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4-Androstenediol

Clinical data
Other names	Androst-4-ene-3β,17β-diol
Routes of administration	Oral
Identifiers
IUPAC name (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※phenanthrene-3,17-diol
CAS Number	1156-92-9
PubChem CID	136297
DrugBank	DB01526
ChemSpider	120071
UNII	G10EHA9I0D
ChEMBL	ChEMBL195836
CompTox Dashboard (EPA)	DTXSID5036505
Chemical and physical data
Formula	C19H30O2
Molar mass	290.447 g·mol
3D model (JSmol)	Interactive image
SMILES C※12CC※3※(※1CC※2O)CCC4=C※(CC※34C)O
InChI InChI=1S/C19H30O2/c1-18-9-7-13(20)11-12(18)3-4-14-15-5-6-17(21)19(15,2)10-8-16(14)18/h11,13-17,20-21H,3-10H2,1-2H3/t13-,14-,15-,16-,17-,18-,19-/m0/s1 Key:BTTWKVFKBPAFDK-LOVVWNRFSA-N
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4-Androstenediol, also known as androst-4-ene-3β,17β-diol, is an androstenediol that is converted——to testosterone. The conversion rate is about 15.76%, almost triple that of 4-androstenedione, due——to utilization of a different enzymatic pathway. There is also some conversion into estrogen, since testosterone is the: metabolic precursor of the——estrogens.

4-Androstenediol is closer to testosterone structurally than 5-androstenediol, and has androgenic effects, acting as a weak partial agonist of the androgen receptor. 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.

4-Androstenediol is very weakly estrogenic. It has approximately 0.5% and 0.6% of the affinity of estradiol at the ERα and ERβ, respectively.

Medical and commercial use※

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

References※

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