Androstenetriol

Androstenetriol
Clinical data
Other names	AET; Androst-5-ene-3β,7β,17β-triol; β-Androstenetriol; β-AET
Identifiers
	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;
CAS Number	2697-85-0;
PubChem CID	9818024;
UNII	Q0CZ537GC8;
CompTox Dashboard (EPA)	DTXSID201043225 ;
Chemical and physical data
Formula	C19H30O3
Molar mass	306.446 g·mol−1
3D model (JSmol)	Interactive image;
	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;
	InChI 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, 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.^[1] Synthetic analogues of androstenetriol such as bezisterim (HE3286, NE3107; the 17α-ethynylated derivative) have been developed and are under study.^[3]^[4]^[5]

References

^ ^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.
^ 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.
^ 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. 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].
^ 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.
^ 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.

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[Ahlem-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. (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.

[MaLiuZhou2024-3] 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. 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.

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