Sisomicin

Sisomicin

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	℞ (Prescription only)
Routes of administration	topical
Identifiers
CAS Number	32385-11-8 Y
ATC code	J01GB08 (WHO)
PubChem	CID: 36119
ChemSpider	33222 Y
UNII	X55XSL74YQ Y
KEGG	D02544 Y
ChEBI	CHEBI:9169 Y
ChEMBL	CHEMBL221886 Y
Chemical data
Formula	C19H37N5O7
Molecular mass	447.53 g/mol
SMILES C[C@@]1(CO[C@@H]([C@@H]([C@H]1NC)O)O[C@H]2[C@@H](C[C@@H]([C@H]([C@@H]2O)O[C@@H]3[C@@H](CC=C(O3)CN)N)N)N)O
InChI InChI=1S/C19H37N5O7/c1-19(27)7-28-18(13(26)16(19)24-2)31-15-11(23)5-10(22)14(12(15)25)30-17-9(21)4-3-8(6-20)29-17/h3,9-18,24-27H,4-7,20-23H2,1-2H3/t9-,10+,11-,12+,13-,14-,15+,16-,17-,18-,19+/m1/s1 Key:URWAJWIAIPFPJE-YFMIWBNJSA-N
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Sisomicin (bactoCeaze or Ensamycin) is an aminoglycoside antibiotic, isolated from the fermentation broth of a new species of the genus Micromonospora. It is a newer broad-spectrum aminoglycoside most structurally related to gentamicin.

Sisomicin is the most predictably active aminoglycoside against gram-positive bacteria. 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). Like other aminoglycosides, most clinical isolates of Pseudomonas aeruginosa remain susceptible to sisomicin. Resistance to sisomicin may be enzymatically or non-enzymatically 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.

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.