2D 3D
	ID	DDInter815
	Drug Type	small molecule
	Molecular Formula	C60H123N15O21
	Molecular Weight	1390.728
	CAS Number	1403-66-3
	Description	Gentamicin is a bactericidal aminoglycoside that was discovered and isolated from _Micromonospora purpurea_ in 1963.[A234349] It is one of the most frequently prescribed aminoglycosides due to its spectrum of activity, low cost, and availability.[A234339,A234354] Gentamicin is effective against both gram-positive and gram-negative organisms but is particularly useful for the treatment of severe gram-negative infections including those caused by _Pseudomonas aeruginosa_.[A233325,A234359,A234364] There is the added benefit of synergy when gentamicin is co-administered with other antibacterials such as beta-lactams.[A234364] This synergistic activity is not only important for the treatment of complex infections, but can also contribute to dose optimization and reduced adverse effects.[A234359,A234364] Although gentamicin is well-established and may be used in a variety of clinical applications, it is also associated with severe adverse effects including nephrotoxicity and ototoxicity which may limit its use.[A234369]
	ATC Classification	S01AA11 S02AA14 D06AX07 S03AA06 J01GB03
IUPAC Name	(2R,3R,4R,5R)-2-{[(1S,2S,3R,4S,6R)-4,6-diamino-3-{[(2R,3R,6S)-3-amino-6-(1-aminoethyl)oxan-2-yl]oxy}-2-hydroxycyclohexyl]oxy}-5-methyl-4-(methylamino)oxane-3,5-diol; (2R,3R,4R,5R)-2-{[(1S,2S,3R,4S,6R)-4,6-diamino-3-{[(2R,3R,6S)-3-amino-6-(aminomethyl)oxan-2-yl]oxy}-2-hydroxycyclohexyl]oxy}-5-methyl-4-(methylamino)oxane-3,5-diol; (2R,3R,4R,5R)-2-{[(1S,2S,3R,4S,6R)-4,6-diamino-3-{[(2R,3R,6S)-3-amino-6-[1-(methylamino)ethyl]oxan-2-yl]oxy}-2-hydroxycyclohexyl]oxy}-5-methyl-4-(methylamino)oxane-3,5-diol
InChI	NPEFREDMMVQEPL-RWPARATISA-N
Canonical SMILES	[H][C@@]1(CN)CC[C@@H](N)[C@@H](O[C@]2([H])[C@@H](N)C[C@@H](N)[C@H](O[C@@]3([H])OC[C@](C)(O)[C@H](NC)[C@H]3O)[C@H]2O)O1.[H][C@]1(CC[C@@H](N)[C@@H](O[C@]2([H])[C@@H](N)C[C@@H](N)[C@H](O[C@@]3([H])OC[C@](C)(O)[C@H](NC)[C@H]3O)[C@H]2O)O1)C(C)N.[H][C@]1(CC[C@@H](N)[C@@H](O[C@]2([H])[C@@H](N)C[C@@H](N)[C@H](O[C@@]3([H])OC[C@](C)(O)[C@H](NC)[C@H]3O)[C@H]2O)O1)C(C)NC
Useful Links	DrugBank ChEBI PubChem Substance KEGG Compound ChemSpider BindingDB PharmGKB Therapeutic Targets Database Guide to Pharmacology Wikipedia ChEMBL