ChemicalBook > CAS DataBase List > Chloroquine diphosphate

Chloroquine diphosphate

Product Name
Chloroquine diphosphate
CAS No.
50-63-5
Chemical Name
Chloroquine diphosphate
Synonyms
CHLOROQUINE PHOSPHATE;CHLOROQUIN PHOSPHATE;wr1522;alermine;h-stadur;khingamin;Melatonine2;klorokinfosfat;Chloropicrin 1;chloroquine bis
CBNumber
CB5467578
Molecular Formula
C18H32ClN3O8P2
Formula Weight
515.86
MOL File
50-63-5.mol
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Chloroquine diphosphate Property

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
BCS Class
1
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.
InChIKey
QKICWELGRMTQCR-UHFFFAOYSA-N
CAS DataBase Reference
50-63-5(CAS DataBase Reference)
EPA Substance Registry System
Chloroquine diphosphate (50-63-5)
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Safety

Hazard Codes 
Xn
Risk Statements 
22-40-20/21/22
Safety Statements 
22-24/25-36
RIDADR 
1544
WGK Germany 
3
RTECS 
VB2450000
F 
10
HazardClass 
6.1(b)
PackingGroup 
III
HS Code 
2933492250
Toxicity
LD50 oral in rat: 623mg/kg
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Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal word
Warning
Hazard statements

H302Harmful if swallowed

Precautionary statements

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P270Do not eat, drink or smoke when using this product.

P301+P312IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.

P501Dispose of contents/container to..…

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N-Bromosuccinimide Price

Sigma-Aldrich
Product number
C6628
Product name
Chloroquine diphosphate salt
Purity
powder or crystals, 98.5-101.0% dry basis
Packaging
25g
Price
$74.4
Updated
2024/03/01
Sigma-Aldrich
Product number
1118000
Product name
Chloroquine phosphate
Purity
United States Pharmacopeia (USP) Reference Standard
Packaging
500mg
Price
$400
Updated
2022/05/15
TCI Chemical
Product number
C2301
Product name
Chloroquine Diphosphate
Purity
>98.0%(HPLC)(T)
Packaging
25g
Price
$69
Updated
2024/03/01
TCI Chemical
Product number
C2301
Product name
Chloroquine Diphosphate
Purity
>98.0%(HPLC)(T)
Packaging
100g
Price
$178
Updated
2024/03/01
Alfa Aesar
Product number
J64459
Product name
Chloroquine diphosphate salt, 98%
Packaging
25g
Price
$115
Updated
2024/03/01
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Chloroquine diphosphate Chemical Properties,Usage,Production

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

Originator

Nivaquine,Specia,France,1949

Uses

Chloroquine 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.

Uses

Standard anti-malarial drug. Substrate for MRP in multidrug resistant cell line and inhibits photoaffinity labelling of MRP by quinoline-based photoactive drug IAAQ

Uses

antimalarial, antiamebic, antirheumatic, intercalating agent

Uses

An antimalarial compound

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

Chloroquine diphosphate Preparation Products And Raw materials

Raw materials

Preparation Products

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Chloroquine diphosphate Suppliers

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View Lastest Price from Chloroquine diphosphate manufacturers

WUHAN CIRCLE POWDER TECHNOLOGY CO.,LTD
Product
chloroquindiphosphate
Price
US $0.00/KG
Min. Order
100g
Purity
98%+
Supply Ability
100kg
Release date
2021-03-17
WUHAN CIRCLE POWDER TECHNOLOGY CO.,LTD
Product
Chloroquine diphosphate 50-63-5
Price
US $0.00/KG
Min. Order
100g
Purity
98%+
Supply Ability
100kg
Release date
2020-09-10
Wuhan Boyuan Import & Export Co., LTD
Product
Chloroquine diphosphate 50-63-5
Price
US $9.00/KG
Min. Order
1KG
Purity
99%
Supply Ability
50000tons
Release date
2023-08-04

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