Sultamicillin

Sultamicillin, sold under the brand name Unasyn among others, is an oral form of the antibiotic combination (codrug or mutual prodrug) ampicillin/sulbactam. It contains esterified ampicillin and sulbactam.

Sultamicillin

Clinical data
AHFS/Drugs.com	International Drug Names
Routes of administration	Oral
ATC code	J01CR04 (WHO)
Identifiers
IUPAC name [(2R)-3,3-Dimethyl-4,4,7-trioxy-4λ^6-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
CAS Number	76497-13-7^N
PubChem CID	444022
ChemSpider	392048^Y
UNII	65DT0ML581
KEGG	D05972^Y
ChEBI	CHEBI:51770^Y
ChEMBL	ChEMBL506110^Y
CompTox Dashboard (EPA)	DTXSID501010077
Chemical and physical data
Formula	C25H30N4O9S2
Molar mass	594.65 g·mol^−1
3D model (JSmol)	Interactive image
SMILES O=C(OCOC(=O)[C@@H]2N1C(=O)C[C@H]1S(=O)(=O)C2(C)C)[C@@H]4N5C(=O)[C@@H](NC(=O)[C@@H](c3ccccc3)N)[C@H]5SC4(C)C
InChI InChI=1S/C25H30N4O9S2/c1-24(2)17(29-20(32)16(21(29)39-24)27-19(31)15(26)12-8-6-5-7-9-12)22(33)37-11-38-23(34)18-25(3,4)40(35,36)14-10-13(30)28(14)18/h5-9,14-18,21H,10-11,26H2,1-4H3,(H,27,31)/t14-,15-,16-,17+,18+,21-/m1/s1^Y Key:OPYGFNJSCUDTBT-PMLPCWDUSA-N^Y
^NY (what is this?)  (verify)

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.

It was patented in 1979 and approved for medical use in 1987.[1]

Medical uses

Medical uses for sultamicillin include:

• Skin and soft tissue infections - furuncles, carbuncles, cellulitis, paronychia, impetigo contagiosa, diabetic foot ulcers and abscesses caused by Staphylococcus aureus and Streptococcus pyogenes.
• Upper respiratory tract infections - pharyngitis and tonsillitis caused by S. pyogenes and S. aureus. Acute and chronic sinusitis caused by S. aureus, S. pneumoniae, H. influenzae and S. progenies. otitis media, particularly suppurative otis media, with or without mastoiditis antrum.
• Lower respiratory tract infections - bacterial pneumonias, bronchitis, bronchiectasis caused by S. pneumoniae, H. influenzae, Staphylococcus aureus and S. progenies. Acute exacerbations of COPD.
• Urinary tract infections - pyelonephritis, cystitis caused by Escherichia coli, Proteus mirabilis, Klebsiella, Enterobacter and Staphylococcus aureus.
• Surgical infections - prophylaxis and treatment of surgical site infections, peri-operative prophylaxis in orthopaedic and cardiovascular surgery.
• Gynecological infections - Caused by beta-lactamase producing strains of E. coli and Bacteroides sp. (including B. fragilis).
• Infections of the gastrointestinal tract - Bacterial esophagitis, treatment of H. pylori infections as a part of MDT in ulcer management.

Chemical evaluation

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

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.

References

1. Fischer J, Ganellin CR (2006). Analogue-based Drug Discovery. John Wiley & Sons. p. 491. ISBN 9783527607495.

Further reading

• Singh GS (January 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.