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C6628

Sigma-Aldrich

Chloroquine diphosphate salt

98.5-101.0% (EP), powder or crystals, autophagy inhibitor

Synonym(s):

N4-(7-chloroquinolin-4-yl)-N1,N1-diethylpentane-1,4-diamine diphosphate, N4-(7-Chloro-4-quinolinyl)-N1,N1-dimethyl-1,4-pentanediamine diphosphate salt

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About This Item

Empirical Formula (Hill Notation):
C18H26ClN3 · 2H3PO4
CAS Number:
50-63-5
Molecular Weight:
515.86
Beilstein/REAXYS Number:
4223142
EC Number:
200-055-2
MDL number:
MFCD00069852
UNSPSC Code:
12352107
PubChem Substance ID:
24278090
NACRES:
NA.77

Key Documents

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Product Name

Chloroquine diphosphate salt, powder or crystals, 98.5-101.0% (EP)

Quality Level

200

assay

98.5-101.0% (EP)

form

powder or crystals

mp

192-198 °C

antibiotic activity spectrum

parasites

mode of action

enzyme | inhibits

SMILES string

OP(O)(O)=O.OP(O)(O)=O.CCN(CC)CCCC(C)Nc1ccnc2cc(Cl)ccc12

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)

InChI key

QKICWELGRMTQCR-UHFFFAOYSA-N

Gene Information

human ... ABCC1(4363)

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General description

Chloroquine effectively eliminates the erythrocytic forms of malaria parasites at all developmental stages, although it does not impact the sporozoites. It also functions as an antibiotic. In addition, it can be utilized at a concentration of 200 mg/mL (PBS, pH 5.0) to dissociate antigen-antibody complexes without denaturing red blood cell antigens. Recent research indicates chloroquine′s potential as an antitumor medication for cancer treatment along with chemotherapy and radiation. Its antimalarial effects are achieved by inhibiting the polymerization of heme into hemozoin, which serves as a food source for the malarial parasite. Chloroquine forms a complex with the drug-hemozoin, capping the polymerizing chain and preventing further polymerization. As a result, free heme accumulates in the food vacuole, exerting toxic effects on the parasite. Additionally, chloroquine acts as an anti-autoimmune therapy by binding to transcriptional factors on T helper 17 cells and inhibiting their differentiation. Chloroquine diphosphate (CQ) is frequently employed as an inhibitor of the autophagic pathway. The combined use of chloroquine diphosphate and salidroside initiates apoptosis in human liver cells by modulating mitochondrial dysfunction and autophagy.
Chloroquine is a member of quinolone family and is a weak intercalating agent. Chloroquine is used for treating amebiasis, rheumatoid arthritis, discoid and systemic lupus erythematosus.

Application

DNA intercalator. Also used to increase transfection efficiency.
Chloroquine diphosphate salt has been used :
  • in in vitro antiplasmodial assays
  • in transfection and infection assays
  • in autophagy inhibition
  • in differentiation of induced pluripotent stem (iPS) cells into cardiomyocytes
  • in flow treatment of infected blood

Biochem/physiol Actions

Standard anti-malarial drug. Substrate for MRP in multidrug resistant cell line and inhibits photoaffinity labeling of MRP by quinoline-based photoactive drug IAAQ (N-[4-[1-hydroxy-2-(dibutylamino)ethyl]quinolin-8-yl]-4-azidosalicylamide).

Features and Benefits

This compound is a featured product for ADME Tox research. Click here to discover more featured ADME Tox products. Learn more about bioactive small molecules for other areas of research at sigma.com/discover-bsm.

Other Notes

2024 CiteAb Award Winner for Supplier Succeeding in Parkinson′s Research

pictograms

Exclamation mark
GHS07

signalword

Warning

hcodes

H302

Hazard Classifications

Acute Tox. 4 Oral

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
109M4003V
039M4131V
029M4020V
098M4093V
028M4005V

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Ecotoxicological evaluation of the antimalarial drug chloroquine
Zurita JL, et al.
Aquatic Toxicology (Amsterdam, Netherlands), 75(2), 97-107 (2005)
Mechanism of inhibition of DNA gyrase by analogues of nalidixic acid: the target of the drugs is DNA
Shen LL and Pernet AG
Proceedings of the National Academy of Sciences of the USA, 82(2), 307-311 (1985)
Pompe disease results in a Golgi-based glycosylation deficit in human induced pluripotent stem cell-derived cardiomyocytes
Raval KK, et al.
The Journal of Biological Chemistry, 290(5), 3121-3136 (2015)
Malaria theranostics using hemozoin-generated vapor nanobubbles
Lukianova-Hleb EY and Lapotko DO
Theranostics, 4(7), 761-761 (2014)
Ototoxicity of chloroquine
Matz GJ and Naunton RF
Archives of Otolaryngology, 88(4), 370-372 (1968)
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