TOY

TOBRAMYCIN

Created: 2002-04-09
Last modified:  2021-03-13

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Chemical Details

Formal Charge0
Atom Count69
Chiral Atom Count14
Bond Count71
Aromatic Bond Count0
2D diagram of TOY

Chemical Component Summary

NameTOBRAMYCIN
Synonyms4-AMINO-2-[4,6-DIAMINO-3-(3-AMINO-6-AMINOMETHYL-5-HYDROXY-TETRAHYDRO-PYRAN-2-YLOXY)-2-HYDROXY-CYCLOHEXYLOXY]-6-HYDROXYMETHYL-TETRAHYDRO-PYRAN-3,5-DIOL
Systematic Name (OpenEye OEToolkits)(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-hydroxy-oxan-2-yl]oxy-2-hydroxy-cyclohexyl]oxy-6-(hydroxymethyl)oxane-3,5-diol
FormulaC18 H37 N5 O9
Molecular Weight467.514
TypeNON-POLYMER

Chemical Descriptors

TypeProgram Version Descriptor
SMILESACDLabs10.04O(C2C(O)C(OC1OC(CN)C(O)CC1N)C(N)CC2N)C3OC(C(O)C(N)C3O)CO
SMILESCACTVS3.341NC[CH]1O[CH](O[CH]2[CH](N)C[CH](N)[CH](O[CH]3O[CH](CO)[CH](O)[CH](N)[CH]3O)[CH]2O)[CH](N)C[CH]1O
SMILESOpenEye OEToolkits1.5.0C1C(C(C(C(C1N)OC2C(C(C(C(O2)CO)O)N)O)O)OC3C(CC(C(O3)CN)O)N)N
Canonical SMILESCACTVS3.341 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
Canonical SMILESOpenEye OEToolkits1.5.0 C1[C@@H]([C@H]([C@@H]([C@H]([C@@H]1N)O[C@@H]2[C@@H]([C@H]([C@@H]([C@H](O2)CO)O)N)O)O)O[C@@H]3[C@@H](C[C@@H]([C@H](O3)CN)O)N)N
InChIInChI1.03 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
InChIKeyInChI1.03 NLVFBUXFDBBNBW-PBSUHMDJSA-N

Drug Info: DrugBank

DrugBank IDDB00684 
NameTobramycin
Groups
  • approved
  • investigational
DescriptionAminoglycosides, many of which are derived directly from _Streptomyces_ spp., are concentration-dependent bactericidal antibiotics with a broad spectrum of activity against Gram-positive and Gram-negative organisms.[A232294] Inhaled tobramycin is notable for its use in treating chronic _Pseudomonas aeruginosa_ infections in cystic fibrosis patients, as _P. aeruginosa_ is notoriously inherently resistant to many antibiotics.[A232294, A232299, L32739] However, tobramycin can also be administered intravenously and topically to treat a variety of infections caused by susceptible bacteria.[L32744, L32749] Its use is limited in some cases by characteristic toxicities such as nephrotoxicity and ototoxicity, yet it remains a valuable option in the face of growing resistance to front-line antibiotics such as β-lactams and cephalosporins.[A232294, A232349, L32739, L32749] Tobramycin was approved by the FDA in 1975 and is currently available in a variety of forms for administration by inhalation, injection, and external application to the eye (ophthalmic).[L32739, L32744, L32749]
Synonyms
  • Tobramycin sulfate
  • Tobramycine
  • 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-streptamine
  • Nebramycin 6
  • Tobramycin hydrochloride
Brand Names
  • Tobramycin Ophthalmic Solution USP 0.3%
  • Sandoz Tobramycin
  • Tobramycin and Dexamethasone
  • Nebcin Inj 40mg/ml
  • Tobramycin Inhalation Solution Pak
IndicationInhaled tobramycin is indicated for the management of cystic fibrosis patients with _Pseudomonas aeruginosa_, but is not recommended in patients under six years of age, those with forced expiratory volume in 1 second (FEV<sub>1</sub>) <25 or >80% predicted, or in those with _Burkholderia cepacia_.[L32739,L45364] Tobramycin applied topically to the eyes is indicated for the treatment of external eye (and adjoining structure) infections by susceptible bacteria.[L32744] Tobramycin injection is indicated in adult and pediatric patients for the treatment of serious bacterial infections, including septicemia (caused by _P. aeruginosa_, _Escherichia coli_, and _Klebsiella_ spp.), lower respiratory tract infections (caused by _P. aeruginosa_, _Klebsiella_ spp., _Enterobacter_ spp., _Serratia_ spp., _E. coli_, and _Staphylococcus aureus_, both penicillinase and non-penicillinase-producing strains), serious central-nervous-system infections (meningitis, caused by susceptible organisms), intra-abdominal infections including peritonitis (caused by _E. coli_, _Klebsiella_ spp., and _Enterobacter_ spp.), skin, bone, and skin structure infections (caused by _P. aeruginosa_, _Proteus_ spp., _E. coli_, _Klebsiella_ spp., _Enterobacter_ spp., _Serratia_ spp. and _S. aureus_), and complicated and recurrent urinary tract infections (caused by _P. aeruginosa_, _Proteus_ spp., _E. coli_, _Klebsiella_ spp., _Enterobacter_ spp., _Serratia_ spp., _S. aureus_, _Providencia_ spp., and _Citrobacter_ spp.).[L32749] Aminoglycosides, including tobramycin, should generally not be used in uncomplicated urinary tract infections or staphylococcal infections unless less toxic antibiotics cannot be used and the bacteria in question are known to be sensitive to aminoglycosides.[L32749,L45359] As with all antibiotics, tobramycin use should be limited to cases where bacterial infections are known or strongly suspected to be caused by sensitive organisms, and the possible emergence of resistance should be monitored closely.[L32739,L32744,L32749]
Categories
  • Agents that produce neuromuscular block (indirect)
  • Aminoglycoside Antibacterials
  • Anti-Bacterial Agents
  • Anti-Infective Agents
  • Antibacterials for Systemic Use
ATC-Code
  • S01AA12
  • J01GB01
CAS number32986-56-4

Drug Targets

NameTarget SequencePharmacological ActionActions
16S ribosomal RNA-unknowninhibitor
23S ribosomal RNA-unknowninhibitor
Bacterial outer membrane-unknownincorporation into and destabilization
Cytoplasmic membrane-unknownincorporation into and destabilization
Drug Info/Drug Targets: DrugBank 3.0: a comprehensive resource for 'omics' research on drugs. Knox C, Law V, Jewison T, Liu P, Ly S, Frolkis A, Pon A, Banco K, Mak C, Neveu V, Djoumbou Y, Eisner R, Guo AC, Wishart DS. Nucleic Acids Res. 2011 Jan; 39 (Database issue):D1035-41. | PMID:21059682

Related Resource References

Resource NameReference
PubChem 36294
ChEMBL CHEMBL1747
ChEBI CHEBI:28864