bulaquine   Click here for help

GtoPdb Ligand ID: 10414

Synonyms: CDRI-80/53 | elubaquine
Antimalarial Ligand
Compound class: Synthetic organic
Comment: Bulaquine is an 8-aminoquinoline derivative that has antimalarial activity and is a synthetic analogue of primaquine.
The INN record for bulaquine indicates that it is a racemic mixture.

The Malaria tab on this ligand page provides additional curator comments of relevance to the Guide to MALARIA PHARMACOLOGY.
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 8
Topological polar surface area 72.48
Molecular weight 369.21
XLogP 3.37
No. Lipinski's rules broken 0
Click here for help
Canonical SMILES COc1cc(NC(CCCNC(=C2CCOC2=O)C)C)c2c(c1)cccn2
Isomeric SMILES COc1cc(NC(CCCN/C(=C/2\CCOC2=O)/C)C)c2c(c1)cccn2
InChI InChI=1S/C21H27N3O3/c1-14(6-4-9-22-15(2)18-8-11-27-21(18)25)24-19-13-17(26-3)12-16-7-5-10-23-20(16)19/h5,7,10,12-14,22,24H,4,6,8-9,11H2,1-3H3/b18-15+
1. Gogtay NJ, Kamtekar KD, Dalvi SS, Mehta SS, Chogle AR, Aigal U, Kshirsagar NA. (2006)
A randomized, parallel study of the safety and efficacy of 45 mg primaquine versus 75 mg bulaquine as gametocytocidal agents in adults with blood schizonticide-responsive uncomplicated falciparum malaria [ISCRTN50134587].
BMC Infect Dis, 6: 16. [PMID:16448575]
2. Krudsood S, Wilairatana P, Tangpukdee N, Chalermrut K, Srivilairit S, Thanachartwet V, Muangnoicharoen S, Luplertlop N, Brittenham GM, Looareesuwan S. (2006)
Safety and tolerability of elubaquine (bulaquine, CDRI 80/53) for treatment of Plasmidium vivax malaria in Thailand.
Korean J Parasitol, 44 (3): 221-8. [PMID:16969059]
3. Zeeman AM, van Amsterdam SM, McNamara CW, Voorberg-van der Wel A, Klooster EJ, van den Berg A, Remarque EJ, Plouffe DM, van Gemert GJ, Luty A et al.. (2014)
KAI407, a potent non-8-aminoquinoline compound that kills Plasmodium cynomolgi early dormant liver stage parasites in vitro.
Antimicrob Agents Chemother, 58 (3): 1586-95. [PMID:24366744]