Structure via PubChem · Public domain (PubChem)
amikacin
Sign in to saveAlso known as 1-N-(L(-)-gamma-amino-alpha-Hydroxybutyryl)kanamycin a, O-3-amino-3-Deoxy-alpha-D-glucopyranosyl-(1->4)-O-(6-amino-6-deoxy-alpha-D-glucopyranosyl-(1->6))-N(3)-(4-amino-L-2-hydroxybutyryl)-2-deoxy-L-streptamine, Amiglyde-v, Amikavet, Briclin, Amicacin, Amikacina
Amikacin is an antibiotic medication used for a number of bacterial infections. This includes joint infections, intra-abdominal infections, meningitis, pneumonia, sepsis, and urinary tract infections. It is also used for the treatment of multidrug-resistant tuberculosis. It is used by injection into a vein using an IV or into a muscle.
OverviewAI-generated
Amikacin is a chemical compound with the formula C₂₂H₄₃N₅O₁₃. It has a mass of 585.286 and a weight of 585.6. The substance possesses a charge of 0, an xlogp value of -7.9, and a topological polar surface area of 332. It contains 13 hydrogen bond donors and 17 hydrogen bond acceptors. The defined daily dose for amikacin is 1.
The compound is associated with the NCI Thesaurus ID C61615 and is categorized under "Amikacin" on Commons. Its canonical SMILES notation is C1C(C(C(C(C1NC(=O)C(CCN)O)OC2C(C(C(C(O2)CO)O)N)O)O)OC3C(C(C(C(O3)CN)O)O)O)N. Amikacin has been referenced by 251 other encyclopedia articles.
Synthesized by Vinony from 17 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.
Key facts
- Drug.Watchedfields
- changed
- Drug.verifiedrevid
- 464364466
- Drug.image
- Amikacin.svg
- Drug.image_class
- skin-invert-image
- Drug.image2
- Amikacin 3D ball-and-stick 4P20.png
- Drug.image_class2
- bg-transparent
- Drug.tradename
- Amikin, Amiglyde-V, Arikayce, others
- Drug.MedlinePlus
- a682661
- Drug.DailyMedID
- Amikacin
- Drug.pregnancy_AU
- D
- Drug.routes_of_administration
- Intramuscular, intravenous, inhalation
- Drug.class
- Aminoglycoside
- Drug.ATC_prefix
- D06
- Drug.ATC_suffix
- AX12
- Drug.ATC_supplemental
- , , , , , ,
- Drug.legal_AU
- S4
- Drug.legal_UK
- POM
- Drug.legal_US
- Rx-only
via Wikipedia infobox
Chemical data
- Formula
- C22H43N5O13
- Molecular weight
- 585.6 g/mol
- IUPAC name
- (2S)-4-amino-N-[(1R,2S,3S,4R,5S)-5-amino-2-[(2S,3R,4S,5S,6R)-4-amino-3,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-4-[(2R,3R,4S,5S,6R)-6-(aminomethyl)-3,4,5-trihydroxyoxan-2-yl]oxy-3-hydroxycyclohexyl]-2-hydroxybutanamide
- SMILES
- C1[C@@H]([C@H]([C@@H]([C@H]([C@@H]1NC(=O)[C@H](CCN)O)O[C@@H]2[C@@H]([C@H]([C@@H]([C@H](O2)CO)O)N)O)O)O[C@@H]3[C@@H]([C@H]([C@@H]([C@H](O3)CN)O)O)O)N
- InChIKey
- LKCWBDHBTVXHDL-RMDFUYIESA-N
- XLogP
- -7.9
- Polar surface area
- 332 Ų
- H-bond donors
- 13
- H-bond acceptors
- 17
- Formal charge
- 0
via PubChem
Research
14,079 papers- Amikacin.Annals of internal medicine · 1981
- Amikacin.Tuberculosis (Edinburgh, Scotland) · 2008
- Amikacin.Lancet (London, England) · 1977
- An overview of amikacin.Therapeutic drug monitoring · 1985
- Amikacin. A new aminoglycoside antibiotic.Minnesota medicine · 1978
via PubMed
~18 min read
Encyclopedic overview
13 sectionsContents
- Medical uses
- Available forms
- Special populations
- Adverse effects
- Contraindications
- Interactions
- Pharmacology
- Mechanism of action
- Resistance
- Pharmacokinetics
- Chemistry
- Veterinary uses
- References
Amikacin is an antibiotic medication used for a number of bacterial infections. This includes joint infections, intra-abdominal infections, meningitis, pneumonia, sepsis, and urinary tract infections. It is also used for the treatment of multidrug-resistant tuberculosis. It is used by injection into a vein using an IV or into a muscle.
Amikacin, like other aminoglycoside antibiotics, can cause hearing loss, balance problems, and kidney problems. Other side effects include paralysis, resulting in the inability to breathe. If used during pregnancy it may cause permanent deafness in the baby. Amikacin works by blocking the function of the bacteria's 30S ribosomal subunit, making it unable to produce proteins.
Excerpted from Wikipedia’s “amikacin” article, available under the CC BY-SA 4.0 licence.