8889. Sulbactam

Nomenclature

CAS number: 68373-14-8
(2S,5R)-3,3-Dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid 4,4-dioxide; penicillanic acid sulfone; penicillanic acid 1,1-dioxide; CP-45899.
C8H11NO5S; mol wt 233.24.
C 41.20%, H 4.75%, N 6.01%, O 34.30%, S 13.75%.

Description and references

Semi-synthetic β-lactamase inhibitor. Prepn and use with β-lactam antibiotics: BE 867859; W. E. Barth, US 4234579 (1978, 1980 both to Pfizer); R. A. Volkmann et al., J. Org. Chem. 47, 3344 (1982). β-Lactamase activity and antibacterial spectrum in vitro: A. R. English et al., Antimicrob. Agents Chemother. 14, 414 (1978); R. N. Jones et al., Diagn. Microbiol. Infect. Dis. 3, 489 (1985). HPLC determn in human plasma and urine: J. Haginaka et al., J. Chromatogr. 341, 115 (1985). Pharmacokinetics in humans: G. Foulds et al., Antimicrob. Agents Chemother. 23, 692 (1983). Clinical study of synergistic effect with ampicillin: S. Mehtar et al., J. Antimicrob. Chemother. 17, 389 (1986); B. V. Stromberg et al., Surg. Gynecol. Obstet. 162, 575 (1986). Review of activity and therapeutic use of sulbactam with ampicillin: D. M. Campoli-Richards, R. N. Brogden, Drugs 33, 577-609 (1987).

Chemical structure

Properties

White, crystalline solid, mp 148-151° (Barth); also reported as mp 154-155.5° (dec) (Barth); also reported as mp 170° (dec) (Volkmann). [α]D20 +251° (c = 0.01 in pH 5.0 buffer). Sol in water.

Derivative

Sodium salt.

Nomenclature

CAS number: 69388-84-7
CP-45899-2; Betamaze (Pfizer).
C8H10NNaO5S; mol wt 255.22.
C 37.65%, H 3.95%, N 5.49%, Na 9.01%, O 31.34%, S 12.56%.

Derivative

Mixture of sodium salt with ampicillin sodium.

Nomenclature

CAS number: 117060-71-6
Loricin (Sigma-Tau); Unacim (Pfizer); Unasyn (inj.) (Pfizer).

Derivative

Mixture of sodium salt with cefoperazone sodium.

Nomenclature

Sulperazone (Pfizer).

Derivative

Compd with ampicillin see Sultamicillin.

Therapeutic Category

In combination with β-lactam antibiotics as antibacterial.

Keywords

Antibacterial Adjuncts; β-Lactamase Inhibitors