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Chloroquine diphosphate
- NSC 14050
- Parent CAS: 54-05-7
- Soluble in water
- MF: C18H26ClN3.2H3PO4
- MW: 515.86
Description
Chloroquine diphosphate is a lysosomotropic antimalarial compound that inhibits hemozoin formation and alters acidic organelle function. In addition to Plasmodium-related pharmacology, it is widely used to perturb lysosomal activity, autophagy and endosomal signaling.
Chloroquine accumulates in acidic vesicles, affecting lysosomes, phagolysosomes and endosomes. This pharmacology supports applications in malaria research, autophagy modulation, TLR/endosomal signaling and cell-death pathway studies.
Key Features
- Inhibits hemozoin/β-hematin formation in malaria models
- Lysosomotropic amine that raises acidic organelle pH
- Modulates autophagy and lysosomal degradation pathways
- Influences endosomal immune signaling and cell-death responses
Applications
- Antimalarial mechanism studies
- Autophagy and lysosome research
- Endosomal TLR and innate immune signaling assays
- Cell stress, apoptosis and necrosis models
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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