4-Androstenediol

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4-Androstenediol
4-Androstenediol.png
4-Androstenediol3D.png
Identifiers
CAS number 1156-92-9 N
PubChem 136297
ChemSpider 120071 YesY
DrugBank DB01526
ChEMBL CHEMBL195836 YesY
Jmol-3D images Image 1
Image 2
Properties
Molecular formula C19H30O2
Molar mass 290.44 g/mol
Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
 N (verify) (what is: YesY/N?)
Infobox references

4-Androstenediol is an androstenediol that is converted to testosterone. The conversion rate is about 15.76%, almost triple that of androstenedione, due to utilization of a different enzymatic pathway. There is no direct conversion to estrogen, though some secondary aromatization does occur through metabolism. 4-Androstenediol is less androgenic, since it does not metabolize into the potent androgen dihydrotestosterone (DHT).[citation needed]

4-Androstenediol is closer to testosterone structurally than 5-androstenediol, and has androgenic effects, acting as a weak partial agonist of the androgen receptor.[1] However, due to its lower intrinsic activity in comparison, in the presence of full agonists like testosterone or dihydrotestosterone (DHT) 4-androstenediol has antagonistic actions, behaving more like an antiandrogen like cyproterone.[1]

Medical and commercial use[edit]

Patrick Arnold holds a 1999 patent on "Use of 4-androstenediol to increase testosterone levels in humans".[2]

References[edit]

  1. ^ a b Chen F, Knecht K, Leu C, et al. (August 2004). "Partial agonist/antagonist properties of androstenedione and 4-androsten-3beta,17beta-diol". The Journal of Steroid Biochemistry and Molecular Biology 91 (4-5): 247–57. doi:10.1016/j.jsbmb.2004.04.009. PMID 15336702. 
  2. ^ http://www.patentstorm.us/patents/5880117/description.html