CYCLOSERINE

CYCLOSERINE

This compound was discovered in 1955 by five independent groups of workers. It has been isolated from three different species of Streptomyces: Streptomyces garyphalus, S lavendulae, and S, orchidaceae. Its structure was established by acid degradation to serine and hydroxylamine and by hydrogenation to D-serine amide. The compound exists in equilibrium with its enol form. In aqueous solutions, cycloserine will form a dipolar ion that, on standing, will dimerize to 2,5- bis (aminoxymethyl) -3,6-diketopiperazine.

Cycloserine is a white to pale yellow hygroscopic, crystalline material that is soluble in water; m.p. 155-156° (decomp). Aqueous solution of cycloserine has a pH around 6. It forms stable salts with strong acids and bases; the neutral or acid solutions are unstable. its racemic mixture is more active than either D-or L-form. It is stored at a temperature not exceeding 25° in airtight containers.

Uses:

Cycloserine is a secondary antituberculous agent and is used when primary agents have been ineffective or when their use is precluded due to intolerance or the presence of resistant organisms. It is also used in the treatment of urinary-tract infections unresponsive to other therapy. Its relatively weak potency and frequent toxic reactions limit its use to the treatment of tuberculosis.

Adverse effect

Adverse effects of cycloserine are dose-related and include anxiety, confusion, disorientation, depression, irritability and paranoia.