Amodiaquine

• Catalog No.: DB00613
• CAS Number: 86-42-0
• M. F.: C20H22ClN3O
• M. W.: 355.86118

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)

• 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