neomycin   Click here for help

GtoPdb Ligand ID: 709

Synonyms: Neo-Rx® | neomycin sulfate
Approved drug PDB Ligand
neomycin is an approved drug (FDA (1964))
Comment: Neomycin is an aminoglycoside antibacterial. Neomycin is active against Gram-negative bacteria, and partially active against Gram-positive bacteria. Standard grade neomycin is a mixture of several related compounds, including neomycin A (neamine), neomycin B (framycetin) and neomycin C, with neomycin B being the most active component. We show the structure of neomycin B here.
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 19
Hydrogen bond donors 13
Rotatable bonds 9
Topological polar surface area 353.11
Molecular weight 614.31
XLogP -6.91
No. Lipinski's rules broken 2
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Isomeric SMILES OC[C@H]1O[C@H]([C@@H]([C@@H]1O[C@H]1O[C@@H](CN)[C@H]([C@@H]([C@H]1N)O)O)O)O[C@@H]1[C@@H](O)[C@H](N)C[C@@H]([C@H]1O[C@H]1O[C@H](CN)[C@H]([C@@H]([C@H]1N)O)O)N
InChI InChI=1S/C23H46N6O13/c24-2-7-13(32)15(34)10(28)21(37-7)40-18-6(27)1-5(26)12(31)20(18)42-23-17(36)19(9(4-30)39-23)41-22-11(29)16(35)14(33)8(3-25)38-22/h5-23,30-36H,1-4,24-29H2/t5-,6+,7-,8+,9-,10-,11-,12+,13-,14-,15-,16-,17-,18-,19-,20-,21-,22-,23+/m1/s1
No information available.
Summary of Clinical Use Click here for help
Used topically in the treatment of eye infections, otitis externa, treatment or prevention of bacterial infections in skin lesions and in the prevention of bacteriuria and gram negative rod bacteremia in abacteriuric patients with indwelling catheters. Also used orally to treat hepatic encephalopathy.
Mechanism Of Action and Pharmacodynamic Effects Click here for help
Neomycin binds to 30S-subunit proteins and 16S rRNA. This leads to misreading of mRNA which in turn leads to the insertion of incorrect amino acids into the polypeptide which leads to the formation of nonfunctional or toxic peptides and breakup of polysomes into nonfunctional monosomes.
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