Testosterone benzoate

{{Short description|Chemical compound}}

{{Drugbox

| Verifiedfields =

| Watchedfields =

| verifiedrevid =

| 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] benzoate

| image = Testosterone_benzoate.svg

| width = 250px

| tradename =

| pregnancy_AU =

| pregnancy_US =

| pregnancy_category =

| legal_AU =

| legal_CA =

| legal_UK =

| legal_US =

| legal_status =

| routes_of_administration = Intramuscular injection

| bioavailability =

| protein_bound =

| metabolism =

| elimination_half-life =

| excretion =

| CAS_number_Ref =

| CAS_number = 2088-71-3

| CAS_supplemental =

| ATC_prefix =

| ATC_suffix =

| ATC_supplemental =

| PubChem = 101474

| IUPHAR_ligand =

| DrugBank_Ref =

| DrugBank =

| ChemSpiderID_Ref =

| ChemSpiderID = 91692

| UNII = 387187KT3E

| KEGG =

| ChEBI =

| ChEMBL =

| synonyms = Testosterone 17β-benzoate; Androst-4-en-17β-ol-3-one 17β-benzoate

| C=26 | H=32 | O=3

| SMILES = C[C@]12CC[C@H]3[C@H]([C@@H]1CC[C@@H]2OC(=O)C4=CC=CC=C4)CCC5=CC(=O)CC[C@]35C

| StdInChI_Ref =

| StdInChI = 1S/C26H32O3/c1-25-14-12-19(27)16-18(25)8-9-20-21-10-11-23(26(21,2)15-13-22(20)25)29-24(28)17-6-4-3-5-7-17/h3-7,16,20-23H,8-15H2,1-2H3/t20-,21-,22-,23-,25-,26-/m0/s1

| StdInChIKey_Ref =

| StdInChIKey = RZJSCADWIWNGKI-IXKNJLPQSA-N

}}

Testosterone benzoate, or testosterone 17β-benzoate, also known as androst-4-en-17β-ol-3-one 17β-benzoate, is a synthetic, injected anabolic–androgenic steroid (AAS) and an androgen ester – specifically, the benzoate C17β ester of testosterone – which was never marketed.{{cite book| vauthors = Yalkowsky SH, He Y, Jain P |title=Handbook of Aqueous Solubility Data, Second Edition|url=https://books.google.com/books?id=cfFzJFthLCIC&pg=PA1313|date=19 April 2016|publisher=CRC Press|isbn=978-1-4398-0246-5|pages=1313–}}{{cite book| vauthors = Archer T, Hansen S |title=Behavioral Biology: Neuroendocrine Axis|url=https://books.google.com/books?id=NMTB6QB4VAYC&pg=PT76|date=5 September 2013|publisher=Psychology Press|isbn=978-1-134-76125-8|pages=76–}} It is a prodrug of testosterone and, when administered via intramuscular injection, is associated with a long-lasting depot effect and extended duration of action.{{cite book|author=CIBA Foundation Symposium|title=Hormones, Psychology and Behaviour, Volume 3: Book I of Colloquia on Endocrinology|url=https://books.google.com/books?id=gFc1uHEKxskC&pg=PA260|date=17 September 2009|publisher=John Wiley & Sons|isbn=978-0-470-71486-7|pages=260–}}{{cite book| vauthors = Schaefer B |title=Natural Products in the Chemical Industry|url=https://books.google.com/books?id=DbO4CQAAQBAJ&pg=PA540|date=26 May 2015|publisher=Springer|isbn=978-3-642-54461-3|pages=540–}}{{cite book| vauthors = Lamparczyk H |title=CRC Handbook of Chromatography: Analysis and Characterization of Steroids|url=https://books.google.com/books?id=qQ9p1vnG-tMC&pg=PA34|date=21 August 1992|publisher=CRC Press|isbn=978-0-8493-3008-7|pages=34–}} The drug was first described in 1936 and was the first androgen ester and ester of testosterone to be synthesized.{{cite journal| vauthors = Parkes AS |title=Increasing the Effectiveness of Testosterone|journal=The Lancet|volume=228|issue=5899|year=1936|pages=674–676|issn=0140-6736|doi=10.1016/S0140-6736(00)80929-0}}