pyronaridine   Click here for help

GtoPdb Ligand ID: 10086

Synonyms: 7351 | Malaridine®
Antimalarial Ligand
Compound class: Synthetic organic
Comment: Pyronaridine is a benzonaphthyridine derivative with potent antimalarial activity.
Note that our structure is an exact match for the chemical structure in the INN record for this compound. PubChem CID 5485198 provides a different InChIKey YFYLPWJKCSESGB-UHFFFAOYSA-N (link in table below).

The Malaria tab on this ligand page provides additional curator comments of relevance to the Guide to MALARIA PHARMACOLOGY.
Click here for help
2D Structure
Click here for help
Click here for structure editor
Physico-chemical Properties
Click here for help
Hydrogen bond acceptors 5
Hydrogen bond donors 2
Rotatable bonds 7
Topological polar surface area 73.75
Molecular weight 517.22
XLogP 4.9
No. Lipinski's rules broken 0
SMILES / InChI / InChIKey
Click here for help
Canonical SMILES COc1ccc2c(n1)c(Nc1cc(CN3CCCC3)c(c(c1)CN1CCCC1)O)c1c(n2)cc(cc1)Cl
Isomeric SMILES COc1ccc2c(n1)c(Nc1cc(CN3CCCC3)c(c(c1)CN1CCCC1)O)c1c(n2)cc(cc1)Cl
InChI InChI=1S/C29H32ClN5O2/c1-37-26-9-8-24-28(33-26)27(23-7-6-21(30)16-25(23)32-24)31-22-14-19(17-34-10-2-3-11-34)29(36)20(15-22)18-35-12-4-5-13-35/h6-9,14-16,36H,2-5,10-13,17-18H2,1H3,(H,31,32)
InChI Key DJUFPMUQJKWIJB-UHFFFAOYSA-N
References
1. Croft SL, Duparc S, Arbe-Barnes SJ, Craft JC, Shin CS, Fleckenstein L, Borghini-Fuhrer I, Rim HJ. (2012)
Review of pyronaridine anti-malarial properties and product characteristics.
Malar. J., 11: 270. [PMID:22877082]
2. Delves M, Plouffe D, Scheurer C, Meister S, Wittlin S, Winzeler EA, Sinden RE, Leroy D. (2012)
The activities of current antimalarial drugs on the life cycle stages of Plasmodium: a comparative study with human and rodent parasites.
PLoS Med., 9 (2): e1001169. [PMID:22363211]
3. (2015)
All chapters.  In  Guidelines for the Treatment of Malaria (World Health Organization) . [PMID:26020088] [ISBN:9789241549127]