Sultamicillin

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Sultamicillin
Sultamicillin.svg
Systematic (IUPAC) name
[(2R)-3,3-Dimethyl-4,4,7-trioxy-4λ6-thia-1-azabicyclo[3.2.0]heptane-2-carbonyl]oxymethyl(2R)-6-{[(2S)-2-amino-2-phenyl-acetyl]amino}-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate
Clinical data
AHFS/Drugs.com International Drug Names
Legal status
?
Routes Oral
Identifiers
CAS number 76497-13-7 N
ATC code J01CR04
PubChem CID 444022
ChemSpider 392048 YesY
UNII 65DT0ML581 YesY
KEGG D05972 YesY
ChEBI CHEBI:51770 YesY
ChEMBL CHEMBL506110 YesY
Chemical data
Formula C25H30N4O9S2 
Mol. mass 594.659 g/mol
 N (what is this?)  (verify)

Sultamicillin is an oral form of the antibiotic combination (codrug or mutual prodrug) ampicillin/sulbactam. It contains esterified ampicillin and sulbactam and is marketed under a number of trade names, including Saltum from Morepen Lab and Unasyn from Pfizer.

The pharmacokinetic properties of sultamicillin are improved compared to a combination of ampicillin and sulbactam. Sultamicillin increases the absorption and decreases the chances of diarrhea and dysentery. The inclusion of sulbactam extends ampicillin's spectrum of action to beta-lactamase producing strains of bacteria. Oral sulbactam with parenteral form provides a regimen of continuous sulbactam therapy throughout the treatment, resulting in better clinical results.

Chemical evaluation[edit]

Sultamicillin is a mutual prodrug of ampicillin and sulbactam. Ampicillin, a semi-synthetic orally active broad spectrum antibiotic, is linked via a methylene group with a beta-lactamase inhibitor. Sultamicillin is chemically oxymethyl penicillinate sulfone ester of ampicillin.

Mechanism of action[edit]

After absorption, sultamicillin releases ampicillin and sulbactam into the system, so all the antibacterial efficacy of sultamicillin is due to ampicillin and sulbactam. Ampicillin exerts antibacterial activity against sensitive organisms by inhibiting biosynthesis of cell wall mucopeptide where as sulbactam irreversibly inhibits most important beta-lactamases that occur in resistant strains.

Indications[edit]

Indications for sultamicillin include:

References[edit]

  • Singh, G.S. (2004). "Beta-lactams in the new millennium. Part-II: Cephems, oxacephems, penams and sulbactam". Mini Reviews in Medicinal Chemistry 4 (1): 93–109. doi:10.2174/1389557043487547. PMID 14754446.