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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

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About This Item

Empirical Formula (Hill Notation):
C18H37N5O9
CAS Number:
Molecular Weight:
467.51
UNSPSC Code:
51281626
NACRES:
NA.85
PubChem Substance ID:
EC Number:
251-322-5
Beilstein/REAXYS Number:
1357507
MDL number:

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Product Name

Tobramycin, Aminoglycoside antibiotic

InChI key

NLVFBUXFDBBNBW-SNGYORCQSA-N

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

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

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

Quality Level

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1 of 4

This Item
PHR1079BP333T1500000
Tobramycin British Pharmacopoeia (BP) Reference Standard

BP333

Tobramycin

antibiotic activity spectrum

Gram-negative bacteria

antibiotic activity spectrum

-

antibiotic activity spectrum

-

antibiotic activity spectrum

-

mode of action

protein synthesis | interferes

mode of action

-

mode of action

-

mode of action

-

Quality Level

200

Quality Level

300

Quality Level

-

Quality Level

-

form

powder

form

-

form

solid

form

-

storage temp.

2-8°C

storage temp.

2-8°C

storage temp.

2-8°C

storage temp.

2-8°C

concentration

≥900 μg/mg (anhydrous)

concentration

-

concentration

-

concentration

-

Application

Tobramycin has been used:
  • to study the effect of tobramycin on bacteriophage infected biofilms[1]
  • to study the effects of antibiotics on Pseudomonas aeruginosa strain[2]
  • as a comparator antibiotic[3]

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.[4]
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.[5]
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.

General description

Chemical structure: aminoglycoside
Tobramycin is an aminoglycoside, broad-spectrum antibiotic produced by Streptomyces tenebrarius.[6] It is effective against gram-negative bacteria, especially the Pseudomonas species.[7]

Other Notes

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

pictograms

Health hazard

signalword

Warning

hcodes

Hazard Classifications

Repr. 2

Storage Class

11 - Combustible Solids

wgk

WGK 3


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Eric G Romanowski et al.
Journal of ocular pharmacology and therapeutics : the official journal of the Association for Ocular Pharmacology and Therapeutics, 32(2), 119-126 (2015-11-07)
The goals of the current study were to determine the in vitro antibacterial activity of tigecycline against multiple clinically relevant ocular pathogens and to evaluate the in vivo ocular tolerability and efficacy of 0.5% tigecycline in a methicillin-resistant Staphylococcus aureus
C Formosa et al.
Scientific reports, 2, 575-575 (2012-08-16)
Drug resistance is a challenge that can be addressed using nanotechnology. We focused on the resistance of the bacteria Pseudomonas aeruginosa and investigated, using Atomic Force Microscopy (AFM), the behavior of a reference strain and of a multidrug resistant clinical
Lindsey B Coulter et al.
Viruses, 6(10), 3778-3786 (2014-10-07)
Bacteriophage infection and antibiotics used individually to reduce biofilm mass often result in the emergence of significant levels of phage and antibiotic resistant cells. In contrast, combination therapy in Escherichia coli biofilms employing T4 phage and tobramycin resulted in greater
Madan Kumar Kharel et al.
FEMS microbiology letters, 230(2), 185-190 (2004-02-06)
The biosynthetic gene cluster for tobramycin, a 2-deoxystreptamine-containing aminoglycoside antibiotic, was isolated from Streptomyces tenebrarius ATCC 17920. A genomic library of S. tenebrarius was constructed, and a cosmid, pST51, was isolated by the probes based on the core regions of
R D Meyer et al.
Applied microbiology, 22(6), 1147-1151 (1971-12-01)
Tobramycin (factor 6 of the nebramycin complex) is a new aminoglycoside antibiotic isolated from Streptomyces tenebrarius which is active against S. aureus, Enterobacteriaceae, and Pseudomonas aeruginosa. Susceptibility to tobramycin of 96 strains of P. aeruginosa, including 45 recent isolates from

Questions

  1. What are the recommandations for the storage time and temperature of an aqueous solution of of Tobramycin please?

    1 answer
    1. The stability of this product in solution has not been determined. However, pharmaceutical preparations in the form of solutions or ointments appear to be fairly stable when refrigerated. See the link below for a publication that may be helpful:
      https://www.cjhp-online.ca/index.php/cjhp/article/view/659.

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