Androstenetriol Explained

Androstenetriol should not be confused with Androstenediol.

Cas Number:2697-85-0
Pubchem:9818024
Unii:Q0CZ537GC8
Synonyms:AET; Androst-5-ene-3β,7β,17β-triol; β-Androstenetriol; β-AET
Iupac Name:(3S,7R,8R,9S,10R,13S,14S,17S)-10,13-Dimethyl-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[''a'']phenanthrene-3,7,17-triol
C:19
H:30
O:3
Stdinchi:1S/C19H30O3/c1-18-7-5-12(20)9-11(18)10-15(21)17-13-3-4-16(22)19(13,2)8-6-14(17)18/h10,12-17,20-22H,3-9H2,1-2H3/t12-,13-,14-,15-,16-,17-,18-,19-/m0/s1
Stdinchikey:OEVZKEVBDIDVOI-YSZCXEEOSA-N
Smiles:C[C@]12CC[C@H]3[C@H]([C@@H]1CC[C@@H]2O)[C@H](C=C4[C@@]3(CC[C@@H](C4)O)C)O

Androstenetriol (AET, androst-5-ene-3β,7β,17β-triol, β-androstenetriol, or β-AET) is a steroid produced in the adrenal glands as a metabolite of dehydroepiandrosterone (DHEA).[1] It is believed to have similar effects as DHEA and androstenediol.[2] A study in rodents found that the compound was a weak androgen and estrogen, but did not bind to the androgen, estrogen, progesterone, or glucocorticoid receptors. Synthetic analogues of androstenetriol such as bezisterim (HE3286, NE3107; the 17α-ethynylated derivative) have been developed and are under study.[3] [4] [5]

Notes and References

  1. Ahlem . Clarence N. . Auci . Dominick L. . Nicoletti . Ferdinando . Pieters . Raymond . Kennedy . Michael R. . Page . Theodore M. . Reading . Christopher L. . Enioutina . Elena Y. . Frincke . James M. . Pharmacology and immune modulating properties of 5-androstene-3β,7β,17β-triol, a DHEA metabolite in the human metabolome . The Journal of Steroid Biochemistry and Molecular Biology . 2011 . 126 . 3 . 87–94 . 10.1016/j.jsbmb.2011.04.010 . 21570467 . 5123272 . 0960-0760.
  2. Dillon . Joseph S. . Dehydroepiandrosterone, Dehydroepiandrosterone Sulfate and Related Steroids: Their Role in Inflammatory, Allergic and Immunological Disorders . Current Drug Targets. Inflammation and Allergy . 2005 . 4 . 3 . 377–385 . 10.2174/1568010054022079. 16101547 .
  3. Ma . Yajing . Liu . Sufang . Zhou . Qingfeng . Li . Zhonghua . Zhang . Zhijian . Yu . Bin . Approved drugs and natural products at clinical stages for treating Alzheimer’s disease . Chinese Journal of Natural Medicines . 22 . 8 . 2024 . 10.1016/S1875-5364(24)60606-0 . 699–710 . Bezisterim, a derivative of the natural anti-inflammatory steroid β-AET, is an orally active NF-κB inhibitor. It has been shown to protect neurons by reducing inflammation and improving glucose utilization, thereby promoting brain health. Clinical results have demonstrated that bezisterim can improve cognition and biomarker levels in AD patients and is currently in phase III clinical trials [68]..
  4. Reading . Chris L . Ahlem . Clarence N . Parameswaran . Narayanan . Rationale for an anti-inflammatory insulin sensitizer in a phase 3 Alzheimer's disease trial . Alzheimer's & Dementia . December 2021 . 17 . S9 . 10.1002/alz.057438. free .
  5. Reading . Christopher L. . Frincke . James M. . White . Steven K. . Molecular Targets for 17α-Ethynyl-5-Androstene-3β,7β,17β-Triol, an Anti-Inflammatory Agent Derived from the Human Metabolome . PLOS ONE . 24 February 2012 . 7 . 2 . e32147 . 10.1371/journal.pone.0032147 . 22384159 . 3286445 . 2012PLoSO...732147R . en . 1932-6203 . free .

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