Amikacin

Amikacin

Clinical data
Trade names	Amikin, others
AHFS/Drugs.com	Monograph
MedlinePlus	a682661
Pregnancy category	AU: D US: D (Evidence of risk)
Routes of administration	intramuscular, intravenous
ATC code	D06AX12 (WHO) J01GB06 (WHO), S01AA21 (WHO)
Legal status
Legal status	UK: POM (Prescription only) US: ℞-only
Pharmacokinetic data
Protein binding	0-11%
Biological half-life	2-3 hours
Excretion	kidney
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 Y
PubChem CID	37768
DrugBank	DB00479 Y
ChemSpider	34635 Y
UNII	84319SGC3C
KEGG	D02543 Y
ChEBI	CHEBI:2637 Y
ChEMBL	CHEMBL177 Y
ECHA InfoCard	100.048.653
Chemical and physical data
Formula	C22H43N5O13
Molar mass	585.603 g/mol
3D model (Jmol)	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 Y Key:LKCWBDHBTVXHDL-RMDFUYIESA-N Y

Amikacin is an antibiotic used for a number of bacterial infections. This includes joint infections, intraabdominal infections, meningitis, pneumonia, sepsis, and urinary tract infections. It is also used for the treatment of multidrug-resistant tuberculosis. It is used either by injection into a vein or muscle.

Common side effects include hearing loss, balance problems, and kidney problems. Other side effects include paralysis resulting in the inability to breathe. If used during pregnancy it may cause permanent deafness in the baby. Amikacin is in the aminoglycoside family of medications. It works by blocking the function of the bacteria's 30S ribosomal subunit, making it unable to make protein.

Amikacin was patented in 1971 and came into commercial use in 1976. 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 13.80 to 130.50 USD for a month. In the United States a typical course of treatment costs 25 to 50 USD. It is made from kanamycin.