Gentamicin

Gentamicin is an antibiotic used to treat several types of bacterial infections. This may include bone infections, endocarditis, pelvic inflammatory disease, meningitis, pneumonia, urinary tract infections, and sepsis among others. It is not effective for gonorrhea or chlamydia infections. It can be given intravenously, by intramuscular injection, or topically. Topical formulations may be used in burns or for infections of the outside of the eye. It is often only used for two days until bacterial cultures determine what specific antibiotics the infection is sensitive to. The dose required should be monitored by blood testing.

Gentamicin
Clinical data
Pronunciation/ˌɛntəˈmsən/
Trade namesCidomycin, Genticyn, Garamycin, others
AHFS/Drugs.comMonograph
MedlinePlusa682275
License data
Pregnancy
category
  • AU: D
Routes of
administration
Intravenous, eye drop, Intramuscular injection, Topical administration, ear drop
Drug classAminoglycoside antibiotic
ATC code
Legal status
Legal status
  • US: WARNING
  • EU: Rx-only
  • In general: ℞ (Prescription only)
Pharmacokinetic data
Bioavailabilitylimited bioavailability by mouth
Protein binding0–10%
Elimination half-life2 h
ExcretionKidney
Identifiers
  • (3R,4R,5R)-2-{[(1S,2S,3R,4S,6R)-4,6-
    diamino-3-{[(2R,3R,6S)-
    3-amino-6-[(1R)-
    1-(methylamino)ethyl]oxan-2-yl]oxy}-
    2-hydroxycyclohexyl]oxy}-5-methyl-
    4-(methylamino)oxane-3,5-diol
CAS Number
PubChem CID
IUPHAR/BPS
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.014.332
Chemical and physical data
FormulaC21H43N5O7
Molar mass477.603 g·mol−1
3D model (JSmol)
  • O[C@]3(C)[C@H](NC)[C@@H](O)[C@@H](O[C@H]2[C@H](N)C[C@H](N)[C@@H](O[C@H]1O[C@H](C(NC)C)CC[C@H]1N)[C@@H]2O)OC3
  • InChI=1S/C21H43N5O7/c1-9(25-3)13-6-5-10(22)19(31-13)32-16-11(23)7-12(24)17(14(16)27)33-20-15(28)18(26-4)21(2,29)8-30-20/h9-20,25-29H,5-8,22-24H2,1-4H3/t9?,10-,11+,12-,13+,14+,15-,16-,17+,18-,19-,20-,21+/m1/s1 Y
  • Key:CEAZRRDELHUEMR-URQXQFDESA-N Y
 NY (what is this?)  (verify)

Gentamicin can cause inner ear problems and kidney problems. The inner ear problems can include problems with balance and hearing loss. These problems may be permanent. If used during pregnancy, it can cause harm to the developing baby. However, it appears to be safe for use during breastfeeding. Gentamicin is a type of aminoglycoside. It works by disrupting the ability of the bacteria to make proteins, which typically kills the bacteria.

Gentamicin is naturally produced by the bacterium Micromonospora purpurea, was patented in 1962, approved for medical use in 1964. The antibiotic is collected from the culture of the Micromonospora by perforating the cell wall of the bacterium. Current research is underway to understand the biosynthesis of this antibiotic in an attempt to increase expression and force secretion of gentamicin for higher titer. Gentamicin is on the World Health Organization's List of Essential Medicines. The World Health Organization classifies gentamicin as critically important for human medicine. It is available as a generic medication.

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