Sulbactam

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]

Sulbactam

Clinical data
AHFS/Drugs.com	International Drug Names
MedlinePlus	a693021
Routes of administration	Injection
ATC code	J01CG01 (WHO)
Legal status
Legal status	UK: POM (Prescription only)
Pharmacokinetic data
Bioavailability	1
Excretion	Kidneys?
Identifiers
IUPAC name (2S,5R)-3,3-Dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid 4,4-dioxide
CAS Number	68373-14-8^Y
PubChem CID	130313
ChemSpider	115306^Y
UNII	S4TF6I2330
KEGG	D08533^Y
ChEBI	CHEBI:9321^Y
ChEMBL	ChEMBL403^Y
CompTox Dashboard (EPA)	DTXSID1023605
ECHA InfoCard	100.063.506
Chemical and physical data
Formula	C8H11NO5S
Molar mass	233.24 g·mol^−1
3D model (JSmol)	Interactive image
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
(verify)

It was patented in 1977 and approved for medical use in 1986.[2]

Medical 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 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.

The combination cefoperazone/sulbactam (Sulperazon) is available in many countries.[3]

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

Mechanism

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

See also

• Tazobactam
• Clavulanate

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.
2. Fischer, Jnos; Ganellin, C. Robin (2006). Analogue-based Drug Discovery. John Wiley & Sons. p. 492. ISBN 9783527607495.
3. "Sulperazon". drugs.com.

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.