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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/REAXYS Number:
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

signalword

Warning

hcodes

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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Hydroxychloroquine sulfate United States Pharmacopeia (USP) Reference Standard

USP

1327000

Hydroxychloroquine sulfate

Hydroxychloroquine sulfate British Pharmacopoeia (BP) Reference Standard

BP1100

Hydroxychloroquine sulfate

Sigma-Aldrich

Sigma-Aldrich

19-148

Bafilomycin A1

Hydroxychloroquine sulfate European Pharmacopoeia (EP) Reference Standard

Y0001839

Hydroxychloroquine sulfate

2-Chloroquinoxaline 98%

Sigma-Aldrich

136301

2-Chloroquinoxaline

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)
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)
Ototoxicity of chloroquine
Matz GJ and Naunton RF
Archives of Otolaryngology, 88(4), 370-372 (1968)

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