Chemistry: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;
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;

Short description: Chemical compound

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]

v · d · 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	14–20 days
Testosterone cypionate	Oil solution	Depovirin	14–20 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 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

↑ The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies. Springer. 14 November 2014. pp. 641–642. ISBN 978-1-4757-2085-3. https://books.google.com/books?id=0vXTBwAAQBAJ&pg=PA641.
↑ Index Nominum 2000: International Drug Directory. Taylor & Francis. January 2000. ISBN 978-3-88763-075-1. https://books.google.com/books?id=5GpcTQD_L2oC&pg=PA976.
↑ Concise Dictionary of Pharmacological Agents: Properties and Synonyms. Springer Science & Business Media. 6 December 2012. ISBN 978-94-011-4439-1. https://books.google.com/books?id=tsjrCAAAQBAJ&pg=PA270.
↑ ^4.0 ^4.1 ^4.2 ^4.3 ^4.4 "Testosterone preparations for clinical use in males". Testosterone: Action, Deficiency, Substitution. Cambridge University Press. 26 July 2012. pp. 309–335. doi:10.1017/CBO9781139003353.016. ISBN 978-1-107-01290-5.
↑ Introduction to Criminalistics: The Foundation of Forensic Science. Academic Press. 6 February 2009. pp. 182–. ISBN 978-0-08-091675-0. https://books.google.com/books?id=JeheoVz6cWwC&pg=PT182.
↑ "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. April 2005. doi:10.1210/jc.2004-0895. PMID 15671109.
↑ "A multicentre study investigating subcutaneous etonogestrel implants with injectable testosterone decanoate as a potential long-acting male contraceptive". Human Reproduction 21 (1): 285–294. January 2006. doi:10.1093/humrep/dei300. PMID 16172147.
↑ Animal Andrology: Theories and Applications. CABI. 30 April 2014. pp. 488–. ISBN 978-1-78064-316-8. https://books.google.com/books?id=hv6dAwAAQBAJ&pg=PA488.

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(incl. AAS)

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| group2 = Antiandrogens
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  | group1 = AR antagonists
  | list1 =

  | group2 = Steroidogenesis
inhibitors

| list2 =

  | group3 = Antigonadotropins
  | list3 =

D₂ receptor antagonists (prolactin releasers) (e.g., domperidone, metoclopramide, risperidone, haloperidol, chlorpromazine, sulpiride)
Estrogens (e.g., bifluranol, [[diethylstilbestrol, estradiol, estradiol esters, ethinylestradiol, ethinylestradiol sulfonate, paroxypropione)
GnRH agonists (e.g., leuprorelin)
GnRH antagonists (e.g., cetrorelix)
Progestogens (incl., chlormadinone acetate, [[cyproterone acetate, hydroxyprogesterone caproate, gestonorone caproate, [[Chemistry:Medroxyprogesterone medroxyprogesterone acetate, Chemistry:Megestrol acetate|megestrol acetate]])

  | group4 = Others
  | list4 =

Androstenedione immunogens: Androvax (androstenedione albumin)
Ovandrotone albumin (Fecundin)

}}

| liststyle = background:#DDDDFF;

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^#WHO-EM
^‡Withdrawn from market
Clinical trials:
- ^†Phase III
- ^§Never to phase III

See also: Androgen receptor modulators; Estrogens and antiestrogens; Progestogens and antiprogestogens; List of androgens/anabolic steroids

}}

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Original source: https://en.wikipedia.org/wiki/Testosterone decanoate. Read more

[Elks2014-1] The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies. Springer. 14 November 2014. pp. 641–642. ISBN 978-1-4757-2085-3. https://books.google.com/books?id=0vXTBwAAQBAJ&pg=PA641.

[IndexNominum2000-2] Index Nominum 2000: International Drug Directory. Taylor & Francis. January 2000. ISBN 978-3-88763-075-1. https://books.google.com/books?id=5GpcTQD_L2oC&pg=PA976.

[MortonHall2012-3] Concise Dictionary of Pharmacological Agents: Properties and Synonyms. Springer Science & Business Media. 6 December 2012. ISBN 978-94-011-4439-1. https://books.google.com/books?id=tsjrCAAAQBAJ&pg=PA270.

[BehreNieschlag2012-4] 4.0 ^4.1 ^4.2 ^4.3 ^4.4 "Testosterone preparations for clinical use in males". Testosterone: Action, Deficiency, Substitution. Cambridge University Press. 26 July 2012. pp. 309–335. doi:10.1017/CBO9781139003353.016. ISBN 978-1-107-01290-5.

[FisherTilstone2009-5] Introduction to Criminalistics: The Foundation of Forensic Science. Academic Press. 6 February 2009. pp. 182–. ISBN 978-0-08-091675-0. https://books.google.com/books?id=JeheoVz6cWwC&pg=PT182.

[HayBrady2005-6] "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. April 2005. doi:10.1210/jc.2004-0895. PMID 15671109.

[Brady2005-7] "A multicentre study investigating subcutaneous etonogestrel implants with injectable testosterone decanoate as a potential long-acting male contraceptive". Human Reproduction 21 (1): 285–294. January 2006. doi:10.1093/humrep/dei300. PMID 16172147.

[ChenowethLorton2014-8] Animal Andrology: Theories and Applications. CABI. 30 April 2014. pp. 488–. ISBN 978-1-78064-316-8. https://books.google.com/books?id=hv6dAwAAQBAJ&pg=PA488.

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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 Transgender hormone therapy (female-to-male)
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

5α-Reductase	Alfatradiol Dutasteride Epristeride Finasteride Saw palmetto extract
Others	Abiraterone acetate Aminoglutethimide Bifluranol Cyproterone acetate Flutamide Ketoconazole Nilutamide Seviteronel^† Spironolactone

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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
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

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