Androstenetriol (AET, androst-5-ene-3β,7β,17β-triol, β-androstenetriol, or βAET) is a steroid produced in the adrenal glands as a metabolite of 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 attach to the androgen, estrogen, progesterone, or glucocorticoid receptors.[1] Synthetic analogs of AET known as HE3286[3] and NE3107 have been developed.[4]

Androstenetriol
Identifiers
  • (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
CAS Number
PubChem CID
UNII
Chemical and physical data
FormulaC19H30O3
Molar mass306.446 g·mol−1
3D model (JSmol)
  • 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
  • InChI=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
  • Key:OEVZKEVBDIDVOI-YSZCXEEOSA-N

References edit

  1. ^ a b 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. (2011). "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. 126 (3): 87–94. doi:10.1016/j.jsbmb.2011.04.010. ISSN 0960-0760. PMID 21570467. S2CID 5123272.
  2. ^ Dillon, Joseph S. (2005). "Dehydroepiandrosterone, Dehydroepiandrosterone Sulfate and Related Steroids: Their Role in Inflammatory, Allergic and Immunological Disorders". Current Drug Targets - Inflammation & Allergy. 4 (3): 377–385. doi:10.2174/1568010054022079. PMID 16101547.
  3. ^ Reading, Christopher L.; Frincke, James M.; White, Steven K. (24 February 2012). "Molecular Targets for 17α-Ethynyl-5-Androstene-3β,7β,17β-Triol, an Anti-Inflammatory Agent Derived from the Human Metabolome". PLOS ONE. 7 (2): e32147. Bibcode:2012PLoSO...732147R. doi:10.1371/journal.pone.0032147. ISSN 1932-6203. PMC 3286445. PMID 22384159.
  4. ^ Reading, Chris L; Ahlem, Clarence N; Parameswaran, Narayanan (December 2021). "Rationale for an anti-inflammatory insulin sensitizer in a phase 3 Alzheimer's disease trial". Alzheimer's & Dementia. 17 (S9). doi:10.1002/alz.057438.