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| Names | |
|---|---|
| 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) | |
| ChEMBL | |
| ChemSpider | |
| ECHA InfoCard | 100.008.487 |
| UNII | |
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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 theirstandard state (at 25 °C [77 °F], 100 kPa). | |
3β-Androstanediol, also known as5α-androstane-3β,17β-diol, and sometimes shortened in the literature to3β-diol, is anendogenoussteroid hormone and ametabolite ofandrogens likedehydroepiandrosterone (DHEA) anddihydrotestosterone (DHT).
3β-Androstanediol is a selective, high-affinityagonist of theERβ, and hence, anestrogen.[2] In contrast to ERβ, 3β-androstanediol does not bind to theandrogen receptor (AR).[3] 3β-Androstanediol has been reported to also bind toERα with lownanomolar affinity, with several-fold lower affinity relative to ERβ.[4][5] It has approximately 3% and 7% of theaffinity ofestradiol at theERα andERβ, respectively.[6] Unlike3α-androstanediol, 3β-androstanediol does not bind to theGABAA receptor.[7]
3β-Androstanediol may be the primary endogenousligand of ERβ in theprostate gland, and as a result of activation of the ERβ, 3β-androstanediol hasantiproliferative effects againstprostate cancercells.[8] Through the ERβ, 3β-androstanediol positively regulatesoxytocinneurons andsignaling in theparaventricular nucleus of hypothalamus,[9][10] and has been found to haveantidepressant,[11]anxiolytic,[12]cognitive-enhancing,[12] andstress-relieving effects via this action.[13][14] Androgens, includingtestosterone and DHT, are known to downregulate thehypothalamic-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]
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3β-Androstanediol is a5α-reduced and17β-hydroxylatedmetabolite ofdehydroepiandrosterone (DHEA) as well as a3β-hydroxylated metabolite of DHT (and by extension oftestosterone).
A determination of the circulating levels of 3β-androstanediol inhumans foundconcentrations of 239 ± 76 pg/ml and 82 ± 45 pg/ml of the compound in normalmale andfemaleserum, respectively.[16]
3β-Androstanediol shows high affinity forsex hormone-binding globulin (SHBG), similar to that of DHT.[17]
3β-Androstanediol, also known as 5α-androstane-3β,17β-diol, is anaturally occurringandrostanesteroid and astructural analogue of DHT (5α-androstan-17β-ol-3-one). A notableepimer of 3β-androstanediol is3α-androstanediol.
17α-Ethynyl-3β-androstanediol is a17α-substitutedderivative of 3β-androstanediol and is an estrogen similarly.[18][19]
