f Index Nominum 2000 International Drug Directory Taylor amp Francis 2000 pp 751 ISBN 978 3 88763 075 1 a b c d Morton IK Hall JM 6 December 2012 Concise Dictionary of Pharmacological Agents Properties and Synonyms Springer Science amp Business Media pp 202 ISBN 978 94 011 4439 1 Archived from the original on 10 January 2023 Retrieved 10 March 2018 a b c d e f g h i 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 a b c d e f g h Norgestrel brand name list from Drugs com Archived from the original on 9 January 2021 Retrieved 17 September 2022 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 a b Ortiz Gomez T Santesmases MJ 22 April 2016 Gendered Drugs and Medicine Historical and Socio Cultural Perspectives Taylor amp Francis pp 175 ISBN 978 1 317 12981 3 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 a b Pohl WG 2004 Die wissenschaftliche Welt von gestern die Preistrager des Ignaz L Lieben Preises 1865 1937 und des Richard Lieben Preises 1912 1928 ein Kapitel osterreichischer Wissenschaftsgeschichte in Kurzbiografien Bohlau Verlag Wien pp 150 ISBN 978 3 205 77303 0 Archived from the original on 12 January 2023 Retrieved 18 April 2018 The contraceptive Eugynon is launched in 1966 Neogynon follows in 1970 Fischer J Ganellin CR 2006 Analogue based Drug Discovery John Wiley amp Sons p 479 ISBN 9783527607495 Carp HJ 9 April 2015 Progestogens in Obstetrics and Gynecology Springer p 112 ISBN 978 3 319 14385 9 Generic Lo Ovral 28 Availability Archived from the original on 2 March 2019 Retrieved 10 March 2018 The Top 300 of 2021 ClinCalc Archived from the original on 15 January 2024 Retrieved 14 January 2024 Ethinyl Estradiol Norgestrel Drug Usage Statistics ClinCalc Archived from the original on 7 October 2021 Retrieved 14 January 2024 Yuzpe AA Smith RP Rademaker AW April 1982 A multicenter clinical investigation employing ethinyl estradiol combined with dl norgestrel as postcoital contraceptive agent Fertility and Sterility 37 4 508 513 doi 10 1016 s0015 0282 16 46157 1 PMID 7040117 a b Endrikat J Gerlinger C Richard S Rosenbaum P Dusterberg B December 2011 Ovulation inhibition doses of progestins a systematic review of the available literature and of marketed preparations worldwide Contraception 84 6 549 57 doi 10 1016 j contraception 2011 04 009 PMID 22078182 Schindler AE Campagnoli C Druckmann R Huber J Pasqualini JR Schweppe KW et al December 2003 Classification and pharmacology of progestins Maturitas 46 Suppl 1 S7 S16 doi 10 1016 j maturitas 2003 09 014 PMID 14670641 a b Knorr K Knorr Gartner H Beller FK Lauritzen C 8 March 2013 Geburtshilfe und Gynakologie Physiologie und Pathologie der Reproduktion Springer Verlag pp 583 ISBN 978 3 642 95583 9 Archived from the original on 11 January 2023 Retrieved 13 August 2022 Leidenberger FA Strowitzki T Ortmann O 29 August 2009 Klinische Endokrinologie fur Frauenarzte Springer Verlag pp 225 227 ISBN 978 3 540 89760 6 Archived from the original on 14 July 2023 Retrieved 13 August 2022 a b Die Gestagene Springer Verlag 27 November 2013 pp 16 17 284 ISBN 978 3 642 99941 3 Archived from the original on 14 July 2023 Retrieved 19 September 2018 Alldredge BK Corelli RL Ernst ME 1 February 2012 Koda Kimble and Young s Applied Therapeutics The Clinical Use of Drugs Lippincott Williams amp Wilkins pp 1072 ISBN 978 1 60913 713 7 Archived from the original on 12 January 2023 Retrieved 3 August 2017 Lavery JP Sanfilippo JS 6 December 2012 Pediatric and Adolescent Obstetrics and Gynecology Springer Science amp Business Media pp 248 ISBN 978 1 4612 5064 7 Archived from the original on 12 January 2023 Retrieved 3 August 2017 Offermanns S Rosenthal W 14 August 2008 Encyclopedia of Molecular Pharmacology Springer Science amp Business Media pp 390 ISBN 978 3 540 38916 3 a b William Andrew Publishing 22 October 2013 Pharmaceutical Manufacturing Encyclopedia 3rd ed Elsevier pp 2935 ISBN 978 0 8155 1856 3 Marks L 2010 Sexual Chemistry A History of the Contraceptive Pill Yale University Press pp 73 ISBN 978 0 300 16791 7 Archived copy PDF Archived PDF from the original on 9 March 2024 Retrieved 13 March 2024 a href Template Cite web html title Template Cite web cite web a CS1 maint archived copy as title link Portal nbsp Medicine Retrieved from https en wikipedia org w index php title Norgestrel amp oldid 1213437088, wikipedia, wiki, book, books, library,

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