Chloroquine

Modify Date: 2024-01-01 19:06:41

Chloroquine structure	Common Name	Chloroquine
	CAS Number	54-05-7	Molecular Weight	319.872
	Density	1.1±0.1 g/cm3	Boiling Point	460.6±40.0 °C at 760 mmHg
	Molecular Formula	C₁₈H₂₆ClN₃	Melting Point	87ºC
	MSDS	N/A	Flash Point	232.3±27.3 °C

Use of Chloroquine

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].

Name	chloroquine
Synonym	More Synonyms

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].
Related Catalog	Signaling Pathways >> Immunology/Inflammation >> Toll-like Receptor (TLR) Research Areas >> Cancer Signaling Pathways >> Anti-infection >> HIV Signaling Pathways >> Anti-infection >> SARS-CoV Signaling Pathways >> Autophagy >> Autophagy
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	[1]. Said A, et al. 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]. Tuomela J, et al. Chloroquine has tumor-inhibitory and tumor-promoting effects in triple-negative breast cancer. Oncol Lett. 2013 Dec;6(6):1665-1672. [3]. Mohamed FE, et al. 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]. Colson P, et al. Chloroquine and hydroxychloroquine as available weapons to fight COVID-19. Int J Antimicrob Agents. 2020;55(4):105932.

Density	1.1±0.1 g/cm3
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

RTECS NUMBER :: VB2360000

CHEMICAL NAME :: Quinoline, 7-chloro-4-((4-(diethylamino)-1-methylbutyl)amino)-

CAS REGISTRY NUMBER :: 54-05-7

LAST UPDATED :: 199707

DATA ITEMS CITED :: 40

MOLECULAR FORMULA :: C18-H26-Cl-N3

MOLECULAR WEIGHT :: 319.92

WISWESSER LINE NOTATION :: T66 BNJ EMY1&3N2&2 IG

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Human - woman

DOSE/DURATION :: 24 mg/kg/12D-I

TOXIC EFFECTS :: Brain and Coverings - changes in surface EEG Behavioral - hallucinations, distorted perceptions Behavioral - changes in motor activity (specific assay)

TYPE OF TEST :: LDLo - Lowest published lethal dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Human - woman

DOSE/DURATION :: 110 mg/kg

TOXIC EFFECTS :: Cardiac - change in rate Cardiac - other changes Gastrointestinal - nausea or vomiting

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Human - woman

DOSE/DURATION :: 3600 mg/kg/3Y

TOXIC EFFECTS :: Sense Organs and Special Senses (Eye) - visual field changes Gastrointestinal - other changes Nutritional and Gross Metabolic - weight loss or decreased weight gain

TYPE OF TEST :: LDLo - Lowest published lethal dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Human - man

DOSE/DURATION :: 86 mg/kg

TOXIC EFFECTS :: Cardiac - change in rate Cardiac - other changes Gastrointestinal - nausea or vomiting

TYPE OF TEST :: LDLo - Lowest published lethal dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Human

DOSE/DURATION :: 20 mg/kg

TOXIC EFFECTS :: Sense Organs and Special Senses (Eye) - diplopia Behavioral - coma Vascular - BP elevation not characterized in autonomic section

TYPE OF TEST :: LDLo - Lowest published lethal dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Human - child

DOSE/DURATION :: 37593 ug/kg

TOXIC EFFECTS :: Brain and Coverings - other degenerative changes Behavioral - convulsions or effect on seizure threshold Cardiac - change in rate

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 330 mg/kg

TOXIC EFFECTS :: Behavioral - convulsions or effect on seizure threshold Behavioral - ataxia Lungs, Thorax, or Respiration - dyspnea

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 102 mg/kg

TOXIC EFFECTS :: Gastrointestinal - other changes

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Subcutaneous

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 190 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intravenous

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 60 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 311 mg/kg

TOXIC EFFECTS :: Behavioral - tremor Behavioral - convulsions or effect on seizure threshold Lungs, Thorax, or Respiration - respiratory depression

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 66 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Subcutaneous

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 150 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intravenous

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 21600 ug/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intramuscular

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 71 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Subcutaneous

SPECIES OBSERVED :: Rodent - rabbit

DOSE/DURATION :: 75 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intravenous

SPECIES OBSERVED :: Rodent - rabbit

DOSE/DURATION :: 8 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

TYPE OF TEST :: LDLo - Lowest published lethal dose

ROUTE OF EXPOSURE :: Intramuscular

SPECIES OBSERVED :: Rodent - rabbit

DOSE/DURATION :: 20 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 560 mg/kg/14D-I

TOXIC EFFECTS :: Behavioral - food intake (animal) Nutritional and Gross Metabolic - weight loss or decreased weight gain Related to Chronic Data - death

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 9800 mg/kg/35W-C

TOXIC EFFECTS :: Behavioral - food intake (animal) Blood - changes in leukocyte (WBC) count Nutritional and Gross Metabolic - weight loss or decreased weight gain

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Mammal - dog

DOSE/DURATION :: 360 mg/kg/30D-I

TOXIC EFFECTS :: Behavioral - tremor Biochemical - Enzyme inhibition, induction, or change in blood or tissue levels - transaminases Related to Chronic Data - death

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Unreported

DOSE :: 420 mg/kg

SEX/DURATION :: female 1-42 day(s) after conception

TOXIC EFFECTS :: Reproductive - Specific Developmental Abnormalities - urogenital system Reproductive - Specific Developmental Abnormalities - other developmental abnormalities

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Unreported

DOSE :: 1155 mg/kg

SEX/DURATION :: female 6-39 week(s) after conception

TOXIC EFFECTS :: Reproductive - Specific Developmental Abnormalities - eye/ear Reproductive - Effects on Newborn - other postnatal measures or effects

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Unreported

DOSE :: 840 mg/kg

SEX/DURATION :: female 1-84 day(s) after conception

TOXIC EFFECTS :: Reproductive - Fertility - abortion

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

DOSE :: 10500 mg/kg

SEX/DURATION :: female 1-15 day(s) after conception

TOXIC EFFECTS :: Reproductive - Effects on Embryo or Fetus - fetotoxicity (except death, e.g., stunted fetus) Reproductive - Specific Developmental Abnormalities - musculoskeletal system Reproductive - Specific Developmental Abnormalities - hepatobiliary system

TYPE OF TEST :: Specific locus test

TYPE OF TEST :: Sex chromosome loss and nondisjunction

MUTATION DATA

TYPE OF TEST :: DNA damage

TEST SYSTEM :: Mammal - species unspecified Lymphocyte

DOSE/DURATION :: 500 umol/L

REFERENCE :: BBACAQ Biochimica et Biophysica Acta. (Elsevier Science Pub. B.V., POB 211, 1000 AE Amsterdam, Netherlands) V.1- 1947- Volume(issue)/page/year: 561,77,1979 *** REVIEWS *** IARC Cancer Review:Animal Inadequate Evidence IMEMDT IARC Monographs on the Evaluation of Carcinogenic Risk of Chemicals to Man. (WHO Publications Centre USA, 49 Sheridan Ave., Albany, NY 12210) V.1- 1972- Volume(issue)/page/year: 13,47,1977 IARC Cancer Review:Human No Adequate Data IMEMDT IARC Monographs on the Evaluation of Carcinogenic Risk of Chemicals to Man. (WHO Publications Centre USA, 49 Sheridan Ave., Albany, NY 12210) V.1- 1972- Volume(issue)/page/year: 13,47,1977 IARC Cancer Review:Group 3 IMSUDL IARC Monographs, Supplement. (WHO Publications Centre USA, 49 Sheridan Ave., Albany, NY 12210) No.1- 1979- Volume(issue)/page/year: 7,56,1987 TOXICOLOGY REVIEW PLMJAP Pahlavi Medical Journal. (Shiraz, Iran) V.1-9, 1970-78. Volume(issue)/page/year: 6,160,1975 TOXICOLOGY REVIEW 32XPAD "Teratology," Berry, C.L., and D.E. Poswillo, eds., New York, Springer, 1975 Volume(issue)/page/year: -,49,1975 TOXICOLOGY REVIEW FNSCA6 Forensic Science. (Lausanne, Switzerland) V.1-11, 1972-78. For pub lisher information, see FSINDR. Volume(issue)/page/year: 2,67,1973 *** NIOSH STANDARDS DEVELOPMENT AND SURVEILLANCE DATA *** NIOSH OCCUPATIONAL EXPOSURE SURVEY DATA : NOES - National Occupational Exposure Survey (1983) NOES Hazard Code - X4820 No. of Facilities: 7 (estimated) No. of Industries: 1 No. of Occupations: 1 No. of Employees: 103 (estimated) No. of Female Employees: 52 (estimated)

Hazard Codes	Xi
HS Code	2933499090

4-Bromo-7-chlor...

CAS#:98519-65-4

Novoldiamine

CAS#:140-80-7

~76%

Chloroquine

CAS#: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

Chloroquine dip...

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Chloroquine

CAS#:54-05-7

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7-chloroquinoli...

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Chloroquine

CAS#:54-05-7

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3-Chloroaniline

CAS#:108-42-9

Chloroquine

CAS#:54-05-7

Literature: De; Byers; Krogstad Journal of Heterocyclic Chemistry, 1997 , vol. 34, # 1 p. 315 - 320

7-Chloro-4-hydr...

CAS#:86-47-5

Chloroquine

CAS#:54-05-7

Literature: De; Byers; Krogstad Journal of Heterocyclic Chemistry, 1997 , vol. 34, # 1 p. 315 - 320

Ethyl 7-chloro-...

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Chloroquine

CAS#:54-05-7

Literature: De; Byers; Krogstad Journal of Heterocyclic Chemistry, 1997 , vol. 34, # 1 p. 315 - 320

Propanedioic ac...

CAS#:3412-99-5

Chloroquine

CAS#:54-05-7

Literature: De; Byers; Krogstad Journal of Heterocyclic Chemistry, 1997 , vol. 34, # 1 p. 315 - 320

uroporphyrin I-...

CAS#:114422-77-4

Chloroquine

CAS#:54-05-7

3-[7,12,17-tris...

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Literature: Constantinidis, I.; Satterlee, James D. Journal of the American Chemical Society, 1988 , vol. 110, # 13 p. 4391 - 4395

4,7-Dichloroqui...

CAS#:86-98-6

Novoldiamine

CAS#:140-80-7

Chloroquine

CAS#:54-05-7

Literature: De; Byers; Krogstad Journal of Heterocyclic Chemistry, 1997 , vol. 34, # 1 p. 315 - 320

Precursor 10
CAS#:98519-65-4 4-Bromo-7-chlor... CAS#:140-80-7 Novoldiamine CAS#:50-63-5 Chloroquine dip... CAS#:86-99-7 7-chloroquinoli...
CAS#:108-42-9 3-Chloroaniline CAS#:86-47-5 7-Chloro-4-hydr... CAS#:16600-22-9 Ethyl 7-chloro-... CAS#:3412-99-5 Propanedioic ac...
CAS#:114422-77-4 uroporphyrin I-... CAS#:86-98-6 4,7-Dichloroqui...
DownStream 1
CAS#:1476-52-4 Desethyl Chloroquine

HS Code	2933499090
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%

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

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China
Product Name: 1,4-Pentanediamine,N4-(7-chloro-4-quinolinyl)-N1,N1-diethyl-
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Price: ￥550/10 mM * 1 mL in DMSO

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Chloroquine

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