Structural Formula Vector Image
Title: Hydroxychloroquine
CAS Registry Number: 118-42-3
CAS Name: 2-[[4-[(7-Chloro-4-quinolinyl)amino]pentyl]ethylamino]ethanol
Additional Names: 7-chloro-4-[4-[ethyl(2-hydroxyethyl)amino]-1-methylbutylamino]quinoline; 7-chloro-4-[4-(N-ethyl-N-b-hydroxyethylamino)-1-methylbutylamino]quinoline; 7-chloro-4-[5-(N-ethyl-N-2-hydroxyethylamino)-2-pentyl]aminoquinoline; oxychloroquine; oxichlorochine
Molecular Formula: C18H26ClN3O
Molecular Weight: 335.87
Percent Composition: C 64.37%, H 7.80%, Cl 10.56%, N 12.51%, O 4.76%
Literature References: Prepd by reacting a mixture of 4,7-dichloroquinoline, phenol and N¢-ethyl-N¢-b-hydroxyethyl-1,4-pentadiamine at 125-130°: Surrey, Hammer, J. Am. Chem. Soc. 72, 1814 (1950); Surrey, US 2546658 (1951 to Sterling Drug). Use in combination with cyclophosphamide and azathioprine, q.q.v. in the treatment of rheumatoid arthritis: D. J. McCarty, G. F. Carrera, J. Am. Med. Assoc. 248, 1718 (1982). Reassessment in the treatment of rheumatoid arthritis: Am. J. Med. 75, no. 1A, 1-56 (1983). Series of articles on clinical use: ibid. 85, Suppl. 4A, 1-71 (1988).
Properties: Crystals from ethylene dichloride and Skellysolve B; mp 89-91°.
Melting point: mp 89-91°
Derivative Type: Diphosphate
Molecular Formula: C18H26ClN3O.2H3PO4
Molecular Weight: 531.86
Percent Composition: C 40.65%, H 6.06%, Cl 6.67%, N 7.90%, O 27.07%, P 11.65%
Properties: Recrystallized from ethanol, mp 168-170° (dec).
Melting point: mp 168-170° (dec)
Derivative Type: Sulfate
CAS Registry Number: 747-36-4
Trademarks: Ercoquin; Plaquenil Sulfate (Winthrop); Quensyl
Molecular Formula: C18H26ClN3O.H2SO4
Molecular Weight: 433.95
Percent Composition: C 49.82%, H 6.50%, Cl 8.17%, N 9.68%, O 18.43%, S 7.39%
Properties: White crystalline powder; odorless but has a bitter taste. pH of aq solns about 4.5. Exists in two forms, the usual form mp ~240°, the other mp ~198°. Freely sol in water. Practically insol in alcohol, chloroform, ether.
Melting point: mp ~240°; mp ~198°
Therap-Cat: Antimalarial; antirheumatic; lupus erythematosus suppressant.
Keywords: Antimalarial; Antiarthritic/Antirheumatic; Lupus Erythematosus Suppressant.

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