Sulbactam is prepared by partial chemical synthesis from
penicillins. The oxidation of the sulfur atom to a sulfone greatly enhances the potency of sulbactam. The
combination of sulbactam and ampicillin (Unasyn) is now clinically popular.
White crystalline solid, melting point 148-151°C; melting point 154-155°C (decomposition) also reported. [α]D20+251° (C=0.01, Ph=5 buffer solution). Soluble in water. Sulbactam Sodium (Sulbactam Sodium): C8H10NNaO5S.[69388-84-7]. White or off-white crystalline powder, soluble in water.
Sulbactam-Sodium,Antibiotic Co.,Bulgaria
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Sulbactam sodium is a semi-synthetic penem antibiotic formed by the oxidation of penicillanic acid to its sulfone and was invented by Barth at Pfizer in 1978. Sulbactam sodium is a weak antibiotic but its action as an irreversible inhibitor of β-lactamase is exploited to block the degradation of other penicillin derivatives. Sulbactam acts as a synergist with cephalosporins and penicillins against Gram positive bacteria and is used commercially in combination with ampicillin.
ChEBI: Sulbactam is a member of penicillanic acids.
Sulbactam sodium is semi-synthetic antibiotic of penicillinic group. Start
material for it's synthesis is 6-aminopenicillanic acid. First 6-aminopenicillanic
acid was isolated in 1957 year from benzylpenicilline as resalt of treating of it
by penicillinaze. Benzylpenicilline is produced by microorganism of genus
Streptomyces.
Further, 6-aminopenicillanic acid reacted with bromine, hydrochloric acid and
NaNO2. As a result the 6,6-dibromopenicillanic acid was obtained.
6,6-Dibromopenicillanic acid was oxidized by KMnO4, to give 6,6-dibromo-1,1-The 6,6-dibromo-1,1-dioxopenicillanic acid in presence of Fe was converted to
the 1,1-dioxopenicillanic acid (sulbactam acid). The sulbactam acid was
treated by sodium 2-ethylhexanoate and crude sulbactam sodium was
obtained.
Sulbactam has very weak antimicrobial activity against most
bacteria. Its only notable activity is against N. gonorrhoeae,
N. meningitidis and Acinetobacter baumannii.
Sulbactam is penicillanic acid sulfone or 1,1-dioxopenicillanicacid. This synthetic penicillin derivative is a potent inhibitorof S. aureus β-lactamase as well as many β-lactamaseselaborated by Gram-negative bacilli. Sulbactam has weak intrinsicantibacterial activity but potentiates the activity ofampicillin and carbenicillin against β-lactamase–producingS. aureus and members of the Enterobacteriaceae family. Itdoes not, however, synergize with either carbenicillin or ticarcillinagainst P. aeruginosa strains resistant to these agents.Failure of sulbactam to penetrate the cell envelope is a possibleexplanation for the lack of synergy.
Fixed-dose combinations of ampicillin sodium and sulbactamsodium, marketed under the trade name Unasyn assterile powders for injection, have been approved for use inthe United States. These combinations are recommended forthe treatment of skin, tissue, intra-abdominal, and gynecologicalinfections caused by β-lactamase–producing strainsof S. aureus, E. coli, Klebsiella spp., P. mirabilis, B. fragilis,and Enterobacter and Acinetobacter spp.
