Kanamycin A

Kanamycin A
Clinical data
Other names	K/KAN/HLK/KM
AHFS/Drugs.com	Monograph
Pregnancy; category	D;
Routes of; administration	By mouth, intravenous, intramuscular
ATC code	A07AA08 (WHO) J01GB04 (WHO) S01AA24 (WHO);
Pharmacokinetic data
Bioavailability	very low after by mouth delivery
Metabolism	Unknown
Elimination 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 ; 8063-07-8 ;
PubChem CID	6032;
DrugBank	DB01172 ;
ChemSpider	5810 ;
UNII	EQK9Q303C5; RUC37XUP2P ;
ChEBI	CHEBI:17630 ;
ChEMBL	ChEMBL1384 ;
PDB ligand	KAN (PDBe, RCSB PDB);
CompTox Dashboard (EPA)	DTXSID3023184 ;
ECHA InfoCard	100.000.374
Chemical and physical data
Formula	C18H36N4O11
Molar mass	484.499 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 ; Key:SBUJHOSQTJFQJX-NOAMYHISSA-N ;
	(verify)

Kanamycin A, often referred to simply as 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. As with most antibiotics, it is ineffective 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 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 was removed from the World Health Organization's List of Essential Medicines in 2019. It is no longer marketed in the United States.

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