Testosterone undecanoate

Testosterone undecanoate

Clinical data
Pronunciation	/tɛˈstɒstəroʊn ənˈdɛkənoʊ.eɪt/ tess-TOSS-tə-rohn ən-DEK-ə-noh-ayt
Trade names	Nebido, Aveed, Andriol, others
Synonyms	Testosterone undecylate; 17β-[(1-Oxoundecyl)oxy]-androst-4-en-3-one
Pregnancy category	US: X (Contraindicated)
Routes of administration	By mouth, intramuscular injection
Drug class	Androgen; Anabolic steroid; Androgen ester
ATC code	G03BA03 (WHO)
Legal status
Legal status	CA: Schedule IV US: Schedule III
Pharmacokinetic data
Bioavailability	Oral: 3–7% Intramuscular: ~100%
Metabolism	Liver
Biological half-life	Tea seed oil: 20.9 days (i.m.) Castor oil: 33.9 days (i.m.)
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
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	456.711 g/mol
3D model (JSmol)	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, sold under the brand names Nebido, Aveed, and Andriol among others, is an androgen and anabolic steroid. 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. It is a synthetic androgen ester which acts as a prodrug of testosterone, and hence is considered to be a natural and bioidentical form of testosterone. Unlike other testosterone esters, testosterone undecanoate is available in both oral and intramuscular formulations. As an intramuscular injection, it is much longer-acting than most other testosterone esters. Along with testosterone cypionate, testosterone enanthate, and testosterone propionate, testosterone undecanoate is one of the most widely used testosterone esters.

Testosterone undecanoate is used in androgen replacement therapy. As an intramuscular injection, it is administered at a dosage of 1,000 mg once every 12 weeks. The oral formulation of testosterone undecanoate must be taken two or three times a day with food.