Chloroquine

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

Chloroquine Structure
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].

 Names

Name chloroquine
Synonym More Synonyms

 Chloroquine Biological Activity

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
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.

 Chemical & Physical Properties

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

 Toxicological Information

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)

 Safety Information

Hazard Codes Xi
HS Code 2933499090

 Synthetic Route

4-Bromo-7-chloroquinoline structure

4-Bromo-7-chlor...

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Novoldiamine

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~76%

Chloroquine Structure

Chloroquine

CAS#:54-05-7
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Chloroquine diphosphate structure

Chloroquine dip...

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~%

Chloroquine Structure

Chloroquine

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7-chloroquinolin-4-ol structure

7-chloroquinoli...

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~%

Chloroquine Structure

Chloroquine

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3-Chloroaniline structure

3-Chloroaniline

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Chloroquine Structure

Chloroquine

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7-Chloro-4-hydroxy-3-quinolinecarboxylic acid structure

7-Chloro-4-hydr...

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~%

Chloroquine Structure

Chloroquine

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Ethyl 7-chloro-4-hydroxy-3-quinolinecarboxylate structure

Ethyl 7-chloro-...

CAS#:16600-22-9

~%

Chloroquine Structure

Chloroquine

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Propanedioic acid,2-[[(3-chlorophenyl)amino]methylene]-, 1,3-diethyl ester structure

Propanedioic ac...

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Chloroquine Structure

Chloroquine

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uroporphyrin I-chloroquine complex structure

uroporphyrin I-...

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~%

Chloroquine Structure

Chloroquine

CAS#:54-05-7

3-[7,12,17-tris-(2-carboxy-ethyl)-3,8,13,18-tetrakis-carboxymethyl-22,24-dihydro-porphin-2-yl]-propionic acid structure

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

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4,7-Dichloroquinoline structure

4,7-Dichloroqui...

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Novoldiamine structure

Novoldiamine

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~%

Chloroquine Structure

Chloroquine

CAS#:54-05-7
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 Customs

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%

 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
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Related Compounds: More...
d-Chloroquine
67459-54-5
Chloroquine D5
1854126-41-2
Chloroquine HCl
3545-67-3
(S)-chloroquine
58175-86-3
(R)-chloroquine
58175-87-4
[2H4]-Chloroquine
1246815-14-4
Deethylchloroquine
61219-61-2
chloroquine sulfate
132-73-0
chloroquine mustard
4213-44-9
Chemsrc provides Chloroquine(CAS#:54-05-7) MSDS, density, melting point, boiling point, structure, formula, molecular weight etc. Articles of Chloroquine are included as well.>> amp version: Chloroquine

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