Skip to Content
Merck
CN
All Photos(1)

Documents

C6628

Sigma-Aldrich

Chloroquine diphosphate salt

98.5-101.0% (EP), powder or crystals, anti-malarial drug

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

Sign Into View Organizational & Contract Pricing
All Photos(1)

About This Item

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

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)

Looking for similar products? Visit Product Comparison Guide

Related Categories

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

Signal Word

Warning

Hazard Statements

H302

Precautionary Statements

P264 - P270 - P301 + P312 - P501

Hazard Classifications

Acute Tox. 4 Oral

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

Already Own This Product?

Find documentation for the products that you have recently purchased in the Document Library.

Visit the Document Library

E2F1 modulates p38 MAPK phosphorylation via transcriptional regulation of ASK1 and Wip1
Hershko T, et al.
The Journal of Biological Chemistry, 281(42), 31309-31316 (2006)
Screening of medicinal plants from Reunion Island for antimalarial and cytotoxic activity
Jonville MC, et al.
Journal of Ethnopharmacology, 120(3), 382-386 (2008)
Malaria theranostics using hemozoin-generated vapor nanobubbles
Lukianova-Hleb EY and Lapotko DO
Theranostics, 4(7), 761-761 (2014)
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)
Combination of chloroquine diphosphate and salidroside induces human liver cell apoptosis via regulation of mitochondrial dysfunction and autophagy
Bing J, et al.
Molecular Medicine Reports, 27, 1-12 (2023)
View All Related Papers

Articles

Autophagy in Cancer Promotes Therapeutic Resistance

We presents an article on Autophagy in Cancer Promotes Therapeutic Resistance

Protein-based Drug Transport

Protein-based drug transporters are expressed in Sf9 cells. Understanding the specific mechanisms of tumor cell transporters is an essential aspect of chemotherapeutic drug design.

Discover Bioactive Small Molecules for ADME/Tox

Discover Bioactive Small Molecules for ADME/Tox

Chromatograms

application for HPLC

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

Contact Technical Service