Etonogestrel

Etonogestrel is a medication which is used as a means of birth control for women. 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. 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. Following removal, fertility quickly returns.

Etonogestrel
Clinical data
Trade namesCirclet, Implanon, Nexplanon, others
Other namesORG-3236; SCH-900702 (with EETooltip ethinylestradiol); 3-Ketodesogestrel; 3-Oxodesogestrel; 11-Methylenelevonorgestrel; 11-Methylene-17α-ethynyl-18-methyl-19-nortestosterone; 11-Methylene-17α-ethynyl-18-methylestr-4-en-17β-ol-3-one
AHFS/Drugs.comProfessional Drug Facts
MedlinePlusa604032
Pregnancy
category
  • AU: B3
Routes of
administration		Subcutaneous implant, vaginal ring
Drug classProgestogen; Progestin
ATC code
Legal status
Legal status
  • AU: S4 (Prescription only)
  • CA: ℞-only
  • UK: POM (Prescription only)
  • US: ℞-only
  • EU: Rx-only
  • In general: ℞ (Prescription only)
Pharmacokinetic data
BioavailabilityImplant: 100%
Vaginal ring: 100%
Protein binding≥98% (66% to albumin, 32% to SHBGTooltip sex hormone-binding globulin)
MetabolismLiver (CYP3A4)
Elimination half-life21–38 hours
ExcretionUrine (major), feces (minor)
Identifiers
  • (8S,9S,10R,13S,14S,17R)-13-Ethyl-17-ethynyl-17-hydroxy-11-methylidene-2,6,7,8,9,10,12,14,15,16-decahydro-1H-cyclopenta[a]phenanthren-3-one
CAS Number
PubChem CID
IUPHAR/BPS
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.053.561
Chemical and physical data
FormulaC22H28O2
Molar mass324.464 g·mol−1
3D model (JSmol)
SMILES
  • CC[C@]12CC(=C)[C@H]3[C@H]([C@@H]1CC[C@]2(C#C)O)CCC4=CC(=O)CC[C@H]34
  • InChI=1S/C22H28O2/c1-4-21-13-14(3)20-17-9-7-16(23)12-15(17)6-8-18(20)19(21)10-11-22(21,24)5-2/h2,12,17-20,24H,3-4,6-11,13H2,1H3/t17-,18-,19-,20+,21-,22-/m0/s1 Y
  • Key:GCKFUYQCUCGESZ-BPIQYHPVSA-N Y
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Etonogestrel birth control implant
Implanon
Background
TypeHormonal
Progestin-only implant
First use1998  Indonesia
SynonymsEtonogestrel contraceptive implant
Trade namesImplanon, Nexplanon, others
AHFS/Drugs.comFDA Professional Drug Information
Failure rates (first year)
Perfect use0.05%
Typical use0.05%
Usage
Duration effect3 to 5 years
ReversibilityYes
User remindersRequires removal after the 3–5 years
Advantages and disadvantages
STI protectionNo
WeightMay cause weight gain
Period disadvantagesMay cause irregular or prolonged bleeding
Period advantagesMinimizes pain. In 33% no periods.
BenefitsLong-term contraception.

Side effects of etonogestrel include menstrual irregularities, breast tenderness, mood changes, acne, headaches, vaginitis, and others. Etonogestrel is a progestin, or a synthetic progestogen, and hence is an agonist of the progesterone receptor, the biological target of progestogens like progesterone. It works by stopping ovulation, thickening the mucus around the opening of the cervix, and altering the lining of the uterus. It has very weak androgenic and glucocorticoid activity and no other important hormonal activity.

Etonogestrel was patented in 1972 and introduced for medical use in 1998. It became available in the United States in 2006. Etonogestrel implants are approved in more than 90 countries and used by about three million women globally as of 2010.

A closely related and more widely known and used progestin, desogestrel, is a prodrug of etonogestrel in the body.

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