Sisomicin

Sisomicin

Clinical data
Trade names	bactoCeaze
AHFS/Drugs.com	International Drug Names
Routes of administration	topical
ATC code	J01GB08 (WHO)
Legal status
Legal status	℞ (Prescription only)
Identifiers
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
CAS Number	32385-11-8
PubChem (CID)	36119
ChemSpider	33222
UNII	X55XSL74YQ
KEGG	D02544
ChEBI	CHEBI:9169
ChEMBL	CHEMBL221886
ECHA InfoCard	100.046.365
Chemical and physical data
Formula	C19H37N5O7
Molar mass	447.53 g/mol
3D model (Jmol)	Interactive image
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
(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).^[3] 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.^[4]

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.^[5][6]

References

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. 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. ME Levison; D Kaye. (Jun 1974). "In vitro comparison of four aminoglycoside antibiotics: sisomicin, gentamicin, tobramycin, and BB-K8.". Antimicrob Agents Chemother. 5 (6): 667–669. doi:10.1128/aac.5.6.667. PMC 429032. PMID 15825423.
4. 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.
5. 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.
6. 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.