Sultamicillin

Title: Sultamicillin
CAS Registry Number: 76497-13-7
CAS Name: (2S,5R,6R)-6-[[(2R)-Aminophenylacetyl]amino]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid [[[(2S,5R)-3,3-dimethyl-4,4-dioxido-7-oxo-4-thia-1-azabicyclo[3.2.0]hept-2-yl]carbonyl]oxy]methyl ester
Additional Names: 1,1-dioxopenicillanoyloxymethyl 6-(D-a-amino-a-phenylacetamido)penicillanate; 6¢-(2-amino-2-phenylacetamido)penicillanoyloxymethyl penicillanate 1,1-dioxide
Manufacturers' Codes: CP-49952; VD-1827
Molecular Formula: C25H30N4O9S2
Molecular Weight: 594.66
Percent Composition: C 50.49%, H 5.08%, N 9.42%, O 24.21%, S 10.78%
Literature References: Orally absorbed double ester of sulbactam and ampicillin, q.q.v. Prepn: E. C. Bigham, DE 3018590; eidem, US 4244951 (1980, 1981 both to Pfizer); and pharmacology: B. Baltzer et al., J. Antibiot. 33, 1183 (1980). HPLC determn and pharmacokinetics: H. J. Rogers et al., J. Antimicrob. Chemother. 11, 435 (1983). Clinical trial in pediatric otitis media: K. H. Chan et al., Pediatr. Infect. Dis. J. 12, 24 (1993). Review of antibacterial activity, pharmacokinetics and therapeutic efficacy: H. A. Friedel et al., Drugs 37, 491-522 (1989).
Properties: mp 190°.
Melting point: mp 190°
Derivative Type: Tosylate
CAS Registry Number: 83105-70-8
Trademarks: Bacimex (Alter); Unacid PD oral (Pfizer); Unacim (Pfizer); Unasyn (Pfizer)
Molecular Formula: C25H30N4O9S2.C7H8O3S
Molecular Weight: 766.86
Percent Composition: C 50.12%, H 4.99%, N 7.31%, O 25.04%, S 12.54%
Therap-Cat: Antibacterial.
Keywords: Antibacterial (Antibiotics); ?Lactams; Penicillins; Antibacterial Adjuncts; ?Lactamase Inhibitors.
Sulthiame Sultopride Sultosilic Acid Sultroponium Sumatrol

Sultamicillin
Sultamicillin.svg
Systematic (IUPAC) name
[(2R)-3,3-dimethyl-4,4,7-trioxo-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.

Sultamicillin with improved pharmacokinetic changes which has led to various changes of ampicillin & sulbactam properties.

Sultamicillin increased the absorption and decreased the chances of diarrhoea and dysentery. Sultamicillin also offered - the oral sulbactam advantage, there by, extending the spectrum of action to resistant strains (betalactamase producing strains). Oral sulbactam with parenteral form provides a regimen of continuous sulbactam therapy throughout the treatment resulting in better clinical results.