| Identification | More | [Name]
Chloroquine diphosphate | [CAS]
50-63-5 | [Synonyms]
7-CHLORO-4-OXO-1H-QUINOLINE-3-CARBOXYLIC ACID
ARALEN PHOSPHATE
CHLOROQUINE DIPHOSPHATE
CHLOROQUINE DIPHOSPHATE SALT
CHLOROQUINE PHOSPHATE
N4-(7-CHLORO-4-QUINOLINYL)-N1,N1-DIMETHYL-1,4-PENTANEDIAMINE DIPHOSPHATE
N4-(7-CHLORO-4-QUINOLINYL)-N1,N1-DIMETHYL-1,4-PENTANEDIAMINE DIPHOSPHATE SALT
n-(7-chloro-4-quinolinyl)-n,n-dimethyl-1,4-pentanediamine diphosphate salt
7-chlor-4-(4-(diaethylamino)-1-methylbutylamino)-chinolindiphosphat
7-chloro-4-((4’-diethylamino-1-methylbutyl)amino)quinolinediphosphate
7-chloro-4-(4-diethylamino-1-methyl-butylamino)-quinolindiphosphate
alermine
aralendiphosphate
chingaminphosphate
chloroquindiphosphate
chloroquinebis(phosphate)
gontochinphosphate
h-stadur
khingamin
klorokinfosfat | [EINECS(EC#)]
200-055-2 | [Molecular Formula]
C18H32ClN3O8P2 | [MDL Number]
MFCD00069852 | [Molecular Weight]
515.86 | [MOL File]
50-63-5.mol |
| Chemical Properties | Back Directory | [Appearance]
White Solid | [Melting point ]
200 °C (dec.) (lit.) | [vapor pressure ]
<0.0000001 kPa ( 25 °C) | [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 | [biological source]
synthetic | [Water Solubility ]
Soluble in water | [Usage]
Standard anti-malarial drug. Substrate for MRP in multidrug resistant cell line and inhibits photoaffinity labelling of MRP by quinoline-based photoactive drug IAAQ | [Detection Methods]
T,NMR | [Merck ]
13,2182 | [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. | [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) | [InChIKey]
QKICWELGRMTQCR-UHFFFAOYSA-N | [SMILES]
OP(O)(O)=O.OP(O)(O)=O.CCN(CC)CCCC(C)Nc1ccnc2cc(Cl)ccc12 | [CAS DataBase Reference]
50-63-5(CAS DataBase Reference) | [Storage Precautions]
Light sensitive | [EPA Substance Registry System]
50-63-5(EPA Substance) |
| Safety Data | Back Directory | [Symbol(GHS) ]
GHS07 | [Signal word ]
Warning | [Hazard statements ]
H302 | [Precautionary statements ]
P264-P270-P301+P312-P501 | [Hazard Codes ]
Xn | [Risk Statements ]
R22:Harmful if swallowed.
R40:Limited evidence of a carcinogenic effect.
R20/21/22:Harmful by inhalation, in contact with skin and if swallowed . | [Safety Statements ]
S22:Do not breathe dust .
S24/25:Avoid contact with skin and eyes .
S36:Wear suitable protective clothing . | [RIDADR ]
1544 | [WGK Germany ]
3
| [RTECS ]
VB2450000
| [F ]
10 | [HazardClass ]
6.1(b) | [PackingGroup ]
III | [HS Code ]
2933492250 | [Storage Class]
11 - Combustible Solids | [Hazard Classifications]
Acute Tox. 4 Oral | [Toxicity]
LD50 oral in rat: 623mg/kg |
| Hazard Information | Back Directory | [Description]
Chloroquine is an aminoquinoline that is an inhibitor of autophagy and has antimalarial, anti-inflammatory, anticancer, and antiviral activities.1,2,3,4,5 Chloroquine inhibits autophagosome-lysosome fusion in HeLa cells when used at a concentration of 100 μM.1 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).3 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.5,6 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).4,7 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.4,8 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]
An antimalarial compound | [Uses]
antimalarial, antiamebic, antirheumatic, intercalating agent | [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 | [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 |
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