3β-Androstanediol
Chemical compound
From Wikipedia, the free encyclopedia
3β-Androstanediol, also known as 5α-androstane-3β,17β-diol, and sometimes shortened in the literature to 3β-diol, is an endogenous steroid hormone and a metabolite of androgens like dehydroepiandrosterone (DHEA) and dihydrotestosterone (DHT).
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| Names | |
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| IUPAC name
5α-Androstane-3β,17β-diol | |
| Systematic IUPAC name
(1S,3aS,3bR,5aS,7S,9aS,9bS,11aS)-9a,11a-Dimethylhexadecahydro-1H-cyclopenta[a]phenanthrene-1,7-diol | |
| Other names
3β-Androstanediol; 3β-Diol; Maxterone | |
| Identifiers | |
3D model (JSmol) |
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| ChEMBL | |
| ChemSpider | |
| ECHA InfoCard | 100.008.487 |
PubChem CID |
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| UNII | |
CompTox Dashboard (EPA) |
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| Properties | |
| C19H32O2 | |
| Molar mass | 292.463 g·mol−1 |
| Melting point | 168–170 °C (334–338 °F; 441–443 K)[1] |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Biological activity
3β-Androstanediol is a selective, high-affinity agonist of the ERβ, and hence, an estrogen.[2] In contrast to ERβ, 3β-androstanediol does not bind to the androgen receptor (AR).[3] 3β-Androstanediol has been reported to also bind to ERα with low nanomolar affinity, with several-fold lower affinity relative to ERβ.[4][5] It has approximately 3% and 7% of the affinity of estradiol at the ERα and ERβ, respectively.[6] Unlike 3α-androstanediol, 3β-androstanediol does not bind to the GABAA receptor.[7]
3β-Androstanediol may be the primary endogenous ligand of ERβ in the prostate gland, and as a result of activation of the ERβ, 3β-androstanediol has antiproliferative effects against prostate cancer cells.[8] Through the ERβ, 3β-androstanediol positively regulates oxytocin neurons and signaling in the paraventricular nucleus of hypothalamus,[9][10] and has been found to have antidepressant,[11] anxiolytic,[12] cognitive-enhancing,[12] and stress-relieving effects via this action.[13][14] Androgens, including testosterone and DHT, are known to downregulate the hypothalamic-pituitary-adrenal axis, and this has been found to be due in part or full to their conversion into 3β-androstanediol rather than to activation of the AR.[13][14][15]
Biochemistry
Testosterone metabolism in humans
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3β-Androstanediol is a 5α-reduced and 17β-hydroxylated metabolite of dehydroepiandrosterone (DHEA) as well as a 3β-hydroxylated metabolite of DHT (and by extension of testosterone).
A determination of the circulating levels of 3β-androstanediol in humans found concentrations of 239 ± 76 pg/ml and 82 ± 45 pg/ml of the compound in normal male and female serum, respectively.[16]
3β-Androstanediol shows high affinity for sex hormone-binding globulin (SHBG), similar to that of DHT.[17]
Chemistry
3β-Androstanediol, also known as 5α-androstane-3β,17β-diol, is a naturally occurring androstane steroid and a structural analogue of DHT (5α-androstan-17β-ol-3-one). A notable epimer of 3β-androstanediol is 3α-androstanediol.
17α-Ethynyl-3β-androstanediol is a 17α-substituted derivative of 3β-androstanediol and is an estrogen similarly.[18][19]