Chloroquine Phosphate

Alias: Quingamine; NSC 14050; Khingamin; Ipsen 225; Gontochin phosphate; Chloroquine dihydrogen phosphate (1:2); Chlorochin diphosphate; Chingamin phosphate; Bemaphate; Aralen diphosphate; Chloroquine; Chloroquine diphosphate; Chingamin; Miniquine, Resochin; Chloroquine; Aralen; Arechin; Tanakan; Chloroquine phosphate; Chloroquine diphosphate; Aralen phosphate; Avloclor; Chingaminum; Chloroquin diphosphate; Delagil; Nivaquine B; Resoquine

Cat No.:V2530 Purity: ≥98%

COA Product Data Instructions for use SDS

Chloroquine phosphate is reported to be highly effective in combating SARS-CoV-2 (COVID-19, CoronaVirus, or the COVID-19 pandemic) infection in vitro.

Chloroquine Phosphate Chemical Structure CAS No.: 50-63-5
Product category: ATM(ATR)

This product is for research use only, not for human use. We do not sell to patients.

Size	Price	Stock	Qty
500mg
1g
2g
5g
10g
50g
Other Sizes

ADD TO CART CHECKOUT BULK INQUIRY

1-708-310-1919 sales@invivochem.com

Official Supplier of:

Business Relationship with 5000+ Clients Globally
Major Universities, Research Institutions, Biotech & Pharma
Citations by Top Journals: Nature, Cell, Science, etc.

Top Publications Citing lnvivochem Products

Nature 2021, 597(7874):119-125.

Cell 2020,183:1202-1218.e25.

Science Adv 2022: 8, eabm9427.

Nature 597, 119–125 (2021)

Cell Stem Cell 2020,26(6):845-861.e12.

Science Trans Med 2023,15(701):eadd7872.

STTT 2023,8(1):91.

Cell Reports 2023,42(4):112313

Science Trans Med 2023, 15: eadd7872.

Cancer Cell 2021,39(4):529-547.e7.

Cancer Discov 2022,12(4):1106-1127.

Immunity 2023,56(3):620-634.e11.

J Am Chem Soc 2022,144:21831-21836.

Cell 2020,183:1202-1218.e25.

Science Adv 2022:8,eabm9427.

Nature 2021,597(7874):119-125.

Cell 2020,183:1202-1218.e25.

PNAS Nexus 2022,1(3):pgac063.

ACS Nano 2023,17(10):9110-9125.

Biomaterial 2023 Sep16:302:122333.

Purity & Quality Control Documentation

Current batch：

Purity: ≥98%

COA

MSDS

NMR

Instructions

Product Description
Bioactivity & Protocols
Physicochemical Properties
Solubility Data
Calculators
Clinical Trial Information
Biological Data

Product Description

Chloroquine phosphate is reported to be highly effective in combating SARS-CoV-2 (COVID-19, CoronaVirus, or the COVID-19 pandemic) infection in vitro. It functions as a strong inhibitor of autophagy and toll-like receptors (TLRs) and a 4-aminoquinoline antimalarial drug that is used to treat and prevent malaria in regions where the disease is known to be susceptible to its effects. In addition to being an ATM activator, it also has anti-rheumatoid properties. Chloroquine diphosphate has been documented as an adjuvant for chemotherapy and radiation therapy to induce autophagy in cells and prevent the proliferation or metastasis of anti-cancer cells. The process by which chloroquine diphosphate induces autophagy in cells involves arresting them in the G1 phase, which up-regulates the expression of p53 and p27 and down-regulates the expression of CDK2 and cyclin D1.

Biological Activity I Assay Protocols (From Reference)

Targets

Plasmodium; Malaria; TLRs; SARS-COV-2; HIV-1

ln Vitro

In vitro activity: Chloroquine is a chemotherapeutic drug used in the clinical management of malaria. Because chloroquine can bind to DNA, it can prevent RNA synthesis and DNA replication, which ultimately leads to cell death. The creation of a toxic heme-chloroquine complex could potentially be connected to the effects of chloroquine. By raising the pH of vacuoles and blocking the actions of vacuolar phospholipase, vacuolar proteases, and heme polymerase, chloroquine prevents the breakdown of trophozoite hemoglobin. There are specific antirheumatic properties of chloroquine. Due to its immuno-modulatory properties, chloroquine inhibits the release and synthesis of interleukin 6 and tumour necrosis factor. Chloroquine also has direct antiviral effects, preventing the replication of various viruses, including retroviruses, coronaviruses, and flaviviruses, at pH-dependent stages. The effects it has on HIV replication have received the most research. Through the process of ion trapping, chloroquine can accumulate within the macrophage phagolysosome, where it possesses strong antifungal properties against both Cryptococcus neoformans and Histoplasma capsulatum through different mechanisms. While chloroquine directly poisons C. neoformans, it inhibits the growth of H. capsulatum through pH-dependent iron deprivation.

ln Vivo

Chloroquine (80 mg/kg, i.p.) has no effect on the growth of triple-negative MDA-MB-231 cells with high or low TLR9 expression levels in the orthotopic mouse model. The mouse xenograft model shows significant tumor growth inhibition upon TLR7 and TLR9 inhibition with IRS-954 or chloroquine. Chloroquine also significantly inhibits the development of HCC in the DEN/NMOR rat model. In a mouse model using a subcutaneous xenograft of 4T1 cells, treatment with chloroquine diphosphate dramatically reduced tumor growth and tumor cell metastasis to the lung, improving the mice's survival. Chloroquine diphosphate worked in concert with 5-FU to significantly increase the tumor growth inhibition caused by 5-FU in BALB/c mice that received subcutaneous injections of colon26 cells.This was achieved by increasing the proportion of apoptotic cells.

Cell Assay

The cells are cultivated in 6-well plates using normal culture medium with either vehicle or 25 or 50 μM chloroquine until they are almost confluent. Afterward, they are rinsed with sterile phosphate-buffered saline (PBS) and continue to culture in serum-free culture medium for the specified durations. Centrifugation is used to quickly harvest the cells in lysis buffer and clarify them after the culture medium is discarded at the predetermined time points. Once the supernatants have been boiled in reducing sodium dodecyl sulphate (SDS) sample buffer, 100 μg of protein is loaded into each lane. The samples are then electrophoresed into 10 or 4–20% gradient polyacrylamide SDS gels before being placed onto a nitrocellulose membrane. TLR9 is detected by incubating the blots with anti-TLR9 antibodies diluted 1:500 in Tris-buffered saline containing 0.1% (v/v) Tween-20 (TBST) for an overnight period at 4°C. Polyclonal rabbit anti-actin is used to confirm equal loading. Horseradish peroxidase-linked secondary antibodies are used in secondary detection. Using an ECL kit, the protein bands can be seen through chemiluminescence.

Animal Protocol

Mice with impaired immunity, four weeks old, have their mammary fat pads injected with a combination of control and TLR9 siRNA MDA-MB-231 cells (5×10⁵ cells in 100 μL) (athymic nude/nu Foxn1). Seven days after the tumor cell inoculation, treatments begin. Every day, the mice receive either a vehicle (PBS) or intraperitoneal (i.p.) chloroquine (80 mg/kg). Every day, the animals are observed for clinical indications. Tumor volumes are estimated using the formula V=(π/6) (d1×d2)^3/2, where d1 and d2 are the perpendicular tumor diameters. Tumor measurements are carried out twice a week. The mice are killed and the tumors are removed for one last measurement after the tumors are left to grow for 22 days. The animals are kept in controlled, pathogen-free environments with 20–21°C temperatures, 30–60% relative humidity, and a 12-hour lighting cycle throughout the trials. Small-animal food pellets are fed to the mice, and they are given access to sterile water whenever they need it.

References

[1]. Chloroquine promotes IL-17 production by CD4+ T cells via p38-dependent IL-23 release by monocyte-derived Langerhans-like cells. J Immunol. 2014 Dec 15;193(12):6135-43.

[2]. Chloroquine has tumor-inhibitory and tumor-promoting effects in triple-negative breast cancer. Oncol Lett. 2013 Dec;6(6):1665-1672.

[3]. Effect of toll-like receptor 7 and 9 targeted therapy to prevent the development of hepatocellular carcinoma. Liver Int. 2014 Jul 2. doi: 10.1111/liv.12626.

[4]. Chloroquine and hydroxychloroquine as available weapons to fight COVID-19. Int J Antimicrob Agents. 2020;55(4):105932.

[5]. Remdesivir and chloroquine effectively inhibit the recently emerged novel coronavirus (2019-nCoV) in vitro. Cell Res. 2020 Mar;30(3):269-271.

[6]. The anti-HIV-1 activity of chloroquine. J Clin Virol. 2001;20(3):131-135.

These protocols are for reference only. InvivoChem does not independently validate these methods.

Physicochemical Properties

Molecular Formula

C18H32CLN3O8P2

Molecular Weight

515.86

Exact Mass

515.14

Elemental Analysis

C, 41.91; H, 6.25; Cl, 6.87; N, 8.15; O, 24.81; P, 12.01

CAS #

50-63-5

Related CAS #

1446-17-9 (phosphate); 151-69-9 (acetate); 132-73-0 (sulfate); 50-63-5(diphosphate); 54-05-7; 3545-67-3 (HCl)

Appearance

White to light yellow crystalline powder

SMILES

CCN(CC)CCCC(C)NC1=C2C=CC(=CC2=NC=C1)Cl.OP(=O)(O)O.OP(=O)(O)O

InChi Key

QKICWELGRMTQCR-UHFFFAOYSA-N

InChi Code

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)

Chemical Name

4-N-(7-chloroquinolin-4-yl)-1-N,1-N-diethylpentane-1,4-diamine;phosphoric acid

Synonyms

Quingamine; NSC 14050; Khingamin; Ipsen 225; Gontochin phosphate; Chloroquine dihydrogen phosphate (1:2); Chlorochin diphosphate; Chingamin phosphate; Bemaphate; Aralen diphosphate; Chloroquine; Chloroquine diphosphate; Chingamin; Miniquine, Resochin; Chloroquine; Aralen; Arechin; Tanakan; Chloroquine phosphate; Chloroquine diphosphate; Aralen phosphate; Avloclor; Chingaminum; Chloroquin diphosphate; Delagil; Nivaquine B; Resoquine

HS Tariff Code

2934.99.9001

Storage

Powder -20°C 3 years

4°C 2 years

In solvent -80°C 6 months

-20°C 1 month

Shipping Condition

Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)

Solubility Data

Solubility (In Vitro)

DMSO: <1 mg/mL

Water: ~100 mg/mL (~193.9 mM)

Ethanol: <1 mg/mL

Preparing Stock Solutions		1 mg	5 mg	10 mg
	1 mM	1.9385 mL	9.6926 mL	19.3851 mL
	5 mM	0.3877 mL	1.9385 mL	3.8770 mL
	10 mM	0.1939 mL	0.9693 mL	1.9385 mL

*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.

Calculator

Mass

Concentration

Volume

Molecular Weight*

Calculate Reset

Molarity Calculator allows you to calculate the mass, volume, and/or concentration required for a solution, as detailed below:

Calculate the Mass of a compound required to prepare a solution of known volume and concentration
Calculate the Volume of solution required to dissolve a compound of known mass to a desired concentration
Calculate the Concentration of a solution resulting from a known mass of compound in a specific volume

See Example

An example of molarity calculation using the molarity calculator is shown below:
What is the mass of compound required to make a 10 mM stock solution in 5 ml of DMSO given that the molecular weight of the compound is 350.26 g/mol?

Enter 350.26 in the Molecular Weight (MW) box
Enter 10 in the Concentration box and choose the correct unit (mM)
Enter 5 in the Volume box and choose the correct unit (mL)
Click the “Calculate” button
The answer of 17.513 mg appears in the Mass box. In a similar way, you may calculate the volume and concentration.

Concentration (Start)

Volume (Start)

Concentration (End)

Volume (End)

Calculate Reset

Dilution Calculator allows you to calculate how to dilute a stock solution of known concentrations. For example, you may Enter C1, C2 & V2 to calculate V1, as detailed below:

What volume of a given 10 mM stock solution is required to make 25 ml of a 25 μM solution?
Using the equation C1V1 = C2V2, where C1=10 mM, C2=25 μM, V2=25 ml and V1 is the unknown:

Enter 10 into the Concentration (Start) box and choose the correct unit (mM)
Enter 25 into the Concentration (End) box and select the correct unit (mM)
Enter 25 into the Volume (End) box and choose the correct unit (mL)
Click the “Calculate” button
The answer of 62.5 μL (0.1 ml) appears in the Volume (Start) box

Molecular formula

Total molecular weight

g/mol

Calculate Reset

Molecular Weight Calculator allows you to calculate the molar mass and elemental composition of a compound, as detailed below:

Note: Chemical formula is case sensitive: C12H18N3O4 c12h18n3o4
Instructions to calculate molar mass (molecular weight) of a chemical compound:

To calculate molar mass of a chemical compound, please enter the chemical/molecular formula and click the “Calculate’ button.

Definitions of molecular mass, molecular weight, molar mass and molar weight:

Molecular mass (or molecular weight) is the mass of one molecule of a substance and is expressed in the unified atomic mass units (u). (1 u is equal to 1/12 the mass of one atom of carbon-12)
Molar mass (molar weight) is the mass of one mole of a substance and is expressed in g/mol.

Volume (to add to vial)

Mass (in vial)

Desired Reconstitution Concentration

Calculate Reset

Reconstitution Calculator allows you to calculate the volume of solvent required to reconstitute your vial.

Enter the mass of the reagent and the desired reconstitution concentration as well as the correct units
Click the “Calculate” button
The answer appears in the Volume (to add to vial) box

In vivo Formulation Calculator (Clear solution)

Step 1: Enter information below (Recommended: An additional animal to make allowance for loss during the experiment)

Dosage mg/kg

Average weight of animals g

Dosing volume per animal μL

Number of animals

Step 2: Enter in vivo formulation (This is only a calculator, not the exact formulation for a specific product. Please contact us first if there is no in vivo formulation in the solubility section.)

% DMSO

% Tween 80

% ddH₂O

Calculate Reset

Calculation results

Working concentration： mg/mL；

Method for preparing DMSO stock solution： mg drug pre-dissolved in μL DMSO (stock solution concentration mg/mL). Please contact us first if the concentration exceeds the DMSO solubility of the batch of drug.

Method for preparing in vivo formulation:：Take μL DMSO stock solution, next add μL PEG300, mix and clarify, next addμL Tween 80, mix and clarify, next add μL ddH₂O，mix and clarify.

Note： (1) Please be sure that the solution is clear before the addition of next solvent. Dissolution methods like vortex, ultrasound or warming and heat may be used to aid dissolving.
(2) Be sure to add the solvent(s) in order.

Clinical Trial Information

NCT Number	Recruitment	interventions	Conditions	Sponsor/Collaborators	Start Date	Phases
NCT03529396	Active Recruiting	Drug: Chloroquine Drug: Primaquine	Vivax Malaria G6PD Deficiency	Fundação de Medicina Tropical Dr. Heitor Vieira Dourado	July 20, 2018	Phase 2
NCT02932007	Active Recruiting	Drug: Chloroquine Phosphate	Atrial Fibrillation	University of South Florida	March 28, 2017	Phase 2
NCT06076837	Not yet recruiting	Drug: Chloroquine Phosphate Drug: Balstilimab	Pancreatic Cancer Metastatic	HonorHealth Research Institute	December 2023	Phase 1
NCT05443178	Recruiting	Drug: Nivaquine ® (Chloroquine)	Tuberculosis Infection	University of Zurich	January 4, 2022	Phase 1
NCT04704999	Not yet recruiting	Drug: Chloroquine Drug: Tafenoquine	Plasmodium Vivax Malaria	University of Oxford	September 18, 2023	Phase 4

Biological Data

Tumour volume reduced with chloroquine and IRS-954. Intrahepatic and extrahepatic tumours (black and red arrows respectively) derived from (a) HuH7 and (b) HepG2 cells injected into NOD-SCID mouse livers. Liver Int . 2015 Mar;35(3):1063-76.

Reduced TLR7, Akt, p-Akt & NF-кB expression with chloroquine in rat HCCs. Liver Int . 2015 Mar;35(3):1063-76.

Zymograms of supernatants from vehicle, 25 or 50 μM chloroquine-treated parental MDA-MB-231 cells or control siRNA or TLR9 siRNA cells after 24 h of treatment in normoxia (N) or hypoxia (H). Oncol Lett . 2013 Dec;6(6):1665-1672.