50-63-5 Usage
Description
Chloroquine diphosphate, also known as chloroquine phosphate, is an aminoquinoline compound that serves as an antimalarial, antiamebic, antirheumatic, and intercalating agent. It is a phosphate salt of chloroquine and is used in various applications due to its diverse properties, such as inhibiting autophagy and exhibiting antimalarial, anti-inflammatory, anticancer, and antiviral activities.
Uses
Used in Antimalarial Applications:
Chloroquine diphosphate is used as an antimalarial drug, effective against chloroquine-sensitive strains of Plasmodium falciparum. It is utilized in the prevention and treatment of malaria, particularly in regions where the disease is prevalent.
Used in Antiamebic Applications:
Chloroquine diphosphate is used as an antiamebic agent, targeting the parasitic protozoa that cause amebiasis. It is particularly effective in treating infections caused by Entamoeba histolytica.
Used in Antirheumatic Applications:
Chloroquine diphosphate is used as an antirheumatic drug, helping to manage the symptoms of rheumatoid arthritis and systemic lupus erythematosus (SLE). It exhibits anti-inflammatory properties that can alleviate pain and reduce inflammation in these conditions.
Used in Anticancer Applications:
Chloroquine diphosphate is used as an anticancer agent, demonstrating inhibitory effects on the growth of various cancer cell lines, including oral squamous cell carcinoma and renal cancer cells. It has also shown potential in reducing tumor growth in mouse models.
Used in Cellular Research:
Chloroquine diphosphate is used as a DNA intercalator and to dissociate antigen-antibody complexes without denaturing red blood cell antigens. It is also used to study the role of endosomal acidification in cellular processes, such as the signaling of intracellular Toll-like receptors (TLRs).
Used in Antiviral Applications:
Chloroquine diphosphate has shown high antiviral activity against Nipah virus (NiV) at concentrations lower than 20 μM. It also prevents infection by severe acute respiratory coronavirus 2 (SARS-CoV-2) in Vero cells.
Used in Drug Resistance Studies:
Chloroquine diphosphate is used as a substrate for multidrug resistance-associated protein (MRP) in multidrug-resistant cell lines. It inhibits photoaffinity labeling of MRP by quinoline-based photoactive drug IAAQ, aiding in the study of drug resistance mechanisms.
Chemical Properties:
Chloroquine diphosphate is a white solid with various applications in the medical and research fields. Its diverse properties make it a valuable compound for treating and studying various diseases and conditions.
Originator
Nivaquine,Specia,France,1949
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
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).
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
Check Digit Verification of cas no
The CAS Registry Mumber 50-63-5 includes 5 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 2 digits, 5 and 0 respectively; the second part has 2 digits, 6 and 3 respectively.
Calculate Digit Verification of CAS Registry Number 50-63:
(4*5)+(3*0)+(2*6)+(1*3)=35
35 % 10 = 5
So 50-63-5 is a valid CAS Registry Number.
InChI:InChI=1/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)
50-63-5Relevant articles and documents
Synthesis method of high-purity chloroquine phosphate
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Paragraph 0043; 0048-0053; 0058-0062; 0067-0070; 0076-0077, (2021/02/10)
The invention relates to the technical field of medicine synthesis, in particular to a synthesis method of chloroquine phosphate, and particularly provides a synthesis method of high-purity chloroquine phosphate. The synthesis method comprises the following steps: (1) condensation: reacting 4, 7-dichloroquinoline with 2-amido-5-diethylamine pentane to obtain a chloroquine crude product; and (2) refining: recrystallizing to obtain chloroquine with higher purity. (3) salifying: stirring and crystallizing the refined chloroquine and phosphoric acid for 2-3 hours, and filtering to obtain a chloroquine phosphate crude product; and (4) purification: recrystallizing the chloroquine phosphate crude product to obtain high-purity chloroquine phosphate. The method is high in atom utilization rate, high in yield, high in product purity, less in solid waste, beneficial to environmental protection and convenient for industrial application, and has a relatively good industrial prospect.
