Levonorgestrel
Hormonal medication used for birth control / From Wikipedia, the free encyclopedia
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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]
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Trade names | Plan B, Julie, Mirena, Plan B One-Step, Liletta, others |
Other names | LNG; 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.com | Monograph |
MedlinePlus | a610021 |
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Routes of administration | By mouth, transdermal patch, intrauterine device, subcutaneous implant |
Drug class | Progestogen (medication); Progestin |
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Bioavailability | 95% (range 85–100%)[4][5] |
Protein binding | 98% (50% to albumin, 48% to SHBGTooltip sex hormone-binding globulin)[4] |
Metabolism | Liver (reduction, hydroxylation, conjugation)[4][6] |
Metabolites | • 5α-Dihydro-LNG[4] |
Elimination half-life | 24–32 hours[4] |
Excretion | Urine: 20–67% Feces: 21–34%[6] |
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ECHA InfoCard | 100.011.227 |
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Formula | C21H28O2 |
Molar mass | 312.453 g·mol−1 |
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Melting point | 235 to 237 °C (455 to 459 °F) |
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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]