leucomethylthioninium   Click here for help

GtoPdb Ligand ID: 9274

Synonyms: leuco-methylthioninium | LMTM | LMTX | TRx-0237 | TRx0237
Compound class: Synthetic organic
Comment: Leucomethylthioninium complexed with bromide or methane sulfonate (LMTX) was designed as a methylthioninium chloride (MTC, or methylene blue) analogue with improved pharmacokinetic properties [1]. MTC and LMTX are tau aggregation inhibitors with potential in Alzheimer's disease (AD) and other tau-opathies. We believe this is the compound being investigated in Phase 3 clinical trials as TRx0237.
2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 1
Hydrogen bond donors 3
Rotatable bonds 2
Topological polar surface area 46.21
Molecular weight 287.15
XLogP 2.68
No. Lipinski's rules broken 0
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Canonical SMILES C[NH+](c1ccc2c(c1)Sc1c(N2)ccc(c1)[NH+](C)C)C
Isomeric SMILES C[NH+](c1ccc2c(c1)Sc1c(N2)ccc(c1)[NH+](C)C)C
InChI InChI=1S/C16H19N3S/c1-18(2)11-5-7-13-15(9-11)20-16-10-12(19(3)4)6-8-14(16)17-13/h5-10,17H,1-4H3/p+2
1. Baddeley TC, McCaffrey J, Storey JM, Cheung JK, Melis V, Horsley D, Harrington CR, Wischik CM. (2015)
Complex disposition of methylthioninium redox forms determines efficacy in tau aggregation inhibitor therapy for Alzheimer's disease.
J Pharmacol Exp Ther, 352 (1): 110-8. [PMID:25320049]
2. Šimić G, Babić Leko M, Wray S, Harrington C, Delalle I, Jovanov-Milošević N, Bažadona D, Buée L, de Silva R, Di Giovanni G et al.. (2016)
Tau Protein Hyperphosphorylation and Aggregation in Alzheimer's Disease and Other Tauopathies, and Possible Neuroprotective Strategies.
Biomolecules, 6 (1): 6. [PMID:26751493]