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Chemical compound
4-Androstenediol
Other names Androst-4-ene-3β,17β-diol
Routes of administration
Oral
(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
CAS Number
PubChem
CID
DrugBank
ChemSpider
UNII
ChEMBL
CompTox Dashboard (
EPA )
Formula C 19 H 30 O 2
Molar mass 290.447 g·mol−1 3D model (
JSmol )
C[C@]12CC[C@H]3[C@H]([C@@H]1CC[C@@H]2O)CCC4=C[C@H](CC[C@]34C)O
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
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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 .
[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 .
[1]
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.
[2]
Medical and commercial use
Patrick Arnold holds a 1999 patent on "Use of 4-androstenediol to increase testosterone levels in humans".
[3]
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 .
S2CID
53267316 .
^ Kuiper GG, Carlsson B, Grandien K, Enmark E, Häggblad J, Nilsson S, Gustafsson JA (1997).
"Comparison of the ligand binding specificity and transcript tissue distribution of estrogen receptors alpha and beta" . Endocrinology . 138 (3): 863–70.
doi :
10.1210/endo.138.3.4979 .
PMID
9048584 .
^
"Use of 4-androstenediol to increase testosterone levels in humans" . Archived from
the original on 2011-03-18. Retrieved 2011-03-18 .
AR Tooltip Androgen receptor
Agonists
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GPRC6A
ER Tooltip Estrogen receptor
Agonists
Steroidal:
2-Hydroxyestradiol
2-Hydroxyestrone
3-Methyl-19-methyleneandrosta-3,5-dien-17β-ol
3α-Androstanediol
3α,5α-Dihydrolevonorgestrel
3β,5α-Dihydrolevonorgestrel
3α-Hydroxytibolone
3β-Hydroxytibolone
3β-Androstanediol
4-Androstenediol
4-Androstenedione
4-Fluoroestradiol
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4-Methoxyestradiol
4-Methoxyestrone
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7α-Methylestradiol
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8,9-Dehydroestradiol
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10β,17β-Dihydroxyestra-1,4-dien-3-one (DHED)
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17α-Ethynyl-3α-androstanediol
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