U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ABSOLUTE
Molecular Formula C22H43N5O13
Molecular Weight 585.6025
Optical Activity UNSPECIFIED
Defined Stereocenters 16 / 16
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of AMIKACIN

SMILES

NCC[C@H](O)C(=O)N[C@@H]1C[C@H](N)[C@@H](O[C@H]2O[C@H](CN)[C@@H](O)[C@H](O)[C@H]2O)[C@H](O)[C@H]1O[C@H]3O[C@H](CO)[C@@H](O)[C@H](N)[C@H]3O

InChI

InChIKey=LKCWBDHBTVXHDL-RMDFUYIESA-N
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

HIDE SMILES / InChI

Description

Amikacin, USP (as the sulfate) is a semi-synthetic aminoglycoside antibiotic derived from kanamycin. Amikacin "irreversibly" binds to specific 30S-subunit proteins and 16S rRNA. Amikacin inhibits protein synthesis by binding to the 30S ribosomal subunit to prevent the formation of an initiation complex with messenger RNA. Specifically Amikacin binds to four nucleotides of 16S rRNA and a single amino acid of protein S12. This interferes with decoding site in the vicinity of nucleotide 1400 in 16S rRNA of 30S subunit. This region interacts with the wobble base in the anticodon of tRNA. This leads to interference with the initiation complex, misreading of mRNA so incorrect amino acids are inserted into the polypeptide leading to nonfunctional or toxic peptides and the breakup of polysomes into nonfunctional monosomes. Amikacin is used for short-term treatment of serious infections due to susceptible strains of Gram-negative bacteria, including Pseudomonas species, Escherichia coli, species of indole-positive and indole-negative Proteus, Providencia species, Klebsiella-Enterobacter-Serratia species, and Acinetobacter (Mima-Herellea) species. Amikacin may also be used to treat Mycobacterium avium and Mycobacterium tuberculosis infections. Amikacin was used for the treatment of gram-negative pneumonia.

CNS Activity

Approval Year

PubMed

PubMed

TitleDatePubMed
[Evaluation of ototoxicity of amikacin (BB-K8) by animal test (author's transl)].
1975 Jun
Antimicrobial susceptibility of Mycobacterium marinum determined by E-test and agar dilution.
2001
Treatment of mycobacterial exit-site infections in patients on continuous ambulatory peritoneal dialysis.
2001
Occurrence of variants with temperature-dependent susceptibility (TDS) to antibiotics among Stenotrophomonas maltophilia clinical strains.
2001
Antimicrobial effect of protein(s) isolated from a marine mollusc Telescopium telescopium.
2001 Apr
Pharmacokinetics of amikacin after single intravenous and intramuscular administration in calves.
2001 Apr
Monotherapy with meropenem versus combination therapy with piperacillin plus amikacin as empiric therapy for neutropenic fever in children with lymphoma and solid tumors.
2001 Apr-Jun
Urinary excretion reflects lung deposition of aminoglycoside aerosols in cystic fibrosis.
2001 Aug
Comparison of 2 techniques for regional antibiotic delivery to the equine forelimb: intraosseous perfusion vs. intravenous perfusion.
2001 Aug
Optimizing antibiotic therapy in the intensive care unit setting.
2001 Aug
Once-a-day individualized amikacin dosing for suspected infection at birth based on population pharmacokinetic models.
2001 Aug
Serum pharmacokinetics and sputum penetration of amikacin 30 mg/kg once daily and of ceftazidime 200 mg/kg/day as a continuous infusion in cystic fibrosis patients.
2001 Aug
Role of megalin in renal handling of aminoglycosides.
2001 Aug
Arsenite-induced multiple antibiotic resistance phenotype in environmental isolates of Yersinia enterocolitica.
2001 Aug
[Clinical effects of combination therapy with cefozopran and amikacin for infections in patients with hematological disorders].
2001 Feb
Changes in electrovestibular brainstem responses after aminoglycoside intoxication in guinea pigs.
2001 Jul
Epidemiology and frequency of resistance among pathogens causing urinary tract infections in 1,510 hospitalized patients: a report from the SENTRY Antimicrobial Surveillance Program (North America).
2001 Jul
Interactions of colistin and rifampin on multidrug-resistant Acinetobacter baumannii.
2001 Jul
Intravitreal antibiotics: the emergency kit.
2001 Jul
Treatment and outcome of nocardia keratitis.
2001 Jul
Penetration of amikacin into aqueous humor of rabbits.
2001 Jul-Aug
In vitro effect of amikacin, imipenem, cefodizime, IFNalpha-2a alone and combinations of antibiotics with IFNalpha-2a on polymorphonuclear leukocyte function in chronic hepatitis patients.
2001 Jul-Aug
In vitro antimicrobial activity of the aminoglycoside arbekacin tested against oxacillin-resistant Staphylococcus aureus isolated in Brazilian hospitals.
2001 Jun
Antibiotic susceptibility and phage typing of methicillin-resistant and -sensitive Staphylococcus aureus clinical isolates at three periods during 1991-1997.
2001 Jun
Blood stream infections in a medical intensive care unit: spectrum and antibiotic susceptibility pattern.
2001 Jun
[Neonatal bacterial infections at the CUH of Dakar].
2001 Jun
Cost-effectiveness of cefepime + netilmicin or ceftazidime + amikacin or meropenem monotherapy in febrile neutropenic children with malignancy in Turkey.
2001 Jun
Antibiotic resistance among Gram-negative non-fermentative bacteria at a teaching hospital in Saudi Arabia.
2001 Jun
Changing antibiotic sensitivity patterns at a university hospital, 1992 through 1999.
2001 Jun
Madura foot: treatment of Nocardia nova infection with antibiotics alone.
2001 Jun
The early bactericidal activity of amikacin in pulmonary tuberculosis.
2001 Jun
Translimbal approach for intravitreal injection in endophthalmitis after phacoemulsification.
2001 Jun
Antimicrobial susceptibility of Pseudomonas aeruginosa: results of a UK survey and evaluation of the British Society for Antimicrobial Chemotherapy disc susceptibility test.
2001 Jun
Retinal vasculitis and posterior pole "hypopyons" as early signs of acute bacterial endophthalmitis.
2001 Jun
Nephrotoxicants induce endothelin release and signaling in renal proximal tubules: effect on drug efflux.
2001 Jun
Pharmacokinetic longitudinal studies of antibiotics administered via a permanent intraosseous device in micropigs.
2001 Jun
Mycobacterium fortuitum wound infection following laparoscopy.
2001 Mar
Meningoencephalitis caused by Bacillus cereus in a neonate.
2001 Mar
Study on antimicrobial susceptibility of bacteria causing neonatal infections: a 12 year study (1987-1998).
2001 Mar
Efficacy and tolerability of piperacillin/tazobactam versus ceftazidime in association with amikacin for treating nosocomial pneumonia in intensive care patients: a prospective randomized multicenter trial.
2001 Mar
[Functional characterization of a multiple-antibiotic resistant plasmid from clinical isolates of methicillin-resistant Staphylococcus aureus].
2001 May
In vitro susceptibility to 15 antibiotics of vibrios isolated from penaeid shrimps in Northwestern Mexico.
2001 May
Bacterial isolates from blood and their susceptibility patterns in critically ill foals: 543 cases (1991-1998).
2001 May 15
Infective endocarditis due to an unusual serotype of Salmonella.
2001 May-Jun
Clinical applications of a novel sustained-release injectable drug delivery system: DepoFoam technology.
2001 May-Jun
Epidemiologic Study of Pseudomonas aeruginosa in critical patients and reservoirs.
2001 May-Jun
Liposome-encapsulated aminoglycosides in pre-clinical and clinical studies.
2001 Sep
Failure of treatment for chronic Mycobacterium abscessus meningitis despite adequate clarithromycin levels in cerebrospinal fluid.
2001 Sep 1
A simple tool for monitoring nebulized amikacin treatments based on a single urine assay.
2001 Spring
Trends in antimicrobial resistance of Salmonella isolated from animals, foods of animal origin, and the environment of animal production in Canada, 1994-1997.
2001 Summer
Patents

Sample Use Guides

In Vivo Use Guide
The recommended dosage for adults, children and older infants with normal renal function is 15 mg/kg/day divided into 2 or 3 equal doses administered at equally divided intervals, i.e., 7.5 mg/kg q12h or 5 mg/kg q8h. Treatment of patients in the heavier weight classes should not exceed 1.5 grams/day. When amikacin is indicated in newborns, it is recommended that a loading dose of 10 mg/kg be administered initially to be followed with 7.5 mg/kg every 12 hours. The usual duration of treatment is 7 to 10 days. It is desirable to limit the duration of treatment to short-term whenever feasible. The total daily dose by all routes of administration should not exceed 15 mg/kg/day.
Route of Administration: Intramuscular
In Vitro Use Guide
Amikacin had a strong bactericidal effect on coccoid bacteria at 8 ug/mL concentration.
Name Type Language
AMIKACIN
EP   HSDB   INN   MART.   MI   USP   USP-RS   VANDF   WHO-DD   WHO-IP  
INN  
Official Name English
AMIKACIN [EP]
Common Name English
AMIKACIN [VANDF]
Common Name English
AMIKACIN [WHO-DD]
Common Name English
AMIKACIN [JAN]
Common Name English
LUKADIN
Common Name English
AMIKACIN [WHO-IP]
Common Name English
NSC-177001
Code English
AMIKACIN [MART.]
Common Name English
AMIKACIN [HSDB]
Common Name English
AMIKACIN [USP]
Common Name English
BAY 41-6551
Code English
O-3-AMINO-3-DEOXY-.ALPHA.-D-GLUCOPYRANOSYL-(1->4)-O-(6-AMINO-6-DEOXY-.ALPHA.-D-GLUCOPYRANOSYL-(1->6))-N(SUP 3)-(4-AMINO-L-2-HYDROXYBUTYRYL)-2-DEOXY-L-STREPTAMINE
Common Name English
AMIKACIN [MI]
Common Name English
AMIKACIN [USP-RS]
Common Name English
AMIKACINUM [WHO-IP LATIN]
Common Name English
AMIKACIN [INN]
Common Name English
POTENTOX
Common Name English
D-STREPTAMINE, O-3-AMINO-3-DEOXY-.ALPHA.-D-GLUCOPYRANOSYL-(1->6)-O-(6-AMINO-6-DEOXY-.ALPHA.-D-GLUCOPYRANOSYL-(1->4))-N(SUP 1)-(4-AMINO-2-HYDROXY-1-OXOBUTYL)-2-DEOXY-, (S)-
Common Name English
Classification Tree Code System Code
NDF-RT N0000175477
Created by admin on Mon Oct 21 19:51:24 UTC 2019 , Edited by admin on Mon Oct 21 19:51:24 UTC 2019
CFR 21 CFR 522.56
Created by admin on Mon Oct 21 19:51:24 UTC 2019 , Edited by admin on Mon Oct 21 19:51:24 UTC 2019
WHO-ATC D06AX12
Created by admin on Mon Oct 21 19:51:24 UTC 2019 , Edited by admin on Mon Oct 21 19:51:24 UTC 2019
WHO-VATC QJ01GB06
Created by admin on Mon Oct 21 19:51:24 UTC 2019 , Edited by admin on Mon Oct 21 19:51:24 UTC 2019
LIVERTOX 37
Created by admin on Mon Oct 21 19:51:24 UTC 2019 , Edited by admin on Mon Oct 21 19:51:24 UTC 2019
NDF-RT N0000007853
Created by admin on Mon Oct 21 19:51:24 UTC 2019 , Edited by admin on Mon Oct 21 19:51:24 UTC 2019
FDA ORPHAN DRUG 217305
Created by admin on Mon Oct 21 19:51:24 UTC 2019 , Edited by admin on Mon Oct 21 19:51:24 UTC 2019
WHO-VATC QD06AX12
Created by admin on Mon Oct 21 19:51:24 UTC 2019 , Edited by admin on Mon Oct 21 19:51:24 UTC 2019
WHO-ESSENTIAL MEDICINES LIST 6.2.4
Created by admin on Mon Oct 21 19:51:24 UTC 2019 , Edited by admin on Mon Oct 21 19:51:24 UTC 2019
FDA ORPHAN DRUG 507715
Created by admin on Mon Oct 21 19:51:24 UTC 2019 , Edited by admin on Mon Oct 21 19:51:24 UTC 2019
CFR 21 CFR 862.3035
Created by admin on Mon Oct 21 19:51:24 UTC 2019 , Edited by admin on Mon Oct 21 19:51:24 UTC 2019
WHO-ATC J01GB06
Created by admin on Mon Oct 21 19:51:24 UTC 2019 , Edited by admin on Mon Oct 21 19:51:24 UTC 2019
FDA ORPHAN DRUG 342011
Created by admin on Mon Oct 21 19:51:24 UTC 2019 , Edited by admin on Mon Oct 21 19:51:24 UTC 2019
FDA ORPHAN DRUG 282109
Created by admin on Mon Oct 21 19:51:24 UTC 2019 , Edited by admin on Mon Oct 21 19:51:24 UTC 2019
WHO-ATC S01AA21
Created by admin on Mon Oct 21 19:51:24 UTC 2019 , Edited by admin on Mon Oct 21 19:51:24 UTC 2019
WHO-ATC J01RA06
Created by admin on Mon Oct 21 19:51:24 UTC 2019 , Edited by admin on Mon Oct 21 19:51:24 UTC 2019
NCI_THESAURUS C2363
Created by admin on Mon Oct 21 19:51:24 UTC 2019 , Edited by admin on Mon Oct 21 19:51:24 UTC 2019
WHO-VATC QS01AA21
Created by admin on Mon Oct 21 19:51:24 UTC 2019 , Edited by admin on Mon Oct 21 19:51:24 UTC 2019
Code System Code Type Description
WHO INTERNATIONAL PHARMACOPEIA
AMIKACIN
Created by admin on Mon Oct 21 19:51:24 UTC 2019 , Edited by admin on Mon Oct 21 19:51:24 UTC 2019
PRIMARY Description: White or almost white powder. Solubility: Freely soluble in water, practically insoluble in acetone R or ethanol (~750 g/l) TS. Category: Antibacterial. Storage: Amikacin should be kept in a tightly closed container, or if sterile, in a hermetically closed container. Labelling: The label states:- where applicable, that the substances is free from bacterial endotoxins,- where applicable, that the substance is sterile. Definition: Amikacin is a semi-synthetic product derived from a fermentation product, kanamycin A. Amikacin contains not less than 96.5% and not more than 102.0% (Assay, Method A) or not less than 98.5% and not more than 101.0% (Assay, Method B) of amikacin (C22H43N5O13), calculated with reference to the anhydrous substance.
NCI_THESAURUS
C61615
Created by admin on Mon Oct 21 19:51:24 UTC 2019 , Edited by admin on Mon Oct 21 19:51:24 UTC 2019
PRIMARY
WIKIPEDIA
AMIKACIN
Created by admin on Mon Oct 21 19:51:24 UTC 2019 , Edited by admin on Mon Oct 21 19:51:24 UTC 2019
PRIMARY
ChEMBL
CHEMBL177
Created by admin on Mon Oct 21 19:51:24 UTC 2019 , Edited by admin on Mon Oct 21 19:51:24 UTC 2019
PRIMARY
CAS
37517-28-5
Created by admin on Mon Oct 21 19:51:24 UTC 2019 , Edited by admin on Mon Oct 21 19:51:24 UTC 2019
PRIMARY
LactMed
37517-28-5
Created by admin on Mon Oct 21 19:51:24 UTC 2019 , Edited by admin on Mon Oct 21 19:51:24 UTC 2019
PRIMARY
MESH
D000583
Created by admin on Mon Oct 21 19:51:24 UTC 2019 , Edited by admin on Mon Oct 21 19:51:24 UTC 2019
PRIMARY
HSDB
37517-28-5
Created by admin on Mon Oct 21 19:51:24 UTC 2019 , Edited by admin on Mon Oct 21 19:51:24 UTC 2019
PRIMARY
EPA CompTox
37517-28-5
Created by admin on Mon Oct 21 19:51:24 UTC 2019 , Edited by admin on Mon Oct 21 19:51:24 UTC 2019
PRIMARY
ECHA (EC/EINECS)
253-538-5
Created by admin on Mon Oct 21 19:51:24 UTC 2019 , Edited by admin on Mon Oct 21 19:51:24 UTC 2019
PRIMARY
PUBCHEM
37768
Created by admin on Mon Oct 21 19:51:24 UTC 2019 , Edited by admin on Mon Oct 21 19:51:24 UTC 2019
PRIMARY
EVMPD
SUB05431MIG
Created by admin on Mon Oct 21 19:51:24 UTC 2019 , Edited by admin on Mon Oct 21 19:51:24 UTC 2019
PRIMARY
INN
3492
Created by admin on Mon Oct 21 19:51:24 UTC 2019 , Edited by admin on Mon Oct 21 19:51:24 UTC 2019
PRIMARY
RXCUI
641
Created by admin on Mon Oct 21 19:51:24 UTC 2019 , Edited by admin on Mon Oct 21 19:51:24 UTC 2019
PRIMARY RxNorm
DRUG BANK
DB00479
Created by admin on Mon Oct 21 19:51:24 UTC 2019 , Edited by admin on Mon Oct 21 19:51:24 UTC 2019
PRIMARY
MERCK INDEX
M1670
Created by admin on Mon Oct 21 19:51:24 UTC 2019 , Edited by admin on Mon Oct 21 19:51:24 UTC 2019
PRIMARY Merck Index