4-Hydroxytestosterone

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[1] 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).[2]

4-Hydroxytestosterone
Skeletal formula of 4-hydroxytestosterone
Ball-and-stick model of the 4-hydroxytestosterone molecule
Clinical data
Other names4,17β-Dihydroxyandrost-4-en-3-one; Androst-4-ene-4,17β-diol-3-one; Desmethylenestebol
Identifiers
  • 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
CAS Number
PubChem CID
DrugBank
ChemSpider
UNII
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC19H28O3
Molar mass304.430 g·mol−1
3D model (JSmol)
  • O=C4C(\O)=C2/[C@]([C@H]1CC[C@@]3([C@@H](O)CC[C@H]3[C@@H]1CC2)C)(C)CC4
  • InChI=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 checkY
  • Key:BQOIJSIMMIDHMO-FBPKJDBXSA-N checkY
 ☒NcheckY (what is this?)  (verify)

See also

References
  1. US 2762818, Levy H, Mednick ML, "4-Hydroxytestosterone and esters", issued 11 September 1956, assigned to GD Searle.
  2. Kohler M, Parr MK, Opfermann G, Thevis M, Schlörer N, Marner FJ, Schänzer W (March 2007). "Metabolism of 4-hydroxyandrostenedione and 4-hydroxytestosterone: Mass spectrometric identification of urinary metabolites". Steroids. 72 (3): 278–86. doi:10.1016/j.steroids.2006.11.018. PMID 17207827. S2CID 34982808.
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