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

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

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
[Multifocal invasive Kingella kingae infection].
1998 Feb
The aminoglycosides.
1999 May
Use of genomics and combinatorial chemistry in the development of new antimycobacterial drugs.
2000 Feb 1
Antimicrobial susceptibility of Mycobacterium marinum determined by E-test and agar dilution.
2001
Cutaneous nocardiosis of the chest wall and pleura--10-year consequences of a hand actinomycetoma.
2001
Molecular diagnosis of a Mycobacterium chelonae infection.
2001
The immunomodulatory effects of gentamicin, imipenem, piperacillin and amphotericin B on LAK effector function in vitro.
2001 Apr
Multiple nocardial abscesses of cerebrum, cerebellum and spinal cord, causing quadriplegia.
2001 Apr
[Combination therapy of antibiotics and intravenous immunoglobulin].
2001 Apr
Urinary excretion reflects lung deposition of aminoglycoside aerosols in cystic fibrosis.
2001 Aug
Arsenite-induced multiple antibiotic resistance phenotype in environmental isolates of Yersinia enterocolitica.
2001 Aug
[Correlation between sensitivity to fosfomycin and the presence of penicillinase PSE-1 in Pseudomonas aeruginosa].
2001 Feb
Antibacterial activity of 41 antimicrobials tested against over 2773 bacterial isolates from hospitalized patients with pneumonia: I--results from the SENTRY Antimicrobial Surveillance Program (North America, 1998).
2001 Feb
Efficacy of meropenem as monotherapy in the treatment of ventilator-associated pneumonia.
2001 Feb
Single-daily ceftriaxone plus amikacin versus thrice-daily ceftazidime plus amikacin as empirical treatment of febrile neutropenia in children with cancer.
2001 Feb
Properties of multidrug-resistant, ESBL-producing Proteus mirabilis isolates and possible role of beta-lactam/beta-lactamase inhibitor combinations.
2001 Feb
Nonenteric Escherichia coli isolates from dogs: 674 cases (1990-1998).
2001 Feb 1
Novel treatment of meningitis caused by multidrug-resistant Mycobacterium tuberculosis with intrathecal levofloxacin and amikacin: case report.
2001 Feb 15
Objective method for differentiating between drug-induced vestibulotoxicity and cochleotoxicity.
2001 Jan
Carriage of class 1 integrons and antibiotic resistance in clinical isolates of Acinetobacter baumannii from northern Spain.
2001 Jan
Nosocomial pneumonia. Diagnostic and therapeutic considerations.
2001 Jan
Disseminated Mycobacterium abscessus infection manifesting as fever of unknown origin and intra-abdominal lymphadenitis: case report and literature review.
2001 Jan
Bilateral infectious keratitis after laser in situ keratomileusis: a case report and review of the literature.
2001 Jan
Review of 49 neonates with acquired fungal sepsis: further characterization.
2001 Jan
Use of a recombinant strain of Mycobacterium avium expressing beta-galactosidase to evaluate the activities of antimycobacterial agents inside macrophages.
2001 Jan
Granulocyte colony-stimulating factor in the treatment of high-risk febrile neutropenia: a multicenter randomized trial.
2001 Jan 3
Interactions of colistin and rifampin on multidrug-resistant Acinetobacter baumannii.
2001 Jul
Penetration of amikacin into aqueous humor of rabbits.
2001 Jul-Aug
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
Mycobacterium fortuitum wound infection following laparoscopy.
2001 Mar
Meningoencephalitis caused by Bacillus cereus in a neonate.
2001 Mar
[Clinical analysis of neutropenic fever associated with hematological disorders].
2001 Mar
Treatment of nosocomial postoperative pneumonia in cancer patients: a prospective randomized study.
2001 Mar
Chryseobacterium (Flavobacterium) meningosepticum outbreak associated with colonization of water taps in a neonatal intensive care unit.
2001 Mar
Hair cell regeneration and recovery of auditory thresholds following aminoglycoside ototoxicity in Bengalese finches.
2001 Mar
[Mycobacterium xenopi: epidemiological and bacteriological features].
2001 Mar-Apr
[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
Antibiotic selective pressure and development of bacterial resistance.
2001 May
Antimicrobial susceptibility of blood culture isolates of viridans streptococci: relationship to a change in empirical antibiotic therapy in febrile neutropenia.
2001 May
Clinical applications of a novel sustained-release injectable drug delivery system: DepoFoam technology.
2001 May-Jun
Liposome-encapsulated aminoglycosides in pre-clinical and clinical studies.
2001 Sep
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.
Substance Class Chemical
Created
by admin
on Mon Oct 21 19:51:24 UTC 2019
Edited
by admin
on Mon Oct 21 19:51:24 UTC 2019
Record UNII
84319SGC3C
Record Status Validated (UNII)
Record Version
  • Download
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
Related Record Type Details
SALT/SOLVATE -> PARENT
BINDER->LIGAND
BINDING
Related Record Type Details
IMPURITY -> PARENT
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.
Related Record Type Details
ACTIVE MOIETY
Name Property Type Amount Referenced Substance Defining Parameters References
Volume of Distribution PHARMACOKINETIC
Biological Half-life PHARMACOKINETIC