T4014

Tobramycin

Aminoglycoside antibiotic

• Synonym(s): 3′-Deoxykanamycin B, 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
• Empirical Formula (Hill Notation): C₁₈H₃₇N₅O₉
• CAS Number: 32986-56-4
• Molecular Weight: 467.51
• Beilstein/REAXYS Number: 1357507
• EC Number: 251-322-5
• MDL number: MFCD00077885
• UNSPSC Code: 51281626
• PubChem Substance ID: 24900188
• NACRES: NA.85

Properties

• biological source: Streptomyces tenebrarius
• form: powder
• storage condition: (Keep container tightly closed in a dry and well-ventilated place. Keep in a dry place.)
• concentration: ≥900 μg/mg (anhydrous)
• color: white to off-white
• antibiotic activity spectrum: Gram-negative bacteria
• mode of action: protein synthesis | interferes
• 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

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 Information

• pictograms: GHS08
• signalword: Warning
• hcodes: H361f
• pcodes: P201 - P202 - P280 - P308 + P313 - P405 - P501
• Hazard Classifications: Repr. 2
• Storage Class: 11 - Combustible Solids
• wgk_germany: WGK 3