Sulbactam

Sulbactam

Systematic (IUPAC) name
(2S,5R)-3,3-Dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid 4,4-dioxide
Clinical data
AHFS/Drugs.com	International Drug Names
MedlinePlus	a693021
Legal status	UK: Prescription-only (POM)
Routes of administration	Injection
Pharmacokinetic data
Bioavailability	1
Excretion	Kidneys?
Identifiers
CAS Registry Number	68373-14-8 Y
ATC code	J01CG01
PubChem	CID 130313
ChemSpider	115306 Y
UNII	S4TF6I2330 Y
KEGG	D08533 Y
ChEBI	CHEBI:9321 Y
ChEMBL	CHEMBL403 Y
Chemical data
Formula	C8H11NO5S
Molecular mass	233.243 g/mol
SMILES O=S2(=O)C([C@@H](N1C(=O)C[C@H]12)C(=O)O)(C)C
InChI 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  Y Key:FKENQMMABCRJMK-RITPCOANSA-N  Y
Y (what is this?)  (verify)

Sulbactam is a β-lactamase inhibitor. This drug is given in combination with β-lactam antibiotics to inhibit β-lactamase, an enzyme produced by bacteria that destroys the antibiotics. ^[1]

Mechanism

Sulbactam is an irreversible inhibitor of β-lactamase; it binds to the enzyme and does not allow it to degrade the antibiotic.

Uses

Sulbactam is able to inhibit the most common forms of β-lactamase but is not able to interact with the ampC cephalosporinase. Thus, it confers little protection against bacteria such as Pseudomonas aeruginosa, Citrobacter, Enterobacter, and Serratia, which often express this gene.

In the United States, sulbactam is combined to form cefoperazone/sulbactam and ampicillin/sulbactam. It does possess some antibacterial activity when administered alone, but it is too weak to have any clinical importance. Its use in the UK is restricted to hospitals.

Recently, its use in treating Acinetobacter septicemia is receiving renewed interest.

See also

• Tazobactam

References

1. ↑ Totir MA, Helfand MS, Carey MP et al. (August 2007). "Sulbactam forms only minimal amounts of irreversible acrylate-enzyme with SHV-1 beta-lactamase". Biochemistry 46 (31): 8980–7. doi:10.1021/bi7006146. PMC 2596720. PMID 17630699.  CS1 maint: Explicit use of et al. (link)

Further reading

• Singh GS (January 2004). "Beta-lactams in the new millennium. Part-II: cephems, oxacephems, penams and sulbactam". Mini Rev Med Chem 4 (1): 93–109. doi:10.2174/1389557043487547. PMID 14754446.