5α-Androstane-3β,17β-diol

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5α-Androstane-3β,17β-diol
3beta-Androstanediol.svg
Names
IUPAC name
(3β,5α,17β)-Androstane-3,17-diol
Systematic IUPAC name
(1S,2S,5S,7S,10R,11S,14S,15S)-2,15-Dimethyltetracyclo[8.7.0.02,7.011,15]heptadecane-5,14-diol
Other names
3β-Androstanediol; 3β-Diol; Maxterone
Identifiers
571-20-0
ChEMBL ChEMBL316048
ChemSpider 211834
Jmol 3D model Interactive image
PubChem 242332
  • InChI=1S/C19H32O2/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/h12-17,20-21H,3-11H2,1-2H3/t12-,13-,14-,15-,16-,17-,18-,19-/m0/s1
    Key: CBMYJHIOYJEBSB-YSZCXEEOSA-N
  • InChI=1/C19H32O2/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/h12-17,20-21H,3-11H2,1-2H3/t12-,13-,14-,15-,16-,17-,18-,19-/m0/s1
    Key: CBMYJHIOYJEBSB-YSZCXEEOBK
  • O[C@H]4CC[C@]3([C@@H](CC[C@H]2[C@@H]1CC[C@H](O)[C@@]1(C)CC[C@@H]23)C4)C
Properties
C19H32O2
Molar mass 292.46 g·mol−1
Melting point 168–170 °C (334–338 °F; 441–443 K) [1]
Vapor pressure {{{value}}}
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

5α-Androstane-3β,17β-diol, also called 3β-androstanediol, and often shortened to 3β-diol, is an endogenous steroid hormone. It is a 5α-reduced and 17β-hydroxylated metabolite of dehydroepiandrosterone (DHEA) as well as a 3β-hydroxylated metabolite of dihydrotestosterone (DHT). 3β-Diol is a selective, potent, high-affinity full agonist of the ERβ, and hence, an estrogen.[2] It has higher affinity for this receptor than estradiol.[2] In contrast to ERβ, 3β-diol does not bind to the androgen receptor (AR).[3] 3β-Diol has been reported to also bind to ERα with low nanomolar affinity, with several-fold lower affinity relative to ERβ.[4][5] Unlike its 3α-isomer, 3α-androstanediol (3α-diol), 3β-diol does not bind to the GABAA receptor.[6]

3β-Diol appears to be the endogenous ligand of ERβ in the prostate gland, and as a result of activation of the ERβ, 3β-diol has antiproliferative effects against prostate cancer cells.[7] Through the ERβ, 3β-diol positively regulates oxytocin neurons and signaling in the paraventricular nucleus of hypothalamus (PVN),[8][9] and has been found to have antidepressant,[10] anxiolytic,[11] cognitive-enhancing,[11] and stress-relieving effects via this action.[12][13] Androgens, including testosterone and dihydrotestosterone (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-diol rather than to activation of the AR.[12][13][14]

A determination of the circulating levels of 3β-diol in humans found concentrations of 239 ± 76 pg/ml and 82 ± 45 pg/ml of the compound in normal male and female serum, respectively.[15]

An orally active synthetic analogue of 3β-diol, 17α-ethynyl-5α-androstane-3α,17β-diol (HE3235, Apoptone), was formerly under investigation for the treatment of prostate cancer and breast cancer.[16]

See also

References

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