Nebido

Testosterone undecanoate
Clinical data

Pronunciation	tess-toss-ter-own un-deck-ah-no-ate
Pregnancy category	X (USA), Teratogenic effects
Routes of administration	Oral, intramuscular injection
ATC code	G03BA03 (WHO)
Legal status
Legal status	CA: Schedule IV US: Schedule III
Pharmacokinetic data
Bioavailability	Oral: 3–7% Intramuscular ~100%
Metabolism	Liver, testis and prostate
Biological half-life	1–12 days
Excretion	Urine
Identifiers
IUPAC name [(8R,9S,10R,13S,14S,17S)-10,13-Dimethyl-3-oxo-1,2,6,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-17-yl] undecanoate
Synonyms	Aveed, Andriol, Undestor, Nebido, Pantestone, Restandol, Cernos Depot, Nebido-R, Reandron 1000 17β-[(1-Oxoundecyl)oxy]-androst-4-en-3-one
CAS Number	5949-44-0^N
PubChem CID	65157
ChemSpider	58664^N
UNII	H16A5VCT9C
KEGG	D06087^Y
ChEMBL	CHEMBL2107067^N
ECHA InfoCard	100.025.193
Chemical and physical data
Formula	C₃₀H₄₈O₃
Molar mass	456.70032 g/mol
3D model (Jmol)	Interactive image
SMILES CCCCCCCCCCC(=O)O[C@H]1CC[C@@H]2[C@@]1(CC[C@H]3[C@H]2CCC4=CC(=O)CC[C@]34C)C
InChI InChI=1S/C30H48O3/c1-4-5-6-7-8-9-10-11-12-28(32)33-27-16-15-25-24-14-13-22-21-23(31)17-19-29(22,2)26(24)18-20-30(25,27)3/h21,24-27H,4-20H2,1-3H3/t24-,25-,26-,27-,29-,30-/m0/s1^N Key:UDSFVOAUHKGBEK-CNQKSJKFSA-N^N

Testosterone undecanoate (USAN, BAN) (brand names Aveed, Andriol, Androxon, Cernos Depot, Nebido, Panteston, Restandol, Nebido-R, Reandron 1000, Undestor), or testosterone undecylate, is an androgen and anabolic steroid and a testosterone ester. It is used in androgen replacement therapy primarily for the treatment of male hypogonadism, and has also been investigated for use as a male contraceptive or as hormone replacement therapy in transgender men. Unlike other testosterone esters, testosterone undecanoate is available in both oral and intramuscular formulations.

Testosterone undecanoate has a very long elimination half-life and mean residence time when given as a depot intramuscular injection. The elimination half-life and mean residence time of testosterone undecanoate are 2.5-fold and 4-fold longer than those of testosterone enanthate (the values for testosterone enanthate being 4.5 days and 8.5 days, respectively).

Testosterone undecanoate is available in Europe and Aveed brand testosterone undecanoate was approved for use in the United States by the FDA in 2014, after three previous rejections due to safety concerns. It is administered at a dosage of 1,000 mg every 12 weeks via intramuscular injection. In addition to parenteral, an oral formulation of testosterone undecanoate (brand name Andriol) is also available in Europe, but must be taken two or three times a day in combination with food.

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Wikipedia