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T4014

Sigma-Aldrich

Tobramycin

Aminoglycoside antibiotic

Synonim(y):

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

Wzór empiryczny (zapis Hilla):
C18H37N5O9
Numer CAS:
32986-56-4
Masa cząsteczkowa:
467.51
Beilstein:
1357507
Numer WE:
251-322-5
Numer MDL:
MFCD00077885
Kod UNSPSC:
51281626
Identyfikator substancji w PubChem:
24900188
NACRES:
NA.85

pochodzenie biologiczne

Streptomyces tenebrarius

Postać

powder

warunki przechowywania

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

stężenie

≥900 μg/mg (anhydrous)

kolor

white to off-white

spektrum działania antybiotyku

Gram-negative bacteria

Tryb działania

protein synthesis | interferes

temp. przechowywania

2-8°C

ciąg SMILES

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

Klucz InChI

NLVFBUXFDBBNBW-SNGYORCQSA-N

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Opis ogólny

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.

Zastosowanie

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

Działania biochem./fizjol.

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.

Inne uwagi

Keep container tightly closed in a dry and well-ventilated place. Keep in a dry place.
This page may contain text that has been machine translated.

Piktogramy

Health hazard
GHS08

Hasło ostrzegawcze

Warning

Zwroty wskazujące rodzaj zagrożenia

H361f

Zwroty wskazujące środki ostrożności

P201 - P202 - P280 - P308 + P313 - P405 - P501

Klasyfikacja zagrożeń

Repr. 2

Kod klasy składowania

11 - Combustible Solids

Klasa zagrożenia wodnego (WGK)

WGK 3

Certyfikaty analizy (CoA)

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Sigma-Aldrich

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Amikacin sulfate salt

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Sigma-Aldrich

A1774

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Ceftazidime

Sigma-Aldrich

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Ceftazidime

Zanamivir for assay European Pharmacopoeia (EP) Reference Standard

Y0001702

Zanamivir for assay

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
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
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
Quentin Vicens et al.
Journal of molecular biology, 326(4), 1175-1188 (2003-02-19)
Aminoglycosides are antibacterial molecules that decrease translation accuracy by binding to the decoding aminoacyl-tRNA site (A site) on 16S ribosomal RNA. We have solved the crystal structure of an RNA fragment containing the A site bound to geneticin at 2.40A
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