65-45-2

Description

Salicylamide is a white crystalline powder that is derived from salicylic acid and used as an analgesic and antipyretic. It is absorbed from the GI tract on oral administration and is rapidly metabolized to inactive metabolites by intestinal mucosa, but not by hydrolysis. Activity appears to reside in the intact molecule. Salicylamide is approximately 40 to 55% plasma protein bound, and it competes with other salicylates and acetaminophen for glucuronide conjugation, decreasing the extent of conjugation of these other drugs. It is also excreted much more rapidly than other salicylates,which accounts for its lower toxicity. It is available inseveral nonprescription products, in combination with acetaminophenand phenyltoloxamine (e.g., Rid-A Pain compound,Cetazone T, Dolorex, Ed-Flex, Lobac) or with aspirin,acetaminophen, and caffeine (e.g., Saleto, BC Powder).

Uses

Medicine (analgesic).

Whereas salicylamide is reported to be as effective as aspirin as an analgetic/antipyretic and is effective in relieving pain associated with arthritic conditions, it does not appear to possess useful anti-inflammatory activity. Thus, indications for the treatment of arthritic disease states are unwarranted, and its use is restricted to the relief of minor aches and pain at a dosage of 325 to 650 mg three or four times per day. Its effects in humans are not reliable, however, and its use is not widely recommended.

Definition

ChEBI: The simplest member of the class of salicylamides derived from salicylic acid.

Air & Water Reactions

Salicylamide darkens on exposure to air. . Insoluble in water.

Fire Hazard

Flash point data for Salicylamide are not available; however, Salicylamide is probably combustible.

Purification Methods

Crystallise the amide from water or repeatedly from CHCl3 [Nishiya et al. J Am Chem Soc 108 3880 1986]. [Beilstein 10 IV 169.] The anilide [87-17-2] M 213.2, m 135o crystallises from H2O. [Beilstein 12 H 500, 12 I 268, 12 II 256, 12 944.]