Synonym
Chloroquine phosphate, Chloroquine diphosphate; Chloroquine; Alermine; Aralen; Aralen diphosphate; Aralen phosphate; Arechin; Avloclor; Bemaphate; Chingamin; Chingamin phosphate; Chingaminum; Chlorochin diphosphate; Chloroquin diphosphate; Chloroquine dihydrogen phosphate (1:2); Chloroquine diphosphate; Chloroquine phosphate; Delagil; Gontochin phosphate; Ipsen 225; Khingamin; Miniquine; Nivaquine B; NSC 14050; Quingamine; Resochin; Resoquine; RP 3377; Sanoquin; SN 7,618; SN 7618; Tanakene; WR 1522.
IUPAC/Chemical Name
N4-(7-chloroquinolin-4-yl)-N1,N1-diethylpentane-1,4-diamine bis(phosphate)
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)
SMILES Code
CC(NC1=CC=NC2=CC(Cl)=CC=C12)CCCN(CC)CC.O=P(O)(O)O.O=P(O)(O)O
Appearance
White to light yellow crystalline powder.
Purity
>98% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
Soluble in DMSO
Shelf Life
>2 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.9001
Biological target:
Chloroquine diphosphate is an antimalarial drug.
In vitro activity:
Chloroquine phosphate was tested for its antiviral potential against SARS-CoV-induced cytopathicity in Vero E6 cell culture. In the virus yield assay, where viral RNA was quantified one and three days postinfection, no significant replication was observed after one day when the cells were treated with 4 μM chloroquine. To inhibit virus replication by 99% three days postinfection, 16 μM chloroquine was needed (Fig. 2).
Reference: Biochem Biophys Res Commun. 2004 Oct 8;323(1):264-8. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7092815/
In vivo activity:
Invasive therapy was applied to investigate the effect of CQ (chloroquine diphosphate) on liver cancer. The results demonstrated that the two drug doses (0.5 and 1.5 mg/kg) used inhibited tumor size (Fig. 3A and B) and weight (Fig. 3C), compared with results in control rats. Subsequently, to further investigate the effect of CQ on the expression of liver cancer markers, the expression levels of the liver cancer stem cell markers, including keratin 19 (K19) and sox9, were determined (24). RT-qPCR results revealed that CQ (1.5 mg/kg) downregulated the expression of K19 and sox9 (Fig. 3D and E). Concerning the survival rate of rats, 7/10, 3/10 and 1/10 rats died in the control group, 0.5 (low-dose) and 1.5 mg/kg (high-dose) CQ treatment groups, respectively (Fig. 4B).
Reference: Oncol Lett. 2021 Mar;21(3):233. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7856698/
|
Solvent |
mg/mL |
mM |
comments |
| Solubility |
| Water |
61.5 |
119.28 |
|
| PBS (pH 7.2) |
10.0 |
19.39 |
|
| DMSO |
1.0 |
1.94 |
|
Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.
Preparing Stock Solutions
The following data is based on the
product
molecular weight
515.86
Batch specific molecular weights may vary
from batch to batch
due to the degree of hydration, which will
affect the solvent
volumes required to prepare stock solutions.
| Concentration / Solvent Volume / Mass |
1 mg |
5 mg |
10 mg |
| 1 mM |
1.15 mL |
5.76 mL |
11.51 mL |
| 5 mM |
0.23 mL |
1.15 mL |
2.3 mL |
| 10 mM |
0.12 mL |
0.58 mL |
1.15 mL |
| 50 mM |
0.02 mL |
0.12 mL |
0.23 mL |
Formulation protocol:
1. Keyaerts E, Vijgen L, Maes P, Neyts J, Van Ranst M. In vitro inhibition of severe acute respiratory syndrome coronavirus by chloroquine. Biochem Biophys Res Commun. 2004 Oct 8;323(1):264-8. doi: 10.1016/j.bbrc.2004.08.085. PMID: 15351731; PMCID: PMC7092815.
2. Hao X, Li W. Chloroquine diphosphate suppresses liver cancer via inducing apoptosis in Wistar rats using interventional therapy. Oncol Lett. 2021 Mar;21(3):233. doi: 10.3892/ol.2021.12494. Epub 2021 Jan 26. PMID: 33613722; PMCID: PMC7856698.
In vitro protocol:
1. Keyaerts E, Vijgen L, Maes P, Neyts J, Van Ranst M. In vitro inhibition of severe acute respiratory syndrome coronavirus by chloroquine. Biochem Biophys Res Commun. 2004 Oct 8;323(1):264-8. doi: 10.1016/j.bbrc.2004.08.085. PMID: 15351731; PMCID: PMC7092815.
In vivo protocol:
1. Hao X, Li W. Chloroquine diphosphate suppresses liver cancer via inducing apoptosis in Wistar rats using interventional therapy. Oncol Lett. 2021 Mar;21(3):233. doi: 10.3892/ol.2021.12494. Epub 2021 Jan 26. PMID: 33613722; PMCID: PMC7856698.
1: Blignaut M, Espach Y, van Vuuren M, Dhanabalan K, Huisamen B. Revisiting the Cardiotoxic Effect of Chloroquine. Cardiovasc Drugs Ther. 2019 Feb;33(1):1-11. doi: 10.1007/s10557-018-06847-9. PMID: 30635818.
2: Goel P, Gerriets V. Chloroquine. 2019 Dec 5. In: StatPearls [Internet]. Treasure Island (FL): StatPearls Publishing; 2020 Jan–. PMID: 31855356.
3: Nguyen AL, Tan AN, Lavrijsen APM. Retinopathie door chloroquine [Chloroquine retinopathy]. Ned Tijdschr Geneeskd. 2018 Dec 17;163:D2904. Dutch. PMID: 30570930.
4: Drugs and Lactation Database (LactMed) [Internet]. Bethesda (MD): National Library of Medicine (US); 2006–. Chloroquine. 2018 Oct 31. PMID: 30000205.
5: Liu WD, Sun W, Hua YQ, Wang SG, Cai ZD. [Effect of rapamycin and chloroquine on osteosarcoma]. Zhonghua Yi Xue Za Zhi. 2017 May 23;97(19):1510-1514. Chinese. doi: 10.3760/cma.j.issn.0376-2491.2017.19.017. PMID: 28535645.
6: Stokkermans TJ, Trichonas G. Chloroquine And Hydroxychloroquine Toxicity. 2019 Jun 4. In: StatPearls [Internet]. Treasure Island (FL): StatPearls Publishing; 2020 Jan–. PMID: 30725771.
7: Ganne P, Srinivasan R. Chloroquine retinopathy. JAMA Ophthalmol. 2015 May;133(5):603-4. doi: 10.1001/jamaophthalmol.2014.6127. PMID: 25974649.
8: Ippolito MM, Jacobson JM, Lederman MM, Winterberg M, Tarning J, Shapiro TA, Flexner C. Effect of Antiretroviral Therapy on Plasma Concentrations of Chloroquine and Desethyl-chloroquine. Clin Infect Dis. 2018 Oct 30;67(10):1617-1620. doi: 10.1093/cid/ciy405. PMID: 29771277; PMCID: PMC6206114.
9: Xue J, Moyer A, Peng B, Wu J, Hannafon BN, Ding WQ. Chloroquine is a zinc ionophore. PLoS One. 2014 Oct 1;9(10):e109180. doi: 10.1371/journal.pone.0109180. PMID: 25271834; PMCID: PMC4182877.
10: Bortoli R, Santiago M. Chloroquine ototoxicity. Clin Rheumatol. 2007 Nov;26(11):1809-10. doi: 10.1007/s10067-007-0662-6. Epub 2007 Jun 27. PMID: 17594118.
11: Nair PA, Patel T. Palmoplantar exfoliation due to chloroquine. Indian J Pharmacol. 2017 Mar-Apr;49(2):205-207. doi: 10.4103/ijp.IJP_659_16. PMID: 28706336; PMCID: PMC5497445.
12: Copeman PW. Chloroquine. Trans St Johns Hosp Dermatol Soc. 1967;53(1):24-45. PMID: 4865867.
13: LiverTox: Clinical and Research Information on Drug-Induced Liver Injury [Internet]. Bethesda (MD): National Institute of Diabetes and Digestive and Kidney Diseases; 2012–. Chloroquine. 2017 Feb 2. PMID: 31643549.
14: Chen X. Hydroxychloroquine and chloroquine. Clin Infect Dis. 2020 Mar 26:ciaa338. doi: 10.1093/cid/ciaa338. Epub ahead of print. PMID: 32215614.
15: Ferner RE, Aronson JK. Chloroquine and hydroxychloroquine in covid-19. BMJ. 2020 Apr 8;369:m1432. doi: 10.1136/bmj.m1432. PMID: 32269046.
16: Touret F, de Lamballerie X. Of chloroquine and COVID-19. Antiviral Res. 2020 May;177:104762. doi: 10.1016/j.antiviral.2020.104762. Epub 2020 Mar 5. PMID: 32147496; PMCID: PMC7132364.
17: Hong W. Combating COVID-19 with Chloroquine. J Mol Cell Biol. 2020 Apr 1:mjaa015. doi: 10.1093/jmcb/mjaa015. Epub ahead of print. PMID: 32236561.
18: Mohr K. Chloroquin [Chloroquine]. Dtsch Med Wochenschr. 1994 Feb 25;119(8):273-4. German. doi: 10.1055/s-0029-1235021. PMID: 8112211.
19: Willkens RF. Chloroquine. Arthritis Rheum. 1972 Mar-Apr;15(2):228-9. PMID: 5027609.
20: Manic G, Obrist F, Kroemer G, Vitale I, Galluzzi L. Chloroquine and hydroxychloroquine for cancer therapy. Mol Cell Oncol. 2014 Jul 15;1(1):e29911. doi: 10.4161/mco.29911. PMID: 27308318; PMCID: PMC4905171.
