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Merck
CN

89549

Tobramycin

≥99.0% (TLC)

Synonym(s):

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:
32986-56-4
Molecular Weight:
467.51
EC Number:
251-322-5
UNSPSC Code:
51101500
MDL number:
MFCD00077885
Beilstein/REAXYS Number:
1357507

Key Documents

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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

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

assay

≥99.0% (TLC)

impurities

≤8% water

solubility

H2O: 50 mg/mL, clear, faintly yellow

mode of action

protein synthesis | interferes

storage temp.

2-8°C

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General description

Chemical structure: aminoglycoside

Biochem/physiol Actions

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.

Regulatory Information

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Catherine G Ambrose et al.
The Journal of bone and joint surgery. American volume, 96(2), 128-134 (2014-01-17)
Prevention of infection associated with uncemented orthopaedic implants could lead to improved implant stability and better patient outcomes. We hypothesized that coating porous metal implants with antibiotic-containing microspheres would prevent infections in grossly contaminated wounds. Bioresorbable polymer microspheres containing tobramycin
Yifat Berkov-Zrihen et al.
Organic letters, 15(24), 6144-6147 (2013-11-15)
A short site-selective strategy for the activation and derivatization of alcohols of the clinically important aminoglycoside tobramycin is reported. The choice of amine protecting group affected the site-selective conversion of secondary alcohols of tobramycin into leaving groups. Temperature-dependent, chemoselective sequential
Stefanie Hennig et al.
Clinical pharmacokinetics, 52(4), 289-301 (2013-02-20)
While several studies have examined the pharmacokinetics of tobramycin in patients with cystic fibrosis (CF), there is no consensus on whether they differ in patients with and without CF. The objectives of this study were to identify covariates which explain
Namrata Sharma et al.
Ophthalmology, 120(6), 1173-1178 (2013-02-19)
To compare the equivalence of moxifloxacin 0.5% with a combination of fortified cefazolin sodium 5% and tobramycin sulfate 1.3% eye drops in the treatment of moderate bacterial corneal ulcers. Randomized, controlled, equivalence clinical trial. Microbiologically proven cases of bacterial corneal
Heleen Van Acker et al.
PloS one, 8(3), e58943-e58943 (2013-03-22)
The presence of persister cells has been proposed as a factor in biofilm resilience. In the present study we investigated whether persister cells are present in Burkholderia cepacia complex (Bcc) biofilms, what the molecular basis of antimicrobial tolerance in Bcc
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