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Amodiaquine

Catalog No. DB00613 Name DrugBank
CAS Number 86-42-0 Website http://www.ualberta.ca/
M. F. C20H22ClN3O Telephone (780) 492-3111
M. W. 355.86118 Fax (780) 492-1071
Purity Email david.wishart@ualberta.ca
Storage Chembase ID: 495

SYNONYMS

IUPAC name
4-[(7-chloroquinolin-4-yl)amino]-2-[(diethylamino)methyl]phenol
IUPAC Traditional name
amodiaquine
Brand Name
Camoquin
Flavoquin
Flavoquine
Camochin
Basoquin
CAM-AQ1
CAM-AQI
Camoquin HCL
Camoquinal
Camoquine
Miaquin
Synonyms
Amodiaquine USP24
Amodiaquine, ring-closed
Amodiaquin
Amodiaquine Hydrochloride

DATABASE IDS

PubChem SID 46506940
CAS Number 86-42-0
PubChem CID 2165

PROPERTIES

Hydrophobicity(logP) 3.7

DETAILS

Description (English)
Item Information
Drug Groups approved
Description A 4-aminoquinoquinoline compound with anti-inflammatory properties. [PubChem]
Indication For treatment of acute malarial attacks in non-immune subjects.
Pharmacology Amodiaquine, a 4-aminoquinoline similar to chloroquine in structure and activity, has been used as both an antimalarial and an anti-inflammatory agent for more than 40 years. Amodiaquine is at least as effective as chloroquine, and is effective against some chloroquine-resistant strains, although resistance to amodiaquine has been reported. The mode of action of amodiaquine has not yet been determined. 4-Aminoquinolines depress cardiac muscle, impair cardiac conductivity, and produce vasodilatation with resultant hypotension. They depress respiration and cause diplopia, dizziness and nausea.
Toxicity LD50 (mouse, intraperitoneal) 225 mg/kg, LD50 (mouse, oral) 550 mg/kg. Symptoms of overdose include headache, drowsiness, visual disturbances, vomiting, hypokalaemia, cardiovascular collapse and cardiac and respiratory arrest. Hypotension, if not treated, may progress rapidly to shock. Electrocardiograms (ECG) may reveal atrial standstill, nodal rhythm, prolonged intraventricular conduction time, broadening of the QRS complex, and progressive bradycardia leading to ventricular fibrillation and/or arrest.
Affected Organisms
Plasmodium
Biotransformation Hepatic biotransformation to desethylamodiaquine (the principal biologically active metabolite) is the predominant route of amodiaquine clearance with such a considerable first pass effect that very little orally administered amodiaquine escapes untransformed into the systemic circulation.
Absorption Rapidly absorbed following oral administration.
Half Life 5.2 ± 1.7 (range 0.4 to 5.5) minutes
References
Jewell H, Maggs JL, Harrison AC, O'Neill PM, Ruscoe JE, Park BK: Role of hepatic metabolism in the bioactivation and detoxication of amodiaquine. Xenobiotica. 1995 Feb;25(2):199-217. [Pubmed]
Harrison AC, Kitteringham NR, Clarke JB, Park BK: The mechanism of bioactivation and antigen formation of amodiaquine in the rat. Biochem Pharmacol. 1992 Apr 1;43(7):1421-30. [Pubmed]
External Links
Wikipedia

REFERENCES

  • Jewell H, Maggs JL, Harrison AC, O'Neill PM, Ruscoe JE, Park BK: Role of hepatic metabolism in the bioactivation and detoxication of amodiaquine. Xenobiotica. 1995 Feb;25(2):199-217. Pubmed
  • Harrison AC, Kitteringham NR, Clarke JB, Park BK: The mechanism of bioactivation and antigen formation of amodiaquine in the rat. Biochem Pharmacol. 1992 Apr 1;43(7):1421-30. Pubmed