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
Routes of administration	Injection
Legal status
Legal status	UK: POM (Prescription only)
Pharmacokinetic data
Bioavailability	1
Excretion	Kidneys?
Identifiers
CAS Number	68373-14-8^Y
ATC code	J01CG01 (WHO)
PubChem	CID 130313
ChemSpider	115306^Y
UNII	S4TF6I2330^Y
KEGG	D08533^Y
ChEBI	CHEBI:9321^Y
ChEMBL	CHEMBL403^Y
Chemical data
Formula	C₈H₁₁NO₅S
Molar 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
(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.

References

↑ 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.

β-lactamase Sensitive (1st Generation)	Benzylpenicillin (G)^# Benzathine benzylpenicillin^# Procaine benzylpenicillin^# Phenoxymethylpenicillin (V)^# Propicillin^‡ Pheneticillin^‡ Azidocillin^‡ Clometocillin^‡ Penamecillin^‡

β-lactamase Resistant (2nd Generation)	Cloxacillin^# (Dicloxacillin Flucloxacillin) Oxacillin Nafcillin Methicillin^‡

Extended Spectrum

Aminopenicillins (3rd Generation)	Amoxicillin^# Ampicillin^# (Pivampicillin Hetacillin^‡ Bacampicillin^‡ Metampicillin^‡ Talampicillin^‡) Epicillin^‡

Carboxypenicillins (4th Generation)	Ticarcillin Carbenicillin^‡ / Carindacillin^‡ Temocillin^‡

Ureidopenicillins (4th Generation)	Piperacillin Azlocillin^‡ Mezlocillin^‡

Other	Mecillinam^‡ (Pivmecillinam^‡) Sulbenicillin^‡

Penems

Faropenem^‡

Carbapenems

Cephalosporins/Cephamycins
(Cephems)

1st Generation (P Ec K)	Cefazolin^# Cefalexin ^# Cefadroxil Cefapirin Cefazedone^‡ Cefazaflur^‡ Cefradine^‡ Cefroxadine^‡ Ceftezole^‡ Cefaloglycin^‡ Cefacetrile^‡ Cefalonium^‡ Cefaloridine^‡ Cefalotin^‡ Cefatrizine^‡

2nd Generation (H E N)	Cefaclor Cefotetan Cephamycin (Cefoxitin Cefprozil Cefuroxime Cefuroxime axetil Cefamandole^‡ Cefminox^‡ Cefonicid^‡ Ceforanide^‡ Cefotiam^‡ Cefbuperazone^‡ Cefuzonam^‡ Cefmetazole)^‡ Carbacephem^‡ (Loracarbef^‡)

3rd Generation	Cefixime^# Ceftriaxone^# Antipseudomonal (Ceftazidime^# Cefoperazone) Cefdinir Cefcapene Cefdaloxime Ceftizoxime Cefmenoxime Cefotaxime Cefpiramide Cefpodoxime Ceftibuten Cefditoren Cefetamet^‡ Cefodizime^‡ Cefpimizole^‡ Cefsulodin^‡ Cefteram^‡ Ceftiolene^‡ Oxacephem (Flomoxef^‡ Latamoxef^‡‡)

4th Generation (Pseudomonas)	Cefepime Cefozopran^‡ Cefpirome^‡ Cefquinome^‡

5th Generation	Ceftaroline fosamil Ceftolozane Ceftobiprole^‡

Veterinary	Ceftiofur Cefquinome Cefovecin

Monobactams

β-lactamase Inhibitors

Combinations

Other

polymyxins/detergent
- Colistin
- Polymyxin B
depolarizing
- Daptomycin
Hydrolyze NAM-NAG
- lysozyme
Gramicidin
Isoniazid
Teixobactin

^#WHO-EM
^‡Withdrawn from market
Clinical trials:
- ^†Phase III
- ^§Never to phase III

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Sulbactam

Mechanism

Uses

See also

References

Further reading