4-[(7-chloroquinolin-4-yl)amino]-2-[(diethylamino)methyl]phenol

• ChemBase ID: 495
• Molecular Formular: C20H22ClN3O
• Molecular Mass: 355.86118
• Monoisotopic Mass: 355.14514002
• SMILES: Clc1cc2nccc(Nc3cc(CN(CC)CC)c(O)cc3)c2cc1
• Canonical SMILES: CCN(Cc1cc(ccc1O)Nc1ccnc2c1ccc(c2)Cl)CC
• InChI: InChI=1S/C20H22ClN3O/c1-3-24(4-2)13-14-11-16(6-8-20(14)25)23-18-9-10-22-19-12-15(21)5-7-17(18)19/h5-12,25H,3-4,13H2,1-2H3,(H,22,23)
• InChIKey: OVCDSSHSILBFBN-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 4-[(7-chloroquinolin-4-yl)amino]-2-[(diethylamino)methyl]phenol
• IUPAC Traditional name: amodiaquine; 4-[(7-chloroquinolin-4-yl)amino]-2-[(diethylamino)methyl]phenol
• Brand Name: Basoquin; CAM-AQ1; CAM-AQI; Camochin; Camoquin; Camoquin HCL; Camoquinal; Camoquine; Flavoquin; Flavoquine; Miaquin
• Synonyms: Amodiaquin; Amodiaquine USP24; Amodiaquine, ring-closed; Amodiaquine Hydrochloride; Amodiaquine; 4-[(7-Chloro-4-quinolinyl)amino]-2-[(diethylamino)methyl]phenol; 4-[(7-Chloro-4-quinolyl)amino]-α-(diethylamino)-o-cresol; Camochin; Camoquin; Camoquinal; Camoquine; Flavoquine; Miaquin; NSC 13453; SN-10751; Amodiaquine

Database IDs

• CAS Number: 86-42-0
• PubChem SID: 46506940; 160963958
• PubChem CID: 2165
• CHEBI ID: 2674
• ATC CODE: P01BA06
• CHEMBL: 682
• Chemspider ID: 2080
• DrugBank ID: DB00613
• KEGG ID: D02922
• Unique Ingredient Identifier: 220236ED28
• Wikipedia Title: Amodiaquine

CALCULATED PROPERTIES

JChem

• Acid pKa: 9.124549
• H Acceptors: 4
• H Donor: 2
• LogD (pH = 5.5): 0.25545564
• LogD (pH = 7.4): 2.2423055
• Log P: 3.7630057
• Molar Refractivity: 103.2911 cm^3
• Polarizability: 40.890427 Å^3
• Polar Surface Area: 48.39 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 4.83
• LOG S: -4.61
• Solubility (Water): 8.80e-03 g/l

PROPERTIES

Physical Property

• Solubility: DMSO; Ethanol; Methanol
• Apperance: Off-White to Pale Yellow Solid
• Melting Point: >208°C (dec.)
• Hydrophobicity(logP): 3.7

Safety Information

• Storage Condition: -20°C Freezer

Pharmacology Properties

• Half Life: 5.2 ± 1.7 (range 0.4 to 5.5) minutes
• Mechanism of Action: acts on the erythrocytic stages of the parasite; Rapidly-acting blood schizonticide; Some gametocytocidal activity

Product Information

• Application(s): Antimalarial drug; Protozoacide

DETAILS

DrugBank - DB00613

• 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

Toronto Research Chemicals - A634200

An antimalarial.

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
• Natarajan, L., et al.: Arzneim.-Forsch., 22, 1230 (1972)
• Kracmer, J., et al.: Pharmazie, 29, 773 (1972)
• Ahmad, I., et al.: Anal. Profiles Drug Subs., 21, 43 (1972)
• Burckhalter, J.H. et al., J.A.C.S., 1948, 70, 1363, (synth)
• Natarajan, P.N. et al., Arzneim.-Forsch., 1972, 22, 1230, (synth)
• Kang, I.P.S. et al., J. Pharm. Pharmacol., 1974, 26, 201, (ir)
• Barrow, A., Xenobiotica, 1974, 4, 669, (metab)
• Winstanley, P.A. et al., Br. J. Clin. Pharmacol., 1990, 29, 479, (tox)
• Ahmad, I. et al., Anal. Profiles Drug Subst., 1992, 21, 43, (rev)
• Martindale, The Extra Pharmacopoeia, 30th edn., Pharmaceutical Press, 1993, 395