S9701

Sulbactam

• Synonym(s): (2S,5R)-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid 4,4-dioxide, Betamaze, CP 45899, CP-45,899, Penicillanic acid 1,1-dioxide, Penicillanic acid S,S-dioxide, Penicillanic acid dioxide, Penicillanic acid sulfone
• Empirical Formula (Hill Notation): C₈H₁₁NO₅S
• CAS Number: 68373-14-8
• Molecular Weight: 233.24
• EC Number: 269-878-2
• MDL number: MFCD00867005
• UNSPSC Code: 12352200
• PubChem Substance ID: 329824632
• NACRES: NA.77

Properties

• Assay: ≥98% (HPLC)
• Quality Level: 100
• form: powder
• optical activity: [α]/D ≥+225°, c = 1 in H₂O
• color: white to tan
• solubility: H₂O: ≥18 mg/mL
• storage temp.: 2-8°C
• SMILES string: CC1(C)[C@@H](N2[C@@H](CC2=O)S1(=O)=O)C(O)=O
• InChI: 1S/C8H11NO5S/c1-8(2)6(7(11)12)9-4(10)3-5(9)15(8,13)14/h5-6H,3H2,1-2H3,(H,11,12)/t5-,6+/m1/s1
• InChI key: FKENQMMABCRJMK-RITPCOANSA-N

Description

General description

Sulbactam is a semi-synthetic penicillinate sulfone derived from 6-aminopenicllanic acid. This β-lactam compound is characterized by a β-lactam ring.

Application

Sulbactam has been used as a β-Lactamase inhibitor in β-lactamase inhibitor assay. It has also been used to evaluate its antimicrobial pharmacodynamic effects against extremely drug-resistant Acinetobacter baumannii. Sulbactam may be used in cell signaling studies.

Biochem/physiol Actions

Sulbactam acts as an irreversible inhibitor of β-lactamases that inactivate β-lactams such as penicillin and cephalosporin. It is also active against bacteroides and certain chromosomally mediated enzymes of Gram-negative bacteria. It exhibits limited antimicrobial activity. However, sulbactam in combination with other potential antibiotics exhibits therapeutic effects against multidrug-resistant Acinetobacter baumannii infections.

Safety Information

• Pictograms: GHS08
• Signal Word: Danger
• Hazard Statements: H317,H334
• Precautionary Statements: P261 - P272 - P280 - P284 - P302 + P352 - P333 + P313
• Hazard Classifications: Resp. Sens. 1 - Skin Sens. 1
• Storage Class Code: 11 - Combustible Solids
• WGK: WGK 3
• Flash Point(F): Not applicable
• Flash Point(C): Not applicable