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gentamicin

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gentamicin

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Also known as gentamicin sulfate, gentamycin, gentamicins

Gentamicin is an aminoglycoside 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 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.

Chemical data

Formula
C21H43N5O7
Molecular weight
477.6 g/mol
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
SMILES
CC(C1CCC(C(O1)OC2C(CC(C(C2O)OC3C(C(C(CO3)(C)O)NC)O)N)N)N)NC
InChIKey
CEAZRRDELHUEMR-UHFFFAOYSA-N
XLogP
-4.1
Polar surface area
200 Ų
H-bond donors
8
H-bond acceptors
12
Formal charge
0

via PubChem

Research

38,434 papers

via PubMed

Wikidata facts

Mass
477.316249
Image
Gentamicin for injection.jpg
Show 5 more facts
Commons category
Gentamicin
chemical formula
C₂₁H₄₃N₅O₇
canonical SMILES
CC(C1CCC(C(O1)OC2C(CC(C(C2O)OC3C(C(C(CO3)(C)O)NC)O)N)N)N)NC
defined daily dose
0.24
NCI Thesaurus ID
C519
Sources (7)

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~20 min read

Article

20 sections
Contents
  • Medical uses
  • Special populations
  • Pregnancy and breastfeeding
  • Elderly
  • Children
  • Contraindications
  • Adverse effects
  • Kidney damage
  • Inner ear
  • Pharmacology
  • Mechanism of action
  • Chemistry
  • Structure
  • Components
  • Biosynthesis
  • Fermentation
  • History
  • Research
  • References
  • Further reading

{{Drugbox | Verifiedfields = changed | verifiedrevid = 443833957 | image = Gentamicin C2.svg | image_class = skin-invert-image | alt = | image2 = Gentamicin C1 ball-and-stick model from xtal 2016.png | image_class2 = bg-transparent | alt2 =

| pronounce = | tradename = Cidomycin, Genticyn, Garamycin, others | Drugs.com = | MedlinePlus = a682275 | DailyMedID = Gentamicin | pregnancy_AU = D | pregnancy_AU_comment = | routes_of_administration = Intravenous, eye drop, Intramuscular injection, Topical administration, ear drop | class = Aminoglycoside antibiotic | ATC_prefix = D06 | ATC_suffix = AX07 | ATC_supplemental =

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