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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
Structure of TOBRAMYCIN SULFATE

SMILES

OS(O)(=O)=O.OS(O)(=O)=O.OS(O)(=O)=O.OS(O)(=O)=O.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.NC[C@H]4O[C@H](O[C@@H]5[C@@H](N)C[C@@H](N)[C@H](O[C@H]6O[C@H](CO)[C@@H](O)[C@H](N)[C@H]6O)[C@H]5O)[C@H](N)C[C@@H]4O

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

HIDE SMILES / InChI

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

Description
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

Curator's Comment: Poor penetrability of tobramycin through the blood-CSF barrier was shown.

Originator

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

Targets

Primary TargetPharmacologyConditionPotency
9.0 µM [IC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Curative
TOBREX

Approved Use

external infections of the eye

Launch Date

1980
Primary
KITABIS PAK

Approved Use

cystic fibrosis

Launch Date

2014
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
3.7 μg/mL
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 sputum
Homo sapiens
population: UNKNOWN
age: UNKNOWN
sex: UNKNOWN
food status: UNKNOWN
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
11.6 μg × h/mL
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

T1/2

ValueDoseCo-administeredAnalytePopulation
1.6 h
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 sputum
Homo sapiens
population: UNKNOWN
age: UNKNOWN
sex: UNKNOWN
food status: UNKNOWN
Funbound

Funbound

ValueDoseCo-administeredAnalytePopulation
100%
300 mg single, respiratory
dose: 300 mg
route of administration: Respiratory
experiment type: SINGLE
co-administered:
TOBRAMYCIN sputum
Homo sapiens
population: UNKNOWN
age: UNKNOWN
sex: UNKNOWN
food status: UNKNOWN
Doses

Doses

DosePopulationAdverse events​
12 mg/kg 1 times / day multiple, intravenous
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
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
Health Status: unhealthy
Age Group: >6 years
Sex: M+F
Sources:
Other AEs: Forced expiratory volume decreased, Rales...
Other AEs:
Forced expiratory volume decreased (31%)
Rales (19%)
Red blood cell sedimentation rate increased (8%)
Dysphonia (6%)
Wheezing (5%)
Sources:
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
Other AEs: Hypersensitivity, Eyelids itchy sensation of...
Other AEs:
Hypersensitivity
Eyelids itchy sensation of
Swelling
Redness of eyelid conjunctiva
Sources:
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
Health Status: unhealthy
Age Group: adult
Sources:
2 mg/kg single, intraperitoneal
Dose: 2 mg/kg
Route: intraperitoneal
Route: single
Dose: 2 mg/kg
Sources:
unhealthy, adult
Health Status: unhealthy
Age Group: adult
Sources:
AEs

AEs

AESignificanceDosePopulation
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
Health Status: unhealthy
Age Group: >6 years
Sex: M+F
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
Health Status: unhealthy
Age Group: >6 years
Sex: M+F
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
Health Status: unhealthy
Age Group: >6 years
Sex: M+F
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
Health Status: unhealthy
Age Group: >6 years
Sex: M+F
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
Health Status: unhealthy
Age Group: >6 years
Sex: M+F
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
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
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
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
PubMed

PubMed

TitleDatePubMed
Ototoxicity of tobramycin: a clinical overview.
1976 Aug
Synthesis and anti-HIV activity of guanidinoglycosides.
2000 Dec 29
Removal of Foscarnet by hemodialysis using dialysate-side values.
2000 Mar
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
Infectious crystalline keratopathy in an immunosuppressed patient.
2001 Apr
Individualized pharmacokinetic monitoring results in less aminoglycoside-associated nephrotoxicity and fewer associated costs.
2001 Apr
[Mupirocin resistant MRSA in Japan].
2001 Apr
Effect of size and disease on estimated deposition of drugs administered using jet nebulization in children with cystic fibrosis.
2001 Apr
The role of nebulized antibiotics in treating serious respiratory infections.
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
[Antibiotic resistance of Staphylococcus aureus in urban experience: 6 month study in Aquitaine].
2001 Feb
Yersinia enterocolitica infection with multiple liver abscesses uncovering a primary hemochromatosis.
2001 Feb
Antibacterial activity of 41 antimicrobials tested against over 2773 bacterial isolates from hospitalized patients with pneumonia: I--results from the SENTRY Antimicrobial Surveillance Program (North America, 1998).
2001 Feb
Disseminated Pseudomonas aeruginosa and necrotizing pneumonia with complete recovery.
2001 Feb
[Effect of subinhibitory levels of aminoglycosides and fluoroquinolines on hydrophobicity and motility of Serratia marcescens].
2001 Feb
Role of bronchoalveolar lavage in immunocompromised patients with pneumonia treated with a broad spectrum antibiotic and antifungal regimen.
2001 Feb
Changes in strategies for optimal antibacterial therapy in cystic fibrosis.
2001 Feb
[Pacemaker-cable endocarditis and spondylodiscitis caused by Citrobacter koseri. Conservative treatment].
2001 Jan
[Acute pyelonephritis. Randomized multicenter double-blind study comparing ciprofloxacin with combined ciprofloxacin and tobramycin].
2001 Jan 13
Aminoglycosides in cystic fibrosis: a descriptive study of current practice in Australia.
2001 Jan-Feb
Perioperative microbiologic profile of the conjunctiva in photorefractive keratectomy.
2001 Jan-Feb
Recent advances in cystic fibrosis.
2001 Jul
Antibiotic therapy in intra-abdominal infections--a review on randomised clinical trials.
2001 Jul 30
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
Ultraviolet recall-like phenomenon occurring after piperacillin, tobramycin, and ciprofloxacin therapy.
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
Effect of some fractions of alveolar surfactant (phospholipids and SP-A) on the bactericidal activity of different antimicrobials against some respiratory pathogens.
2001 Mar
Aminoglycoside ototoxicity.
2001 Mar
Cystic fibrosis.
2001 Mar
Management of corneal epithelial defects following laser in situ keratomileusis.
2001 Mar-Apr
In vitro susceptibilities to topical antibiotics of bacteria isolated from the surface of clinically symptomatic eyes.
2001 Mar-Apr
[Functional characterization of a multiple-antibiotic resistant plasmid from clinical isolates of methicillin-resistant Staphylococcus aureus].
2001 May
Transmucosal transport of tobramycin incorporated in solid lipid nanoparticles (SLN) after duodenal administration to rats. Part II--tissue distribution.
2001 May
Cost-effectiveness of ceftazidime by continuous infusion versus intermittent infusion for nosocomial pneumonia.
2001 May
In vitro characteristics of tobramycin aerosol from ultrasonic and jet nebulizers.
2001 May
Efficacy of once-daily tobramycin monotherapy for acute pulmonary exacerbations of cystic fibrosis: a preliminary study.
2001 May
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
Aminoglycoside binding to human and bacterial A-Site rRNA decoding region constructs.
2001 Oct
Gene expression in Pseudomonas aeruginosa biofilms.
2001 Oct 25
[Survey of the antibiotic sensitivity of Pseudomonas aeruginosa in France and the distribution of beta-lactam resistance mechanisms: the GERPB 1999 study].
2001 Sep
Microbiological and immunologic considerations with aerosolized drug delivery.
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
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
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 Mon Mar 31 18:25:30 GMT 2025
Edited
by admin
on Mon Mar 31 18:25:30 GMT 2025
Record UNII
HJT0RXD7JK
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
NEBCIN
Preferred Name English
TOBRAMYCIN SULFATE
MART.   MI   ORANGE BOOK   USP   VANDF   WHO-DD  
Common Name English
TOBRAMYCIN SULFATE (2:5)
Common Name English
GERNEBCIN
Common Name English
TOBRAMYCIN SULFATE [USP IMPURITY]
Common Name English
STREPTAMINE, O-3-AMINO-3-DEOXY-.ALPHA.-D-GLUCOPYRANOSYL-(1-6)-O-(2,6-DIAMINO-2,3,6-TRIDEOXY-ALPHA-D-RIBOHEXOPYRANOSYL-(1-4))-2-DEOXY-, D-, SULPHATE (SALT)
Common Name English
TOBRADISTIN
Common Name English
NEBICINA
Common Name English
TOBRAMYCIN SULFATE [MI]
Common Name English
TOBRAMYCIN SULPHATE
Common Name English
D-STREPTAMINE, O-3-AMINO-3-DEOXY-ALPHA-D-GLUCOPYRANOSYL-(1.FWDARW.6)-O-(2,6-DIAMINO-2,3,6-TRIDEOXY-ALPHA-D-RIBO-HEXOPYRANOSYL- (1.FWDARW.4))-2-DEOXY-, SULPHATE (2:5) (SALT)
Common Name English
Tobramycin sulfate [WHO-DD]
Common Name English
TOBRAMYCIN SULFATE [ORANGE BOOK]
Common Name English
TOBRA
Common Name English
OBRACIN
Common Name English
TOBRAMYCIN SULFATE [USP MONOGRAPH]
Common Name English
TOBRAMYCIN SULFATE [MART.]
Common Name English
STREPTAMINE, O-3-AMINO-3-DEOXY-.ALPHA.-D-GLUCOPYRANOSYL-(1-6)-O-(2,6-DIAMINO-2,3,6-TRIDEOXY-ALPHA-D-RIBOHEXOPYRANOSYL-(1-4))-2-DEOXY-, D-, SULFATE (SALT)
Common Name English
TOBRAMYCIN SULFATE [VANDF]
Common Name English
D-STREPTAMINE, O-3-AMINO-3-DEOXY-ALPHA-D-GLUCOPYRANOSYL-(1.FWDARW.6)-O-(2,6-DIAMINO-2,3,6-TRIDEOXY-ALPHA-D-RIBO-HEXOPYRANOSYL- (1.FWDARW.4))-2-DEOXY-, SULFATE (2:5) (SALT)
Common Name English
Classification Tree Code System Code
FDA ORPHAN DRUG 536416
Created by admin on Mon Mar 31 18:25:30 GMT 2025 , Edited by admin on Mon Mar 31 18:25:30 GMT 2025
NCI_THESAURUS C2363
Created by admin on Mon Mar 31 18:25:30 GMT 2025 , Edited by admin on Mon Mar 31 18:25:30 GMT 2025
Code System Code Type Description
FDA UNII
HJT0RXD7JK
Created by admin on Mon Mar 31 18:25:30 GMT 2025 , Edited by admin on Mon Mar 31 18:25:30 GMT 2025
PRIMARY
PUBCHEM
11954252
Created by admin on Mon Mar 31 18:25:30 GMT 2025 , Edited by admin on Mon Mar 31 18:25:30 GMT 2025
PRIMARY
CAS
79645-27-5
Created by admin on Mon Mar 31 18:25:30 GMT 2025 , Edited by admin on Mon Mar 31 18:25:30 GMT 2025
SUPERSEDED
MERCK INDEX
m10917
Created by admin on Mon Mar 31 18:25:30 GMT 2025 , Edited by admin on Mon Mar 31 18:25:30 GMT 2025
PRIMARY Merck Index
EPA CompTox
DTXSID50964441
Created by admin on Mon Mar 31 18:25:30 GMT 2025 , Edited by admin on Mon Mar 31 18:25:30 GMT 2025
PRIMARY
CAS
49842-07-1
Created by admin on Mon Mar 31 18:25:30 GMT 2025 , Edited by admin on Mon Mar 31 18:25:30 GMT 2025
PRIMARY
DAILYMED
HJT0RXD7JK
Created by admin on Mon Mar 31 18:25:30 GMT 2025 , Edited by admin on Mon Mar 31 18:25:30 GMT 2025
PRIMARY
ChEMBL
CHEMBL1747
Created by admin on Mon Mar 31 18:25:30 GMT 2025 , Edited by admin on Mon Mar 31 18:25:30 GMT 2025
PRIMARY
ECHA (EC/EINECS)
256-499-2
Created by admin on Mon Mar 31 18:25:30 GMT 2025 , Edited by admin on Mon Mar 31 18:25:30 GMT 2025
PRIMARY
NCI_THESAURUS
C893
Created by admin on Mon Mar 31 18:25:30 GMT 2025 , Edited by admin on Mon Mar 31 18:25:30 GMT 2025
PRIMARY
SMS_ID
100000091585
Created by admin on Mon Mar 31 18:25:30 GMT 2025 , Edited by admin on Mon Mar 31 18:25:30 GMT 2025
PRIMARY
EVMPD
SUB04896MIG
Created by admin on Mon Mar 31 18:25:30 GMT 2025 , Edited by admin on Mon Mar 31 18:25:30 GMT 2025
PRIMARY
RXCUI
7276
Created by admin on Mon Mar 31 18:25:30 GMT 2025 , Edited by admin on Mon Mar 31 18:25:30 GMT 2025
PRIMARY RxNorm
DRUG BANK
DBSALT000317
Created by admin on Mon Mar 31 18:25:30 GMT 2025 , Edited by admin on Mon Mar 31 18:25:30 GMT 2025
PRIMARY
Related Record Type Details
PARENT -> SALT/SOLVATE
Related Record Type Details
ACTIVE MOIETY