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T4014

Sigma-Aldrich

Tobramicina

Aminoglycoside antibiotic

Sinonimo/i:

Nebramicina Fattore 6, O-[3-amino-3-deossi-α-D-glucopiranosil-(1→6)]-O-[2,6-diamino-2,3,6-trideossi-α-D-riboesopiranosil-(1→4)]-2-deossi-D-streptamina

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About This Item

Formula empirica (notazione di Hill):
C18H37N5O9
Numero CAS:
32986-56-4
Peso molecolare:
467.51
Beilstein:
1357507
Numero CE:
251-322-5
Numero MDL:
MFCD00077885
Codice UNSPSC:
51281626
ID PubChem:
24900188
NACRES:
NA.85

Origine biologica

Streptomyces tenebrarius

Livello qualitativo

200

Stato

powder

Condizioni di stoccaggio

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

Concentrazione

≥900 μg/mg (anhydrous)

Colore

white to off-white

Spettro attività antibiotica

Gram-negative bacteria

Modalità d’azione

protein synthesis | interferes

Temperatura di conservazione

2-8°C

Stringa SMILE

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
NLVFBUXFDBBNBW-SNGYORCQSA-N

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Descrizione generale

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.

Applicazioni

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

Azioni biochim/fisiol

La tobramicina è un aminoglicoside.
Modalità d′azione: Si lega alla subunità ribosomiale 70S, inibisce la traslocazione e suscita errori di codifica.
Spettro di attività: Batteri gram negativi. Non efficace nei confronti di Enterococci.
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.

Altre note

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

Pittogrammi

Health hazard
GHS08

Avvertenze

Warning

Indicazioni di pericolo

H361f

Classi di pericolo

Repr. 2

Codice della classe di stoccaggio

11 - Combustible Solids

Classe di pericolosità dell'acqua (WGK)

WGK 3

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Certificati d'analisi (COA)

Lot/Batch Number
SLCD1941
069M4783V
069M4782V
SLCC4418
SLCB7407

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Sigma-Aldrich

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Sigma-Aldrich

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Sigma-Aldrich

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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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