tobramycin   Click here for help

GtoPdb Ligand ID: 10930

Synonyms: Bethkis® | Kitabis® | Tobi Podhaler® | Tobradex® (tobramycin + dexamethasone) | Vantobra®
Approved drug PDB Ligand
tobramycin is an approved drug (FDA (1975), EMA (2011))
Comment: Tobramycin is an aminoglycoside antibiotic that was originally isolated from Streptomyces tenebrarius. It is particularly effective against Gram-negative infections (especially Pseudomonas spp. infections). Like other aminoglycosides it is ototoxic and nephrotoxic.
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 14
Hydrogen bond donors 10
Rotatable bonds 6
Topological polar surface area 268.17
Molecular weight 467.26
XLogP -5.38
No. Lipinski's rules broken 2
SMILES / InChI / InChIKey
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Canonical SMILES NC[C@H]1O[C@H](O[C@@H]2[C@@H](N)C[C@H]([C@@H]([C@H]2O)O[C@H]2O[C@H](CO)[C@H]([C@@H]([C@H]2O)N)O)N)[C@@H](C[C@@H]1O)N
Isomeric SMILES NC[C@H]1O[C@H](O[C@@H]2[C@@H](N)C[C@H]([C@@H]([C@H]2O)O[C@H]2O[C@H](CO)[C@H]([C@@H]([C@H]2O)N)O)N)[C@@H](C[C@@H]1O)N
InChI 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
InChI Key NLVFBUXFDBBNBW-PBSUHMDJSA-N
Classification Click here for help
Compound class Natural product or derivative
Approved drug? Yes (FDA (1975), EMA (2011))
IUPAC Name Click here for help
(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
International Nonproprietary Names Click here for help
INN number INN
2990 tobramycin
Synonyms Click here for help
Bethkis® | Kitabis® | Tobi Podhaler® | Tobradex® (tobramycin + dexamethasone) | Vantobra®
Database Links Click here for help
CAS Registry No. 32986-56-4 (source: WHO INN record)
ChEMBL Ligand CHEMBL1747
DrugBank Ligand DB00684
DrugCentral Ligand 2684
GtoPdb PubChem SID 405560371
PubChem CID 36294
RCSB PDB Ligand TOY
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