4-Hydroxytestosterone

{{Short description|Chemical compound}}

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| verifiedrevid = 477222394

| IUPAC_name = 4,17-Dihydroxy-10,13-dimethyl-1,2,6,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-cyclopenta[a]phenanthren-3-one

| image = 4-Hydroxytestosterone.svg

| alt = Skeletal formula of 4-hydroxytestosterone

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| image2 = 4-Hydroxytestosterone-3D-balls.png

| alt2 = Ball-and-stick model of the 4-hydroxytestosterone molecule

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| CAS_number_Ref = {{cascite|changed|??}}

| CAS_number = 2141-17-5

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| PubChem = 160615

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| DrugBank = DB01485

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| ChemSpiderID = 141138

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| UNII = 912GOZ167T

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| synonyms = 4,17β-Dihydroxyandrost-4-en-3-one; Androst-4-ene-4,17β-diol-3-one; Desmethylenestebol

| C=19 | H=28 | O=3

| SMILES = O=C4C(\O)=C2/[C@]([C@H]1CC[C@@]3([C@@H](O)CC[C@H]3[C@@H]1CC2)C)(C)CC4

| StdInChI_Ref = {{stdinchicite|correct|chemspider}}

| StdInChI = 1S/C19H28O3/c1-18-10-8-15(20)17(22)14(18)4-3-11-12-5-6-16(21)19(12,2)9-7-13(11)18/h11-13,16,21-22H,3-10H2,1-2H3/t11-,12-,13-,16-,18+,19-/m0/s1

| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}

| StdInChIKey = BQOIJSIMMIDHMO-FBPKJDBXSA-N

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4-Hydroxytestosterone (4-OHT), also known as 4,17β-dihydroxyandrost-4-en-3-one, is a synthetic anabolic-androgenic steroid (AAS) and a derivative of testosterone that was never marketed. It was first patented by G.D. Searle & Company in 1955{{cite patent | country = US | number = 2762818 | inventor = Levy H, Mednick ML | assign1 = GD Searle | title = 4-Hydroxytestosterone and esters | postscript = . | pridate = 26 May 1955 | gdate = 11 September 1956 }} and is testosterone with a hydroxy group at the four position. 4-OHT has moderate anabolic, mild androgenic, and anti-aromatase properties and is similar to the steroid clostebol (4-chlorotestosterone).{{cite journal | vauthors = Kohler M, Parr MK, Opfermann G, Thevis M, Schlörer N, Marner FJ, Schänzer W | title = Metabolism of 4-hydroxyandrostenedione and 4-hydroxytestosterone: Mass spectrometric identification of urinary metabolites | journal = Steroids | volume = 72 | issue = 3 | pages = 278–86 | date = March 2007 | pmid = 17207827 | doi = 10.1016/j.steroids.2006.11.018 | s2cid = 34982808 }}