Back أميكاسين Arabic آمیکاسین AZB Амикацин Bulgarian Amikacina Catalan Amicacin CY Amikacin German Amikacina Spanish Amikazina EU آمیکاسین FA Amikasiini Finnish

Amikacin

Amikacin
Clinical data
Trade namesAmikin, Amiglyde-V, Arikayce, others
AHFS/Drugs.comMonograph
MedlinePlusa682661
License data
Pregnancy
category
Routes of
administration		Intramuscular, intravenous, inhalation
Drug classAminoglycoside
ATC code
Legal status
Legal status
Pharmacokinetic data
Bioavailability>90%[8]
Protein binding0–11%
MetabolismMostly unmetabolized
Elimination half-life2–3 hours
ExcretionKidney
Identifiers
  • (2S)-4-Amino-N-[(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,5R,6R)-6-(aminomethyl)-3,4,5-trihydroxy-oxan-2-yl]oxy-3-hydroxy-cyclohexyl]-2-hydroxybutanamide
CAS Number
PubChem CID
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.048.653 Edit this at Wikidata
Chemical and physical data
FormulaC22H43N5O13
Molar mass585.608 g·mol−1
3D model (JSmol)
  • O=C(N[C@H]3[C@H](O[C@H]1O[C@@H]([C@@H](O)[C@H](N)[C@H]1O)CO)[C@@H](O)[C@H](O[C@H]2O[C@H](CN)[C@@H](O)[C@H](O)[C@H]2O)[C@@H](N)C3)[C@@H](O)CCN
  • InChI=1S/C22H43N5O13/c23-2-1-8(29)20(36)27-7-3-6(25)18(39-22-16(34)15(33)13(31)9(4-24)37-22)17(35)19(7)40-21-14(32)11(26)12(30)10(5-28)38-21/h6-19,21-22,28-35H,1-5,23-26H2,(H,27,36)/t6-,7+,8-,9+,10+,11-,12+,13+,14+,15-,16+,17-,18+,19-,21+,22+/m0/s1 checkY
  • Key:LKCWBDHBTVXHDL-RMDFUYIESA-N checkY
  (verify)

Amikacin is an antibiotic medication used for a number of bacterial infections.[9] This includes joint infections, intra-abdominal infections, meningitis, pneumonia, sepsis, and urinary tract infections.[9] It is also used for the treatment of multidrug-resistant tuberculosis.[10] It is used by injection into a vein using an IV or into a muscle.[9]

Amikacin, like other aminoglycoside antibiotics, can cause hearing loss, balance problems, and kidney problems.[9] Other side effects include paralysis, resulting in the inability to breathe.[9] If used during pregnancy it may cause permanent deafness in the baby.[9][1] Amikacin works by blocking the function of the bacteria's 30S ribosomal subunit, making it unable to produce proteins.[9]

Amikacin was patented in 1971, and came into commercial use in 1976.[11][12] It is on the World Health Organization's List of Essential Medicines.[13] It is derived from kanamycin.[9]

  1. ^ a b "Amikacin Use During Pregnancy". Drugs.com. 2 December 2019. Retrieved 13 March 2020.
  2. ^ "FDA-sourced list of all drugs with black box warnings (Use Download Full Results and View Query links.)". nctr-crs.fda.gov. FDA. Retrieved 22 October 2023.
  3. ^ "Prescription medicines: registration of new generic medicines and biosimilar medicines, 2017". Therapeutic Goods Administration (TGA). 21 June 2022. Retrieved 30 March 2024.
  4. ^ "Amikacin 250 mg/ml Injection - Summary of Product Characteristics (SmPC)". (emc). 16 September 2015. Retrieved 13 March 2020.
  5. ^ Cite error: The named reference Arikayce FDA label was invoked but never defined (see the help page).
  6. ^ "Arikayce liposomal EPAR". European Medicines Agency. 21 July 2020. Retrieved 4 March 2023.
  7. ^ "Arikayce liposomal Product information". Union Register of medicinal products. Retrieved 3 March 2023.
  8. ^ Cite error: The named reference plumb was invoked but never defined (see the help page).
  9. ^ a b c d e f g h "Amikacin Sulfate". The American Society of Health-System Pharmacists. Archived from the original on 20 December 2016. Retrieved 8 December 2016.
  10. ^ World Health Organization (2009). Stuart MC, Kouimtzi M, Hill SR (eds.). WHO Model Formulary 2008. World Health Organization. p. 137. hdl:10665/44053. ISBN 9789241547659.
  11. ^ Fischer J, Ganellin CR (2006). Analogue-based Drug Discovery. John Wiley & Sons. p. 507. ISBN 9783527607495. Archived from the original on 20 December 2016.
  12. ^ Oxford Handbook of Infectious Diseases and Microbiology. OUP Oxford. 2009. p. 56. ISBN 9780191039621. Archived from the original on 24 November 2015.
  13. ^ World Health Organization (2019). World Health Organization model list of essential medicines: 21st list 2019. Geneva: World Health Organization. hdl:10665/325771. WHO/MVP/EMP/IAU/2019.06. License: CC BY-NC-SA 3.0 IGO.