Andriol

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
NY (what is this?)

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. The Reandron 1000 formulation (Nebido in the United States) contains 1000 mg of testosterone undecanoate suspended in castor oil with benzyl benzoate for solubilisation and as a preservative, and is administered by intramuscular injection. As an excipient, benzyl benzoate has been reported as a cause of anaphylaxis in a case in Australia. Bayer includes this report in information for health professionals and recommends that physicians "should be aware of the potential for serious allergic reactions" to preparations of this type. In Australia, reports to ADRAC, which evaluates reports of adverse drug reactions for the Therapeutic Goods Administration, show several reports of allergic issues since the anaphylaxis case from 2011.

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).