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T4014 Sigma-Aldrich

Tobramycin

Aminoglycoside antibiotic

Synonym: Nebramycin Factor 6, O-[3-Amino-3-deoxy-α-D-glucopyranosyl-(1→6)]-O-[2,6-diamino-2,3,6-trideoxy-α-D-ribohexopyranosyl-(1→4)]-2-deoxy-D-streptamine

  • CAS Number 32986-56-4

  • Empirical Formula (Hill Notation) C18H37N5O9

  • Molecular Weight 467.51

  •  Beilstein/REAXYS Number 1357507

  •  EC Number 251-322-5

  •  MDL number MFCD00077885

  •  PubChem Substance ID 24900188

  •  NACRES NA.85

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Properties

Related Categories Aminoglycosides, Antibacterial, Antibiotics, Antibiotics A to Z, Antibiotics T-Z,
Quality Level   200
biological source   Streptomyces tenebrarius
assay   ≥900 μg/mg anhydrous basis
form   powder
color   white to off-white
Mode of action   protein synthesis | interferes
antibiotic activity spectrum   Gram-negative bacteria
storage temp.   2-8°C
SMILES string   NC[C@H]1O[C@H](O[C@@H]2[C@@H](N)C[C@@H](N)[C@H](O[C@H]3O[C@H](CO)[C@@H](O)[C@@H](N)[C@H]3O)[C@H]2O)[C@H](N)C[C@@H]1O
InChI   1S/C18H37N5O9/c19-3-9-8(25)2-7(22)17(29-9)31-15-5(20)1-6(21)16(14(15)28)32-18-13(27)11(23)12(26)10(4-24)30-18/h5-18,24-28H,1-4,19-23H2/t5-,6+,7+,8-,9+,10+,11+,12+,13+,14-,15+,16-,17+,18+/m0/s1
InChI key   NLVFBUXFDBBNBW-SNGYORCQSA-N

Description

General description

Chemical structure: aminoglycoside

Tobramycin is an aminoglycoside, broad-spectrum antibiotic produced by Streptomyces tenebrarius. It is effective against gram-negative bacteria, especially the Pseudomonas species.

Application

Tobramycin has been used:
• to study the effect of tobramycin on bacteriophage infected biofilms
• to study the effects of antibiotics on Pseudomonas aeruginosa strain
• as a comparator antibiotic

Packaging

100, 500 mg in glass bottle

Biochem/physiol Actions

Tobramycin binds irreversibly to one of two aminoglycoside binding sites on the 30S ribosomal subunit, inhibiting bacterial protein synthesis. Tobramycin may also destabilize bacterial membranes by binding to 16S rRNA (ribosomal RNA). It inhibits translocation and elicits miscoding.
Tobramycin is used to treat Pseudomonas aeruginosa lung infections and is used in combination with other antibiotics to treat urinary tract infections, gynecologic infections, peritonitis, endocarditis, pneumonia, sepsis, respiratory infections, osteomyelitis, and other soft-tissue infections. It is a potential therapy for sinus infections.

Tobramycin is an aminoglycoside.
Mode of Action: Binds to 70S ribosomal subunit; inhibits translocation; elicits miscoding.
Spectrum of Activity: Gram negative bacteria. Not effective against Enterococci.

Other Notes

Keep container tightly closed in a dry and well-ventilated place. Keep in a dry place.

Safety & Documentation

Safety Information

RIDADR 
NONH for all modes of transport
WGK Germany 
WGK 2
RTECS 
WK2100000
Flash Point(F) 
Not applicable
Flash Point(C) 
Not applicable

Documents

Certificate of Analysis (COA)

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Certificate of Origin (COO)

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Protocols & Articles
Peer-Reviewed Papers
15

References

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