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Substance Name: Chloroquine phosphate [USP:BAN]
RN: 50-63-5
UNII: 6E17K3343P
InChIKey: QKICWELGRMTQCR-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-N3.2H3-O4-P

Molecular Weight

  • 515.8648
 

Classification Codes

  • Analgesics
  • Analgesics, Non-Narcotic
  • Anthelmintics
  • Anti-Amebic
  • Anti-Infective Agents
  • Anti-Inflammatory Agents
  • Anti-Inflammatory Agents, Non-Steroidal
  • Antimalarial
  • Antimalarials
  • Antinematodal Agents
  • Antiparasitic Agents
  • Antiprotozoal Agents
  • Antirheumatic Agents
  • Drug / Therapeutic Agent
  • Filaricides
  • Human Data
  • Mutation Data
  • Peripheral Nervous System Agents
  • Reproductive Effect
  • Sensory System Agents
  • Suppressant (Lupus Erythematosus)
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Names and Synonyms

Name of Substance

  • Chloroquine diphosphate
  • Chloroquine phosphate [USP:BAN]

Synonyms

  • 3377 RP
  • 7-Chlor-4-(4-(diaethylamino)-1-methylbutylamino)-chinolindiphosphat
  • 7-Chlor-4-(4-(diaethylamino)-1-methylbutylamino)-chinolindiphosphat [German]
  • 7-Chloro-4-((4-(diethylamino)-1-methylbutyl)amino)quinoline phosphate (1:2)
  • AI3-14952
  • Alermine
  • Aralen
  • Aralen diphosphate
  • Aralen phosphate
  • Arechin
  • Avloclor
  • Bemaphate
  • CCRIS 1554
  • Chingamin
  • Chingamin phosphate
  • Chingaminum
  • Chlorochin diphosphate
  • Chloroquin diphosphate
  • Chloroquine dihydrogen phosphate (1:2)
  • Chloroquine diphosphate
  • Chloroquine phosphate
  • Delagil
  • dl-Chloroquine diphosphate
  • EINECS 200-055-2
  • Gontochin phosphate
  • H-Stadur
  • Ipsen 225
  • Khingamin
  • Miniquine
  • Nivaquine B
  • NSC 14050
  • Quingamine
  • Resochin
  • Resoquine
  • RP 3377
  • Sanoquin
  • SN 7,618
  • SN 7618
  • Tanakan
  • Tanakan (antimalarial)
  • Tanakene
  • UNII-6E17K3343P
  • WR 1522

Systematic Names

  • 1,4-Pentanediamine, N(sup 4)-(7-chloro-4-quinolinyl)-N(sup 1),N(sup 1)-diethyl-, phosphate (1:2)
  • 1,4-Pentanediamine, N4-(7-chloro-4-quinolinyl)-N',N'-diethyl-, (+-)-, phosphate (1:2)
  • 1,4-Pentanediamine, N4-(7-chloro-4-quinolinyl)-N1,N1-diethyl-, phosphate (1:2)
  • Chloroquine bis(phosphate)
  • Chloroquine phosphate
  • N(4)-(7-Chloro-4-quinolinyl)-N(1),N(1)-diethyl-1,4-pentanediamine, phosphate (1:2)
  • Quinoline, 7-chloro-4-((4-(diethylamino)-1-methylbutyl)amino)-, phosphate (1:2) (8CI)
  • Quinoline, 7-chloro-4-(4-diethylamino-1-methyl-butylamino)-, diphosphate

Registry Numbers

CAS Registry Number

  • 50-63-5

FDA UNII

  • 6E17K3343P

Other Registry Numbers

  • 6384-82-3
  • 69698-56-2

System Generated Number

  • 0000050635

Molecular Formulas

Molecular Formula

  • C18-H26-Cl-N3.2H3-O4-P

Molecular Formula Fragments

  • C18-H26-Cl-N3
  • COMPONENT
  • H3-O4-P

Structure Descriptors

InChI

InChI=1S/C18H26ClN3.2H3O4P/c1-4-22(5-2)12-6-7-14(3)21-17-10-11-20-18-13-15(19)8-9-16(17)18;2*1-5(2,3)4/h8-11,13-14H,4-7,12H2,1-3H3,(H,20,21);2*(H3,1,2,3,4)

InChIKey

QKICWELGRMTQCR-UHFFFAOYSA-N

Smiles

CCN(CC)CCCC(C)Nc1ccnc2cc(Cl)ccc12.OP(=O)(O)O.OP(=O)(O)O

Toxicity

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
bird - domestic LD50 intravenous 64500ug/kg (64.5mg/kg)   Arzneimittel-Forschung. Drug Research. Vol. 20, Pg. 1775, 1970.
child LDLo oral 250mg/kg (250mg/kg) BEHAVIORAL: COMA Archiv fuer Toxikologie. Vol. 23, Pg. 204, 1968.
dog LDLo intravenous 8mg/kg (8mg/kg) BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY) "A Survey of Antimalarial Drugs, 1941-1945," Wiselogle, F.Y., 2 vols., Ann Arbor, MI, J.W. Edwards, 1946Vol. 1, Pg. 390, 1946.
man LDLo oral 179mg/kg (179mg/kg)   Archiv fuer Toxikologie. Vol. 23, Pg. 204, 1968.
man TDLo oral 8571ug/kg (8.571mg/kg) GASTROINTESTINAL: OTHER CHANGES

GASTROINTESTINAL: NAUSEA OR VOMITING		 Human Toxicology. Vol. 8, Pg. 387, 1989.
man TDLo oral 8571ug/kg (8.571mg/kg) GASTROINTESTINAL: NAUSEA OR VOMITING

GASTROINTESTINAL: OTHER CHANGES

GASTROINTESTINAL: ULCERATION OR BLEEDING FROM DUODENUM		 Human Toxicology. Vol. 8, Pg. 387, 1989.
mouse LD50 intraperitoneal 68mg/kg (68mg/kg) BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD "A Survey of Antimalarial Drugs, 1941-1945," Wiselogle, F.Y., 2 vols., Ann Arbor, MI, J.W. Edwards, 1946Vol. 1, Pg. 389, 1946.
mouse LD50 oral 500mg/kg (500mg/kg)   Tropenmedizin und Parasitologie. Vol. 30, Pg. 308, 1979.
mouse LD50 subcutaneous 200mg/kg (200mg/kg)   Annals of Tropical Medicine and Parasitology. Vol. 74, Pg. 393, 1980.
rat LD50 oral 623mg/kg (623mg/kg)   EHP, Environmental Health Perspectives. Vol. 106(Suppl,
women LDLo oral 298mg/kg (298mg/kg) LUNGS, THORAX, OR RESPIRATION: OTHER CHANGES

CARDIAC: OTHER CHANGES

BEHAVIORAL: COMA		 Journal of Forensic Sciences. Vol. 41, Pg. 1077, 1996.
women TDLo oral 138mg/kg (138mg/kg) BEHAVIORAL: COMA

VASCULAR: BP LOWERING NOT CHARACTERIZED IN AUTONOMIC SECTION

LUNGS, THORAX, OR RESPIRATION: OTHER CHANGES		 Japanese Journal of Toxicology. Vol. 12, Pg. 159, 1999.
women TDLo oral 167mg/kg (167mg/kg) LUNGS, THORAX, OR RESPIRATION: RESPIRATORY DEPRESSION

CARDIAC: EKG CHANGES NOT DIAGNOSTIC OF ABOVE

VASCULAR: BP LOWERING NOT CHARACTERIZED IN AUTONOMIC SECTION		 Journal of Toxicology, Clinical Toxicology. Vol. 19, Pg. 1067, 1982/1983.
women TDLo oral 600mg/kg/17W- (600mg/kg) BEHAVIORAL: CHANGES IN MOTOR ACTIVITY (SPECIFIC ASSAY)

SENSE ORGANS AND SPECIAL SENSES: OTHER: EYE

PERIPHERAL NERVE AND SENSATION: SPASTIC PARALYSIS WITH OR WITHOUT SENSORY CHANGE		 Postgraduate Medical Journal. Vol. 55, Pg. 569, 1979.