Kanamycin A

Not to be confused with Kanamycin B or Keanumycin.

Kanamycin A
Clinical data
Other namesK/KAN/HLK/KM[1]
AHFS/Drugs.comMonograph
Pregnancy
category
  • D
Routes of
administration		By mouth, intravenous, intramuscular
ATC code
Pharmacokinetic data
Bioavailabilityvery low after by mouth delivery
MetabolismUnknown
Elimination half-life2 hours 30 minutes
ExcretionUrine (as unchanged drug)
Identifiers
  • 2-(aminomethyl)- 6-[4,6-diamino-3- [4-amino-3,5-dihydroxy-6-(hydroxymethyl) tetrahydropyran-2-yl]oxy- 2-hydroxy- cyclohexoxy]- tetrahydropyran- 3,4,5-triol
CAS Number
PubChem CID
DrugBank
ChemSpider
UNII
ChEBI
ChEMBL
PDB ligand
CompTox Dashboard (EPA)
ECHA InfoCard100.000.374 Edit this at Wikidata
Chemical and physical data
FormulaC18H36N4O11
Molar mass484.503 g·mol−1
3D model (JSmol)
  • O([C@@H]2[C@@H](O)[C@H](O[C@H]1O[C@H](CN)[C@@H](O)[C@H](O)[C@H]1O)[C@@H](N)C[C@H]2N)[C@H]3O[C@@H]([C@@H](O)[C@H](N)[C@H]3O)CO
  • InChI=1S/C18H36N4O11/c19-2-6-10(25)12(27)13(28)18(30-6)33-16-5(21)1-4(20)15(14(16)29)32-17-11(26)8(22)9(24)7(3-23)31-17/h4-18,23-29H,1-3,19-22H2/t4-,5+,6-,7-,8+,9-,10-,11-,12+,13-,14-,15+,16-,17-,18-/m1/s1 checkY
  • Key:SBUJHOSQTJFQJX-NOAMYHISSA-N checkY
  (verify)

Kanamycin A,[2] often referred to simply as kanamycin, is an antibiotic used to treat severe bacterial infections and tuberculosis.[3] It is not a first line treatment.[3] It is used by mouth, injection into a vein, or injection into a muscle.[3] Kanamycin is recommended for short-term use only, usually from 7 to 10 days.[3] Since antibiotics only show activity against bacteria, it is ineffective in viral infections.[3]

Common side effects include hearing and balance problems.[3] Kidney problems may also occur.[3] Kanamycin is not recommended during pregnancy as it may harm the baby.[3] It is likely safe during breastfeeding.[4] Kanamycin is in the aminoglycoside family of medications.[3] It works by blocking the production of proteins that are required for bacterial survival.[3]

Kanamycin was first isolated in 1957 by Hamao Umezawa from the bacterium Streptomyces kanamyceticus.[3][5] It was removed from the World Health Organization's List of Essential Medicines in 2019.[6][7] It is no longer marketed in the United States.[3]

  1. ^ "Antibiotic abbreviations list". Retrieved 22 June 2023.
  2. ^ Elks J, Ganellin DR (1990). The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies. Springer. pp. 717–. doi:10.1007/BF00171763. S2CID 122125855.
  3. ^ a b c d e f g h i j k l "Kanamycin Sulfate". The American Society of Health-System Pharmacists. Archived from the original on 10 September 2017. Retrieved 6 December 2016.
  4. ^ "Kanamycin (Kantrex) Use During Pregnancy". www.drugs.com. Archived from the original on 20 December 2016. Retrieved 7 December 2016.
  5. ^ Sneader W (2005). Drug Discovery: A History. John Wiley & Sons. p. 302. ISBN 9780471899792.
  6. ^ World Health Organization (2019). Executive summary: the selection and use of essential medicines 2019: report of the 22nd WHO Expert Committee on the selection and use of essential medicines. Geneva: World Health Organization. hdl:10665/325773. WHO/MVP/EMP/IAU/2019.05. License: CC BY-NC-SA 3.0 IGO.
  7. ^ World Health Organization (2019). The selection and use of essential medicines: report of the WHO Expert Committee on Selection and Use of Essential Medicines, 2019 (including the 21st WHO Model List of Essential Medicines and the 7th WHO Model List of Essential Medicines for Children). Geneva: World Health Organization. hdl:10665/330668. ISBN 9789241210300. ISSN 0512-3054. WHO technical report series;1021.