Etonogestrel

Etonogestrel
ATC Code G03AC08
Formula C22H28O2
Molar Mass (g·mol−1) 324.464
Physical State solid
Melting Point (°C) 196-200
PKS Value 10.4
CAS Number 54048-10-1
PUB Number 6917715
Drugbank ID DB00294
Solubility moderate in water / poor in ethanol

Basics

Etonogestrel is a medication used as a contraceptive in women. It is available as an implant placed under the skin of the upper arm under the brand names Nexplanon and Implanon, and in combination with ethinyl estradiol, an estrogen, as a vaginal ring under the brand names NuvaRing and Circlet. Etonogestrel is effective as a birth control agent within 8 hours of insertion and lasts at least three or four years. After removal, the possibility of conception is restored relatively quickly.

Pharmacology

Pharmacodynamics

Etonogestrel is a progestogen, i.e. an agonist of the progesterone receptor. It has androgenic activity, but much less than other common progestins (e.g.: levonorgestrel and norethisterone) and does not cause a decrease in sex hormone-binding globulin levels. In addition to its progestagenic and weak androgenic activity, etonogestrel also binds to the glucocorticoid receptor and has very weak glucocorticoid activity. Etonogestrel has no other hormonal activity.

Pharmacokinetics

The bioavailability of etonogestrel when administered as a subcutaneous implant or vaginal ring is 100%. Plasma protein binding of the drug is at least 98%, with 66% bound to albumin and 32% bound to sex hormone-binding globulin. Etonogestrel is metabolized in the liver by the enzyme CYP3A4. The elimination half-life of etonogestrel is approximately 25 to 29 hours. After removal of an implant containing etonogestrel, concentrations of the drug were below the limit of detection after one week. Most of etonogestrel is excreted in the urine and a small amount in the stool.

Toxicity

Side effects

Common side effects of Etonogestrel may include menstrual irregularities, amenorrhea, headache, nausea, breast tenderness, and mood changes (e.g., depression), as well as weight gain, acne, and hirsutism. Etonogestrel may also cause changes in total, LDL, and HDL cholesterol.

Rare side effects of etonogestrel include vaginal infections, contact lens intolerance, vomiting, hair loss, dysmenorrhea, ovarian cysts, and fatigue, while rare side effects include rash, urticaria, and erythema nodosum. Breast discharge, ectopic pregnancy, and exacerbation of angioedema may also occur with the use of etonogestrel.

Toxicological Data

LD50 (rat, oral): > 2000 mg/kg

Markus Falkenstätter

Markus Falkenstätter
Author

Markus Falkenstätter ist Autor zu pharmazeutischen Themen in der Medizin-Redaktion von Medikamio. Er befindet sich im letzten Semester seines Pharmaziestudiums an der Universität Wien und liebt das wissenschaftliche Arbeiten im Bereich der Naturwissenschaften.

Mag. pharm Stefanie Lehenauer

Mag. pharm Stefanie Lehenauer
Lector

Stefanie Lehenauer ist seit 2020 freie Autorin bei Medikamio und studierte Pharmazie an der Universität Wien. Sie arbeitet als Apothekerin in Wien und ihre Leidenschaft sind pflanzliche Arzneimittel und deren Wirkung.

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