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
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2D Structure

An image of the ligand's 2D structure. For small molecules with SMILES these are drawn using the NCI/CADD Chemical Identifier Resolver. Click on the image to access the chemical structure search tool with the ligand pre-loaded in the structure editor. For other types of ligands, e.g. longer nucleotides and peptides, a manually drawn representation of the molecule may be provided.

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Physico-chemical Properties
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Physico-chemical Properties

Calculated molecular properties are available for small molecules and natural products (not peptides). Properties were generated using the CDK toolkit. All properties were selected to enable the prediction of the Lipinski Rule-of-Five profile or ‘druglikeness’ for each ligand. For more info on each category see the help pages.

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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
SMILES / InChI / InChIKey
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SMILES / InChI / InChIKey

SMILES (Simplified Molecular Input Line Entry Specification) A specification for unambiguously describing the structure of chemical molecules using short ASCII strings. Canonical SMILES specify a unique representation of the 2D structure without chiral or isotopic specifications. Isomeric SMILES include chiral specification and isotopes.

Standard InChI (IUPAC International Chemical Identifier) and InChIKey InChI is a non-proprietary, standard, textual identifier for chemical substances designed to facilitate linking of information and database searching. An InChIKey is a simplified version of a full InChI, designed for easier web searching.

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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+
InChI Key ADCOUXIGWFEYJP-OBGWFSINSA-N
References
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]