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Substance Name: Chloroquine [USP:INN:BAN]
RN: 54-05-7
UNII: 886U3H6UFF
InChIKey: WHTVZRBIWZFKQO-UHFFFAOYSA-N

Note

  • The prototypical antimalarial agent with a mechanism that is not well understood. It has also been used to treat rheumatoid arthritis, systemic lupus erythematosus, and in the systemic therapy of amebic liver abscesses.

Molecular Formula

  • C18-H26-Cl-N3

Molecular Weight

  • 319.8774
 

Classification Codes

Classification Codes

  • Amebicides
  • Anti-Amebic
  • Anti-Infective Agents
  • Antimalarial
  • Antimalarials
  • Antiparasitic Agents
  • Antiprotozoal Agents
  • Antirheumatic Agents
  • Drug / Therapeutic Agent
  • Human Data
  • Mutation Data
  • Reproductive Effect
  • Tumor Data

Superlist Classification Code

  • Overall Carcinogenic Evaluation: Group 3

Names and Synonyms

Name of Substance

  • Chloroquine
  • Chloroquine [USP:INN:BAN]

MeSH Heading

  • Chloroquine

Synonyms

  • (+-)-Chloroquine
  • 1,4-Pentanediamine, N(4)-(7-chloro-4-quinolinyl)-N(1),N(1)-diethyl-
  • 7-Chloro-4-((4-(diethylamino)-1-methylbutyl)amino)quinoline
  • Amokin
  • Aralen
  • Arthrochin
  • Artrichin
  • Bemaco
  • Bemasulph
  • Benaquin
  • Bipiquin
  • BRN 0482809
  • Capquin
  • CCRIS 3439
  • Chemochin
  • Chloraquine
  • Chlorochin
  • Chlorochinum
  • Chloroquina
  • Chloroquine
  • Chloroquine (VAN)
  • Chloroquinium
  • Chloroquinum
  • Chloroquinum [INN-Latin]
  • Chlorquin
  • Cidanchin
  • Clorochina
  • Clorochina [DCIT]
  • Cloroquina
  • Cloroquina [INN-Spanish]
  • Cocartrit
  • CQ
  • Dichinalex
  • EINECS 200-191-2
  • Elestol
  • Gontochin
  • Heliopar
  • HSDB 3029
  • Imagon
  • Iroquine
  • Khingamin
  • Klorokin
  • Lapaquin
  • Malaquin
  • Malaren
  • Malarex
  • Mesylith
  • N(sup 4)-(7-Chloro-4-quinolinyl)-N(sup 1),N(sup 1)-diethyl-1,4-pentanediamine
  • N4-(7-Chloro-4-quinolinyl)-N1,N1-diethyl-1,4-pentanediamine
  • Neochin
  • Nivaquine
  • NSC 187208
  • Pfizerquine
  • Quinachlor
  • Quinercyl
  • Quinilon
  • Quinoline, 7-chloro-4-((4-(diethylamino)-1-methylbutyl)amino)-
  • Quinoscan
  • Reumachlor
  • Ronaquine
  • Roquine
  • RP 3377
  • Silbesan
  • Siragan
  • Solprina
  • Sopaquin
  • ST 21
  • ST 21 (pharmaceutical)
  • Tresochin
  • Trochin
  • UNII-886U3H6UFF
  • W 7618
  • WIN 244

Systematic Names

  • 1,4-Pentanediamine, N(sup 4)-(7-chloro-4-quinolinyl)-N(sup 1),N(sup 1)-diethyl-
  • 1,4-Pentanediamine, N4-(7-chloro-4-quinolinyl)-N1,N1-diethyl-
  • Chloroquine
  • Quinoline, 7-chloro-4-((4-(diethylamino)-1-methylbutyl)amino)-

Superlist Name

  • Chloroquine

Registry Numbers

CAS Registry Number

  • 54-05-7

FDA UNII

  • 886U3H6UFF

Other Registry Number

  • 56598-66-4

System Generated Number

  • 0000054057

Structure Descriptors

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)

InChIKey

WHTVZRBIWZFKQO-UHFFFAOYSA-N

Smiles

CCN(CC)CCCC(C)Nc1ccnc2c1ccc(c2)Cl

Toxicity

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
child LDLo oral 37593ug/kg (37.593mg/kg) BRAIN AND COVERINGS: OTHER DEGENERATIVE CHANGES

CARDIAC: CHANGE IN RATE

BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD		 Annals of Emergency Medicine. Vol. 19, Pg. 47, 1990.
human LDLo oral 20mg/kg (20mg/kg) VASCULAR: BP ELEVATION NOT CHARACTERIZED IN AUTONOMIC SECTION

SENSE ORGANS AND SPECIAL SENSES: DIPLOPIA: EYE

BEHAVIORAL: COMA		 Journal Europeen de Toxicologie. Vol. 6, Pg. 86, 1973.
man LDLo oral 86mg/kg (86mg/kg) CARDIAC: OTHER CHANGES

GASTROINTESTINAL: NAUSEA OR VOMITING

CARDIAC: CHANGE IN RATE		 New England Journal of Medicine. Vol. 318, Pg. 1, 1988.
mouse LD50 intramuscular 71mg/kg (71mg/kg)   Zhongguo Yaoli Xuebao. Acta Pharmacologica Sinica. Chinese Journal of Pharmacology. Vol. 4, Pg. 69, 1983.
mouse LD50 intraperitoneal 66mg/kg (66mg/kg)   Arzneimittel-Forschung. Drug Research. Vol. 32, Pg. 1219, 1982.
mouse LD50 intravenous 21600ug/kg (21.6mg/kg)   Zhongguo Yaoli Xuebao. Acta Pharmacologica Sinica. Chinese Journal of Pharmacology. Vol. 4, Pg. 69, 1983.
mouse LD50 oral 311mg/kg (311mg/kg) LUNGS, THORAX, OR RESPIRATION: RESPIRATORY DEPRESSION

BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD

BEHAVIORAL: TREMOR		 Oyo Yakuri. Pharmacometrics. Vol. 7, Pg. 753, 1973.
mouse LD50 subcutaneous 150mg/kg (150mg/kg)   Journal Europeen de Toxicologie. Vol. 6, Pg. 86, 1973.
rabbit LD50 intravenous 8mg/kg (8mg/kg)   Therapie. Vol. 25, Pg. 823, 1970.
rabbit LD50 subcutaneous 75mg/kg (75mg/kg)   Journal Europeen de Toxicologie. Vol. 6, Pg. 86, 1973.
rabbit LDLo intramuscular 20mg/kg (20mg/kg)   Yaoxue Xuebao. Acta Pharmaceutica Sinica. Pharmaceutical Journal. Vol. 15, Pg. 630, 1980.
rat LD50 intraperitoneal 102mg/kg (102mg/kg) GASTROINTESTINAL: OTHER CHANGES Pharmacology: International Journal of Experimental and Clinical Pharmacology. Vol. 13, Pg. 401, 1975.
rat LD50 intravenous 60mg/kg (60mg/kg)   Archives Internationales de Pharmacodynamie et de Therapie. Vol. 163, Pg. 38, 1966.
rat LD50 oral 330mg/kg (330mg/kg) LUNGS, THORAX, OR RESPIRATION: DYSPNEA

BEHAVIORAL: ATAXIA

BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD		 Journal of Toxicology, Clinical Toxicology. Vol. 20, Pg. 271, 1983.
rat LD50 subcutaneous 190mg/kg (190mg/kg)   Archives Internationales de Pharmacodynamie et de Therapie. Vol. 163, Pg. 38, 1966.
women LDLo oral 110mg/kg (110mg/kg) CARDIAC: OTHER CHANGES

CARDIAC: CHANGE IN RATE

GASTROINTESTINAL: NAUSEA OR VOMITING		 New England Journal of Medicine. Vol. 318, Pg. 1, 1988.
women LDLo oral 180mg/kg (180mg/kg) BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD

CARDIAC: PULSE RATE INCREASE WITHOUT FALL IN BP

VASCULAR: BP LOWERING NOT CHARACTERIZED IN AUTONOMIC SECTION		 Medical Journal of Australia. Vol. 160, Pg. 231, 1994.
women TDLo oral 24mg/kg/12D-I (24mg/kg) BEHAVIORAL: "HALLUCINATIONS, DISTORTED PERCEPTIONS"

BRAIN AND COVERINGS: CHANGES IN SURFACE EEG

BEHAVIORAL: CHANGES IN MOTOR ACTIVITY (SPECIFIC ASSAY)		 Annals of Internal Medicine. Vol. 123, Pg. 76, 1995.
women TDLo oral 3600mg/kg/3Y (3600mg/kg)   Tropical and Geographical Medicine. Vol. 32, Pg. 216, 1980.
women TDLo oral 3600mg/kg/3Y (3600mg/kg) GASTROINTESTINAL: OTHER CHANGES

SENSE ORGANS AND SPECIAL SENSES: VISUAL FIELD CHANGES: EYE		 Tropical and Geographical Medicine. Vol. 32, Pg. 216, 1980.

Physical Properties

Physical Property Value Units Temp (deg C) Source
Melting Point 289 dec deg C   EXP
pKa Dissociation Constant 10.1 (none)   EXP
log P (octanol-water) 4.63 (none)   EXP
Water Solubility 10.6 mg/L 25 EST
Vapor Pressure 1.92E-07 mm Hg 25 EST
Henry's Law Constant 1.07E-12 atm-m3/mole 25 EST
Atmospheric OH Rate Constant 1.59E-10 cm3/molecule-sec 25 EST

Physical property data is provided to ChemIDplus by SRC, Inc.