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
Pregnancy cat.	?
Legal status	POM (UK)
Routes	Injection
Pharmacokinetic data
Bioavailability	1
Excretion	Kidneys?
Identifiers
CAS 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
Mol. 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 beta-lactamase inhibitor. This molecule is given in combination with beta-lactam antibiotics to inhibit beta-lactamase, an enzyme produced by bacteria that destroys the antibiotics.

Mechanism

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

Uses

Sulbactam is able to inhibit the most common forms of beta-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 Acinetebacter septicemia is receiving renewed interest,

See also

Tazobactam

References

• 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.