Kanamycin

Kanamycin A
Clinical data

AHFS/Drugs.com	Monograph
Pregnancy category	D
Routes of administration	By mouth, intravenous, intramuscular
ATC code	A07AA08 (WHO) J01GB04 (WHO) S01AA24 (WHO)
Legal status
Legal status	?
Pharmacokinetic data
Bioavailability	very low after by mouth delivery
Metabolism	Unknown
Biological half-life	2 hours 30 minutes
Excretion	Urine (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^Y
PubChem (CID)	6032
DrugBank	DB01172^Y
ChemSpider	5810^Y
UNII	RUC37XUP2P^Y
ChEBI	CHEBI:17630^Y
ChEMBL	CHEMBL1384^Y
PDB ligand ID	KAN (PDBe, RCSB PDB)
Chemical and physical data
Formula	C₁₈H₃₆N₄O₁₁
Molar mass	484.499
3D model (Jmol)	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^Y Key:SBUJHOSQTJFQJX-NOAMYHISSA-N^Y

Kanamycin A, often referred to as simple kanamycin, is an antibiotic used to treat severe bacterial infections and tuberculosis. It is not a first line treatment. It is used by mouth, injection into a vein, or injection into a muscle. Kanamycin is recommended for short-term use only, usually from 7 to 10 days. It is not effective in viral infections.

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

Kanamycin was first isolated in 1957 by Hamao Umezawa from the bacterium Streptomyces kanamyceticus. It is on the World Health Organization's List of Essential Medicines, the most effective and safe medicines needed in a health system. The wholesale cost in the developing world is 0.85 to 1.52 USD per dose as of 2014. It is no longer commercially available in the United States.

Kanamycin is indicated for short term treatment of bacterial infections caused by one or more of the following pathogens: E. coli, Proteus species (both indole-positive and indole-negative), Enterobacter aerogenes, Klebsiella pneumoniae, Serratia marcescens, and Acinetobacter species. In cases of serious infection when the causative organism is unknown, Kanamycin injection in conjunction with a penicillin- or cephalosporin-type drug may be given initially before obtaining results of susceptibility testing.

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