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
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
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
Originator
Approval Year
PubMed
Title | Date | PubMed |
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[Evaluation of ototoxicity of amikacin (BB-K8) by animal test (author's transl)]. | 1975 Jun |
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Antimicrobial susceptibility of Mycobacterium marinum determined by E-test and agar dilution. | 2001 |
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Treatment of mycobacterial exit-site infections in patients on continuous ambulatory peritoneal dialysis. | 2001 |
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Occurrence of variants with temperature-dependent susceptibility (TDS) to antibiotics among Stenotrophomonas maltophilia clinical strains. | 2001 |
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Antimicrobial effect of protein(s) isolated from a marine mollusc Telescopium telescopium. | 2001 Apr |
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Pharmacokinetics of amikacin after single intravenous and intramuscular administration in calves. | 2001 Apr |
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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 |
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Urinary excretion reflects lung deposition of aminoglycoside aerosols in cystic fibrosis. | 2001 Aug |
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Comparison of 2 techniques for regional antibiotic delivery to the equine forelimb: intraosseous perfusion vs. intravenous perfusion. | 2001 Aug |
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Optimizing antibiotic therapy in the intensive care unit setting. | 2001 Aug |
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Once-a-day individualized amikacin dosing for suspected infection at birth based on population pharmacokinetic models. | 2001 Aug |
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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 |
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Role of megalin in renal handling of aminoglycosides. | 2001 Aug |
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Arsenite-induced multiple antibiotic resistance phenotype in environmental isolates of Yersinia enterocolitica. | 2001 Aug |
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[Clinical effects of combination therapy with cefozopran and amikacin for infections in patients with hematological disorders]. | 2001 Feb |
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Changes in electrovestibular brainstem responses after aminoglycoside intoxication in guinea pigs. | 2001 Jul |
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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 |
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Interactions of colistin and rifampin on multidrug-resistant Acinetobacter baumannii. | 2001 Jul |
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Intravitreal antibiotics: the emergency kit. | 2001 Jul |
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Treatment and outcome of nocardia keratitis. | 2001 Jul |
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Penetration of amikacin into aqueous humor of rabbits. | 2001 Jul-Aug |
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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 |
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In vitro antimicrobial activity of the aminoglycoside arbekacin tested against oxacillin-resistant Staphylococcus aureus isolated in Brazilian hospitals. | 2001 Jun |
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Antibiotic susceptibility and phage typing of methicillin-resistant and -sensitive Staphylococcus aureus clinical isolates at three periods during 1991-1997. | 2001 Jun |
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Blood stream infections in a medical intensive care unit: spectrum and antibiotic susceptibility pattern. | 2001 Jun |
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[Neonatal bacterial infections at the CUH of Dakar]. | 2001 Jun |
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Cost-effectiveness of cefepime + netilmicin or ceftazidime + amikacin or meropenem monotherapy in febrile neutropenic children with malignancy in Turkey. | 2001 Jun |
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Antibiotic resistance among Gram-negative non-fermentative bacteria at a teaching hospital in Saudi Arabia. | 2001 Jun |
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Changing antibiotic sensitivity patterns at a university hospital, 1992 through 1999. | 2001 Jun |
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Madura foot: treatment of Nocardia nova infection with antibiotics alone. | 2001 Jun |
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The early bactericidal activity of amikacin in pulmonary tuberculosis. | 2001 Jun |
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Translimbal approach for intravitreal injection in endophthalmitis after phacoemulsification. | 2001 Jun |
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Antimicrobial susceptibility of Pseudomonas aeruginosa: results of a UK survey and evaluation of the British Society for Antimicrobial Chemotherapy disc susceptibility test. | 2001 Jun |
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Retinal vasculitis and posterior pole "hypopyons" as early signs of acute bacterial endophthalmitis. | 2001 Jun |
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Nephrotoxicants induce endothelin release and signaling in renal proximal tubules: effect on drug efflux. | 2001 Jun |
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Pharmacokinetic longitudinal studies of antibiotics administered via a permanent intraosseous device in micropigs. | 2001 Jun |
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Mycobacterium fortuitum wound infection following laparoscopy. | 2001 Mar |
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Meningoencephalitis caused by Bacillus cereus in a neonate. | 2001 Mar |
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Study on antimicrobial susceptibility of bacteria causing neonatal infections: a 12 year study (1987-1998). | 2001 Mar |
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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 |
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[Functional characterization of a multiple-antibiotic resistant plasmid from clinical isolates of methicillin-resistant Staphylococcus aureus]. | 2001 May |
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In vitro susceptibility to 15 antibiotics of vibrios isolated from penaeid shrimps in Northwestern Mexico. | 2001 May |
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Bacterial isolates from blood and their susceptibility patterns in critically ill foals: 543 cases (1991-1998). | 2001 May 15 |
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Infective endocarditis due to an unusual serotype of Salmonella. | 2001 May-Jun |
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Clinical applications of a novel sustained-release injectable drug delivery system: DepoFoam technology. | 2001 May-Jun |
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Epidemiologic Study of Pseudomonas aeruginosa in critical patients and reservoirs. | 2001 May-Jun |
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Liposome-encapsulated aminoglycosides in pre-clinical and clinical studies. | 2001 Sep |
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Failure of treatment for chronic Mycobacterium abscessus meningitis despite adequate clarithromycin levels in cerebrospinal fluid. | 2001 Sep 1 |
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A simple tool for monitoring nebulized amikacin treatments based on a single urine assay. | 2001 Spring |
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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 |
Sample Use Guides
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
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Classification Tree | Code System | Code | ||
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NDF-RT |
N0000175477
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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
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WHO-ATC |
D06AX12
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WHO-VATC |
QJ01GB06
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LIVERTOX |
37
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NDF-RT |
N0000007853
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FDA ORPHAN DRUG |
217305
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WHO-VATC |
QD06AX12
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WHO-ESSENTIAL MEDICINES LIST |
6.2.4
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FDA ORPHAN DRUG |
507715
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CFR |
21 CFR 862.3035
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WHO-ATC |
J01GB06
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FDA ORPHAN DRUG |
342011
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FDA ORPHAN DRUG |
282109
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WHO-ATC |
S01AA21
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WHO-ATC |
J01RA06
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NCI_THESAURUS |
C2363
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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
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Code System | Code | Type | Description | ||
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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
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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. | ||
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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
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PRIMARY | |||
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AMIKACIN
Created by
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PRIMARY | |||
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CHEMBL177
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PRIMARY | |||
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37517-28-5
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PRIMARY | |||
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37517-28-5
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PRIMARY | |||
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D000583
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PRIMARY | |||
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37517-28-5
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PRIMARY | |||
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37517-28-5
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PRIMARY | |||
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253-538-5
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37768
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PRIMARY | |||
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SUB05431MIG
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3492
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641
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PRIMARY | RxNorm | ||
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DB00479
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PRIMARY | |||
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M1670
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PRIMARY | Merck Index |
ACTIVE MOIETY
SALT/SOLVATE (PARENT)