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Kanamycin A information


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
  • A07AA08 (WHO) J01GB04 (WHO) S01AA24 (WHO)
Pharmacokinetic data
Bioavailabilityvery low after by mouth delivery
MetabolismUnknown
Elimination half-life2 hours 30 minutes
ExcretionUrine (as unchanged drug)
Identifiers
IUPAC name
  • 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
  • 59-01-8 checkY
  • 8063-07-8 checkY
PubChem CID
  • 6032
DrugBank
  • DB01172 checkY
ChemSpider
  • 5810 checkY
UNII
  • EQK9Q303C5
  • RUC37XUP2P checkY
ChEBI
  • CHEBI:17630 checkY
ChEMBL
  • ChEMBL1384 checkY
PDB ligand
  • KAN (PDBe, RCSB PDB)
CompTox Dashboard (EPA)
  • DTXSID3023184 Edit this at Wikidata
ECHA InfoCard100.000.374 Edit this at Wikidata
Chemical and physical data
FormulaC18H36N4O11
Molar mass484.503 g·mol−1
3D model (JSmol)
  • Interactive image
SMILES
  • 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
  • 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] As with most antibiotics, 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.

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In molecular biology, kanamycin nucleotidyltransferase EC 2.7.7.- (KNTase) is an enzyme which is involved in conferring resistance to aminoglycoside antibiotics...

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Holden HM (November 1993). "Molecular structure of kanamycin nucleotidyltransferase determined to 3.0-A resolution". Biochemistry. 32 (45): 11977–11984....

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anti-addictive drug, as well as its occasional recreational use as a dissociative.[citation needed] Kanamycin is an aminoglycoside antibiotic which induces deafness...

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

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susceptibility to several antibiotics, such as colistin sulphate, clindamycin and kanamycin A or penicillin has been reported. Page Species: Anaerococcus murdochii...

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