Gentamicin
Chemical Information
Gentamicin is a bactericidal aminoglycoside that was discovered and isolated from Micromonospora purpurea in 1963. It is one of the most frequently prescribed aminoglycosides due to its spectrum of activity, low cost, and availability. 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. There is the added benefit of synergy when gentamicin is co-administered with other antibacterials such as beta-lactams. This synergistic activity is not only important for the treatment of complex infections, but can also contribute to dose optimization and reduced adverse effects. 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.
| CAS Number | 1403-66-3 |
| PubChem CID | 3467 |
| IUPAC Name | 2-[4,6-diamino-3-[3-amino-6-[1-(methylamino)ethyl]oxan-2-yl]oxy-2-hydroxycyclohexyl]oxy-5-methyl-4-(methylamino)oxane-3,5-diol |
| Molecular Formula | C21H43N5O7 |
| Molecular Weight | 477.6 |
| XLogP | -4.1 |
| Topological Polar Surface Area | 200 |
| Hydrogen Bond Donor Count | 8 |
| Hydrogen Bond Acceptor Count | 12 |
| Rotatable Bond Count | 7 |
| Heavy Atom Count | 33 |
| Formal Charge | 0 |
| Complexity | 636 |
| Property | Value |
|---|---|
| Molecular Weight | 477.6 |
| XLogP3 | -4.1 |
| Hydrogen Bond Donor Count | 8 |
| Hydrogen Bond Acceptor Count | 12 |
| Rotatable Bond Count | 7 |
| Exact Mass | 477.31624873 |
| Monoisotopic Mass | 477.31624873 |
| Topological Polar Surface Area | 200 Ų |
| Heavy Atom Count | 33 |
| Formal Charge | 0 |
| Complexity | 636 |
| Isotope Atom Count | 0 |
| Defined Atom Stereocenter Count | 0 |
| Undefined Atom Stereocenter Count | 13 |
| Defined Bond Stereocenter Count | 0 |
| Undefined Bond Stereocenter Count | 0 |
| Covalently-Bonded Unit Count | 1 |
| Compound Is Canonicalized | Yes |
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