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T1783

Sigma-Aldrich

Tobramycin sulfate salt

aminoglycoside antibiotic

Synonym(s):

Nebramycin Factor 6 sulfate

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About This Item

Empirical Formula (Hill Notation):
C18H37N5O9 · xH2SO4
Molecular Weight:
467.51 (free base basis)
MDL number:
MFCD00133864
UNSPSC Code:
51281677
PubChem Substance ID:
329826686
NACRES:
NA.85

biological source

Streptomyces tenebrarius

form

powder

potency

634-739 μg per mg

storage condition

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

color

white to off-white

solubility

H2O: soluble 50 mg/mL

antibiotic activity spectrum

Gram-negative bacteria

Mode of action

protein synthesis | interferes

storage temp.

2-8°C

SMILES string

OS(O)(=O)=O.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.H2O4S/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;1-5(2,3)4/h5-18,24-28H,1-4,19-23H2;(H2,1,2,3,4)/t5-,6+,7+,8-,9+,10+,11-,12+,13+,14-,15+,16-,17+,18+;/m0./s1

InChI key

ZEUUPKVZFKBXPW-TWDWGCDDSA-N

Related Categories

General description

Chemical structure: aminoglycoside

Application

Tobramycin is an aminoglycoside, broad-spectrum antibiotic produced by Streptomyces tenebrarius. It is effective against gram-negative bacteria, especially the pseudomonas species. It is not effective against Enterococci. It is used to inhibit bacterial protein synthesis at the level of 30S (16S rRNA) and 70S ribosomal complex assembly. It 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. Product T1783 has been used to study antibiotic resistance.

Biochem/physiol Actions

Tobramycin binds irreversibly to one of two aminoglycoside binding sites on the 30 S ribosomal subunit, inhibiting bacterial protein synthesis. Tobramycin may also destabilize bacterial membranes by binding to 16 S r-RNA. It inhibits translocation and elicits miscoding. Tobramycin binds to an RNA aptamer, which is structurally similar to the A site of 16S rRNA.
Tobramycin sulfate 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.

Packaging

100MG,500MG

Caution

Hygroscopic

Other Notes

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

Pictograms

Health hazardExclamation mark
GHS08,GHS07

Signal Word

Danger

Hazard Statements

H312 + H332,H360

Hazard Classifications

Acute Tox. 4 Dermal - Acute Tox. 4 Inhalation - Repr. 1B

Storage Class Code

6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Erica B Ricker et al.
Biofouling, 33(10), 855-866 (2017-10-19)
Upon formation of a biofilm, bacteria undergo several changes that prevent eradication with antimicrobials alone. Due to this resistance, the standard of care for infected medical implants is explantation of the infected implant and surrounding tissue, followed by eventual reimplantation
Patrik Mlynarcik et al.
Biomedical papers of the Medical Faculty of the University Palacky, Olomouc, Czechoslovakia, 161(1), 58-67 (2016-11-26)
Planktonic stationary and exponential cultures of Pseudomonas aeruginosa are highly resistant to killing by bactericidal antimicrobials because of the presence of persisters, cells that are multidrug tolerant and play a key role in the recalcitrance of biofilm infections. The aim
David Moreno-González et al.
Talanta, 171, 74-80 (2017-05-30)
An analytical method for the determination of eleven aminoglycosides in different types of milk and milk-based functional products has been optimized and validated. A hydrophilic interaction chromatography (HILIC) column was proposed for the separation of analytes by ultra-high performance liquid
Hessel Van der Weide et al.
Antibiotics (Basel, Switzerland), 9(3) (2020-03-07)
Background: Recent scientific reports on the use of high dose tigecycline monotherapy as a "drug of last resort" warrant further research into the use of this regimen for the treatment of severe multidrug-resistant, Gram-negative bacterial infections. In the current study
Lokender Kumar et al.
PloS one, 14(3), e0214411-e0214411 (2019-03-27)
Antimicrobial biopolymers provide a biodegradable, sustainable, safe, and cheap approach to drug delivery and wound dressing to control bacterial infection and improve wound healing respectively. Here, we report a one-step method of making antimicrobial alginate polymer from sodium alginate and
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Articles

Inhibition of Protein Synthesis by Antibiotics

Protein synthesis is a complex, multi-step process involving many enzymes as well as conformational alignment. However, the majority of antibiotics that block bacterial protein synthesis interfere with the processes at the 30S subunit or 50S subunit of the 70S bacterial ribosome.

Protocols

Aminoglycoside Analysis in Pork Muscle using Molecularly Imprinted Polymer Cleanup and LC/MS/MS Detection

Extraction and quantitative analysis of aminoglycosides in porcine tissue, using molecular imprinted polymer solid phase extraction followed by LC-MS/MS.

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