2163. Chloroquine

Nomenclature

CAS number: 54-05-7
N4-(7-Chloro-4-quinolinyl)-N1,N1-diethyl-1,4-pentanediamine; 7-chloro-4-(4-diethylamino-1-methylbutylamino)quinoline; SN-7618; RP-3377.
C18H26ClN3; mol wt 319.87.
C 67.59%, H 8.19%, Cl 11.08%, N 13.14%.

Description and references

Prepd by the condensation of 4,7-dichloroquinoline with 1-diethylamino-4-aminopentane: DE 683692 (1939); H. Andersag et al., US 2233970 (1941 to Winthrop); Surrey, Hammer, J. Am. Chem. Soc. 68, 113 (1946). Review: Hahn in Antibiotics vol. 3, J. W. Corcoran, F. E. Hahn, Eds. (Springer-Verlag, New York, 1975) pp 58-78. Comprehensive description: D. D. Hong, Anal. Profiles Drug Subs. 5, 61-85 (1976). Comparative clinical trial with dapsone in rheumatoid arthritis: P. D. Fowler et al., Ann. Rheum. Dis. 43, 200 (1984); with penicillamine: T. Gibson et al., Br. J. Rheumatol. 26, 279 (1987).

Chemical structure

Properties

mp 87°.

Derivative

Diphosphate.

Nomenclature

CAS number: 50-63-5
Arechin (Polfa); Avloclor (AstraZeneca); Malaquin (Ahn Gook); Resochin (Bayer).
C18H26ClN3.2H3PO4; mol wt 515.86.
C 41.91%, H 6.25%, Cl 6.87%, N 8.15%, P 12.01%, O 24.81%.

Properties

Bitter, colorless crystals. Dimorphic. One modification, mp 193-195°; the other, mp 215-218°. Freely sol in water; pH of 1% soln about 4.5; less sol at neutral and alkaline pH. Stable to heat in solns of pH 4.0 to 6.5. Practically insol in alcohol, benzene, chloroform, ether.

Derivative

Sulfate.

Nomenclature

CAS number: 132-73-0
Aralen (Sanofi-Synthelabo); Nivaquine (Aventis).
C18H26ClN3.H2SO4; mol wt 417.95.
C 51.73%, H 6.75%, Cl 8.48%, N 10.05%, S 7.67%, O 15.31%.

Therapeutic Category

Antimalarial; antiamebic; antirheumatic. Lupus erythematosus suppressant.

Keywords

Antiamebic; Antiarthritic/Antirheumatic; Antimalarial; Lupus Erythematosus Suppressant