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C6628 Sigma-Aldrich

Chloroquine diphosphate salt

powder or crystals, 98.5-101.0% dry basis

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

  • CAS Number 50-63-5

  • Empirical Formula (Hill Notation) C18H26ClN3 · 2H3PO4

  • Molecular Weight 515.86

  •  Beilstein/REAXYS Number 4223142

  •  EC Number 200-055-2

  •  MDL number MFCD00069852

  •  PubChem Substance ID 24278090

  •  NACRES NA.77

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Properties

Related Categories Antibiotics, Antibiotics A to Z, Antibiotics by Mechanism of Action, Antibiotics  A-F, Antiparasitic / Antiprotozoal / Anthelminthic,
Quality Level   200
assay   98.5-101.0% dry basis
form   powder or crystals
mp   193-198 °C
  200 °C (dec.) (lit.)
solubility   alcohols: very slightly soluble
  methanol: very slightly soluble
  water: freely soluble
Mode of action   enzyme | inhibits
antibiotic activity spectrum   parasites
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)

Description

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

Packaging

25, 50, 100, 250 g in glass bottle

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.

This compound is also offered as part of Sigma′s Library of Pharmacologically Active Compounds (LOPAC®1280), a biologically annotated collection of high-quality, ready-to-screen compounds. Click here to learn more.

Legal Information

LOPAC is a registered trademark of Sigma-Aldrich Co. LLC

Safety & Documentation

Safety Information

Symbol 
GHS07  GHS07
Signal word 
Warning
Hazard statements 
Personal Protective Equipment 
RIDADR 
NONH for all modes of transport
WGK Germany 
3
RTECS 
VB2450000
Protocols & Articles

Articles

Autophagy in Cancer Promotes Therapeutic Resistance

Autophagy is a highly regulated process by which long-lived proteins, organelles, and protein aggregates are captured within autophagosomes, which are then fused with lysosomes for degradation.1 Auto...
Keywords: Apoptosis, Autophagy, Cancer, Degradations, Metabolites, transformation

Discover Bioactive Small Molecules for ADME/Tox

A significant number of drugs that fail in clinical trials have been associated with safety issues, including unexpected drug-drug interactions (DDI) or lack of efficacy due to poor pharmacokinetics....
Keywords: Absorption, Bioactive small molecules, Clinical, Metabolism

Drug Transport

Protein-based drug transporters are found in most tissues including liver, kidney, intestine, and brain. Because of their complexity and genetic heterogeneity, these proteins are often produced as re...
Robert Gates
Biofiles Volume 6 Article 1
Keywords: Absorption, Anti-inflammatory agents, Antibiotics, Antimicrobials, Apoptosis, Cancer, Catalog, Cytotoxins, Detoxification, Enzyme-linked immunosorbent assay, Gene expression, Genetic, High performance liquid chromatography, Immunohistochemistry, Mass spectrometry, Metabolites, Methods, Phosphorylations, Separation, The Reporter, Transfection, Type, Western blot

HPLC Analysis of Chloroquine Enantiomers on Astec® CHIROBIOTIC® V

From our library of Articles, Sigma-Aldrich presents HPLC Analysis of Chloroquine Enantiomers on Astec® CHIROBIOTIC® V
Keywords: Chromatography, High performance liquid chromatography, Pharmaceutical

Peer-Reviewed Papers
15

References

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