Cycloserine
Title: Cycloserine
CAS Registry Number: 68-41-7
CAS Name: D-4-Amino-3-isoxazolidinone
Additional Names: D-4-amino-3-isoxazolidone; orientomycin
Manufacturers' Codes: PA-94; 106-7
Trademarks: Closina; Farmiserina (Farmitalia); Micoserina; Oxamycin (Merck & Co.); Seromycin (Lilly)
Molecular Formula: C3H6N2O2
Molecular Weight: 102.09
Percent Composition: C 35.29%, H 5.92%, N 27.44%, O 31.34%
Literature References: Antibiotic substance produced by Streptomyces garyphalus sive orchidaceus: Kuehl, Jr., et al., J. Am. Chem. Soc. 77, 2344 (1955); Hidy et al., ibid. 2345; Shull, Sardinas, Antibiot. Chemother. 5, 398 (1955); Shull et al., US 2773878 (1956 to Pfizer); Harned, US 2789983 (1957 to Commercial Solvents); GB 768007 (1957 to Commercial Solvents), C.A. 51, 10847e (1957); US 3124590 (1964 to Commercial Solvents); Howe, US 2845433 (1958 to Merck & Co.). Synthesis: Stammer et al., J. Am. Chem. Soc. 77, 2346 (1955); Peck, US 2772280 (1956 to Merck & Co.); Plattner et al., Helv. Chim. Acta 40, 1531 (1957); Holly, Stammer, US 2840565 (1958 to Merck & Co.). Prepn of crystalline calcium and magnesium salts: Harris et al., US 2832788 (1958 to Merck & Co.). HPLC determn in plasma and urine: D. G. Musson et al., J. Chromatogr. 414, 121 (1987). Comprehensive description: J. W. Lamb, Anal. Profiles Drug Subs. 1, 53-64 (1972); H. A. El-Obeid, A. A. Al-Badr, ibid. 18, 567-597 (1989).
Properties: Crystals, decomp 155-156°. [a]D23 +116° (c = 1.17); [a]25546 +137° (c = 5 in 2N NaOH). uv max: 226 nm (E1%1cm 402). Sol in water, slightly sol in methanol, propylene glycol. Aq solns have a pH around 6. Forms salts with acids and bases. Neutral or acid solns are unstable. Aq solns buffered to pH 10 with sodium carbonate can be stored without loss for one week at refrigerator temps.
Optical Rotation: [a]D23 +116° (c = 1.17); [a]25546 +137° (c = 5 in 2N NaOH)
Absorption maximum: uv max: 226 nm (E1%1cm 402)
Therap-Cat: Antibacterial (tuberculostatic).
Keywords: Antibacterial (Antibiotics); Antibacterial (Tuberculostatic).

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