Structural Formula Vector Image
Title: Sulbactam
CAS Registry Number: 68373-14-8
CAS Name: (2S,5R)-3,3-Dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid 4,4-dioxide
Additional Names: penicillanic acid sulfone; penicillanic acid 1,1-dioxide
Manufacturers' Codes: CP-45899
Molecular Formula: C8H11NO5S
Molecular Weight: 233.24
Percent Composition: C 41.20%, H 4.75%, N 6.01%, O 34.30%, S 13.75%
Literature References: Semi-synthetic b-lactamase inhibitor. Prepn and use with b-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). b-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).
Properties: White, crystalline solid, mp 148-151° (Barth); also reported as mp 154-155.5° (dec) (Barth); also reported as mp 170° (dec) (Volkmann). [a]D20 +251° (c = 0.01 in pH 5.0 buffer). Sol in water.
Melting point: mp 148-151° (Barth); mp 154-155.5° (dec) (Barth); mp 170° (dec) (Volkmann)
Optical Rotation: [a]D20 +251° (c = 0.01 in pH 5.0 buffer)
Derivative Type: Sodium salt
CAS Registry Number: 69388-84-7
Manufacturers' Codes: CP-45899-2
Trademarks: Betamaze (Pfizer)
Molecular Formula: C8H10NNaO5S
Molecular Weight: 255.22
Percent Composition: C 37.65%, H 3.95%, N 5.49%, Na 9.01%, O 31.34%, S 12.56%
Derivative Type: Mixture of sodium salt with ampicillin sodium
CAS Registry Number: 117060-71-6
Trademarks: Loricin (Sigma-Tau); Unacim (Pfizer); Unasyn (inj.) (Pfizer)
Derivative Type: Mixture of sodium salt with cefoperazone sodium
Trademarks: Sulperazone (Pfizer)
Derivative Type: Compd with ampicillin see Sultamicillin
Therap-Cat: In combination with b-lactam antibiotics as antibacterial.
Keywords: Antibacterial Adjuncts; ?Lactamase Inhibitors.

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