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Chloroquine diphosphate
- NSC 14050
- Parent CAS: 54-05-7
- Soluble in water
- MF: C18H26ClN3.2H3PO4
- MW: 515.86
Description
Classical antimalarial drug (CQ) with lysosomotropic effects causing necrosis and apoptosis. Inhibitor of hemozoin (β-hematin) formation in malaria (Plasmodium strains) affected red blood cells. Nowadays, most of the Plasmodium falciparum strains are resistant to this drug. Chloroquine was found to inhibit the human thiamine transporter ThTr-2 (SLC19A3), and to inhibit cell growth and to induce cell death in A549 lung cancer cells.
*Drug Reference Standard Grade
Caution: Axon Ligands™ are for research purposes only! Not intended for human consumption!
More Information
| Parent CAS No. | 54-05-7 |
|---|---|
| Chemical Name | N4-(7-chloroquinolin-4-yl)-N1,N1-diethylpentane-1,4-diamine bis(phosphate) |
| SMILES | C(N(CC)CC)CCC(NC1C2C(N=CC=1)=CC(Cl)=CC=2)C.P(O)(O)(O)=O.P(O)(O)(O)=O |
| MFCD | MFCD00069852 |
| InChi | InChI=1S/C18H26ClN3.2H3O4P/c1-4-22(5-2)12-6-7-14(3)21-17-10-11-20-18-13-15(19)8-9-16(17)18;2*1-5(2,3)4/h8-11,13-14H,4-7,12H2,1-3H3,(H,20,21);2*(H3,1,2,3,4) |
| InChiKey | QKICWELGRMTQCR-UHFFFAOYSA-N |
| CID | 64927 |
| Short Description | Antimalarial drug |
References
- O. Dechy-Cabaret et al. Preparation and antimalarial activities of "trioxaquines", new modular molecules with a trioxane skeleton linked to a 4-aminoquinoline. Chembiochem. 2000 Nov 17;1(4):281-3.
- C. Fan et al. Chloroquine inhibits cell growth and induces cell death in A549 lung cancer cells. Bioorg Med Chem. 2006 May 1;14(9):3218-22.
- Z. Huang et al. Discovering thiamine transporters as targets of chloroquine using a novel functional genomics strategy. PLoS Genet. 2012;8(11):e1003083.
- J. Gildenhuys et al. The single crystal X-ray structure of β-hematin DMSO solvate grown in the presence of chloroquine, a β-hematin growth-rate inhibitor. J Am Chem Soc. 2013 Jan 23;135(3):1037-47.
- L. Tanenbaum et al. Antimalarial agents. Chloroquine, hydroxychloroquine, and quinacrine. Arch Dermatol. 1980 May;116(5):587-91.
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