WARNING: This product is for research use only, not for human or veterinary use.
Hodoodo CAT#: H531010
CAS#: 50-63-5 (diphosphate)
Description: Chloroquine is a medication used to prevent and to treat malaria in areas where malaria is known to be sensitive to its effects. Chloroquine has antiviral effects. It increases late endosomal and lysosomal pH, resulting in impaired release of the virus from the endosome or lysosome – release of the virus requires a low pH. The virus is therefore unable to release its genetic material into the cell and replicate. Chloroquine also seems to act as a zinc ionophore, that allows extracellular zinc to enter the cell and inhibit viral RNA-dependent RNA polymerase.
Hodoodo Cat#: H531010
Name: Chloroquine Phosphate
CAS#: 50-63-5 (diphosphate)
Chemical Formula: C18H32ClN3O8P2
Exact Mass: 0.00
Molecular Weight: 515.865
Elemental Analysis: C, 41.91; H, 6.25; Cl, 6.87; N, 8.15; O, 24.81; P, 12.01
Related CAS #: 54-05-7 (free base) 132-73-0 (sulfate) 1446-17-9 (phosphate) 3545-67-3 (HCl) 50-63-5 (diphosphate) 151-69-9 (acetate)
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
More Info:
| 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 | Max Conc. mg/mL | Max Conc. mM | |
|---|---|---|---|
| Solubility | |||
| Water | 61.5 | 119.28 | |
| PBS (pH 7.2) | 10.0 | 19.39 | |
| DMSO | 1.0 | 1.94 |
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.
