Sisomicin

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Sisomicin
Sisomicin.svg
Clinical data
Trade names Baymicin, bactoCeaze
AHFS/Drugs.com International Drug Names
Routes of
administration
topical
ATC code
Legal status
Legal status
  • In general: ℞ (Prescription only)
Identifiers
  • (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 InfoCard 100.046.365 OOjs UI icon edit-ltr-progressive.svg
Chemical and physical data
Formula C19H37N5O7
Molar mass 447.533 g·mol−1
3D model (JSmol)
  • 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=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 X mark.svgN
  • Key:URWAJWIAIPFPJE-YFMIWBNJSA-N X mark.svgN
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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 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]

Related Research Articles

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<span class="mw-page-title-main">Gentamicin</span> Antibiotic medication

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<span class="mw-page-title-main">Aminoglycoside</span> Antibacterial drug

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<i>Micromonospora</i> Genus of bacteria

Micromonospora is a genus of bacteria of the family Micromonosporaceae. The genus name was first proposed in 1923 by Danish physician Jeppe Ørskov in an attempt to classify what at the time was considered "ray fungi" based on morphology. Members of this genus are found throughout natural soil and sediment environments, as well as in association with roots of plants of various species. The genus is well known for its ability to produce a variety of medically relevant products.

<span class="mw-page-title-main">Colistin</span> Antibiotic

Colistin, also known as polymyxin E, is an antibiotic medication used as a last-resort treatment for multidrug-resistant Gram-negative infections including pneumonia. These may involve bacteria such as Pseudomonas aeruginosa, Klebsiella pneumoniae, or Acinetobacter. It comes in two forms: colistimethate sodium can be injected into a vein, injected into a muscle, or inhaled, and colistin sulfate is mainly applied to the skin or taken by mouth. Colistimethate sodium is a prodrug; it is produced by the reaction of colistin with formaldehyde and sodium bisulfite, which leads to the addition of a sulfomethyl group to the primary amines of colistin. Colistimethate sodium is less toxic than colistin when administered parenterally. In aqueous solutions it undergoes hydrolysis to form a complex mixture of partially sulfomethylated derivatives, as well as colistin. Resistance to colistin began to appear as of 2015.

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<i>Pseudomonas aeruginosa</i> Species of bacterium

Pseudomonas aeruginosa is a common encapsulated, gram-negative, aerobic–facultatively anaerobic, rod-shaped bacterium that can cause disease in plants and animals, including humans. A species of considerable medical importance, P. aeruginosa is a multidrug resistant pathogen recognized for its ubiquity, its intrinsically advanced antibiotic resistance mechanisms, and its association with serious illnesses – hospital-acquired infections such as ventilator-associated pneumonia and various sepsis syndromes.

<span class="mw-page-title-main">Tobramycin</span> Chemical compound

Tobramycin is an aminoglycoside antibiotic derived from Streptomyces tenebrarius that is used to treat various types of bacterial infections, particularly Gram-negative infections. It is especially effective against species of Pseudomonas.

<i>Stenotrophomonas maltophilia</i> Species of bacterium

Stenotrophomonas maltophilia is an aerobic, nonfermentative, Gram-negative bacterium. It is an uncommon bacterium and human infection is difficult to treat. Initially classified as Bacterium bookeri, then renamed Pseudomonas maltophilia, S. maltophilia was also grouped in the genus Xanthomonas before eventually becoming the type species of the genus Stenotrophomonas in 1993.

<span class="mw-page-title-main">Netilmicin</span> Chemical compound

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<span class="mw-page-title-main">Oritavancin</span> Pharmaceutical drug

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Kerry L. LaPlante is an American pharmacist, academic and researcher. She is a Professor of Pharmacy and the Chair of the Department of Pharmacy Practice at the University of Rhode Island, an Adjunct Professor of Medicine at Brown University, an Infectious Diseases Pharmacotherapy Specialist, and the Director of the Rhode Island Infectious Diseases Fellowship and Research Programs at the Veterans Affairs Medical Center in Providence, Rhode Island.

References

  1. 1 2 3 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. S2CID   1035277.
  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. S2CID   46971853.