UE2343   Click here for help

GtoPdb Ligand ID: 12037

Synonyms: compound 4 [PMID: 28012176] | UE-2343 | Xanamem®
Compound class: Synthetic organic
Comment: UE2343 is an oral, brain-penetrant hydroxysteroid 11-beta dehydrogenase 1 (11-βHSD1) inhibitor that was developed to reduce brain levels of the stress hormone cortisol, as a mechanism to improve memory in Alzheimer's disease patients [1-2]. It failed to provide efficacy in a phase 2 clinical trial.
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 6
Hydrogen bond donors 2
Rotatable bonds 4
Topological polar surface area 123.24
Molecular weight 381.13
XLogP 0.85
No. Lipinski's rules broken 0
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Canonical SMILES O=C(N1[C@@H]2CC[C@H]1CC(C2)(O)c1ncccn1)c1csc(c1)c1c[nH]nc1
Isomeric SMILES C1C[C@H]2CC(C[C@@H]1N2C(=O)c1csc(c1)c1c[nH]nc1)(c1ncccn1)O
InChI InChI=1S/C19H19N5O2S/c25-17(12-6-16(27-11-12)13-9-22-23-10-13)24-14-2-3-15(24)8-19(26,7-14)18-20-4-1-5-21-18/h1,4-6,9-11,14-15,26H,2-3,7-8H2,(H,22,23)/t14-,15+,19?
1. Ritchie CW, Miller T, Ketelbey JW. (2020)
Results and drug development summary for Xanamem, a potent inhibitor of the 11β-HSD1 enzyme.
Alzheimer's and Dementia,. DOI: 10.1002/alz.038876
2. Webster SP, McBride A, Binnie M, Sooy K, Seckl JR, Andrew R, Pallin TD, Hunt HJ, Perrior TR, Ruffles VS et al.. (2017)
Selection and early clinical evaluation of the brain-penetrant 11β-hydroxysteroid dehydrogenase type 1 (11β-HSD1) inhibitor UE2343 (Xanamem™).
Br J Pharmacol, 174 (5): 396-408. [PMID:28012176]