Chloroquine monophosphate

Base Information

• Chemical Name: Chloroquine monophosphate
• CAS No.: 50-63-5
• Molecular Formula: C18H26ClN3^.2(H3PO4)
• Molecular Weight: 515.868
• Hs Code.: 2933492250
• NSC Number: 756681,14050
• UNII: 7FY24HE2G3
• DSSTox Substance ID: DTXSID10932343
• Wikidata: Q27268205
• NCI Thesaurus Code: C26646
• ChEMBL ID: CHEMBL1326
• Mol file: 50-63-5.mol

Synonyms:EGb 761;EGb-761;EGb761;GBE 761;GBE 761 ONC;GBE-761;Ginkgo biloba extract;Ginkgo biloba extract 761;Ginkgo leaf extract;Rokan;Tanakan;Tebofortran;Tebokan;Tebonin

Chemical Property of Chloroquine monophosphate

Chemical Property:

• Appearance/Colour: White Solid
• Vapor Pressure: 1.15E-08mmHg at 25°C
• Melting Point: 200 °C (dec.)(lit.)
• Boiling Point: 460.6 °C at 760 mmHg
• PKA: pKa 8.10(H2O t = 20 c = 0.0025) (Uncertain)
• Flash Point: 232.3 °C
• PSA: 203.30000
• Density: ==
• LogP: 3.02640
• Storage Temp.: Desiccate at RT
• Solubility.: H2O: 50 mg/mL, clear
• Water Solubility.: Soluble in water
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 8
• Exact Mass: 417.1584211
• Heavy Atom Count: 27
• Complexity: 359

Purity/Quality:

99%min, ^*data from raw suppliers

Chloroquine Diphosphate Salt ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 22-40-20/21/22
• Safety Statements: 22-24/25-36

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCN(CC)CCCC(C)NC1=C2C=CC(=CC2=NC=C1)Cl.OP(=O)(O)O
• Recent ClinicalTrials: Phase II Studies Of Donepezil And Ginkgo Biloba In Irradiated Brain Tumor
• Recent EU Clinical Trials: Monocenter, prospective, randomized placebo-controlled, double blind phase II trial to evaluate protective effects of Gingko biloba extract EGb 761? on temporary hearing damage caused by noise.
• 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.
• 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. Standard anti-malarial drug. Substrate for MRP in multidrug resistant cell line and inhibits photoaffinity labelling of MRP by quinoline-based photoactive drug IAAQ antimalarial, antiamebic, antirheumatic, intercalating agent An antimalarial compound
• Therapeutic Function: Antimalarial

Technology Process of Chloroquine monophosphate

There total 1 articles about Chloroquine monophosphate which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 80.32%

Chloroquine (54-05-7) → chloroquine phosphate (50-63-5,69698-56-2)

Guidance literature:

With phosphoric acid; In ethanol;

Reference yield: 94.0%

chloroquine phosphate (50-63-5,69698-56-2) → Chloroquine (54-05-7)

Guidance literature:

With sodium hydroxide; In water; ethyl acetate; at 0 ℃; for 1h;

Reference yield:

chloroquine phosphate (50-63-5,69698-56-2) → (R)-(-)-chloroquine (54-05-7,56598-66-4,58175-86-3,58175-87-4)

Guidance literature:

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

With diethylamine; sodium hydroxide; In hexane; water; ethyl acetate; isopropyl alcohol;

upstream raw materials:

Chloroquine

Downstream raw materials:

Chloroquine

(R)-(-)-chloroquine

(S)-(+)-chloroquine phosphate

(R)-chloroquine phosphate

Refernces

• 1、 -. "Preparation process of chloroquine phosphate (by machine translation)". Paragraph 0041; 0043-0045; 0047-0049; 0051-0053; 0055-0057. . Retrieved 2020/09/23.