9083. Tazobactam

Nomenclature

CAS number: 89786-04-9
(2S,3S,5R)-3-Methyl-7-oxo-3-(1H-1,2,3-triazol-1-ylmethyl)-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid 4,4-dioxide; 2β-[(1,2,3-triazol-1-yl)methyl]-2α-methylpenam-3α-carboxylic acid 1,1-dioxide; YTR-830H; CL-298741.
C10H12N4O5S; mol wt 300.29.
C 40.00%, H 4.03%, N 18.66%, O 26.64%, S 10.68%.

Description and references

β-Lactamase inhibitor. Prepn: R. G. Micetich et al., EP 97446; eidem, US 4562073 (1984, 1985 both to Taiho); R. G. Micetich et al., J. Med. Chem. 30, 1469 (1987). Degradation in solution: T. Marunaka et al., Chem. Pharm. Bull. 36, 4478 (1988); in solid state: E. Matsushima et al., ibid. 4593. β-Lactamase inhibiting activity in comparison with clavulanic acid and sulbactam, q.q.v., vs aerobes: M. R. Jacobs et al., Antimicrob. Agents Chemother. 29, 980 (1986); vs anaerobes: P. C. Appelbaum et al., ibid. 30, 789. HPLC determn in biological materials: T. Marunaka et al., J. Chromatogr. 431, 87 (1988). Clinical trial in combination with piperacillin, q.v.: I. M. Gould et al., Drugs Exp. Clin. Res. 17, 187 (1991).

Chemical structure

Derivative

Sodium salt.

Nomenclature

CAS number: 89785-84-2
YTR-830; CL-307579.
C10H11N4NaO5S; mol wt 322.27.
C 37.27%, H 3.44%, N 17.39%, Na 7.13%, O 24.82%, S 9.95%.

Properties

Amorphous solid, mp >170° (dec).

Derivative

Combination of sodium salt with piperacillin sodium.

Nomenclature

Tazocilline (Wyeth); Tazocin (Wyeth); Zosyn (Wyeth).

Therapeutic Category

In combination with β-lactam antibiotics as antibacterial.

Keywords

Antibacterial Adjuncts; β-Lactamase Inhibitors