Details
Stereochemistry | ABSOLUTE |
Molecular Formula | 2C18H37N5O9.5H2O4S |
Molecular Weight | 1425.421 |
Optical Activity | UNSPECIFIED |
Defined Stereocenters | 28 / 28 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
OS(O)(=O)=O.OS(O)(=O)=O.OS(O)(=O)=O.OS(O)(=O)=O.OS(O)(=O)=O.[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.[H][C@]6(O[C@@H]4[C@@H](N)C[C@@H](N)[C@H](O[C@@]5([H])O[C@H](CO)[C@@H](O)[C@H](N)[C@H]5O)[C@H]4O)O[C@H](CN)[C@@H](O)C[C@H]6N
InChI
InChIKey=NZKFUBQRAWPZJP-BXKLGIMVSA-N
InChI=1S/2C18H37N5O9.5H2O4S/c2*19-3-9-8(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;5*1-5(2,3)4/h2*5-18,24-28H,1-4,19-23H2;5*(H2,1,2,3,4)/t2*5-,6+,7+,8-,9+,10+,11-,12+,13+,14-,15+,16-,17+,18+;;;;;/m00...../s1
Molecular Formula | H2O4S |
Molecular Weight | 98.078 |
Charge | 0 |
Count |
|
Stereochemistry | ACHIRAL |
Additional Stereochemistry | No |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Optical Activity | NONE |
Molecular Formula | C18H37N5O9 |
Molecular Weight | 467.5145 |
Charge | 0 |
Count |
|
Stereochemistry | ABSOLUTE |
Additional Stereochemistry | No |
Defined Stereocenters | 14 / 14 |
E/Z Centers | 0 |
Optical Activity | UNSPECIFIED |
DescriptionCurator's Comment: Description was created based on several resourses, including http://www.drugbank.ca/drugs/DB00684
Curator's Comment: Description was created based on several resourses, including http://www.drugbank.ca/drugs/DB00684
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
Sources: https://www.karger.com/Article/Pdf/237996
Curator's Comment: Poor penetrability of tobramycin through the blood-CSF barrier was shown.
Originator
Sources: http://www.ncbi.nlm.nih.gov/pubmed/?term=4208289
Curator's Comment: Tobramycin is the generic ingredient in eleven branded drugs marketed by Amneal Pharms, Chiesi Usa Inc, Akorn Inc, Fera Pharms, Pulmoflow Inc, Alcon, Alcon Labs Inc, Bausch And Lomb, Novartis Pharms, Alcon Pharms Ltd, Apotex Inc, Novartis, Teva Pharms Usa, Akorn, Lilly, Mylan Labs Ltd, Hospira, Hikma Maple , X Gen Pharms, Igi Labs Inc, Fresenius Kabi Usa, Apothecon, Watson Labs Inc, and Xellia Pharms Aps, and is included in forty-five NDAs. Nebramycin, an antibiotic complex of at least seven factors, was first described in 1967 by Stark et al.
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: CHEMBL1641336 Sources: http://www.drugbank.ca/drugs/DB00684#targets |
9.0 µM [IC50] |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Curative | TOBREX Approved Useexternal infections of the eye Launch Date3.45427214E11 |
|||
Primary | KITABIS PAK Approved Usecystic fibrosis Launch Date1.39216316E12 |
Cmax
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
3.7 μg/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/4208289/ |
80 mg single, intramuscular dose: 80 mg route of administration: Intramuscular experiment type: SINGLE co-administered: |
TOBRAMYCIN plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN |
|
814 μg/mL |
300 mg single, respiratory dose: 300 mg route of administration: Respiratory experiment type: SINGLE co-administered: |
TOBRAMYCIN unknown | Homo sapiens population: UNKNOWN age: UNKNOWN sex: UNKNOWN food status: UNKNOWN |
AUC
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
11.6 μg × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/4208289/ |
80 mg single, intramuscular dose: 80 mg route of administration: Intramuscular experiment type: SINGLE co-administered: |
TOBRAMYCIN plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN |
T1/2
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
1.6 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/4208289/ |
80 mg single, intramuscular dose: 80 mg route of administration: Intramuscular experiment type: SINGLE co-administered: |
TOBRAMYCIN plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN |
|
4.4 h |
300 mg single, respiratory dose: 300 mg route of administration: Respiratory experiment type: SINGLE co-administered: |
TOBRAMYCIN unknown | Homo sapiens population: UNKNOWN age: UNKNOWN sex: UNKNOWN food status: UNKNOWN |
Funbound
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
100% |
300 mg single, respiratory dose: 300 mg route of administration: Respiratory experiment type: SINGLE co-administered: |
TOBRAMYCIN unknown | Homo sapiens population: UNKNOWN age: UNKNOWN sex: UNKNOWN food status: UNKNOWN |
Doses
Dose | Population | Adverse events |
---|---|---|
12 mg/kg 1 times / day multiple, intravenous (mean) Highest studied dose Dose: 12 mg/kg, 1 times / day Route: intravenous Route: multiple Dose: 12 mg/kg, 1 times / day Sources: |
unhealthy, 2 months - 27 years Health Status: unhealthy Condition: cystic fibrosis Age Group: 2 months - 27 years Sources: |
|
300 mg 2 times / day multiple, respiratory Recommended Dose: 300 mg, 2 times / day Route: respiratory Route: multiple Dose: 300 mg, 2 times / day Sources: |
unhealthy, >6 years n = 190 Health Status: unhealthy Age Group: >6 years Sex: M+F Population Size: 190 Sources: |
Other AEs: Forced expiratory volume decreased, Rales... Other AEs: Forced expiratory volume decreased (31%) Sources: Rales (19%) Red blood cell sedimentation rate increased (8%) Dysphonia (6%) Wheezing (5%) |
3 mg 3 times / day multiple, ophthalmic Recommended Dose: 3 mg, 3 times / day Route: ophthalmic Route: multiple Dose: 3 mg, 3 times / day Sources: |
unhealthy, adult Health Status: unhealthy Age Group: adult Sources: |
Other AEs: Hypersensitivity, Eyelids itchy sensation of... Other AEs: Hypersensitivity Sources: Eyelids itchy sensation of Swelling Redness of eyelid conjunctiva |
1.5 mg/kg 3 times / day multiple, intramuscular Dose: 1.5 mg/kg, 3 times / day Route: intramuscular Route: multiple Dose: 1.5 mg/kg, 3 times / day Sources: |
unhealthy, adult n = 28 Health Status: unhealthy Condition: gram-negative bacilli infection Age Group: adult Population Size: 28 Sources: |
|
2 mg/kg single, intraperitoneal Dose: 2 mg/kg Route: intraperitoneal Route: single Dose: 2 mg/kg Sources: |
unhealthy, adult n = 5 Health Status: unhealthy Condition: end stage renal disease Age Group: adult Population Size: 5 Sources: |
AEs
AE | Significance | Dose | Population |
---|---|---|---|
Rales | 19% | 300 mg 2 times / day multiple, respiratory Recommended Dose: 300 mg, 2 times / day Route: respiratory Route: multiple Dose: 300 mg, 2 times / day Sources: |
unhealthy, >6 years n = 190 Health Status: unhealthy Age Group: >6 years Sex: M+F Population Size: 190 Sources: |
Forced expiratory volume decreased | 31% | 300 mg 2 times / day multiple, respiratory Recommended Dose: 300 mg, 2 times / day Route: respiratory Route: multiple Dose: 300 mg, 2 times / day Sources: |
unhealthy, >6 years n = 190 Health Status: unhealthy Age Group: >6 years Sex: M+F Population Size: 190 Sources: |
Wheezing | 5% | 300 mg 2 times / day multiple, respiratory Recommended Dose: 300 mg, 2 times / day Route: respiratory Route: multiple Dose: 300 mg, 2 times / day Sources: |
unhealthy, >6 years n = 190 Health Status: unhealthy Age Group: >6 years Sex: M+F Population Size: 190 Sources: |
Dysphonia | 6% | 300 mg 2 times / day multiple, respiratory Recommended Dose: 300 mg, 2 times / day Route: respiratory Route: multiple Dose: 300 mg, 2 times / day Sources: |
unhealthy, >6 years n = 190 Health Status: unhealthy Age Group: >6 years Sex: M+F Population Size: 190 Sources: |
Red blood cell sedimentation rate increased | 8% | 300 mg 2 times / day multiple, respiratory Recommended Dose: 300 mg, 2 times / day Route: respiratory Route: multiple Dose: 300 mg, 2 times / day Sources: |
unhealthy, >6 years n = 190 Health Status: unhealthy Age Group: >6 years Sex: M+F Population Size: 190 Sources: |
Eyelids itchy sensation of | 3 mg 3 times / day multiple, ophthalmic Recommended Dose: 3 mg, 3 times / day Route: ophthalmic Route: multiple Dose: 3 mg, 3 times / day Sources: |
unhealthy, adult Health Status: unhealthy Age Group: adult Sources: |
|
Hypersensitivity | 3 mg 3 times / day multiple, ophthalmic Recommended Dose: 3 mg, 3 times / day Route: ophthalmic Route: multiple Dose: 3 mg, 3 times / day Sources: |
unhealthy, adult Health Status: unhealthy Age Group: adult Sources: |
|
Redness of eyelid conjunctiva | 3 mg 3 times / day multiple, ophthalmic Recommended Dose: 3 mg, 3 times / day Route: ophthalmic Route: multiple Dose: 3 mg, 3 times / day Sources: |
unhealthy, adult Health Status: unhealthy Age Group: adult Sources: |
|
Swelling | 3 mg 3 times / day multiple, ophthalmic Recommended Dose: 3 mg, 3 times / day Route: ophthalmic Route: multiple Dose: 3 mg, 3 times / day Sources: |
unhealthy, adult Health Status: unhealthy Age Group: adult Sources: |
Overview
CYP3A4 | CYP2C9 | CYP2D6 | hERG |
---|---|---|---|
OverviewOther
Other Inhibitor | Other Substrate | Other Inducer |
---|---|---|
Drug as perpetrator
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
Page: 8.0 |
minor | |||
Page: 8.0 |
minor | |||
Page: 8.0 |
minor | |||
Page: 7.0 |
no | |||
Page: 8.0 |
no | |||
Page: 1612.0 |
no | |||
Page: 7.0 |
yes | |||
Page: 7.0 |
yes |
Drug as victim
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
Page: 2908.0 |
yes |
PubMed
Title | Date | PubMed |
---|---|---|
New and emerging therapies for pulmonary complications of cystic fibrosis. | 2001 |
|
The effect of apramycin on colonization of pathogenic Escherichia coli in the intestinal tract of chicks. | 2001 Apr |
|
Fungal keratitis in a daily disposable soft contact lens wearer. | 2001 Apr |
|
The role of nebulized antibiotics in treating serious respiratory infections. | 2001 Aug |
|
Pharmacokinetics and pharmacodynamics of aztreonam and tobramycin in hospitalized patients. | 2001 Aug |
|
Mycobacterium keratitis following hyperopic laser in situ keratomileusis. | 2001 Aug |
|
Prevalence and analysis of risk factors for infections caused by resistant Escherichia coli strains in Anhui, China. | 2001 Aug |
|
In vitro elution of tobramycin from bioabsorbable polycaprolactone beads. | 2001 Aug |
|
Serratia Marcescens corneal ulcer as a complication of orthokeratology. | 2001 Aug |
|
Selective decontamination of the digestive tract in severely burned pediatric patients. | 2001 Aug |
|
Aminoglycosides in cystic fibrosis: a descriptive study of current practice in Australia. | 2001 Jan-Feb |
|
[Susceptibilities of bacteria isolated from patients with lower respiratory infectious diseases to antibiotics (1999)]. | 2001 Jul |
|
Drug interference in clinical chemistry: recommendation of drugs and their concentrations to be used in drug interference studies. | 2001 Jul |
|
Recent advances in cystic fibrosis. | 2001 Jul |
|
Tobramycin (Cystic Fibrosis Foundation/PathoGenesis). | 2001 Jun |
|
Effective bactericidal activity of tobramycin and vancomycin eluted from acrylic bone cement. | 2001 Jun |
|
Changing antibiotic sensitivity patterns at a university hospital, 1992 through 1999. | 2001 Jun |
|
Continuous versus intermittent administration of ceftazidime in intensive care unit patients with nosocomial pneumonia. | 2001 Jun |
|
Population kinetics of tobramycin in neonates. | 2001 Jun |
|
Mucositis reduction by selective elimination of oral flora in irradiated cancers of the head and neck: a placebo-controlled double-blind randomized study. | 2001 Jun 1 |
|
In vitro selection of RNA against kanamycin B. | 2001 Jun 30 |
|
Statement on the application of the ToBI test for batch potency testing of tetanus vaccines for human use. | 2001 Mar-Apr |
|
[Cloning of the sugar related biosynthesis gene cluster from Streptomyces tenebrarius H6]. | 2001 May |
|
Natural antibiotic susceptibility of recently established coryneform bacteria. | 2001 May |
|
Transmucosal transport of tobramycin incorporated in solid lipid nanoparticles (SLN) after duodenal administration to rats. Part II--tissue distribution. | 2001 May |
|
Inhibition of the HIV-1 rev-RRE complex formation by unfused aromatic cations. | 2001 May |
|
Clinical applications of a novel sustained-release injectable drug delivery system: DepoFoam technology. | 2001 May-Jun |
|
Epidemiologic Study of Pseudomonas aeruginosa in critical patients and reservoirs. | 2001 May-Jun |
|
A comparison of cortisporin and ciprofloxacin otic drops as prophylaxis against post-tympanostomy otorrhea. | 2001 Nov 1 |
|
Effects of antibiotics on morphologic characteristics and migration of canine corneal epithelial cells in tissue culture. | 2001 Oct |
|
Bacillus cereus keratitis associated with contact lens wear. | 2001 Oct |
|
Efficacy and safety of aerosolized tobramycin in cystic fibrosis. | 2001 Oct |
|
Genotypic characterization of Pseudomonas aeruginosa strains recovered from patients with cystic fibrosis after initial and subsequent colonization. | 2001 Oct |
|
Aminoglycoside binding to human and bacterial A-Site rRNA decoding region constructs. | 2001 Oct |
|
High-rising terminals and fall-rise tunes in Australian English. | 2001 Oct-Dec |
|
The changing nature of aminoglycoside resistance mechanisms and prevalence of newly recognized resistance mechanisms in Turkey. | 2001 Sep |
|
Isolation and culture of airway epithelial cells from chronically infected human lungs. | 2001 Sep |
|
[Survey of the antibiotic sensitivity of Pseudomonas aeruginosa in France and the distribution of beta-lactam resistance mechanisms: the GERPB 1999 study]. | 2001 Sep |
|
Reduction in gram-positive pneumonia and antibiotic consumption following the use of a SDD protocol including nasal and oral mupirocin. | 2001 Sep |
|
Recovery from vestibular ototoxicity. | 2001 Sep |
|
Defining a pulmonary exacerbation in cystic fibrosis. | 2001 Sep |
|
A simple infection model using pre-colonized implants to reproduce rat chronic Staphylococcus aureus osteomyelitis and study antibiotic treatment. | 2001 Sep |
|
Treatment of chronic rhinosinusitis refractory to other treatments with topical antibiotic therapy delivered by means of a large-particle nebulizer: results of a controlled trial. | 2001 Sep |
|
Microbiological and immunologic considerations with aerosolized drug delivery. | 2001 Sep |
|
Treatment With tobramycin solution for inhalation in bronchiectasis patients with Pseudomonas aeruginosa. | 2001 Sep |
|
Administration of aerosolized antibiotics in cystic fibrosis patients. | 2001 Sep |
|
Evaluating possible pharmacokinetic interactions between tobramycin, piperacillin, and a combination of piperacillin and tazobactam in patients with various degrees of renal impairment. | 2001 Sep |
|
Characterization of paired mucoid/non-mucoid Pseudomonas aeruginosa isolates from Danish cystic fibrosis patients: antibiotic resistance, beta-lactamase activity and RiboPrinting. | 2001 Sep |
|
Effect of inhaled tobramycin on early Pseudomonas aeruginosa colonisation in patients with cystic fibrosis. | 2001 Sep 22 |
|
Aerosols and anti-infectious agents. | 2001 Spring |
Patents
Sample Use Guides
In Vivo Use Guide
Curator's Comment: Tobramycin does not pass the gastro-intestinal tract, so for systemic use it can only be given intravenously or intramuscularly http://www.accessdata.fda.gov/drugsatfda_docs/label/2011/063111s014lbl.pdf. Dosage is different for different infections. Ophthalmic route of administration is also possible, as indicated here http://www.accessdata.fda.gov/scripts/cder/drugsatfda/index.cfm?fuseaction=Search.DrugDetails or for TOBREX http://www.accessdata.fda.gov/drugsatfda_docs/label/2012/050541s024lbl.pdf
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
Sources: http://www.ncbi.nlm.nih.gov/pubmed/?term=11112146
Curator's Comment: Low dose tobramycin (4 ug/ml) as a single agent was bactericidal against only 16% of Pseudomonas aeruginosa isolates; however, 72% of isolates were killed with high-dose tobramycin (200 ug/ml).
High-dose tobramycin (200 ug/ml) killed 72% of Pseudomonas aeruginosa isolates
Substance Class |
Chemical
Created
by
admin
on
Edited
Fri Dec 15 16:20:30 UTC 2023
by
admin
on
Fri Dec 15 16:20:30 UTC 2023
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Record UNII |
HJT0RXD7JK
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Record Status |
Validated (UNII)
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Record Version |
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Classification Tree | Code System | Code | ||
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FDA ORPHAN DRUG |
536416
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NCI_THESAURUS |
C2363
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HJT0RXD7JK
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11954252
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79645-27-5
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m10917
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DTXSID50964441
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49842-07-1
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HJT0RXD7JK
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CHEMBL1747
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256-499-2
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C893
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100000091585
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7276
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DBSALT000317
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