DSM421   Click here for help

GtoPdb Ligand ID: 10020

PDB Ligand Antimalarial Ligand
Compound class: Synthetic organic
Comment: DSM421 was being developed as a backup compound to DSM265, the clinical lead for the triazolopyrimidine structural class of antimalarial compounds, but it has not been progressed due to unpredicted off-target toxicity [1,3].

The Malaria tab on this ligand page provides additional curator comments of relevance to the Guide to MALARIA PHARMACOLOGY.
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 5
Hydrogen bond donors 1
Rotatable bonds 4
Topological polar surface area 68
Molecular weight 358.1
XLogP 2.83
No. Lipinski's rules broken 0
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Canonical SMILES Cc1cc(Nc2ccc(nc2)C(F)(F)F)n2c(n1)nc(n2)C(F)(F)C
Isomeric SMILES Cc1cc(Nc2ccc(nc2)C(F)(F)F)n2c(n1)nc(n2)C(F)(F)C
InChI InChI=1S/C14H11F5N6/c1-7-5-10(22-8-3-4-9(20-6-8)14(17,18)19)25-12(21-7)23-11(24-25)13(2,15)16/h3-6,22H,1-2H3
1. Lynch 3rd JJ, Rossignol E, Moehrle JJ, Van Vleet TR, Marsh KC, Parman T, Mirsalis J, Ottinger SE, Segreti JA, Rao M et al.. (2019)
Increased stress associated with head-out plethysmography testing can exacerbate respiratory effects and lead to mortality in rats.
J Pharmacol Toxicol Methods, 99: 106580. [PMID:31085318]
2. Phillips M, Charman SA, Rathod PK, Matthews D, Waterson D. (2016)
New substituted triazolopyrimidines as anti-malarial agents.
Patent number: WO2016151521A1. Assignee: Board of Regents of the University Of Texas System, University of Washington, Medicines for Malaria Venture. Priority date: 26/03/2015. Publication date: 29/09/2016.
3. Phillips MA, White KL, Kokkonda S, Deng X, White J, El Mazouni F, Marsh K, Tomchick DR, Manjalanagara K, Rudra KR et al.. (2016)
A Triazolopyrimidine-Based Dihydroorotate Dehydrogenase Inhibitor with Improved Drug-like Properties for Treatment and Prevention of Malaria.
ACS Infect Dis, 2 (12): 945-957. [PMID:27641613]