Pyrazinamide
Title: Pyrazinamide
CAS Registry Number: 98-96-4
CAS Name: Pyrazinecarboxamide
Additional Names: pyrazinoic acid amide; pyrazine carboxylamide
Manufacturers' Codes: D-50
Trademarks: Pezetamid (Hefa-Frenon); Pyrafat (Fatol); Pirilène (Cassenne); Piraldina (Bracco); Tebrazid (Searle); Unipyranamide (Unichem); Zinamide (Merck & Co.)
Molecular Formula: C5H5N3O
Molecular Weight: 123.11
Percent Composition: C 48.78%, H 4.09%, N 34.13%, O 13.00%
Literature References: Prepn: O. Dalmer, E. Walter, DE 632257 (1936 to E. Merck); eidem, US 2149279 (1939 to Merck & Co.); S. A. Hall, P. E. Spoerri, J. Am. Chem. Soc. 62, 664 (1940). Structure-activity study: S. Kushner et al., ibid. 74, 3617 (1952). Pharmacology: I. M. Weiner, J. P. Tinker, J. Pharmacol. Exp. Ther. 180, 411 (1972). HPLC determn in biological samples: J. E. Conte, Jr. et al., J. Chromatogr. Sci. 38, 33 (2000). Clinical pharmacokinetics: C. A. Peloquin et al., Pharmacotherapy 18, 1205 (1998). Clinical trial in combination with rifampicin and isoniazid, q.q.v.: S. K. Teo, Int. J. Tuberc. Lung Dis. 3, 126 (1999); in prevention of tuberculosis: F. Gordin et al., J. Am. Med. Assoc. 283, 1445 (2000). Comprehensive description: E. Feldner, D. Pitre, Anal. Profiles Drug Subs. 12, 433-462 (1983). Review of clinical experience: M. A. Steele, R. M. Des Prez, Chest 94, 845-850 (1988).
Properties: Crystals from water or alcohol, mp 189-191°. Begins to sublime at 60°. pKa 0.5. uv max: 269 nm (E1%1cm 660). Soly (mg/ml): water 15; methanol 13.8; abs ethanol 5.7; isopropanol 3.8; ether 1.0; isooctane 0.01; chloroform 7.4. Aq solns are neutral.
Melting point: mp 189-191°
pKa: pKa 0.5
Absorption maximum: uv max: 269 nm (E1%1cm 660)
Therap-Cat: Antibacterial (tuberculostatic).
Keywords: Antibacterial (Tuberculostatic).

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