Synonym
Chloroquine; Imagon; RP 3377; RP-3377; RP3377; NSC 187208; NSC-187208; NSC187208;
IUPAC/Chemical Name
N4-(7-chloroquinolin-4-yl)-N1,N1-diethylpentane-1,4-diamine
InChi Key
WHTVZRBIWZFKQO-UHFFFAOYSA-N
InChi Code
InChI=1S/C18H26ClN3/c1-4-22(5-2)12-6-7-14(3)21-17-10-11-20-18-13-15(19)8-9-16(17)18/h8-11,13-14H,4-7,12H2,1-3H3,(H,20,21)
SMILES Code
CC(NC1=CC=NC2=CC(Cl)=CC=C12)CCCN(CC)CC
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
>3 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
2934.99.03.00
Biological target:
Chloroquine is an autophagy and toll-like receptors (TLRs) inhibitor.
In vitro activity:
This study first tested the cytotoxicity of CQ (Chloroquine) on OS cells using the CCk-8 assay, and the results showed cell viability at 24 h, 48 h, and 72 h in a concentration gradient of CQ (Figure 1A), and the IC50 values at 24 h and 48 h in 143B and U-2OS cells (Figure 1B). Specifically, the IC50 value in 143B at 24h and 48h were 53.06 μM and 24.54 μM respectively, and were 66.3 μM and 27.81 μM in U2OS, respectively. As illustrated in Figure 1C, the proliferation of OS cells was significantly inhibited by CQ with increasing concentration. Furthermore, the flow cytometry results showed that with increasing CQ concentration, more apoptosis occurred in OS cells (Figure 1D). These results indicated that CQ was cytotoxic to OS cells, inhibited their proliferation and induced apoptosis in vitro in a dose-and time-dependent manner.
Reference: Aging (Albany NY). 2021 Jun 24;13. https://www.aging-us.com/article/203196/text
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 |
| DMSO |
82.0 |
256.35 |
|
| Ethanol |
82.0 |
256.35 |
|
| Water |
1.0 |
3.13 |
|
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
319.87
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. Chen C, Zhang H, Yu Y, Huang Q, Wang W, Niu J, Lou J, Ren T, Huang Y, Guo W. Chloroquine suppresses proliferation and invasion and induces apoptosis of osteosarcoma cells associated with inhibition of phosphorylation of STAT3. Aging (Albany NY). 2021 Jun 24;13. doi: 10.18632/aging.203196. Epub ahead of print. PMID: 34170850.
2. Han NR, Ko SG, Moon PD, Park HJ. Chloroquine attenuates thymic stromal lymphopoietin production via suppressing caspase-1 signaling in mast cells. Biomed Pharmacother. 2021 Jun 17;141:111835. doi: 10.1016/j.biopha.2021.111835. Epub ahead of print. PMID: 34146852.
3. 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.
4. Vergote V, Laenen L, Mols R, Augustijns P, Van Ranst M, Maes P. Chloroquine, an Anti-Malaria Drug as Effective Prevention for Hantavirus Infections. Front Cell Infect Microbiol. 2021 Mar 15;11:580532. doi: 10.3389/fcimb.2021.580532. PMID: 33791230; PMCID: PMC8006394.
In vitro protocol:
1. Chen C, Zhang H, Yu Y, Huang Q, Wang W, Niu J, Lou J, Ren T, Huang Y, Guo W. Chloroquine suppresses proliferation and invasion and induces apoptosis of osteosarcoma cells associated with inhibition of phosphorylation of STAT3. Aging (Albany NY). 2021 Jun 24;13. doi: 10.18632/aging.203196. Epub ahead of print. PMID: 34170850.
2. Han NR, Ko SG, Moon PD, Park HJ. Chloroquine attenuates thymic stromal lymphopoietin production via suppressing caspase-1 signaling in mast cells. Biomed Pharmacother. 2021 Jun 17;141:111835. doi: 10.1016/j.biopha.2021.111835. Epub ahead of print. PMID: 34146852.
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.
2. Vergote V, Laenen L, Mols R, Augustijns P, Van Ranst M, Maes P. Chloroquine, an Anti-Malaria Drug as Effective Prevention for Hantavirus Infections. Front Cell Infect Microbiol. 2021 Mar 15;11:580532. doi: 10.3389/fcimb.2021.580532. PMID: 33791230; PMCID: PMC8006394.
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.
