4-Androstenediol

4-Androstenediol

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Names
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[a]phenanthrene-3,17-diol
Other names Androst-4-ene-3β,17β-diol
Identifiers
CAS Number	1156-92-9 N
ChEMBL	ChEMBL195836 Y
ChemSpider	120071 Y
DrugBank	DB01526 Y
Jmol 3D model	Interactive image Interactive image
PubChem	136297
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 Y Key: BTTWKVFKBPAFDK-LOVVWNRFSA-N Y InChI=1/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-LOVVWNRFBP
SMILES C[C@]12CC[C@H]3[C@H]([C@@H]1CC[C@@H]2O)CCC4=C[C@H](CC[C@]34C)O O[C@@H]4/C=C2\[C@]([C@H]1CC[C@@]3([C@@H](O)CC[C@H]3[C@@H]1CC2)C)(C)CC4
Properties
Chemical formula	C19H30O2
Molar mass	290.44 g/mol
Vapor pressure	{{{value}}}
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

Δ⁴-Androstenediol is an androstenediol that is converted to testosterone. The conversion rate is about 15.76%, almost triple that of Δ⁴-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.

Δ⁴-Androstenediol is closer to testosterone structurally than Δ⁵-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), Δ⁴-androstenediol has antagonistic actions, behaving more like an antiandrogen.

Medical and commercial use

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