Tobramycin (CED0001670)

Record Information
Version1.0
Creation Date2016-05-22 03:47:25 UTC
Update Date2026-05-14 16:46:00 UTC
Accession NumberCHEM016913
Identification
Common NameTobramycin
ClassSmall Molecule
Description
Tobramycin is an organic compound with the formula C18H37N5O9 and an average molecular weight of 467.51 g/mol. Tobramycin belongs to the carbohydrates and carbohydrate conjugates, a subclass of organooxygen compounds within the organic compounds. It functions as a biological inhibitor (PMC10491871). The compound is found in or released from 27 recorded sources. These include healthcare, pharmaceuticals and veterinary products, specifically antibiotics, antiinfectives, and aminoglycoside antibacterials. Other sources include food, food processing and cookware, such as processing meats; household items, including credit card holders; building and construction materials, such as roofs, fencing, tents or canopies, and ceilings; household cleaning and consumer products, including pipe accessories, ash trays, cigar cigarettes, non electric simulated smoking devices, other smoking requisites, and one more; and electrical and electronic equipment, including antennas, auxiliary devices, electric switches, electric hearing aids, electrically stimulated smoking devices, and seven more. Recorded exposure routes for the substance include oral, intravenous, intramuscular, respiratory, ophthalmic, and inhalation. Regarding its health effects, tobramycin is used as a treatment for osteomyelitis (PMC9668588) and cystic fibrosis (PMC11773326). Additionally, it has a therapeutic effect on inflammation (PMC11664836).
Contaminant Type
  • Human Neurotoxin
Chemical Structure
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
3'-Deoxykanamycin bChEBI
Nebramycin 6ChEBI
Nebramycin factir 6ChEBI
O-3-Amino-3-deoxy-alpha-D-glucopyranosyl-(1-4)-O-(2,6-diamino-2,3,6-trideoxy-alpha-D-ribohexopyranosyl-(1-4))-2-deoxy-D-streptamineChEBI
TobracinChEBI
TobrexChEBI
Nebramycin factor 6Kegg
TobiKegg
BethkisKegg
O-3-Amino-3-deoxy-a-D-glucopyranosyl-(1-4)-O-(2,6-diamino-2,3,6-trideoxy-a-D-ribohexopyranosyl-(1-4))-2-deoxy-D-streptamineGenerator
O-3-Amino-3-deoxy-α-D-glucopyranosyl-(1-4)-O-(2,6-diamino-2,3,6-trideoxy-α-D-ribohexopyranosyl-(1-4))-2-deoxy-D-streptamineGenerator
TOBHMDB
SPRC-AB01HMDB
Tobramycin solution for inhalationHMDB
Tobramycin sulfateHMDB
ObracinHMDB
NebcinHMDB
NebicinHMDB
BrulamycinHMDB
Sulfate, tobramycinHMDB
Chemical FormulaC18H37N5O9
Average Molecular Mass467.515 g/mol
Monoisotopic Mass467.259 g/mol
CAS Registry Number32986-56-4
IUPAC Name(2S,3R,4S,5S,6R)-4-amino-2-{[(1S,2S,3R,4S,6R)-4,6-diamino-3-{[(2R,3R,5S,6R)-3-amino-6-(aminomethyl)-5-hydroxyoxan-2-yl]oxy}-2-hydroxycyclohexyl]oxy}-6-(hydroxymethyl)oxane-3,5-diol
Traditional Nametobramycin
SMILESNC[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 IdentifierInChI=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 KeyNLVFBUXFDBBNBW-PBSUHMDJSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as 4,6-disubstituted 2-deoxystreptamines. These are 2-deoxystreptamine aminoglycosides that are glycosidically linked to a pyranose of furanose unit at the C4- and C6-positions.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassCarbohydrates and carbohydrate conjugates
Direct Parent4,6-disubstituted 2-deoxystreptamines
Alternative Parents
Substituents
  • 4,6-disubstituted 2-deoxystreptamine
  • Glycosyl compound
  • O-glycosyl compound
  • Aminocyclitol or derivatives
  • Cyclohexanol
  • Cyclohexylamine
  • Cyclitol or derivatives
  • Monosaccharide
  • Oxane
  • Cyclic alcohol
  • 1,2-aminoalcohol
  • Secondary alcohol
  • Organoheterocyclic compound
  • Acetal
  • Oxacycle
  • Alcohol
  • Organonitrogen compound
  • Primary aliphatic amine
  • Hydrocarbon derivative
  • Organopnictogen compound
  • Organic nitrogen compound
  • Amine
  • Primary alcohol
  • Primary amine
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
ApplicationsNot Available
Biological Roles
Chemical RolesNot Available
Organoleptic EffectsNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility53.7 g/LALOGPS
logP-3ALOGPS
logP-6.5ChemAxon
logS-0.94ALOGPS
pKa (Strongest Acidic)12.54ChemAxon
pKa (Strongest Basic)9.83ChemAxon
Physiological Charge5ChemAxon
Hydrogen Acceptor Count14ChemAxon
Hydrogen Donor Count10ChemAxon
Polar Surface Area268.17 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity106.69 m³·mol⁻¹ChemAxon
Polarizability47.18 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyDeposition DateView
Predicted GC-MSPredicted GC-MS Spectrumsplash10-000t-9331300000-a064abea38315acb9ea8Not AvailableView Spectrum
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1D NMR1H NMR Spectrum (1D, D2O, predicted)Not AvailableNot AvailableView Spectrum
1D NMR13C NMR Spectrum (1D, D2O, predicted)Not AvailableNot AvailableView Spectrum
Toxicity Profile
Mechanism of ToxicityNot Available
Carcinogenicity (IARC Classification)Not Available
Minimum Risk LevelNot Available
SymptomsNot Available
TreatmentNot Available
Toxicity Values
Toxicity ValueUnitValue RangeOrganismDose DescriptorRoute of ExposurePredicted or ExperimentalReference
7024.0Log mg/kg[4000:12000]RatLD50oralpredictedNot Available
Health Effects
Health EffectRelationshipDirectionReference
inflammationhas_therapeutic_effect_onNot AvailablePMC11664836
cystic fibrosisis_treatment_forNot AvailablePMC11773326
osteomyelitisis_treatment_forNot AvailablePMC9668588
Exposure Sources
Source IDSourceSectorReference
233BrushesPersonal care & cosmeticsNot Available
306AntibioticsHealthcare, pharmaceuticals & veterinary productsNot Available
344Aminoglycoside antibacterialsHealthcare, pharmaceuticals & veterinary productsNot Available
395AntiinfectivesHealthcare, pharmaceuticals & veterinary productsNot Available
495CeilingsBuilding & ConstructionNot Available
496FencingBuilding & ConstructionNot Available
499RoofsBuilding & ConstructionNot Available
503Tents Or CanopiesBuilding & ConstructionNot Available
506AntennasElectrical & Electronic EquipmentNot Available
507Auxiliary DevicesElectrical & Electronic EquipmentNot Available
516Electric Hearing AidsElectrical & Electronic EquipmentNot Available
517Electric SwitchesElectrical & Electronic EquipmentNot Available
518Electrically Stimulated Smoking DevicesElectrical & Electronic EquipmentNot Available
520Emergency Protective DevicesElectrical & Electronic EquipmentNot Available
525Line Transmission SystemsElectrical & Electronic EquipmentNot Available
527MagnetsElectrical & Electronic EquipmentNot Available
529Power CablesElectrical & Electronic EquipmentNot Available
530Radio Transmission SystemsElectrical & Electronic EquipmentNot Available
537Television SystemsElectrical & Electronic EquipmentNot Available
539Video GamesElectrical & Electronic EquipmentNot Available
552Processing MeatsFood, food processing & cookwareNot Available
554Ash TraysHousehold cleaning & consumer productsNot Available
556Cigar CigarettesHousehold cleaning & consumer productsNot Available
559Non Electric Simulated Smoking DevicesHousehold cleaning & consumer productsNot Available
560Other Smoking RequisitesHousehold cleaning & consumer productsNot Available
562Pipe AccessoriesHousehold cleaning & consumer productsNot Available
566Tobacco PipesHousehold cleaning & consumer productsNot Available
572Credit Card HoldersHousehold itemsNot Available
578Making CigarsIndustrial manufacturing & chemical processingNot Available
579Manufacture Of Iron Or SteelIndustrial manufacturing & chemical processingNot Available
581Paper Making MachinesIndustrial manufacturing & chemical processingNot Available
598Fertiliser DistributorsAgriculture & land managementNot Available
602MolluscicidesAgriculture & land managementNot Available
609AftershavePersonal care & cosmeticsNot Available
612Body Washing Or Cleaning ImplementsPersonal care & cosmeticsNot Available
613DepilatoriesPersonal care & cosmeticsNot Available
617Lip Care ProductsPersonal care & cosmeticsNot Available
619Manicure PedicurePersonal care & cosmeticsNot Available
630ToysRecreation & sports surfacesNot Available
631Anthraquinone DyesTextiles, leather & furnishingsNot Available
633Azo DyesTextiles, leather & furnishingsNot Available
643HeadwearTextiles, leather & furnishingsNot Available
650Purses Luggage Hand BagsTextiles, leather & furnishingsNot Available
651Purses Money Bags WalletsTextiles, leather & furnishingsNot Available
653SewingTextiles, leather & furnishingsNot Available
658Touch FastenersTextiles, leather & furnishingsNot Available
662Yarns Or ThreadsTextiles, leather & furnishingsNot Available
663Sanitary EquipmentWastewater, sanitation & biosolidsNot Available
Pathways
4 pathways
Tobramycin Action Pathway
Tobramycin Action Pathway
Tobramycin Action Pathway (new)
Tobramycin Action Pathway (new)
Netilmicin Action Pathway
Netilmicin Action Pathway
Tobramycin Drug Metabolism Action Pathway
Tobramycin Drug Metabolism Action Pathway
Targets
StructureProteinUniProt IDOrganismRelationshipDetails
Gap junction beta-2 protein structureClick to view 3D structureGap junction beta-2 proteinP29033HumansPredicted (SEA)0.311397
Click to view 3D structureHuman immunodeficiency virus type 1 REVQ77Y21Human immunodeficiency virus 1Predicted (SEA)0.0778492
Beta-ketoacyl-[acyl-carrier-protein] synthase III structureClick to view 3D structureBeta-ketoacyl-[acyl-carrier-protein] synthase IIIP0A6R0Escherichia coli (strain K12)Predicted (SEA)0.0778492
Gap junction alpha-1 protein structureClick to view 3D structureGap junction alpha-1 proteinP17302HumansPredicted (SEA)0.389246
Click to view 3D structure3-oxoacyl-[acyl-carrier-protein] synthase 3C3TDZ2Escherichia coliPredicted (SEA)0.311397
Heparanase structureClick to view 3D structureHeparanaseQ9Y251HumansPredicted (SEA)0.544945
CD44 antigen structureClick to view 3D structureCD44 antigenP16070HumansPredicted (SEA)2.17978
Click to view 3D structureCD44 antigenP15379Mus musculusPredicted (SEA)2.17978
Click to view 3D structureAlpha-amylaseQ7M328Sus scrofa domesticusPredicted (SEA)1.24559
Click to view 3D structureLectinB4EH87Burkholderia cenocepacia (strain ATCC BAA-245 / DSM 16553 / LMG 16656/ NCTC 13227 / J2315 / CF5610) (Burkholderia cepacia (strain J2315))Predicted (SEA)8.32987
Click to view 3D structureType 1 fimbrin D-mannose specific adhesinP08191Escherichia coli K-12Predicted (SEA)9.88685
Click to view 3D structureEndo-beta-N-acetylglucosaminidaseQ9ZB22Arthrobacter protophormiaePredicted (SEA)3.58106
Click to view 3D structureKiller cell lectin-like receptor subfamily B member 1AP27471Rattus norvegicusPredicted (SEA)2.72472
Click to view 3D structureN-acetyllactosaminide alpha-1,3-galactosyltransferaseP50127Sus scrofaPredicted (SEA)8.87481
Galectin-3 structureClick to view 3D structureGalectin-3P17931HumansPredicted (SEA)16.8933
Click to view 3D structureSucrase-isomaltase, intestinalP23739Rattus norvegicusPredicted (SEA)9.41976
Click to view 3D structureLysosomal alpha-glucosidaseQ6P7A9Rattus norvegicusPredicted (SEA)9.57545
Click to view 3D structurePeptidoglycan-N-acetylglucosamine deacetylaseQ8DP63Streptococcus pneumoniae (strain ATCC BAA-255 / R6)Predicted (SEA)33.2416
Click to view 3D structureE-selectinP98105Rattus norvegicusPredicted (SEA)4.28171
Click to view 3D structureAdenosine deaminaseP56658Bos taurusPredicted (SEA)79.0948
Maltase-glucoamylase structureClick to view 3D structureMaltase-glucoamylaseO43451HumansPredicted (SEA)29.2713
Galectin-9 structureClick to view 3D structureGalectin-9O00182HumansPredicted (SEA)49.6678
Sialic acid-binding Ig-like lectin 7 structureClick to view 3D structureSialic acid-binding Ig-like lectin 7Q9Y286HumansPredicted (SEA)3.50322
Carbonic anhydrase 12 structureClick to view 3D structureCarbonic anhydrase 12O43570HumansPredicted (SEA)3842.25
Click to view 3D structureCytidine deaminaseP56389Mus musculusPredicted (SEA)47.0988
Concentrations
Not Available
External Links
DrugBank IDDB00684
HMDB IDHMDB0014822
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDTOY
Wikipedia LinkTobramycin
Chemspider ID33377
ChEBI ID28864
PubChem Compound ID36294
Kegg Compound IDC00397
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=11000679
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=11072877
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=11459219
4. https://www.ncbi.nlm.nih.gov/pubmed/?term=11478352
5. https://www.ncbi.nlm.nih.gov/pubmed/?term=14961139
6. https://www.ncbi.nlm.nih.gov/pubmed/?term=15813341
7. https://www.ncbi.nlm.nih.gov/pubmed/?term=16205136
8. https://www.ncbi.nlm.nih.gov/pubmed/?term=16239129
9. https://www.ncbi.nlm.nih.gov/pubmed/?term=16478137
10. https://www.ncbi.nlm.nih.gov/pubmed/?term=16650821
11. https://www.ncbi.nlm.nih.gov/pubmed/?term=17150225
12. https://www.ncbi.nlm.nih.gov/pubmed/?term=18331849
13. https://www.ncbi.nlm.nih.gov/pubmed/?term=19072156
14. https://www.ncbi.nlm.nih.gov/pubmed/?term=19220547
15. https://www.ncbi.nlm.nih.gov/pubmed/?term=19340717
16. https://www.ncbi.nlm.nih.gov/pubmed/?term=19465435
17. https://www.ncbi.nlm.nih.gov/pubmed/?term=20000576
18. https://www.ncbi.nlm.nih.gov/pubmed/?term=20884302
19. https://www.ncbi.nlm.nih.gov/pubmed/?term=20938669
20. https://www.ncbi.nlm.nih.gov/pubmed/?term=21275493
21. https://www.ncbi.nlm.nih.gov/pubmed/?term=21343445
22. https://www.ncbi.nlm.nih.gov/pubmed/?term=21357290
23. https://www.ncbi.nlm.nih.gov/pubmed/?term=21396748
24. https://www.ncbi.nlm.nih.gov/pubmed/?term=21414310
25. https://www.ncbi.nlm.nih.gov/pubmed/?term=21429824
26. https://www.ncbi.nlm.nih.gov/pubmed/?term=21438171
27. https://www.ncbi.nlm.nih.gov/pubmed/?term=21530479
28. https://www.ncbi.nlm.nih.gov/pubmed/?term=21592592
29. https://www.ncbi.nlm.nih.gov/pubmed/?term=21726492
30. https://www.ncbi.nlm.nih.gov/pubmed/?term=21756818
31. https://www.ncbi.nlm.nih.gov/pubmed/?term=21796931
32. https://www.ncbi.nlm.nih.gov/pubmed/?term=21815282