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.
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2D Structure
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Physico-chemical Properties
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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
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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
Guide to Malaria Pharmacology Comments
Pyronaridine was synthesized in the early 1970s in China (as part of Project 523) and used in that jurisdiction for the treatment of malaria as a monotherapy. Clinical data show excellent antimalarial efficacy against P. falciparum (including chloroquine resistant strains) and combination therapy studies also show promise against P. vivax [1].
Pyronaridine is listed in the World Health Organisation's 21st Essential Medicines List (2019) as an antimalarial for curative treatment in combination with artesunate (trade name Pyramax®). This is one of the new artemisinin-based combination therapies (ACTs) registered and used in some countries but not yet recommended by the WHO for unrestricted use [3].