Back ليفونورغيستريل Arabic لوونورژسترول AZB Levonorgestrel Catalan Levonorgestrel German Λεβονοργεστρέλη Greek Levonorgestrel Spanish لوونورژسترول Persian Levonorgestreeli Finnish Lévonorgestrel French Levonorgestrel Hausa

Levonorgestrel

Not to be confused with Medication abortion.
Levonorgestrel
Clinical data
Trade namesPlan B, Julie, Mirena, Plan B One-Step, Liletta, others
Other namesLNG; LNG-EC; d-Norgestrel; d(–)-Norgestrel; D-Norgestrel; WY-5104; SH-90999; NSC-744007; 18-Methylnorethisterone; 17α-Ethynyl-18-methyl-19-nortestosterone; 17α-Ethynyl-18-methylestr-4-en-17β-ol-3-one; 13β-Ethyl-17α-hydroxy-18,19-dinorpregn-4-en-20-yn-3-one
AHFS/Drugs.comMonograph
MedlinePlusa610021
Pregnancy
category
Routes of
administration		By mouth, transdermal patch, intrauterine device, subcutaneous implant
Drug classProgestogen (medication); Progestin
ATC code
Legal status
Legal status
Pharmacokinetic data
Bioavailability95% (range 85–100%)[4][5]
Protein binding98% (50% to albumin, 48% to SHBGTooltip sex hormone-binding globulin)[4]
MetabolismLiver (reduction, hydroxylation, conjugation)[4][6]
Metabolites• 5α-Dihydro-LNG[4]
Elimination half-life24–32 hours[4]
ExcretionUrine: 20–67%
Feces: 21–34%[6]
Identifiers
  • (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
CAS Number
PubChem CID
IUPHAR/BPS
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.011.227 Edit this at Wikidata
Chemical and physical data
FormulaC21H28O2
Molar mass312.453 g·mol−1
3D model (JSmol)
Melting point235 to 237 °C (455 to 459 °F)
  • CC[C@]12CC[C@H]3[C@H]([C@@H]1CC[C@]2(C#C)O)CCC4=CC(=O)CC[C@H]34
  • 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 checkY
  • Key:WWYNJERNGUHSAO-XUDSTZEESA-N checkY
  (verify)

Levonorgestrel is a hormonal medication which is used in a number of birth control methods.[3][7] It is combined with an estrogen to make combination birth control pills.[8] As an emergency birth control, sold under the brand names Plan B One-Step and Julie, among others, it is useful within 72 hours of unprotected sex.[3][7][9] The more time that has passed since sex, the less effective the medication becomes, and it does not work after pregnancy (implantation) has occurred.[7] Levonorgestrel works by preventing ovulation or fertilization from occurring.[10] It decreases the chances of pregnancy by 57–93%.[11] In an intrauterine device (IUD), such as Mirena among others, it is effective for the long-term prevention of pregnancy.[7] A levonorgestrel-releasing implant is also available in some countries.[12]

Common side effects include nausea, breast tenderness, headaches, and increased, decreased, or irregular menstrual bleeding.[7] When used as an emergency contraceptive, if pregnancy occurs, there is no evidence that its use harms the fetus.[7] It is safe to use during breastfeeding.[7] Birth control that contains levonorgestrel will not change the risk of sexually transmitted infections.[7] It is a progestin and has effects similar to those of the hormone progesterone.[7] It works primarily by preventing ovulation and closing off the cervix to prevent the passage of sperm.[7]

Levonorgestrel was patented in 1960 and introduced for medical use together with ethinylestradiol in 1970.[13][14] It is on the World Health Organization's List of Essential Medicines.[15] It is available as a generic medication.[16] In the United States, levonorgestrel-containing emergency contraceptives are available over the counter (OTC) for all ages.[17] In 2020, it was the 323rd most commonly prescribed medication in the United States, with more than 800 thousand prescriptions.[18]

  1. ^ a b "Levonorgestrel Use During Pregnancy". Drugs.com. 23 March 2020. Archived from the original on 2 July 2020. Retrieved 29 June 2020.
  2. ^ "Jaydess 13.5 mg intrauterine delivery system - Summary of Product Characteristics (SmPC)". (emc). 1 July 2022. Archived from the original on 13 April 2021. Retrieved 1 July 2022.
  3. ^ a b c "Plan B One-Step- levonorgestrel tablet". DailyMed. 21 December 2022. Retrieved 26 December 2022.
  4. ^ a b c d e Cite error: The named reference pmid16112947 was invoked but never defined (see the help page).
  5. ^ Cite error: The named reference pmid8842581 was invoked but never defined (see the help page).
  6. ^ a b Cite error: The named reference ShoupeHaseltine2012 was invoked but never defined (see the help page).
  7. ^ a b c d e f g h i j "Progestins (Etonogestrel, Levonorgestrel, Norethindrone)". The American Society of Health-System Pharmacists. Archived from the original on 2015-09-07. Retrieved Aug 21, 2015.
  8. ^ Postgraduate Gynecology. Jaypee Brothers Medical Pub. 2011. p. 159. ISBN 9789350250822. Archived from the original on 2015-09-26.
  9. ^ "Levonorgestrel 1.5 mg Tablet Emergency Contraceptive: New Drug Application 21998, Supplement 5" (PDF). U.S. Food and Drug Administration.
  10. ^ "Now Is the Time to Change Label on Emergency Contraceptives". Relias Media | Online Continuing Medical Education | Relias Media - Continuing Medical Education Publishing. Retrieved 2022-08-16.
  11. ^ Gemzell-Danielsson K (November 2010). "Mechanism of action of emergency contraception". Contraception. 82 (5): 404–409. doi:10.1016/j.contraception.2010.05.004. PMID 20933113.
  12. ^ "Chapter 1". Research on reproductive health at WHO : biennial report 2000-2001. Geneva: World health organization. 2002. ISBN 9789241562089. Archived from the original on 2015-09-26.
  13. ^ Fischer J, Ganellin CR (2006). Analogue-based Drug Discovery. John Wiley & Sons. p. 479. ISBN 9783527607495. Archived from the original on 2021-08-28. Retrieved 2020-08-05.
  14. ^ Cite error: The named reference Roth2014 was invoked but never defined (see the help page).
  15. ^ World Health Organization (2019). World Health Organization model list of essential medicines: 21st list 2019. Geneva: World Health Organization. hdl:10665/325771. WHO/MVP/EMP/IAU/2019.06. License: CC BY-NC-SA 3.0 IGO.
  16. ^ Hamilton RJ (2014). Tarascon pocket pharmacopoeia : 2014 deluxe lab-pocket edition (15th ed.). Sudbury: Jones & Bartlett Learning. pp. 310–312. ISBN 9781284053999. Archived from the original on 2015-09-26.
  17. ^ "FDA approves Plan B One-Step emergency contraceptive for use without a prescription for all women of child-bearing potential" (Press release). June 20, 2013. Archived from the original on 14 January 2016. Retrieved 2 February 2016.
  18. ^ "Levonorgestrel - Drug Usage Statistics". ClinCalc. Retrieved 7 October 2022.

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