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HomeProduct name listChloroquine diphosphate

Chloroquine diphosphate

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

  • CAS NO.:50-63-5
  • Empirical Formula: C18H32ClN3O8P2
  • Molecular Weight: 515.86
  • MDL number: MFCD00069852
  • EINECS: 200-055-2
  • SAFETY DATA SHEET (SDS)
  • Update Date: 2024-11-09 19:38:33
Chloroquine diphosphate  Structural

What is Chloroquine diphosphate ?

Description

Chloroquine is an aminoquinoline that is an inhibitor of autophagy and has antimalarial, anti-inflammatory, anticancer, and antiviral activities. Chloroquine inhibits autophagosome-lysosome fusion in HeLa cells when used at a concentration of 100 μM. It is active against the chloroquine-sensitive GC03 strain of P. falciparum (IC50 = 29.2 nM) but has decreased activity against mutant pfcrt P. falciparum (IC50s = 100-150 nM). Chloroquine prevents infection by severe acute respiratory coronavirus 2 (SARS-CoV-2) in Vero cells (EC50 = 1.13 μM) but does not inhibit SARS-CoV replication in the lungs in a mouse model of SARS-CoV infection. It inhibits the growth of human SSC25 and CAL 27 oral squamous cell carcinoma cells (IC50s = 29.9 and 17.3 μM, respectively), as well as A498, SN12C, RXF 393, and 769-P renal cancer cells (IC50s = 16, 62, 81, and 25 μM, respectively). It reduces tumor growth in a CAL 27 mouse xenograft model and a 4T1 mouse allograft model when administered at a dose of 50 mg/kg. Formulations containing chloroquine have been used in the prevention of malaria, as well as the treatment of rheumatoid arthritis and systemic lupus erythematosus (SLE), and have been associated with cardiotoxicity and myopathy.

Chemical properties

White Solid. Chloroquine diphosphate exists as a crystalline solid with a solubility of approximately 10 mg/ml in PBS (pH 7.2).

Originator

Nivaquine,Specia,France,1949

The Uses of Chloroquine diphosphate

Chloroquine diphosphate is a standard antimalarial drug. It is a substrate for MRP in multidrug-resistant cell lines and inhibits the photoaffinity labelling of MRP by the quinoline photoreactive drug IAAQ. Chloroquine is a weak intercalating agent for the treatment of amebiasis, rheumatoid arthritis, discoid lupus erythematosus and systemic lupus erythematosus. Chloroquine diphosphate has also been used to study the role of endosomal acidification in cellular processes such as intracellular TLR signalling. Chloroquine diphosphate is also used to study the role of endosomal acidification in cellular processes such as intracellular TLR signalling. It is also used as a DNA intermediate to dissociate antigen-antibody complexes without denaturing red blood cell antigens. Chloroquine has very high antiviral activity against NiV at concentrations below 20 μM, but very low activity against other viruses.

Manufacturing Process

105 g of 4,7-dichloroquinoline (MP 93 to 94°C) are heated with 200 g of 1- diethylamino-4-aminopentane for 7 hours in an oil bath to 180°C while stirring, until a test portion dissolved in diluted nitric acid does not show a precipitation with sodium acetate solution. The mixture is dissolved in diluted acetic acid and made alkaline by adding sodium lye.
The base is extracted with ether, dried with potassium carbonate, the ether removed by distillation and the residue fractionated. The 4-(5'- diethylaminopentyl-2'-amino)-7-chloroquinoline (BP 212 to 214C/0.2 mm) is obtained. On cooling the compound solidifies crystalline. It melts, recrystallized from benzene, at 88°C. The base combines with phosphoric acid to yield a diphosphate salt.

Therapeutic Function

Antimalarial

General Description

Chloroquine phosphate is a phosphate salt of chloroquine. It belongs to the class of aminoquinoline drugs utilized as antimalarials and amebicides.

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).

storage

Desiccate at RT

References

1) Frieboes et al. (2014), Chloroquine-mediated cell death in metastatic pancreatic adenocarcinoma through inhibition of autophagy; JOP, 15 189 2) Jiang et al. (2010), Antitumor and antimetastatic activities of chloroquine diphosphate in a murine model of breast cancer; Biomed. Pharmacother., 64 609 3) Choi et al. (2014), Chloroquine eliminates cancer stem cells through deregulation of Jak2 and DNMT1; Stem Cells, 32 2309 4) Mulcahy Levy et al. (2014), Autophagy inhibition improves chemosensitivity in BRAFV600E brain tumors; Cancer Discov., 4 773

Properties of Chloroquine diphosphate

Melting point: 200 °C (dec.) (lit.)
storage temp.  protect from light
solubility  H2O: 50 mg/mL, clear
form  solid
pka pKa 8.10(H2O t = 20 c = 0.0025) (Uncertain)
color  White
PH pH(100g/l, 25℃) : 3.8~4.3
Water Solubility  Soluble in water
Merck  14,2163
BRN  4223142
Stability: Stable for 2 years from date of purchase as supplied. Solutions in distilled water may be stored at -20° for up to 3 months.
CAS DataBase Reference 50-63-5(CAS DataBase Reference)
EPA Substance Registry System Chloroquine diphosphate (50-63-5)

Safety information for Chloroquine diphosphate

Signal word Warning
Pictogram(s)
ghs
Exclamation Mark
Irritant
GHS07
GHS Hazard Statements H302:Acute toxicity,oral
Precautionary Statement Codes P264:Wash hands thoroughly after handling.
P264:Wash skin thouroughly after handling.
P270:Do not eat, drink or smoke when using this product.
P301+P312:IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.
P501:Dispose of contents/container to..…

Computed Descriptors for Chloroquine diphosphate

InChIKey QKICWELGRMTQCR-UHFFFAOYSA-N

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