Sisomicin

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Sisomicin
Sisomicin.svg
Systematic (IUPAC) name
(2R,3R,4R,5R)-2-{[(1S,2S,3R,4S,6R)-4,6-diamino-3-{[(2S,3R)-3-amino-6-(aminomethyl)-3,4-dihydro-2H-pyran-2-yl]oxy}-2-hydroxycyclohexyl]oxy}-5-methyl-4-(methylamino)oxane-3,5-diol
Clinical data
Trade names bactoCeaze
AHFS/Drugs.com International Drug Names
Legal status
  • Rx Only
Routes topical
Identifiers
CAS number  YesY
ATC code J01GB08
PubChem CID 36119
UNII X55XSL74YQ YesY
KEGG D02544 YesY
ChEMBL CHEMBL606051 N
Chemical data
Formula C19H37N5O7 
Mol. mass 447.53 g/mol
 N (what is this?)  (verify)

Sisomicin (bactoCeaze or Ensamycin) is an aminoglycoside antibiotic, isolated from the fermentation broth of a new species of the genus Micromonospora.[1] It is a newer broad-spectrum aminoglycoside most structurally related to gentamicin.

Sisomicin is the most predictably active aminoglycoside against gram-positive bacteria.[2] Like most other aminoglycosides, Sisomicin is bactericidal for sensitive clinical isolates. The Minimum Bactericidal Concentrations (MBC) have been found to be equivalent or very close to the Minimum Inhibitory Concentrations (MIC).[2] Like other aminoglycosides, most clinical isolates of Pseudomonas aeruginosa remain susceptible to sisomicin. Resistance to sisomicin may enzymatically or non-enzymatically be mediated. Sisomicin is inactivated by the same enzymes as gentamicin but it is active against many, not all, organisms that resist gentamicin by non-enzymatic mechanisms.[3]

Some studies show that sisomicin has been effective in the treatment of infections that either had failed to respond to other drugs or were due to microorganisms resistant in vitro to other aminoglycosides.[4][5]

References[edit]

  1. ^ M. J. Weinstein, J. A. Marquez, R. T. Testa, G. H. Wagman, E. M. Oden, J. A. Waitz (Nov 1970). "Antibiotic 6640, a new Micromonospora-produced aminoglycoside antibiotic.". J. Antibiot. 23 (11): 551–554. doi:10.7164/antibiotics.23.551. PMID 5487129. 
  2. ^ a b WE Sanders Jr, CC Sanders. (Mar–Apr 1980). "Sisomicin: a review of eight years' experience.". Rev Infect Dis. 2 (2): 182–195. doi:10.1093/clinids/2.2.182. PMID 6994206. 
  3. ^ I Phillips, BA King, KP Shannon. (Mar 1978). "The mechanisms of resistance to aminoglycosides in the genus Pseudomonas.". J Antimicrob Chemother. 4 (2): 121–129. doi:10.1093/jac/4.2.121. PMID 649532. 
  4. ^ ME Levison, D Kaye. (Mar 1979). "A randomized comparative trial of three aminoglycosides--comparison of continuous infusions of gentamicin, amikacin and sisomicin combined with carbenicillin in the treatment of infections in neutropenic patients with malignancies.". Medicine (Baltimore). 58 (2): 159–170. doi:10.1097/00005792-197903000-00004. PMID 431401. 
  5. ^ DG Maki, WA Craig, WA Agger. (Jun 1979). "A comparative clinical trial of sisomicin and gentamicin in major gram-negative infections.". Infection 7(Suppl. 3) 5 (6): 298–300. doi:10.1007/bf01646260.