In today's world, 3α-Androstanediol is a topic that has gained great relevance and has captured the attention of people of all ages and cultures. Whether due to its impact on society or its influence on daily life, 3α-Androstanediol has become a point of interest for those seeking to better understand the world around them. As we delve deeper into this article, we will explore the various facets of 3α-Androstanediol and discuss its importance in different areas. From its historical relevance to its impact today, 3α-Androstanediol continues to be a topic of discussion and debate that deserves our attention and reflection.
Names | |
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IUPAC name
5α-Androstane-3α,17β-diol
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Systematic IUPAC name
(1S,3aS,3bR,5aS,7R,9aS,9bS,11aS)-9a,11a-Dimethylhexadecahydro-1H-cyclopentaphenanthrene-1,7-diol | |
Other names
Hombreol
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Identifiers | |
3D model (JSmol)
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ChEBI | |
ChemSpider | |
ECHA InfoCard | 100.015.862 |
PubChem CID
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UNII | |
CompTox Dashboard (EPA)
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Properties | |
C19H32O2 | |
Molar mass | 292.463 g·mol−1 |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa).
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3α-Androstanediol also known as 5α-androstane-3α,17β-diol and sometimes shortened in the literature to 3α-diol, is an endogenous steroid hormone and neurosteroid and a metabolite of androgens like dihydrotestosterone (DHT).
3α-Androstanediol is an inhibitory androstane neurosteroid and weak androgen and estrogen.
As a neurosteroid, it acts as a potent positive allosteric modulator of the GABAA receptor, and has been found to have rewarding, anxiolytic, pro-sexual, and anticonvulsant effects. As androgens such as testosterone and DHT are known to have many of the same effects as 3α-diol and are converted into it in vivo, it is thought that this compound may in part be responsible for said effects.
Relative to its isomer 3β-androstanediol, which is a potent estrogen, 3α-androstanediol has substantially lower, though still significant affinity for the estrogen receptors, with a several-fold preference for ERβ over ERα. It has approximately 0.07% and 0.3% of the affinity of estradiol at the ERα and ERβ, respectively.
Testosterone metabolism in humans
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3α-Androstanediol shows high affinity for sex hormone-binding globulin (SHBG), similar to that of testosterone.
3α-Androstanediol, also known as 5α-androstane-3α,17β-diol, is a naturally occurring androstane steroid and a structural analogue of DHT (5α-androstan-17β-ol-3-one). A notable positional isomer of 3α-androstanediol is 3β-androstanediol.
An orally active synthetic analogue of 3α-androstanediol, 17α-ethynyl-3α-androstanediol (HE-3235, Apoptone), was formerly under investigation for the treatment of prostate cancer and breast cancer.