Atophan

ATOPHAN, 2-phenylquinoline-4-carboxylic acid, phenylcinchonic acid, Atophanum, Acidum phenylcinchoninicum, is obtained by the action of benzaldehyde and pyruvic acid on aniline or acetophenone on isatin. Yellowish crystalline powder or colorless needles, melts at 210-213°, bitter taste; insoluble in water, easily soluble in alcohol and ether, as well as in aqueous solutions of alkalis with the formation of alkali salts, or in aqueous acids with the formation of corresponding salts (amphoteric compound). In concentrated sulfuric acid with slight heating, it dissolves forming a yellow-colored solution; solution in HCl with bromine water gives an orange-yellow precipitate; alcoholic solution with ferric chloride gives a reddish-brown coloring [other reactions - see Ф (VII), 1925].

A. is used in gout, joint rheumatism and other rheumatic diseases. When introduced into the body (0.5 - 3.0), it causes increased excretion of uric acid, apparently acting in a peculiar way on the kidneys and thereby causing increased passage of uric acid through the kidneys; a day after taking A., the excretion of uric acid by the kidneys falls even below normal. The effect on the kidneys apparently belongs not to A. itself, but to the oxyatophan (8-hydroxy-2-phenylquinoline-4-carboxylic acid) formed from it in the body.

Atophan and its derivatives exert not only anti-gout but also a clearly expressed antiseptic, anti-inflammatory and analgesic effect, almost to the same degree as salicylate preparations. Lit.: Kravkov N., Osnovy farmakologii, M.-L., 1928; Frankel S., Die Arzneimittelsynthese, Berlin, 1927; Hagers Handbuch d. pharmazeutischen Praxis, B., 1925.