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Androstenetriol

From Wikipedia, the free encyclopedia
Chemical compound
Not to be confused withAndrostenediol.
Pharmaceutical compound
Androstenetriol
Clinical data
Other namesAET; Androst-5-ene-3β,7β,17β-triol; β-Androstenetriol; β-AET
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
PubChemCID
UNII
CompTox Dashboard(EPA)
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

Androstenetriol (AET,androst-5-ene-3β,7β,17β-triol,β-androstenetriol, orβ-AET) is asteroid produced in theadrenal glands as ametabolite ofdehydroepiandrosterone (DHEA).[1] It is believed to have similar effects as DHEA andandrostenediol.[2] A study in rodents found that the compound was a weakandrogen andestrogen, but did not bind to theandrogen,estrogen,progesterone, orglucocorticoid receptors.[1]Syntheticanalogues of androstenetriol such asbezisterim (HE3286, NE3107; the 17α-ethynylatedderivative) have been developed and are under study.[3][4][5]

References

[edit]
  1. ^abAhlem, 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 and Allergy.4 (3):377–385.doi:10.2174/1568010054022079.PMID 16101547.
  3. ^Ma, Yajing; Liu, Sufang; Zhou, Qingfeng; Li, Zhonghua; Zhang, Zhijian; Yu, Bin (2024)."Approved drugs and natural products at clinical stages for treating Alzheimer's disease"(PDF).Chinese Journal of Natural Medicines.22 (8):699–710.doi:10.1016/S1875-5364(24)60606-0.PMID 39197961.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 (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.
  5. ^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.
Precursors
Corticosteroids
Glucocorticoids
Mineralocorticoids
Sex steroids
Androgens
Estrogens
Progestogens
Neurosteroids
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