Chloroquine diphosphate

Chloroquine diphosphate Basic information
Product Name:Chloroquine diphosphate
Synonyms:7-chlor-4-(4-(diaethylamino)-1-methylbutylamino)-chinolindiphosphat;ARALEN PHOSPHATE;CHLOROQUINE DIPHOSPHATE;CHLOROQUINE DIPHOSPHATE SALT;CHLOROQUINE PHOSPHATE;7-CHLORO-4-OXO-1H-QUINOLINE-3-CARBOXYLIC ACID;CHLOROQUINE PHOSPHATE BP;CHLOROQUINE PHOSPHATE BP98
CAS:50-63-5
MF:C18H32ClN3O8P2
MW:515.86
EINECS:200-055-2
Product Categories:Inhibitors;ARALEN;Heterocycles;Intermediates & Fine Chemicals;Pharmaceuticals;Miscellaneous Enzyme;API;50-63-5
Mol File:50-63-5.mol
Chloroquine diphosphate Structure
Chloroquine diphosphate Chemical Properties
Melting point 200 °C (dec.) (lit.)
storage temp. protect from light
solubility H2O: 50 mg/mL, clear
pkapKa 8.10(H2O t = 20 c = 0.0025) (Uncertain)
form solid
color White
PHpH(100g/l, 25℃) : 3.8~4.3
Water Solubility Soluble in water
Merck 14,2163
BRN 4223142
BCS Class1
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.
InChIKeyQKICWELGRMTQCR-UHFFFAOYSA-N
CAS DataBase Reference50-63-5(CAS DataBase Reference)
EPA Substance Registry SystemChloroquine diphosphate (50-63-5)
Safety Information
Hazard Codes Xn
Risk Statements 22-40-20/21/22
Safety Statements 22-24/25-36
RIDADR 1544
WGK Germany 3
RTECS VB2450000
10
HazardClass 6.1(b)
PackingGroup III
HS Code 2933492250
ToxicityLD50 oral in rat: 623mg/kg
MSDS Information
ProviderLanguage
SigmaAldrich English
Chloroquine diphosphate Usage And Synthesis
DescriptionChloroquine 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 PropertiesWhite Solid
OriginatorNivaquine,Specia,France,1949
UsesChloroquine diphosphate salt is used to study the role of endosomal acidification in cellular processes, such as the signaling of intracellular TLRs. It can be used as DNA intercalator & to dissociate antigen antibody complexes without denaturing red blood cell antigens. Chloroquine showed very high antiviral activity against NiV but very little activity against the other viruses at concentrations lower than 20 μM.
UsesStandard anti-malarial drug. Substrate for MRP in multidrug resistant cell line and inhibits photoaffinity labelling of MRP by quinoline-based photoactive drug IAAQ
Usesantimalarial, antiamebic, antirheumatic, intercalating agent
UsesAn antimalarial compound
Manufacturing Process105 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 FunctionAntimalarial
General DescriptionChloroquine phosphate is a phosphate salt of chloroquine. It belongs to the class of aminoquinoline drugs utilized as antimalarials and amebicides.
Biochem/physiol ActionsStandard 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).
storageDesiccate at RT
References1) 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
Chloroquine diphosphate Preparation Products And Raw materials
Raw materials2-Amino-5-diethylaminopentane-->4,7-Dichloroquinoline-->Phosphoric acid
4-(4-AMINOBUTYL)AMINO-7-CHLOROQUINOLINE 7-Chloro-4-quinolinamine N,N-Dimethylformamide ETHANE 5,7-Dichloro-8-hydroxyquinaldine BISDESETHYL CHLOROQUINE 2-Chloroquinoline Chloroquine diphosphate Dimethyl sulfide Dimethyl fumarate Diphosphate CHLOROQUINE Dimethyl sebacate Dimethyl sulfoxide 7-Chloro-2-methylquinoline Dimethyl ether Dimethyl carbonate Dimethyl sulfate

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