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Amikacin information


Amikacin
Clinical data
Trade namesAmikin, Amiglyde-V, Arikayce, others
AHFS/Drugs.comMonograph
MedlinePlusa682661
License data
  • US DailyMed: Amikacin
Pregnancy
category
  • AU: D[1]
Routes of
administration
Intramuscular, intravenous, inhalation
Drug classAminoglycoside
ATC code
  • D06AX12 (WHO) J01GB06 (WHO), S01AA21 (WHO), J01RA06 (WHO), QD06AX12 (WHO), QJ01GB06 (WHO), QS01AA21 (WHO), QJ01RA06 (WHO)
Legal status
Legal status
  • AU: S4 (Prescription only)[3]
  • UK: POM (Prescription only)[4]
  • US: WARNING[2]Rx-only[5]
  • EU: Rx-only[6][7]
Pharmacokinetic data
Bioavailability>90%[8]
Protein binding0–11%
MetabolismMostly unmetabolized
Elimination half-life2–3 hours
ExcretionKidney
Identifiers
IUPAC name
  • (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
  • 37517-28-5 checkY
PubChem CID
  • 37768
DrugBank
  • DB00479 checkY
ChemSpider
  • 34635 checkY
UNII
  • 84319SGC3C
KEGG
  • D02543 checkY
  • as salt: D00865 checkY
ChEBI
  • CHEBI:2637 checkY
ChEMBL
  • ChEMBL177 checkY
CompTox Dashboard (EPA)
  • DTXSID3022586 Edit this at Wikidata
ECHA InfoCard100.048.653 Edit this at Wikidata
Chemical and physical data
FormulaC22H43N5O13
Molar mass585.608 g·mol−1
3D model (JSmol)
  • Interactive image
SMILES
  • 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
  • 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.

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of combinations of cephalothin, dicloxacillin, imipenem, vancomycin and amikacin against methicillin-resistant Staphylococcus spp. strains". Ann. Clin....

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B Aztreonam (monobactam) Aminoglycosides - particularly tobramycin and amikacin Antibiotics that usually have activity against vancomycin-resistant Enterococcus...

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Enterobacter

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carbapenem) is often the antibiotic of choice. Aminoglycosides such as amikacin have been found to be very effective, as well. Quinolones can be an effective...

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[e.g. cefepime, ceftazidime ], or an aminoglycoside [i.e. gentamicin, amikacin]) Antibiotics directed against Gram-positive bacteria need to be included...

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when administered with a macrolide and ethambutol, as well as the drugs amikacin and clarithromycin. However, in the United States, clofazimine is considered...

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Aminoglycoside

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streptomycin is an example of a non-deoxystreptamine aminoglycoside. Kanamycin A Amikacin Tobramycin Dibekacin Gentamicin Sisomicin Netilmicin Neomycins B, C Neomycin...

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Continuous fever

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diseases include chloramphenicol, cefotaxime, ciprofloxacin, gentamicin and amikacin. Intermittent fever Relapsing fever Undulant fever Remittent fever Neutropenic...

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WHO Model List of Essential Medicines

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Complementary: Oxamniquineα Complementary: Albendazoleα Mebendazoleα Praziquantelα Amikacin Amoxicillin Amoxicillin/clavulanic acid (amoxicillin + clavulanic acid)...

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et al., 2022 as cited in Tavares-Carreon et al., 2023), aminoglycoside amikacin, gentamicin and tobramycin (Bertrand & Dowzicky, 2012; Sader et al., 2014...

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talampicillin 1975 – tobramycin 1975 – bacampicillin 1975 – ticarcillin 1976 – amikacin 1977 – azlocillin 1977 – cefadroxil 1977 – cefamandole 1977 – cefoxitin...

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Hypersensitivity

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pyrazinamide. For drug-resistant TB, a combination of antibiotics such as amikacin, kanamycin, or capreomycin should be used. The most common drugs to treat...

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Ampicillin

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February 2018. Retrieved 22 February 2018. "Drug interactions between amikacin and ampicillin". Drugs.com. Archived from the original on 23 February 2018...

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Hattori M (1992). "[Comparative study of cefpiramide + amikacin versus piperacillin + amikacin in granulocytopenic patients: a randomized, prospective...

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Klebsiella pneumoniae

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with multidrug-resistant Klebsiella species, a combination therapy with amikacin and meropenem has been suggested. Multiple drug-resistant K. pneumoniae...

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Semen extender

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used in combination with clavulanic acid under the designation Timentin), amikacin sulfate, penicillin, and gentamicin are commonly used. The latter - gentamicin...

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Dicloxacillin

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of combinations of cephalothin, dicloxacillin, imipenem, vancomycin and amikacin against methicillin-resistant Staphylococcus spp. strains". Annals of Clinical...

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Mycobacterium

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vesicles, fevers, chills, muscle aches. clarithromycin, azithromycin, amikacin, cefoxitin, imipenem. 3000 (US, Annual estimated) M. abscessus complex...

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Pharmacokinetics

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Blaschke T, Sandhaus RA (Sep 1999). "Phase I Pharmacokinetics of Liposomal Amikacin (MiKasome) in Human Subjects: Dose Dependence and Urinary Clearance". Abstr...

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Schedule H

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ALPRAZOLAM 16. ALPROSTADIL 17. AMANTADINE HYDROCHLORIDE 18. AMIFOSTINE 19. AMIKACIN SULPHATE 20. AMILORIDE HYDROCHLORIDE 21. AMINEPTINE 22. AMINOGLUTETHIMIDE...

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hearing loss that might have been related to treatment with the antibiotic amikacin although the researchers believed the more likely cause was slight differences...

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originally isolated from the sputum of a human patient. It is susceptible to amikacin, clarithromycin, and rifampin. Kim BJ, Hong SH, Yu HK, Park YG, Jeong J...

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Pseudomonas

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Nocardia

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usually substituted when a sulfa cannot be given; high-dose imipenem and amikacin have also been used in severe or refractory cases. Linezolid appears to...

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Antimicrobial resistance

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serious side-effects; for example, antibiotics like aminoglycosides (such as amikacin, gentamicin, kanamycin, streptomycin, etc.) used for the treatment of drug-resistant...

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Piperacillin

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piperacillin-tazobactam has produced results showing an increase in their affinity with amikacin and gentamicin in vitro, enabling the process of simultaneous Y-site infusion...

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Acute radiation syndrome

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coverage: e.g., cefepime, ceftazidime, or an aminoglycoside: i.e. gentamicin, amikacin). The prognosis for ARS is dependent on the exposure dose, with anything...

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