User:Mr. Ibrahem/Levonorgestrel

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Not to be confused with Norgestrel.
Mr. Ibrahem/Levonorgestrel
Clinical data
Trade namesPlan B, others
Other namesLNG; 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; progestin
Legal status
Legal status
  • US: ℞-only / OTC
  • In general: ℞ (Prescription only)
Pharmacokinetic data
Bioavailability95% (range 85–100%)[2][3]
Protein binding98% (50% to albumin, 48% to SHBGTooltip sex hormone-binding globulin)[2]
MetabolismLiver (reduction, hydroxylation, conjugation)[2][4]
Metabolites• 5α-Dihydro-@@@6@@@[2]
Elimination half-life24–32 hours[2]
ExcretionUrine: 20–67%
Feces: 21–34%[4]
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
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.[6] It is combined with an estrogen to make combination birth control pills.[8] As an emergency birth control, sold under the brand name Plan B among others, it is useful within 120 hours of unprotected sex.[6] The more time that has passed since sex, the less effective the medication becomes, and it does not work after pregnancy (implantation) has occurred.[6] It decreases the chances of pregnancy by 57 to 93%.[9] In an intrauterine device (IUD), such as Mirena among others, it is effective for the long-term prevention of pregnancy.[6] A levonorgestrel-releasing implant is also available in some countries.[10]

Common side effects include nausea, breast tenderness, headaches, and increased, decreased, or irregular menstrual bleeding.[6] When used as an emergency contraceptive, if pregnancy occurs, there is no evidence that its use harms the baby.[6] It is safe to use during breastfeeding.[6] Birth control that contains levonorgestrel will not change the risk of sexually transmitted infections.[6] It is a progestin and has effects similar to those of the hormone progesterone.[6] It works primarily by preventing ovulation and closing off the cervix to prevent the passage of sperm.[6]

Levonorgestrel was patented in 1960 and introduced for medical use together with ethinylestradiol in 1970.[11][12] It is on the World Health Organization's List of Essential Medicines.[13] It is available as a generic medication.[14] The wholesale cost in the developing world is between $0.23 and $1.65 US for the dose required for emergency birth control.[15] In the United States, levonorgestrel-containing emergency birth control is available over the counter (OTC) for all ages.[16] In 2016, it was the 223rd most commonly prescribed medication in the United States, with more than two million prescriptions.[17]

References[edit]

  1. ^ a b c "Levonorgestrel Use During Pregnancy". Drugs.com. 23 March 2020. Retrieved 29 June 2020.
  2. ^ a b c d e f Kuhl H (August 2005). "Pharmacology of estrogens and progestogens: influence of different routes of administration". Climacteric. 8 Suppl 1: 3–63. doi:10.1080/13697130500148875. PMID 16112947. S2CID 24616324.
  3. ^ Fotherby K (August 1996). "Bioavailability of orally administered sex steroids used in oral contraception and hormone replacement therapy". Contraception. 54 (2): 59–69. doi:10.1016/0010-7824(96)00136-9. PMID 8842581.
  4. ^ a b Shoupe, Donna; Haseltine, Florence P. (6 December 2012). Contraception. Springer Science & Business Media. pp. 22–. ISBN 978-1-4612-2730-4.
  5. ^ "LEVONORGESTREL oral - Essential drugs". medicalguidelines.msf.org. Retrieved 31 August 2020.
  6. ^ a b c d e f g h i j k "Progestins (Etonogestrel, Levonorgestrel, Norethindrone)". The American Society of Health-System Pharmacists. Archived from the original on 2015-09-07. Retrieved Aug 21, 2015.
  7. ^ "WHOCC - ATC/DDD Index". www.whocc.no. Retrieved 31 August 2020.
  8. ^ Postgraduate Gynecology. Jaypee Brothers Medical Pub. 2011. p. 159. ISBN 9789350250822. Archived from the original on 2015-09-26.
  9. ^ Gemzell-Danielsson, K (November 2010). "Mechanism of action of emergency contraception". Contraception. 82 (5): 404–9. doi:10.1016/j.contraception.2010.05.004. PMID 20933113.
  10. ^ "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.
  11. ^ Fischer, Jnos; Ganellin, C. Robin (2006). Analogue-based Drug Discovery. John Wiley & Sons. p. 479. ISBN 9783527607495.
  12. ^ Roth, Klaus (2014). Chemische Leckerbissen. John Wiley & Sons. pp. 77–. ISBN 978-3-527-33739-2. [Levonorgestrel (24): The product generated by Smith's norgestrel total synthesis was a racemate, so half of each consisted of the left- and the right-handed enantiomer. Chemists at Schering discovered that only the levorotatory enantiomer was effective [49] and developed a biotechnological process for the preparation of the pure levorotatory enantiomer. This was the active ingredient levonorgestrel born. With the single-acting enantiomer, the dose and thus the liver burden could be halved again. The resulting Neogynon® contained 0.25 mg levonorgestrel and 0.05 mg ethinylestradiol and was introduced in 1970.]
  13. ^ 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.
  14. ^ Hamilton, Richard J. (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.
  15. ^ "Levonorgestrel". International Drug Price Indicator Guide. Archived from the original on 22 January 2018. Retrieved 21 August 2015.
  16. ^ "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.
  17. ^ "Levonorgestrel - Drug Usage Statistics". ClinCalc. Retrieved 11 April 2020.
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