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50-63-5

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50-63-5 Usage

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

Different sources of media describe the Uses of 50-63-5 differently. You can refer to the following data:
1. 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.
2. Standard anti-malarial drug. Substrate for MRP in multidrug resistant cell line and inhibits photoaffinity labelling of MRP by quinoline-based photoactive drug IAAQ
3. antimalarial, antiamebic, antirheumatic, intercalating agent
4. 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).

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)

50-63-5 Well-known Company Product Price

  • Brand
  • (Code)Product description
  • CAS number
  • Packaging
  • Price
  • Detail
  • TCI America

  • (C2301)  Chloroquine Diphosphate  >98.0%(HPLC)(T)

  • 50-63-5

  • 25g

  • 315.00CNY

  • Detail
  • TCI America

  • (C2301)  Chloroquine Diphosphate  >98.0%(HPLC)(T)

  • 50-63-5

  • 100g

  • 950.00CNY

  • Detail
  • TCI America

  • (C2301)  Chloroquine Diphosphate  >98.0%(HPLC)(T)

  • 50-63-5

  • 500g

  • 2,690.00CNY

  • Detail
  • Sigma-Aldrich

  • (PHR1258)  Chloroquine phosphate  pharmaceutical secondary standard; traceable to USP

  • 50-63-5

  • PHR1258-1G

  • 878.44CNY

  • Detail
  • USP

  • (1118000)  Chloroquine phosphate  United States Pharmacopeia (USP) Reference Standard

  • 50-63-5

  • 1118000-500MG

  • 4,662.45CNY

  • Detail
  • Sigma

  • (C6628)  Chloroquinediphosphatesalt  solid, ≥98%

  • 50-63-5

  • C6628-25G

  • 684.45CNY

  • Detail
  • Sigma

  • (C6628)  Chloroquinediphosphatesalt  solid, ≥98%

  • 50-63-5

  • C6628-50G

  • 1,263.60CNY

  • Detail
  • Sigma

  • (C6628)  Chloroquinediphosphatesalt  solid, ≥98%

  • 50-63-5

  • C6628-100G

  • 2,283.84CNY

  • Detail
  • Sigma

  • (C6628)  Chloroquinediphosphatesalt  solid, ≥98%

  • 50-63-5

  • C6628-250G

  • 4,089.15CNY

  • Detail

50-63-5SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 11, 2017

Revision Date: Aug 11, 2017

1.Identification

1.1 GHS Product identifier

Product name Chloroquine Diphosphate

1.2 Other means of identification

Product number -
Other names 1,4-Pentanediamine, N4-(7-chloro-4-quinolinyl)-N1,N1-diethyl-, phosphate (1:2)

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:50-63-5 SDS

50-63-5Synthetic route

Chloroquine
54-05-7

Chloroquine

chloroquine phosphate
50-63-5

chloroquine phosphate

Conditions
ConditionsYield
With phosphoric acid In ethanol80.32%
With phosphoric acid In ethanol at 60 - 65℃;66.11%
chloroquine phosphate
50-63-5

chloroquine phosphate

Chloroquine
54-05-7

Chloroquine

Conditions
ConditionsYield
With sodium hydroxide In water; ethyl acetate at 0℃; for 1h;94%
With sodium hydroxide In water at 0℃; for 0.5h;94%
With sodium hydroxide In water
With sodium hydroxide In dichloromethane; water
potassium tetrachloroplatinate(II)
10025-99-7

potassium tetrachloroplatinate(II)

chloroquine phosphate
50-63-5

chloroquine phosphate

trans-Pt(chloroquine diphosphate)2(Cl)2

trans-Pt(chloroquine diphosphate)2(Cl)2

Conditions
ConditionsYield
In water at 20℃; for 18h;87.8%
silver tetrafluoroborate
14104-20-2

silver tetrafluoroborate

[ruthenium(II)(η6-1-methyl-4-isopropyl-benzene)(chloride)(μ-chloride)]2
52462-29-0

[ruthenium(II)(η6-1-methyl-4-isopropyl-benzene)(chloride)(μ-chloride)]2

water
7732-18-5

water

chloroquine phosphate
50-63-5

chloroquine phosphate

[Ru(II)(η6-p-cymene)(η6-chloroquineH2)](BF4)2(H2PO4)2*2H2O

[Ru(II)(η6-p-cymene)(η6-chloroquineH2)](BF4)2(H2PO4)2*2H2O

Conditions
ConditionsYield
In water under N2; Ru complex dissolved in water at 55°C, addn. of silver salt and chloroquine diphosphate, mixt. stirred at 55°C for 20 h; filtration throught Celite, filtrate evapd., residue dried under vac. for 20 h; elem. anal.;78%
potassium pentacyanonitrosylchromate(III) monohydrate

potassium pentacyanonitrosylchromate(III) monohydrate

chloroquine phosphate
50-63-5

chloroquine phosphate

{Cr(NO)(CN)2(chloroquine)(H2O)}

{Cr(NO)(CN)2(chloroquine)(H2O)}

Conditions
ConditionsYield
In acetic acid byproducts: CH3COOK, HCN, H2O; aq. acetic acid; heated at 80°C for 20-30 min.; added with shaking; CO2 passed for 2 h; filtered by suction; washed (diluted acetic acid, water); dried over silica gel in a vac. at room temp.; elem. anal.; TGA;46%
chloroquine phosphate
50-63-5

chloroquine phosphate

β‐cyclodextrin
7585-39-9

β‐cyclodextrin

C42H70O35*C18H26ClN3

C42H70O35*C18H26ClN3

Conditions
ConditionsYield
In water at 40 - 45℃; for 96h; Thermodynamic data;
chloroquine phosphate
50-63-5

chloroquine phosphate

alpha cyclodextrin
10016-20-3

alpha cyclodextrin

C36H60O30*C18H26ClN3

C36H60O30*C18H26ClN3

Conditions
ConditionsYield
In water at 40 - 45℃; for 96h; Thermodynamic data;
chloroquine phosphate
50-63-5

chloroquine phosphate

(+)-Chloroquine

(+)-Chloroquine

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: sodium hydroxide / water; ethyl acetate / 1 h / 0 °C
2: diethylamine / hexane; isopropyl alcohol / 35 °C / Resolution of racemate
View Scheme
Multi-step reaction with 2 steps
1: sodium hydroxide / water / 0.5 h / 0 °C
2: diethylamine / isopropyl alcohol; hexane / 35 °C / Resolution of racemate
View Scheme
chloroquine phosphate
50-63-5

chloroquine phosphate

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: sodium hydroxide / water; ethyl acetate / 1 h / 0 °C
2: diethylamine / hexane; isopropyl alcohol / 35 °C / Resolution of racemate
View Scheme
Multi-step reaction with 2 steps
1: sodium hydroxide / water / 0.5 h / 0 °C
2: diethylamine / isopropyl alcohol; hexane / 35 °C / Resolution of racemate
View Scheme
chloroquine phosphate
50-63-5

chloroquine phosphate

7-chloro-4-[4-diethylamino-L-methylbutylamino]quinoline diphosphate

7-chloro-4-[4-diethylamino-L-methylbutylamino]quinoline diphosphate

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: sodium hydroxide / water; ethyl acetate / 1 h / 0 °C
2: diethylamine / hexane; isopropyl alcohol / 35 °C / Resolution of racemate
3: phosphoric acid / ethanol / 2 h / Reflux
View Scheme
Multi-step reaction with 3 steps
1: sodium hydroxide / water / 0.5 h / 0 °C
2: diethylamine / isopropyl alcohol; hexane / 35 °C / Resolution of racemate
3: phosphoric acid / ethanol / 2 h / Reflux
View Scheme
chloroquine phosphate
50-63-5

chloroquine phosphate

(R)-(-)-chloroquine diphosphate

(R)-(-)-chloroquine diphosphate

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: sodium hydroxide / water; ethyl acetate / 1 h / 0 °C
2: diethylamine / hexane; isopropyl alcohol / 35 °C / Resolution of racemate
3: phosphoric acid / ethanol / 2 h / Reflux
View Scheme
Multi-step reaction with 3 steps
1: sodium hydroxide / water / 0.5 h / 0 °C
2: diethylamine / isopropyl alcohol; hexane / 35 °C / Resolution of racemate
3: phosphoric acid / ethanol / 2 h / Reflux
View Scheme

50-63-5Upstream product

50-63-5Relevant articles and documents

Synthesis method of high-purity chloroquine phosphate

-

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.

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