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Details

Stereochemistry ABSOLUTE
Molecular Formula C18H37N5O9.ClH
Molecular Weight 503.975
Optical Activity UNSPECIFIED
Defined Stereocenters 14 / 14
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of TOBRAMYCIN HYDROCHLORIDE

SMILES

Cl.[H][C@]3(O[C@@H]1[C@@H](N)C[C@@H](N)[C@H](O[C@@]2([H])O[C@H](CO)[C@@H](O)[C@H](N)[C@H]2O)[C@H]1O)O[C@H](CN)[C@@H](O)C[C@H]3N

InChI

InChIKey=CVDADWBWFLWJNQ-TWDWGCDDSA-N
InChI=1S/C18H37N5O9.ClH/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;1H/t5-,6+,7+,8-,9+,10+,11-,12+,13+,14-,15+,16-,17+,18+;/m0./s1

HIDE SMILES / InChI

Description

Tobramycin, an aminoglycoside antibiotic obtained from cultures of Streptomyces tenebrarius, it is effective against gram-negative bacteria, especially the pseudomonas species. Tobramycin is used in combination with other antibiotics to treat urinary tract infections, gynecologic infections, peritonitis, endocarditis, pneumonia, bacteremia and sepsis, respiratory infections including those associated with cystic fibrosis, osteomyelitis, and diabetic foot and other soft-tissue infections. It acts primarily by disrupting protein synthesis, leading to altered cell membrane permeability, progressive disruption of the cell envelope, and eventual cell death. Tobramycin has in vitro activity against a wide range of gram-negative organisms including Pseudomonas aeruginosa. 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 memebrane by binding to 16 S 16 S r-RNA. An active transport mechanism for aminoglycoside uptake is necessary in the bacteria in order to attain a significant intracellular concentration of tobramycin. KITABIS PAK (co-packaging of tobramycin inhalation solution and PARI LC PLUS Reusable Nebulizer) is indicated for the management of cystic fibrosis in adults and pediatric patients 6 years of age and older with P. aeruginosa.

CNS Activity

Originator

Approval Year

Targets

Primary TargetPharmacologyConditionPotency
9.0 µM [IC50]

Conditions

ConditionModalityTargetsHighest PhaseProduct
Curative
TOBREX
Primary
KITABIS PAK

Cmax

ValueDoseCo-administeredAnalytePopulation
3.7 μg/mL
80 mg single, intramuscular
TOBRAMYCIN plasma
Homo sapiens
814 μg/mL
300 mg single, respiratory
TOBRAMYCIN unknown
Homo sapiens

AUC

ValueDoseCo-administeredAnalytePopulation
11.6 μg × h/mL
80 mg single, intramuscular
TOBRAMYCIN plasma
Homo sapiens

T1/2

ValueDoseCo-administeredAnalytePopulation
1.6 h
80 mg single, intramuscular
TOBRAMYCIN plasma
Homo sapiens
4.4 h
300 mg single, respiratory
TOBRAMYCIN unknown
Homo sapiens

Funbound

ValueDoseCo-administeredAnalytePopulation
100%
300 mg single, respiratory
TOBRAMYCIN unknown
Homo sapiens

Doses

AEs

Overview

CYP3A4CYP2C9CYP2D6hERG

OverviewOther

Drug as perpetrator​

Drug as victim

PubMed

Sample Use Guides

In Vivo Use Guide
KITABIS PAK is a co-packaging of tobramycin inhalation solution ampules with a PARI LC PLUS Reusable Nebulizer. Administer as follows: One single-use ampule (300 mg /5 mL) of tobramycin inhalation solution twice a day by oral inhalation in alternating periods of 28 days on drug, followed by 28 days off drug. The 300 mg/5mL dose of tobramycin inhalation solution is the same for all patients regardless of age or weight. The doses should be taken as close to 12 hours apart as possible; they should not be taken less than 6 hours apart.
Route of Administration: Respiratory
In Vitro Use Guide
High-dose tobramycin (200 ug/ml) killed 72% of Pseudomonas aeruginosa isolates