Structure via PubChem · Public domain (PubChem)
gentamicin
Sign in to saveAlso 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.
OverviewAI-generated
Gentamicin is a chemical compound with the formula C₂₁H₄₃N₅O₇. It has a molecular mass of 477.316249 and a weight of 477.6. The substance carries a charge of 0 and possesses an xlogp value of -4.1. Its topological polar surface area is 200, with 8 hydrogen bond donors and 12 hydrogen bond acceptors.
The defined daily dose for gentamicin is 0.24. The compound is associated with a PubMed query count of 38434. It is referenced by 378 other encyclopedia articles.
Synthesized by Vinony from 18 facts across 4 sources: Wikidata, PubMed, PubChem, Vinony graph. Generated from structured data (not the Wikipedia text) and checked against those facts — may still contain errors.
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- Gentamicin vestibulotoxicity.Otolaryngology--head and neck surgery : official journal of American Academy of Otolaryngology-Head and Neck Surgery · 1994
- Gentamicin in 1978.Annals of internal medicine · 1978
- Gentamicin-induced anaphylaxis.Irish journal of medical science · 2007
- Use of Gentamicin as Empiric Coverage for Ventilator-Associated Pneumonia: The "Con" Perspective.Surgical infections · 2016
- Microbial biosynthesis and applications of gentamicin: a critical appraisal.Critical reviews in biotechnology · 2008
via PubMed
~20 min read
Encyclopedic overview
20 sectionsContents
- 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 =
Excerpted from Wikipedia’s “gentamicin” article, available under the CC BY-SA 4.0 licence.