4-Androstenediol
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4-Androstenediol
| 4-Androstenediol | |
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(3S,8R,9S,10R,13S,14S,17S)-10,13-dimethyl-2,3,6,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthrene-3,17-diol |
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Other names
Androst-4-ene-3β,17β-diol |
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| Identifiers | |
| CAS number | 1156-92-9 |
| PubChem | 136297 |
| ChemSpider | 120071  |
| DrugBank | DB01526 |
| ChEMBL | CHEMBL195836 |
| Jmol-3D images | Image 1 Image 2 |
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| Properties | |
| Molecular formula | C19H30O2 |
| Molar mass | 290.44 g/mol |
 (verify) (what is:  / ?)Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) |
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| 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
Patrick Arnold holds a 1999 patent on "Use of 4-androstenediol to increase testosterone levels in humans".[2]
References
- ^ 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. http://linkinghub.elsevier.com/retrieve/pii/S0960-0760(04)00288-2.
- ^ http://www.patentstorm.us/patents/5880117/description.html
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