Testosterone decanoate

{{short description|Chemical compound}}

{{Drugbox

| Verifiedfields =

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| 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] decanoate

| image = Testosterone decanoate.svg

| image_class = skin-invert-image

| width = 250px

| image2 = Testosterone decanoate molecule ball.png

| width2 = 250px

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| routes_of_administration = Intramuscular injection

| bioavailability =

| protein_bound =

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| CAS_number_Ref =

| CAS_number = 5721-91-5

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| PubChem = 155143

| DrugBank_Ref =

| DrugBank = DB16001

| ChemSpiderID_Ref =

| ChemSpiderID = 136680

| UNII = IJW60LAO6S

| ChEBI = 35000

| ChEMBL = 1473654

| KEGG = D08573

| synonyms = Testosterone decylate; Testosterone 17β-decanoate

| C=29 | H=46 | O=3

| SMILES = CCCCCCCCCC(=O)O[C@H]1CC[C@@H]2[C@@]1(CC[C@H]3[C@H]2CCC4=CC(=O)CC[C@]34C)C

| StdInChI_Ref =

| StdInChI = 1S/C29H46O3/c1-4-5-6-7-8-9-10-11-27(31)32-26-15-14-24-23-13-12-21-20-22(30)16-18-28(21,2)25(23)17-19-29(24,26)3/h20,23-26H,4-19H2,1-3H3/t23-,24-,25-,26-,28-,29-/m0/s1

| StdInChIKey_Ref =

| StdInChIKey = LBERVHLCXUMDOT-MPZZESAYSA-N

| melting_point= 49.1

}}

Testosterone decanoate ({{abbrlink|BAN|British Approved Name}}) is an androgen and anabolic steroid and a testosterone ester.{{cite book| vauthors = Elks J |title=The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies|url=https://books.google.com/books?id=0vXTBwAAQBAJ&pg=PA641|date=14 November 2014|publisher=Springer|isbn=978-1-4757-2085-3|pages=641–642}}{{cite book|title=Index Nominum 2000: International Drug Directory|url=https://books.google.com/books?id=5GpcTQD_L2oC&pg=PA976|date=January 2000|publisher=Taylor & Francis|isbn=978-3-88763-075-1}}{{cite book| vauthors = Morton IK, Hall JM |title=Concise Dictionary of Pharmacological Agents: Properties and Synonyms|url=https://books.google.com/books?id=tsjrCAAAQBAJ&pg=PA270|date=6 December 2012|publisher=Springer Science & Business Media|isbn=978-94-011-4439-1}}{{cite book | vauthors = Behre HM, Nieschlag E, Nieschlag E, Behre HM, Nieschlag S |chapter=Testosterone preparations for clinical use in males| veditors = Nieschlag E, Behre HM, Nieschlag S |pages=309–335|doi=10.1017/CBO9781139003353.016|title=Testosterone: Action, Deficiency, Substitution|date=26 July 2012|publisher=Cambridge University Press|isbn=978-1-107-01290-5}} It is a component of Sustanon, along with testosterone propionate, testosterone phenylpropionate, and testosterone isocaproate.{{cite book| vauthors = Fisher BA, Tilstone WJ, Woytowicz C |title=Introduction to Criminalistics: The Foundation of Forensic Science|url=https://books.google.com/books?id=JeheoVz6cWwC&pg=PT182|date=6 February 2009|publisher=Academic Press|isbn=978-0-08-091675-0|pages=182–}} The medication has not been marketed as a single-drug preparation. Testosterone decanoate has been investigated as a potential long-acting injectable male contraceptive.{{cite journal | vauthors = Hay CJ, Brady BM, Zitzmann M, Osmanagaoglu K, Pollanen P, Apter D, Wu FC, Anderson RA, Nieschlag E, Devroey P, Huhtaniemi I, Kersemaekers WM | display-authors = 6 | title = A multicenter phase IIb study of a novel combination of intramuscular androgen (testosterone decanoate) and oral progestogen (etonogestrel) for male hormonal contraception | journal = The Journal of Clinical Endocrinology and Metabolism | volume = 90 | issue = 4 | pages = 2042–2049 | date = April 2005 | pmid = 15671109 | doi = 10.1210/jc.2004-0895 | doi-access = free }}{{cite journal | vauthors = Brady BM, Amory JK, Perheentupa A, Zitzmann M, Hay CJ, Apter D, Anderson RA, Bremner WJ, Pollanen P, Nieschlag E, Wu FC, Kersemaekers WM | display-authors = 6 | title = A multicentre study investigating subcutaneous etonogestrel implants with injectable testosterone decanoate as a potential long-acting male contraceptive | journal = Human Reproduction | volume = 21 | issue = 1 | pages = 285–294 | date = January 2006 | pmid = 16172147 | doi = 10.1093/humrep/dei300 | doi-access = }}{{cite book| vauthors = Chenoweth PJ, Lorton S |title=Animal Andrology: Theories and Applications|url=https://books.google.com/books?id=hv6dAwAAQBAJ&pg=PA488|date=30 April 2014|publisher=CABI|isbn=978-1-78064-316-8|pages=488–}} It has a longer duration of action than testosterone enanthate, but its duration is not as prolonged as that of testosterone undecanoate.

{{Parenteral durations of androgens/anabolic steroids}}