Sulbactam Chemical Properties

Melting point:

154-157℃

alpha 

D20 +251° (c = 0.01 in pH 5.0 buffer)

Boiling point:

567.7±50.0 °C(Predicted)

Density 

1.62±0.1 g/cm3(Predicted)

storage temp. 

2-8°C

solubility 

H2O: ≥18mg/mL

form 

lyophilized powder

pka

2.62±0.40(Predicted)

color 

white to tan

optical activity

[α]/D ≥+225°, c = 1 in H2O

Water Solubility 

Soluble in water at 18mg/ml

Merck 

14,8889

Stability:

Hygroscopic

InChIKey

FKENQMMABCRJMK-RITPCOANSA-N

CAS DataBase Reference

68373-14-8

Safety Information

Hazard Codes 

Xn

Risk Statements 

22

Safety Statements 

24/25

WGK Germany 

3

HS Code 

29349990

MSDS

• Language:English Provider:Sulbactam

Sulbactam Usage And Synthesis

Description

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.

Originator

Sulbactam-Sodium,Antibiotic Co.,Bulgaria

Uses

antidepressant, dopamine uptake inhibitor

Uses

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.

Uses

A β-lactamase inhibitor.

Definition

ChEBI: Sulbactam is a member of penicillanic acids.

Manufacturing Process

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.

Therapeutic Function

Beta-lactamase inhibitor

Antimicrobial activity

Sulbactam has very weak antimicrobial activity against most bacteria. Its only notable activity is against N. gonorrhoeae, N. meningitidis and Acinetobacter baumannii.

Clinical Use

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.

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