Levonorgestrel | DrugBank Online

Step 2

Edgren RA, Stanczyk FZ: Nomenclature of the gonane progestins. Contraception. 1999 Dec;60(6):313. [PubMed:10715364] Sitruk-Ware R: New progestagens for contraceptive use. Hum Reprod Update. 2006 Mar-Apr;12(2):169-78. Epub 2005 Nov 16. [PubMed:16291771] Kahlenborn C, Peck R, Severs WB: Mechanism of action of levonorgestrel emergency contraception. Linacre Q. 2015 Feb;82(1):18-33. doi: 10.1179/2050854914Y.0000000026. [PubMed:25698840] Kook K, Gabelnick H, Duncan G: Pharmacokinetics of levonorgestrel 0.75 mg tablets. Contraception. 2002 Jul;66(1):73-6. [PubMed:12169384] Sambol NC, Harper CC, Kim L, Liu CY, Darney P, Raine TR: Pharmacokinetics of single-dose levonorgestrel in adolescents. Contraception. 2006 Aug;74(2):104-9. doi: 10.1016/j.contraception.2006.01.011. Epub 2006 Jun 16. [PubMed:16860047] Natavio M, Stanczyk FZ, Molins EAG, Nelson A, Jusko WJ: Pharmacokinetics of the 1.5 mg levonorgestrel emergency contraceptive in women with normal, obese and extremely obese body mass index. Contraception. 2019 May;99(5):306-311. doi: 10.1016/j.contraception.2019.01.003. Epub 2019 Jan 28. [PubMed:30703352] Shohel M, Rahman MM, Zaman A, Uddin MM, Al-Amin MM, Reza HM: A systematic review of effectiveness and safety of different regimens of levonorgestrel oral tablets for emergency contraception. BMC Womens Health. 2014 Apr 4;14:54. doi: 10.1186/1472-6874-14-54. [PubMed:24708837] Polis CB, Phillips SJ, Hillier SL, Achilles SL: Levonorgestrel in contraceptives and multipurpose prevention technologies: does this progestin increase HIV risk or interact with antiretrovirals? AIDS. 2016 Nov 13;30(17):2571-2576. doi: 10.1097/QAD.0000000000001229. [PubMed:27525548] Raymond EG, Coeytaux F, Gemzell-Danielsson K, Moore K, Trussell J, Winikoff B: Embracing post-fertilisation methods of family planning: a call to action. J Fam Plann Reprod Health Care. 2013 Oct;39(4):244-6. doi: 10.1136/jfprhc-2013-100702. [PubMed:24062495] Beatty MN, Blumenthal PD: The levonorgestrel-releasing intrauterine system: Safety, efficacy, and patient acceptability. Ther Clin Risk Manag. 2009 Jun;5(3):561-74. doi: 10.2147/tcrm.s5624. Epub 2009 Aug 3. [PubMed:19707273] Juchem M, Pollow K: Binding of oral contraceptive progestogens to serum proteins and cytoplasmic receptor. Am J Obstet Gynecol. 1990 Dec;163(6 Pt 2):2171-83. doi: 10.1016/0002-9378(90)90559-p. [PubMed:2175153] Stanczyk FZ, Roy S: Metabolism of levonorgestrel, norethindrone, and structurally related contraceptive steroids. Contraception. 1990 Jul;42(1):67-96. [PubMed:2143719] Brinton LA, Felix AS: Menopausal hormone therapy and risk of endometrial cancer. J Steroid Biochem Mol Biol. 2014 Jul;142:83-9. doi: 10.1016/j.jsbmb.2013.05.001. Epub 2013 May 13. [PubMed:23680641] Townsend S: Norplant: safe and highly effective. Netw Res Triangle Park N C. 1990 Dec;11(4):6-8. [PubMed:12283720] Mozzanega B, Nardelli GB: UPA and LNG in emergency contraception: the information by EMA and the scientific evidences indicate a prevalent anti-implantation effect. Eur J Contracept Reprod Health Care. 2019 Jan 18:1-7. doi: 10.1080/13625187.2018.1555662. [PubMed:30656992] Gemzell-Danielsson K, Berger C, Lalitkumar PG: Mechanisms of action of oral emergency contraception. Gynecol Endocrinol. 2014 Oct;30(10):685-7. doi: 10.3109/09513590.2014.950648. Epub 2014 Aug 12. [PubMed:25117156] Christina Vrettakos; Tushar Bajaj (2019). Levonorgestrel. Stat Pearls NIH. Levonorgestrel FDA label [Link] Alesse 28 FDA label [Link] FDA label, Mirena IUD [Link] Kyleena IUD FDA label [Link] Jaydess monograph [Link] Levonorgestrel MSDS [Link] Medicines UK, levonorgestrel [Link] Birth control pill overdose, Medline [Link] Climara pro FDA label [Link] Cleveland clinic: hormone therapy [Link] Norplant FDA label [Link]

Step 3

Maruo T, Ohara N, Matsuo H, Xu Q, Chen W, Sitruk-Ware R, Johansson ED: Effects of levonorgestrel-releasing IUS and progesterone receptor modulator PRM CDB-2914 on uterine leiomyomas. Contraception. 2007 Jun;75(6 Suppl):S99-103. Epub 2007 Mar 21. [PubMed:17531625] Hompes PG, Mijatovic V: Endometriosis: the way forward. Gynecol Endocrinol. 2007 Jan;23(1):5-12. [PubMed:17484506] Creinin MD, Schlaff W, Archer DF, Wan L, Frezieres R, Thomas M, Rosenberg M, Higgins J: Progesterone receptor modulator for emergency contraception: a randomized controlled trial. Obstet Gynecol. 2006 Nov;108(5):1089-97. [PubMed:17077229] Bray JD, Jelinsky S, Ghatge R, Bray JA, Tunkey C, Saraf K, Jacobsen BM, Richer JK, Brown EL, Winneker RC, Horwitz KB, Lyttle CR: Quantitative analysis of gene regulation by seven clinically relevant progestins suggests a highly similar mechanism of action through progesterone receptors in T47D breast cancer cells. J Steroid Biochem Mol Biol. 2005 Dec;97(4):328-41. Epub 2005 Sep 12. [PubMed:16157482] Christina Vrettakos; Tushar Bajaj (2019). Levonorgestrel. Stat Pearls NIH.

Step 4

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Step 5

Vereide AB, Kaino T, Sager G, Arnes M, Orbo A: Effect of levonorgestrel IUD and oral medroxyprogesterone acetate on glandular and stromal progesterone receptors (PRA and PRB), and estrogen receptors (ER-alpha and ER-beta) in human endometrial hyperplasia. Gynecol Oncol. 2006 May;101(2):214-23. Epub 2005 Dec 1. [PubMed:16325240] Vijayanathan V, Venkiteswaran S, Nair SK, Verma A, Thomas TJ, Zhu BT, Thomas T: Physiologic levels of 2-methoxyestradiol interfere with nongenomic signaling of 17beta-estradiol in human breast cancer cells. Clin Cancer Res. 2006 Apr 1;12(7 Pt 1):2038-48. [PubMed:16609013] Lv XH, Shi DZ: Effects of levonorgestrel on reproductive hormone levels and their receptor expression in Mongolian gerbils (Meriones unguiculatus). Exp Anim. 2011;60(4):363-71. doi: 10.1538/expanim.60.363. [PubMed:21791876] Garcia-Becerra R, Borja-Cacho E, Cooney AJ, Jackson KJ, Lemus AE, Perez-Palacios G, Larrea F: The intrinsic transcriptional estrogenic activity of a non-phenolic derivative of levonorgestrel is mediated via the estrogen receptor-alpha. J Steroid Biochem Mol Biol. 2002 Nov;82(4-5):333-41. [PubMed:12589940] Lemus AE, Vilchis F, Damsky R, Chavez BA, Garcia GA, Grillasca I, Perez-Palacios G: Mechanism of action of levonorgestrel: in vitro metabolism and specific interactions with steroid receptors in target organs. J Steroid Biochem Mol Biol. 1992 Mar;41(3-8):881-90. [PubMed:1562565]

Step 6

Shields-Botella J, Duc I, Duranti E, Puccio F, Bonnet P, Delansorne R, Paris J: An overview of nomegestrol acetate selective receptor binding and lack of estrogenic action on hormone-dependent cancer cells. J Steroid Biochem Mol Biol. 2003 Nov;87(2-3):111-22. [PubMed:14672731] Freyberger A, Weimer M, Tran HS, Ahr HJ: Assessment of a recombinant androgen receptor binding assay: initial steps towards validation. Reprod Toxicol. 2010 Aug;30(1):2-8. doi: 10.1016/j.reprotox.2009.10.001. Epub 2009 Oct 13. [PubMed:19833195] Kloosterboer HJ, Vonk-Noordegraaf CA, Turpijn EW: Selectivity in progesterone and androgen receptor binding of progestagens used in oral contraceptives. Contraception. 1988 Sep;38(3):325-32. [PubMed:3139361] Christina Vrettakos; Tushar Bajaj (2019). Levonorgestrel. Stat Pearls NIH.

Step 7

Hammond GL, Abrams LS, Creasy GW, Natarajan J, Allen JG, Siiteri PK: Serum distribution of the major metabolites of norgestimate in relation to its pharmacological properties. Contraception. 2003 Feb;67(2):93-9. [PubMed:12586319] Hammond GL, Rabe T, Wagner JD: Preclinical profiles of progestins used in formulations of oral contraceptives and hormone replacement therapy. Am J Obstet Gynecol. 2001 Aug;185(2 Suppl):S24-31. [PubMed:11521119] Alvarez F, Brache V, Tejada AS, Cochon L, Faundes A: Sex hormone binding globulin and free levonorgestrel index in the first week after insertion of Norplant implants. Contraception. 1998 Oct;58(4):211-4. [PubMed:9866001] Song S, Chen JK, He ML, Fotherby K: Effect of some oral contraceptives on serum concentrations of sex hormone binding globulin and ceruloplasmin. Contraception. 1989 Apr;39(4):385-99. [PubMed:2498034]

Step 8

Juchem M, Pollow K: Binding of oral contraceptive progestogens to serum proteins and cytoplasmic receptor. Am J Obstet Gynecol. 1990 Dec;163(6 Pt 2):2171-83. doi: 10.1016/0002-9378(90)90559-p. [PubMed:2175153] PharmGKB, Levonorgestrel [Link]

Step 9

Moreno I, Quinones L, Catalan J, Miranda C, Roco A, Sasso J, Tamayo E, Caceres D, Tchernitchin AN, Gaete L, Saavedra I: [Influence of CYP3A4/5 polymorphisms in the pharmacokinetics of levonorgestrel: a pilot study]. Biomedica. 2012 Oct-Dec;32(4):570-7. doi: 10.1590/S0120-41572012000400012. [PubMed:23715232] Edelman A, Munar M, Elman MR, Koop D, Cherala G: Effect of the ethinylestradiol/levonorgestrel combined oral contraceptive on the activity of cytochrome P4503A in obese women. Br J Clin Pharmacol. 2012 Sep;74(3):510-4. doi: 10.1111/j.1365-2125.2012.04209.x. [PubMed:22299599] Hatorp V, Hansen KT, Thomsen MS: Influence of drugs interacting with CYP3A4 on the pharmacokinetics, pharmacodynamics, and safety of the prandial glucose regulator repaglinide. J Clin Pharmacol. 2003 Jun;43(6):649-60. [PubMed:12817528] Levonorgestrel FDA label [Link]

Step 10

Moreno I, Quinones L, Catalan J, Miranda C, Roco A, Sasso J, Tamayo E, Caceres D, Tchernitchin AN, Gaete L, Saavedra I: [Influence of CYP3A4/5 polymorphisms in the pharmacokinetics of levonorgestrel: a pilot study]. Biomedica. 2012 Oct-Dec;32(4):570-7. doi: 10.1590/S0120-41572012000400012. [PubMed:23715232] Edelman A, Munar M, Elman MR, Koop D, Cherala G: Effect of the ethinylestradiol/levonorgestrel combined oral contraceptive on the activity of cytochrome P4503A in obese women. Br J Clin Pharmacol. 2012 Sep;74(3):510-4. doi: 10.1111/j.1365-2125.2012.04209.x. [PubMed:22299599] Neary M, Lamorde M, Olagunju A, Darin KM, Merry C, Byakika-Kibwika P, Back DJ, Siccardi M, Owen A, Scarsi KK: The Effect of Gene Variants on Levonorgestrel Pharmacokinetics When Combined With Antiretroviral Therapy Containing Efavirenz or Nevirapine. Clin Pharmacol Ther. 2017 Sep;102(3):529-536. doi: 10.1002/cpt.667. Epub 2017 May 30. [PubMed:28187506]