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C6628

Sigma-Aldrich

Chloroquine diphosphate salt

powder or crystals, 98.5-101.0% (EP)

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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
Empirical Formula (Hill Notation):
C18H26ClN3 · 2H3PO4
CAS Number:
Molecular Weight:
515.86
Beilstein:
4223142
EC Number:
MDL number:
PubChem Substance ID:
NACRES:
NA.77

Quality Level

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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This Item
PHR12581118000C7874
vibrant-m

C6628

Chloroquine diphosphate salt

vibrant-m

PHR1258

Chloroquine phosphate

vibrant-m

1118000

Chloroquine phosphate

Quality Level

200

Quality Level

300

Quality Level

-

Quality Level

100

assay

98.5-101.0% (EP)

assay

-

assay

-

assay

≥98% (HPLC)

mp

192-198 °C

mp

200 °C (dec.) (lit.)

mp

200 °C (dec.) (lit.)

mp

-

antibiotic activity spectrum

parasites

antibiotic activity spectrum

-

antibiotic activity spectrum

-

antibiotic activity spectrum

-

mode of action

enzyme | inhibits

mode of action

-

mode of action

-

mode of action

-

General description

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.

Pictograms

Exclamation mark

Signal Word

Warning

Hazard Statements

Precautionary Statements

Hazard Classifications

Acute Tox. 4 Oral

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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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)
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)
Screening of medicinal plants from Reunion Island for antimalarial and cytotoxic activity
Jonville MC, et al.
Journal of Ethnopharmacology, 120(3), 382-386 (2008)

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