Name | chloroquine |
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Synonyms |
UNII:886U3H6UFF
Bemaco (±)-Chloroquine N-(7-Chloro-4-quinolinyl)-N,N-diethyl-1,4-pentanediamine [3H]-Chloroquine sn7618 N-(7-Chloroquinolin-4-yl)-N,N-diethylpentane-1,4-diamine CHLOROQUINE 1,4-Pentanediamine, N-(7-chloro-4-quinolinyl)-N,N-diethyl- 1,4-Pentanediamine, N4-(7-chloro-4-quinolinyl)-N1,N1-diethyl- N4-(7-Chloroquinolin-4-yl)-N1,N1-diethylpentane-1,4-diamine Amokin rp3377 N4-(7-chloroquinoline-4-yl)-N1,N1-diethyl-pentane-1,4-diamine Imagon Aralen w7618 3377 RP win244 |
Description | Chloroquine is an antimalarial and anti-inflammatory agent widely used to treat malaria and rheumatoid arthritis. Chloroquine is a autophagy and toll-like receptors (TLRs) inhibitor. Chloroquine is highly effective in the control of SARS-CoV-2 (COVID-19) infection in vitro (EC50=1.13 μM)[1][2][3][4]. |
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Related Catalog | |
Target |
TLRs, HIV, SARS-CoV-2, Autophagy[1][2][3][4] |
In Vitro | Chloroquine (CHQ, 20 μM) inhibits IL-12p70 release and reduces Th1-priming capacity of activated human monocyte-derived Langerhans-like cells (MoLC). Chloroquine (20 μM) enhances IL-1–induced IL-23 secretion in MoLC and subsequently increases IL-17A release by primed CD4+ T cells[1]. Chloroquine (25 μM) suppresses MMP-9 mRNA expression in normoxia and hypoxia in parental MDA-MB-231 cells. Chloroquine has cell-, dose- and hypoxia-dependent effects on MMP-2, MMP-9 and MMP-13 mRNA expression[2]. TLR7 and TLR9 inhibition using IRS-954 or chloroquine significantly reduces HuH7 cell proliferation in vitro[3]. Chloroquine (0.01-100μM; 48 hours) potently blocked virus infection (vero E6 cells infected with SARS-CoV-2) at low-micromolar concentration (EC50=1.13 μM). Chloroquine blocks virus infection by increasing endosomal pH required for virus/cell fusion, as well as interfering with the glycosylation of cellular receptors of SARS-CoV[4]. |
In Vivo | Chloroquine (80 mg/kg, i.p.) does not prevent the growth of the triple-negative MDA-MB-231 cells with high or low TLR9 expression levels in the orthotopic mouse model[2]. TLR7 and TLR9 inhibition using IRS-954 or chloroquine significantly inhibits tumour growth in the mouse xenograft model. HCC development in the DEN/NMOR rat model is also significantly inhibited by Chloroquine[3]. |
References |
Density | 1.1±0.1 g/cm3 |
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Boiling Point | 460.6±40.0 °C at 760 mmHg |
Melting Point | 87ºC |
Molecular Formula | C18H26ClN3 |
Molecular Weight | 319.872 |
Flash Point | 232.3±27.3 °C |
Exact Mass | 319.181519 |
PSA | 28.16000 |
LogP | 4.69 |
Vapour Pressure | 0.0±1.1 mmHg at 25°C |
Index of Refraction | 1.592 |
CHEMICAL IDENTIFICATION
HEALTH HAZARD DATAACUTE TOXICITY DATA
MUTATION DATA
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Hazard Codes | Xi |
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HS Code | 2933499090 |
~76% 54-05-7 |
Literature: Margolis, Brandon J.; Long, Kimberly A.; Laird, Dana L. T.; Ruble, J. Craig; Pulley, Shon R. Journal of Organic Chemistry, 2007 , vol. 72, # 6 p. 2232 - 2235 |
~% 54-05-7 |
Literature: Kuter, David; Benjamin, Stefan J.; Egan, Timothy J. Journal of Inorganic Biochemistry, 2014 , vol. 133, p. 40 - 49 |
~% 54-05-7 |
Literature: De; Byers; Krogstad Journal of Heterocyclic Chemistry, 1997 , vol. 34, # 1 p. 315 - 320 |
~% 54-05-7 |
Literature: De; Byers; Krogstad Journal of Heterocyclic Chemistry, 1997 , vol. 34, # 1 p. 315 - 320 |
~% 54-05-7 |
Literature: De; Byers; Krogstad Journal of Heterocyclic Chemistry, 1997 , vol. 34, # 1 p. 315 - 320 |
~% 54-05-7 |
Literature: De; Byers; Krogstad Journal of Heterocyclic Chemistry, 1997 , vol. 34, # 1 p. 315 - 320 |
~% 54-05-7 |
Literature: De; Byers; Krogstad Journal of Heterocyclic Chemistry, 1997 , vol. 34, # 1 p. 315 - 320 |
~% 54-05-7 |
Literature: Constantinidis, I.; Satterlee, James D. Journal of the American Chemical Society, 1988 , vol. 110, # 13 p. 4391 - 4395 |
~% 54-05-7 |
Literature: De; Byers; Krogstad Journal of Heterocyclic Chemistry, 1997 , vol. 34, # 1 p. 315 - 320 |
Precursor 10 | |
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DownStream 1 | |
HS Code | 2933499090 |
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Summary | 2933499090. other compounds containing in the structure a quinoline or isoquinoline ring-system (whether or not hydrogenated), not further fused. VAT:17.0%. Tax rebate rate:13.0%. . MFN tariff:6.5%. General tariff:20.0% |