Testosterone stearate

{{Short description|Chemical compound}}

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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] octadecanoate

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| routes_of_administration = Oral, intramuscular injection

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| CAS_number = 6024-71-1

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| PubChem = 57463467

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| ChemSpiderID = 58539759

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| C=37 | H=62 | O=3

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

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| StdInChI = 1S/C37H62O3/c1-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-35(39)40-34-23-22-32-31-21-20-29-28-30(38)24-26-36(29,2)33(31)25-27-37(32,34)3/h28,31-34H,4-27H2,1-3H3/t31-,32-,33-,34-,36-,37-/m0/s1

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| StdInChIKey = FHJSGESOWQSDBH-MXFPRFFXSA-N

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

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Testosterone stearate, also known as testosterone octadecanoate, testosterone 17β-stearate, and androst-4-en-17β-ol-3-one 17β-stearate, is an injected anabolic-androgenic steroid (AAS) and an androgen ester – specifically, the C17β stearate (octadecanoate) ester of testosterone – which was never marketed.{{cite book| vauthors = Josephy E, Radt F |title=Elsevier's Encyclopaedia of Organic Chemistry: Series III: Carboisocyclic Condensed Compounds|url=https://books.google.com/books?id=HqHzCAAAQBAJ&pg=PA3048|date=1 December 2013|publisher=Springer|isbn=978-3-662-25863-7|pages=3048–}} 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. Testosterone stearate may occur naturally in the body.{{cite book| vauthors = Oettel M, Schillinger E |title=Estrogens and Antiestrogens I: Physiology and Mechanisms of Action of Estrogens and Antiestrogens|url=https://books.google.com/books?id=0BfrCAAAQBAJ&pg=PA236|date=6 December 2012|publisher=Springer Science & Business Media|isbn=978-3-642-58616-3|pages=236–}}

It has been said that with longer-chain esters of testosterone like testosterone stearate, the duration of action may be so protracted that the magnitude of effect with typical doses may be too low to be appreciable.{{cite book|title=Vitamins and Hormones|url=https://books.google.com/books?id=u_JhtsPyH90C&pg=PA384|date=1 January 1944|publisher=Academic Press|isbn=978-0-08-086599-7|pages=384–}}