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T4014

Tobramycin

Name: Tobramycin
Brand: SIGMA

Aminoglycoside antibiotic

别名:

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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关于此项目

经验公式（希尔记法）:

C₁₈H₃₇N₅O₉

化学文摘社编号:

32986-56-4

分子量:

467.51

UNSPSC Code:

51281626

NACRES:

NA.85

PubChem Substance ID:

24900188

EC Number:

251-322-5

Beilstein/REAXYS Number:

1357507

MDL number:

MFCD00077885

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属性

biological source

Streptomyces tenebrarius

Quality Level

200

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

说明

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.

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pictograms

GHS08

signalword

Warning

hcodes

H361f

pcodes

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

Hazard Classifications

Repr. 2

存储类别

11 - Combustible Solids

wgk

WGK 3

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Effect of bacteriophage infection in combination with tobramycin on the emergence of resistance in Escherichia coli and Pseudomonas aeruginosa biofilms.

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

Isolation and characterization of the tobramycin biosynthetic gene cluster from Streptomyces tenebrarius.

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

Crystal structure of geneticin bound to a bacterial 16S ribosomal RNA A site oligonucleotide.

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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全球贸易项目编号

货号	GTIN
T4014-100MG	04061837345357
T4014-500MG	04061837345371