Testosterone decanoate

Testosterone decanoate
Clinical data
Other names	Testosterone 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	5721-91-5;
PubChem CID	155143;
DrugBank	DB16001;
ChemSpider	136680;
UNII	IJW60LAO6S;
KEGG	D08573;
ChEBI	CHEBI:35000;
ChEMBL	ChEMBL1473654;
CompTox Dashboard (EPA)	DTXSID5046198 ;
ECHA InfoCard	100.024.752
Chemical and physical data
Formula	C29H46O3
Molar mass	442.684 g·mol−1
3D model (JSmol)	Interactive image;
Melting point	49.1 °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;

Testosterone decanoate (BANTooltip British Approved Name) 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]

v
t
e
Parenteral durations of androgens/anabolic steroids
Medication	Form	Major brand names	Duration
Testosterone	Aqueous suspension	Andronaq, Sterotate, Virosterone	2–3 days
Testosterone propionate	Oil solution	Androteston, Perandren, Testoviron	3–4 days
Testosterone phenylpropionate	Oil solution	Testolent	8 days
Testosterone isobutyrate	Aqueous suspension	Agovirin Depot, Perandren M	14 days
Mixed testosterone esters^a	Oil solution	Triolandren	10–20 days
Mixed testosterone esters^b	Oil solution	Testosid Depot	14–20 days
Testosterone enanthate	Oil solution	Delatestryl	14–28 days
Testosterone cypionate	Oil solution	Depovirin	14–28 days
Mixed testosterone esters^c	Oil solution	Sustanon 250	28 days
Testosterone undecanoate	Oil solution	Aveed, Nebido	100 days
Testosterone buciclate^d	Aqueous suspension	20 Aet-1, CDB-1781^e	90–120 days
Nandrolone phenylpropionate	Oil solution	Durabolin	10 days
Nandrolone decanoate	Oil solution	Deca Durabolin	21–28 days
Methandriol	Aqueous suspension	Notandron, Protandren	8 days
Methandriol bisenanthoyl acetate	Oil solution	Notandron Depot	16 days
Metenolone acetate	Oil solution	Primobolan	3 days
Metenolone enanthate	Oil solution	Primobolan Depot	14 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.

References

^ 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.
^ Index Nominum 2000: International Drug Directory. Taylor & Francis. January 2000. ISBN 978-3-88763-075-1.
^ 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.
^ ^a ^b ^c ^d ^e 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.
^ 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.
^ 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): 2042–2049. doi:10.1210/jc.2004-0895. PMID 15671109.
^ 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): 285–294. doi:10.1093/humrep/dei300. PMID 16172147.
^ 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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[Elks2014-1] 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.

[IndexNominum2000-2] Index Nominum 2000: International Drug Directory. Taylor & Francis. January 2000. ISBN 978-3-88763-075-1.

[MortonHall2012-3] 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.

[BehreNieschlag2012-4] 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.

[FisherTilstone2009-5] 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.

[HayBrady2005-6] 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): 2042–2049. doi:10.1210/jc.2004-0895. PMID 15671109.

[Brady2005-7] 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): 285–294. doi:10.1093/humrep/dei300. PMID 16172147.

[ChenowethLorton2014-8] 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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v t e Testosterone
Topics	Testosterone (as a hormone) Testosterone (as a medication) Pharmacodynamics of testosterone Pharmacokinetics of testosterone Androgen (as a hormone) Androgen/anabolic steroid (as a medication) Androgen replacement therapy Masculinizing hormone therapy
Esters	Androgen ester Testosterone ester Testosterone buciclate Testosterone caproate Testosterone cypionate Testosterone decanoate Testosterone enanthate Testosterone isobutyrate Testosterone isocaproate Testosterone phenylpropionate Testosterone propionate Testosterone undecanoate Mixed testosterone esters
Related	Dihydrotestosterone (DHT; androstanolone) Methyltestosterone Nandrolone (19-nortestosterone) Dehydroepiandrosterone (DHEA; prasterone) Estradiol

See also

References