Sisomicin

Sisomicin (bactoCeaze, ensamycin, and initially antibiotic 6640[1] and rickamicin[1]), is an aminoglycoside antibiotic, isolated from the fermentation broth of Micromonospora inositola.[1] It is a newer broad-spectrum aminoglycoside most structurally related to gentamicin.

Sisomicin
Clinical data
Trade namesBaymicin, bactoCeaze
AHFS/Drugs.comInternational Drug Names
Routes of
administration		topical
ATC code
Legal status
Legal status
  • In general: ℞ (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
PubChem CID
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.046.365
Chemical and physical data
FormulaC19H37N5O7
Molar mass447.533 g·mol−1
3D model (JSmol)
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 N
  • Key:URWAJWIAIPFPJE-YFMIWBNJSA-N N
 NY (what is this?)  (verify)

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 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. Weinstein MJ, Marquez JA, Testa RT, Wagman GH, Oden EM, Waitz JA (November 1970). "Antibiotic 6640, a new Micromonospora-produced aminoglycoside antibiotic". The Journal of Antibiotics. 23 (11): 551–4. doi:10.7164/antibiotics.23.551. PMID 5487129.
  2. Sanders WE, Sanders CC (Mar–Apr 1980). "Sisomicin: a review of eight years' experience". Reviews of Infectious Diseases. 2 (2): 182–95. doi:10.1093/clinids/2.2.182. PMID 6994206.
  3. Levison ME, Kaye D (June 1974). "In vitro comparison of four aminoglycoside antibiotics: sisomicin, gentamicin, tobramycin, and BB-K8". Antimicrobial Agents and Chemotherapy. 5 (6): 667–9. doi:10.1128/aac.5.6.667. PMC 429032. PMID 15825423.
  4. Phillips I, King BA, Shannon KP (March 1978). "The mechanisms of resistance to aminoglycosides in the genus Pseudomonas". Journal of Antimicrobial Chemotherapy. 4 (2): 121–9. doi:10.1093/jac/4.2.121. PMID 649532.
  5. Keating MJ, Bodey GP, Valdivieso M, Rodriguez V (March 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. 58 (2): 159–70. doi:10.1097/00005792-197903000-00004. PMID 431401.
  6. Maki DG, Craig WA, Agger WA (Jun 1979). "A comparative clinical trial of sisomicin and gentamicin in major gram-negative infections". Infection. 7: S298–S300. doi:10.1007/bf01646260.
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