Etonogestrel
Chemical compound / From Wikipedia, the free encyclopedia
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Etonogestrel is a medication which is used as a means of birth control for women.[4][5][12][13] It is available as an implant placed under the skin of the upper arm under the brand names Nexplanon and Implanon. It is a progestin that is also used in combination with ethinylestradiol, an estrogen, as a vaginal ring under the brand names NuvaRing and Circlet.[14] Etonogestrel is effective as a means of birth control and lasts at least three or four years with some data showing effectiveness for five years.[9][11] Following removal, fertility quickly returns.[15]
Clinical data | |
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Trade names | Circlet, Implanon, Nexplanon, others |
Other names | ORG-3236; SCH-900702 (with EETooltip ethinylestradiol); 3-Ketodesogestrel; 3-Oxodesogestrel; 11-Methylenelevonorgestrel;[1] 11-Methylene-17α-ethynyl-18-methyl-19-nortestosterone; 11-Methylene-17α-ethynyl-18-methylestr-4-en-17β-ol-3-one |
AHFS/Drugs.com | Professional Drug Facts |
MedlinePlus | a604032 |
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Routes of administration | Subcutaneous implant, vaginal ring |
Drug class | Progestogen; Progestin |
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Pharmacokinetic data | |
Bioavailability | Implant: 100%[4] Vaginal ring: 100%[5] |
Protein binding | ≥98% (66% to albumin, 32% to SHBGTooltip sex hormone-binding globulin)[4] |
Metabolism | Liver (CYP3A4)[4][5] |
Elimination half-life | 21–38 hours[6][7][4][5] |
Excretion | Urine (major), feces (minor)[4][5] |
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ECHA InfoCard | 100.053.561 |
Chemical and physical data | |
Formula | C22H28O2 |
Molar mass | 324.464 g·mol−1 |
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Etonogestrel birth control implant | |
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Background | |
Type | Hormonal Progestin-only implant |
First use | 1998 Indonesia |
Synonyms | Etonogestrel contraceptive implant |
Trade names | Implanon, Nexplanon, others |
AHFS/Drugs.com | FDA Professional Drug Information |
Failure rates (first year) | |
Perfect use | 0.05%[8] |
Typical use | 0.05%[8] |
Usage | |
Duration effect | 3 to 5 years[9][10] |
Reversibility | Yes |
User reminders | Requires removal after the 3–5 years[11] |
Advantages and disadvantages | |
STI protection | No |
Weight | May cause weight gain |
Period disadvantages | May cause irregular or prolonged bleeding |
Period advantages | Minimizes pain. In 33% no periods. |
Benefits | Long-term contraception. |
Side effects of etonogestrel include menstrual irregularities, breast tenderness, mood changes, acne, headaches, vaginitis, and others.[4] Etonogestrel is a progestin, or a synthetic progestogen, and hence is an agonist of the progesterone receptor, the biological target of progestogens like progesterone.[16] It works by stopping ovulation, thickening the mucus around the opening of the cervix, and altering the lining of the uterus.[17] It has very weak androgenic and glucocorticoid activity and no other important hormonal activity.[16]
Etonogestrel was patented in 1972 and introduced for medical use in 1998.[18][19][20] It became available in the United States in 2006.[18][19] Etonogestrel implants are approved in more than 90 countries and used by about three million women globally as of 2010.[17][21]
A closely related and more widely known and used progestin, desogestrel, is a prodrug of etonogestrel in the body.[16]