Testosterone decanoate

Testosterone decanoate (BAN) is an androgen and anabolic steroid and a testosterone ester.[1][2][3][4] It is a component of Sustanon, along with testosterone propionate, testosterone phenylpropionate, and testosterone isocaproate.[4][5] The medication has not been marketed as a single-drug preparation.[4] Testosterone decanoate has been investigated as a potential long-acting injectable male contraceptive.[4][6][7][8] It has a longer duration of action than testosterone enanthate, but its duration is not as prolonged as that of testosterone undecanoate.[4]

Parenteral durations of androgens/anabolic steroids
MedicationFormMajor brand namesDuration
TestosteroneAqueous suspensionAndronaq, Sterotate, Virosterone2–3 days
Testosterone propionateOil solutionAndroteston, Perandren, Testoviron3–4 days
Testosterone phenylpropionateOil solutionTestolent8 days
Testosterone isobutyrateAqueous suspensionAgovirin Depot, Perandren M14 days
Mixed testosterone estersaOil solutionTriolandren10–20 days
Mixed testosterone estersbOil solutionTestosid Depot14–20 days
Testosterone enanthateOil solutionDelatestryl14–28 days
Testosterone cypionateOil solutionDepovirin14–28 days
Mixed testosterone esterscOil solutionSustanon 25028 days
Testosterone undecanoateOil solutionAveed, Nebido100 days
Testosterone buciclatedAqueous suspension20 Aet-1, CDB-1781e90–120 days
Nandrolone phenylpropionateOil solutionDurabolin10 days
Nandrolone decanoateOil solutionDeca Durabolin21–28 days
MethandriolAqueous suspensionNotandron, Protandren8 days
Methandriol bisenanthoyl acetateOil solutionNotandron Depot16 days
Metenolone acetateOil solutionPrimobolan3 days
Metenolone enanthateOil solutionPrimobolan Depot14 days
Note: All are via i.m. injection. Footnotes: a = TP, TV, and TUe. b = TP and TKL. c = TP, TPP, TiCa, and TD. d = Studied but never marketed. e = Developmental code names. Sources: See template.
Testosterone decanoate
Clinical data
Other namesTestosterone decylate; Testosterone 17β-decanoate
Routes of
administration		Intramuscular injection
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] decanoate
CAS Number
PubChem CID
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.024.752
Chemical and physical data
FormulaC29H46O3
Molar mass442.684 g·mol−1
3D model (JSmol)
Melting point49.1 °C (120.4 °F)
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
InChI
  • InChI=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
  • Key:LBERVHLCXUMDOT-MPZZESAYSA-N

See also

References
  1. Elks J (14 November 2014). The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies. Springer. pp. 641–642. ISBN 978-1-4757-2085-3.
  2. Index Nominum 2000: International Drug Directory. Taylor & Francis. January 2000. ISBN 978-3-88763-075-1.
  3. Morton IK, Hall JM (6 December 2012). Concise Dictionary of Pharmacological Agents: Properties and Synonyms. Springer Science & Business Media. ISBN 978-94-011-4439-1.
  4. Behre HM, Nieschlag E, Nieschlag E, Behre HM, Nieschlag S (26 July 2012). "Testosterone preparations for clinical use in males". In Nieschlag E, Behre HM, Nieschlag S (eds.). Testosterone: Action, Deficiency, Substitution. Cambridge University Press. pp. 309–335. doi:10.1017/CBO9781139003353.016. ISBN 978-1-107-01290-5.
  5. Fisher BA, Tilstone WJ, Woytowicz C (6 February 2009). Introduction to Criminalistics: The Foundation of Forensic Science. Academic Press. pp. 182–. ISBN 978-0-08-091675-0.
  6. Hay CJ, Brady BM, Zitzmann M, Osmanagaoglu K, Pollanen P, Apter D, et al. (April 2005). "A multicenter phase IIb study of a novel combination of intramuscular androgen (testosterone decanoate) and oral progestogen (etonogestrel) for male hormonal contraception". The Journal of Clinical Endocrinology and Metabolism. 90 (4): 2042–9. doi:10.1210/jc.2004-0895. PMID 15671109.
  7. Brady BM, Amory JK, Perheentupa A, Zitzmann M, Hay CJ, Apter D, et al. (January 2006). "A multicentre study investigating subcutaneous etonogestrel implants with injectable testosterone decanoate as a potential long-acting male contraceptive". Human Reproduction. 21 (1): 285–94. doi:10.1093/humrep/dei300. PMID 16172147.
  8. Chenoweth PJ, Lorton S (30 April 2014). Animal Andrology: Theories and Applications. CABI. pp. 488–. ISBN 978-1-78064-316-8.
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