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Identification
NameAmikacin
Accession NumberDB00479  (APRD00550)
TypeSmall Molecule
GroupsApproved, Vet Approved
DescriptionAmikacin is a semi-synthetic aminoglycoside antibiotic derived from kanamycin A. Similar to other aminoglycosides, amikacin disrupts bacterial protein synthesis by binding to the 30S ribosome of susceptible organisms. Binding interferes with mRNA binding and tRNA acceptor sites leading to the production of non-functional or toxic peptides. Other mechanisms not fully understood may confer the bactericidal effects of amikacin. Amikacin is also nephrotoxic and ototoxic.
Structure
Thumb
Synonyms
1-N-(L(-)-gamma-amino-alpha-Hydroxybutyryl)kanamycin a
Amicacin
Amiglyde-v
Amikacin
Amikacina
Amikacine
Amikacinum
Amikavet
Briclin
O-3-amino-3-Deoxy-alpha-D-glucopyranosyl-(1->4)-O-(6-amino-6-deoxy-alpha-D-glucopyranosyl-(1->6))-N(3)-(4-amino-L-2-hydroxybutyryl)-2-deoxy-L-streptamine
External Identifiers Not Available
Approved Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Amikacin Sulfate Injection USPliquid250 mgintramuscular; intravenousSandoz Canada Incorporated2001-01-29Not applicableCanada
Amikinsolution250 mgintramuscular; intravenousBristol Myers Squibb Canada1977-12-312006-05-29Canada
Approved Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Amikacin Sulfateinjection250 mg/mLintramuscular; intravenousWest Ward Pharmaceuticals Corp.2015-08-01Not applicableUs
Amikacin Sulfateinjection, solution250 mg/mLintramuscular; intravenousHeritage Pharmaceuticals Inc.2013-12-24Not applicableUs
Amikacin Sulfateinjection250 mg/mLintramuscular; intravenousWest Ward Pharmaceuticals Corp.2015-08-01Not applicableUs
Amikacin Sulfateinjection, solution250 mg/mLintramuscular; intravenousFresenius Kabi USA, LLC2015-12-09Not applicableUs
Amikacin Sulfateinjection, solution500 mg/2mLintramuscular; intravenousTeva Parenteral Medicines, Inc.1993-10-01Not applicableUs
Amikacin Sulfateinjection, solution50 mg/mLintramuscular; intravenousFresenius Kabi USA, LLC2015-12-09Not applicableUs
Amikacin Sulfateinjection, solution1 g/4mLintramuscular; intravenousTeva Parenteral Medicines, Inc.1993-10-01Not applicableUs
Approved Over the Counter ProductsNot Available
Unapproved/Other Products Not Available
International Brands
NameCompany
AmexelAbbott
AmukinBristol-Myers Squibb
BiklinBristol-Myers Squibb
ErkacinBrown & Burk
FarcyclinFaran Laboratories
FlexeliteBros
KaminBosch
NovaminBristol-Myers Squibb
SelaxaProel
SelemycinMedochemie
SikacinShiteh Organic
TipkinT P Drug
TybikinM & H
UkajectUnimed Pharm
UnikinUnion
UzixRafarm
XylanalEpsilon
Brand mixturesNot Available
Salts
Name/CASStructureProperties
Amikacin Sulfate
39831-55-5
Thumb
  • InChI Key: FXKSEJFHKVNEFI-GCZBSULCSA-N
  • Monoisotopic Mass: 781.220494971
  • Average Mass: 781.759
DBSALT000351
Categories
UNII84319SGC3C
CAS number37517-28-5
WeightAverage: 585.6025
Monoisotopic: 585.285736487
Chemical FormulaC22H43N5O13
InChI KeyInChIKey=LKCWBDHBTVXHDL-RMDFUYIESA-N
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
IUPAC Name
(2S)-4-amino-N-[(1R,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,5S,6R)-6-(aminomethyl)-3,4,5-trihydroxyoxan-2-yl]oxy}-3-hydroxycyclohexyl]-2-hydroxybutanamide
SMILES
NCC[[email protected]](O)C(=O)N[C@@H]1C[[email protected]](N)[C@@H](O[[email protected]]2O[[email protected]](CN)[C@@H](O)[[email protected]](O)[[email protected]]2O)[[email protected]](O)[[email protected]]1O[[email protected]]1O[[email protected]](CO)[C@@H](O)[[email protected]](N)[[email protected]]1O
Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as amino sugars. These are sugars having one alcoholic hydroxy group replaced by an amino group; systematically known as x-amino-x-deoxymonosaccharides. These compounds do not include Glycosylamines.
KingdomOrganic compounds
Super ClassOrganooxygen compounds
ClassCarbohydrates and carbohydrate conjugates
Sub ClassAminosaccharides
Direct ParentAmino sugars
Alternative Parents
Substituents
  • 4,6-disubstituted 2-deoxystreptamine
  • Aminoglycoside core
  • 2-deoxystreptamine aminoglycoside
  • Gamma amino acid or derivatives
  • Glucosamine
  • Amino sugar
  • O-glycosyl compound
  • Glycosyl compound
  • Cyclohexylamine
  • Cyclohexanol
  • Fatty acyl
  • Oxane
  • N-acyl-amine
  • Monosaccharide
  • Fatty amide
  • Cyclic alcohol
  • 1,3-aminoalcohol
  • Secondary carboxylic acid amide
  • Secondary alcohol
  • Polyol
  • Carboxamide group
  • 1,2-diol
  • 1,2-aminoalcohol
  • Oxacycle
  • Organoheterocyclic compound
  • Carboxylic acid derivative
  • Carboxylic acid amide
  • Acetal
  • Hydrocarbon derivative
  • Primary amine
  • Primary alcohol
  • Organonitrogen compound
  • Primary aliphatic amine
  • Carbonyl group
  • Amine
  • Alcohol
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External Descriptors
Pharmacology
IndicationFor 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.
PharmacodynamicsAmikacin is an aminoglycoside antibiotic. Aminoglycosides work by binding to the bacterial 30S ribosomal subunit, causing misreading of t-RNA, leaving the bacterium unable to synthesize proteins vital to its growth. Aminoglycosides are useful primarily in infections involving aerobic, Gram-negative bacteria, such as Pseudomonas, Acinetobacter, and Enterobacter. In addition, some mycobacteria, including the bacteria that cause tuberculosis, are susceptible to aminoglycosides. Infections caused by Gram-positive bacteria can also be treated with aminoglycosides, but other types of antibiotics are more potent and less damaging to the host. In the past the aminoglycosides have been used in conjunction with penicillin-related antibiotics in streptococcal infections for their synergistic effects, particularly in endocarditis. Aminoglycosides are mostly ineffective against anaerobic bacteria, fungi and viruses.
Mechanism of actionAminoglycosides like Amikacin "irreversibly" bind 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.
Related Articles
AbsorptionRapidly absorbed after intramuscular administration. Rapid absorption occurs from the peritoneum and pleura. Poor oral and topical absorption. Poorly absorbed from bladder irrigations and intrathecal administration.
Volume of distribution
  • 24 L [normal adult subjects]
Protein binding0-11%
MetabolismNot Available
Route of eliminationAmikacin is excreted primarily by glomerular filtration.
Half life2-3 hours
Clearance
  • 100 mL/min
ToxicityMild and reversible nephrotoxicity may be observed in 5 - 25% of patients. Amikacin accumulates in proximal renal tubular cells. Tubular cell regeneration occurs despite continued drug exposure. Toxicity usually occurs several days following initiation of therapy. May cause irreversible ototoxicity. Otoxocity appears to be correlated to cumulative lifetime exposure. Drug accumulation in the endolymph and perilymph of the inner ear causes irreversible damage to hair cells of the cochlea or summit of ampullar cristae in the vestibular complex. High frequency hearing is lost first with progression leading to loss of low frequency hearing. Further toxicity may lead to retrograde degeneration of the 8th cranial (vestibulocochlear) nerve. Vestibular toxicity may cause vertigo, nausea, vomiting, dizziness and loss of balance.
Affected organisms
  • Enteric bacteria and other eubacteria
Pathways
PathwayCategorySMPDB ID
Amikacin Action PathwayDrug actionSMP00253
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption-0.9405
Blood Brain Barrier-0.9659
Caco-2 permeable-0.7583
P-glycoprotein substrateSubstrate0.5129
P-glycoprotein inhibitor INon-inhibitor0.7336
P-glycoprotein inhibitor IINon-inhibitor0.8383
Renal organic cation transporterNon-inhibitor0.8614
CYP450 2C9 substrateNon-substrate0.816
CYP450 2D6 substrateNon-substrate0.8309
CYP450 3A4 substrateNon-substrate0.5664
CYP450 1A2 substrateNon-inhibitor0.9381
CYP450 2C9 inhibitorNon-inhibitor0.9237
CYP450 2D6 inhibitorNon-inhibitor0.9249
CYP450 2C19 inhibitorNon-inhibitor0.9128
CYP450 3A4 inhibitorNon-inhibitor0.9434
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.8866
Ames testNon AMES toxic0.6813
CarcinogenicityNon-carcinogens0.9635
BiodegradationNot ready biodegradable0.5512
Rat acute toxicity1.7506 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9926
hERG inhibition (predictor II)Non-inhibitor0.6366
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397 )
Pharmacoeconomics
Manufacturers
  • Abbott laboratories
  • Abbott laboratories hosp products div
  • Astrazeneca lp
  • Baxter healthcare corp anesthesia and critical care
  • Bedford laboratories div ben venue laboratories inc
  • Hospira inc
  • Teva parenteral medicines inc
  • Apothecon inc div bristol myers squibb
Packagers
Dosage forms
FormRouteStrength
Injectionintramuscular; intravenous250 mg/mL
Injection, solutionintramuscular; intravenous1 g/4mL
Injection, solutionintramuscular; intravenous250 mg/mL
Injection, solutionintramuscular; intravenous50 mg/mL
Injection, solutionintramuscular; intravenous500 mg/2mL
Liquidintramuscular; intravenous250 mg
Solutionintramuscular; intravenous250 mg
Prices
Unit descriptionCostUnit
Amikacin sulfate powder26.01USD g
Amikacin (pf) 500 mg/2 ml2.53USD ml
Amikacin 250 mg/ml vial2.19USD ml
Amikacin (pf) 100 mg/2 ml1.8USD ml
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
PatentsNot Available
Properties
StateSolid
Experimental Properties
PropertyValueSource
melting point203-204 °CPhysProp
water solubility1.85E+005 mg/L (at 25 °C)YALKOWSKY,SH & DANNENFELSER,RM (1992)
logP-7.4Not Available
logS-0.5ADME Research, USCD
Predicted Properties
PropertyValueSource
Water Solubility49.7 mg/mLALOGPS
logP-3.2ALOGPS
logP-8.6ChemAxon
logS-1.1ALOGPS
pKa (Strongest Acidic)12.1ChemAxon
pKa (Strongest Basic)9.79ChemAxon
Physiological Charge4ChemAxon
Hydrogen Acceptor Count17ChemAxon
Hydrogen Donor Count13ChemAxon
Polar Surface Area331.94 Å2ChemAxon
Rotatable Bond Count10ChemAxon
Refractivity129.84 m3·mol-1ChemAxon
Polarizability58.2 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Mass Spec (NIST)Not Available
Spectra
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, NegativeNot Available
References
Synthesis Reference

Alberto Mangia, Vicenzo Giobbio, Giorgio Ornato, “Novel process for the synthesis of amikacin.” U.S. Patent US4902790, issued August, 1984.

US4902790
General References
  1. Edson RS, Terrell CL: The aminoglycosides. Mayo Clin Proc. 1999 May;74(5):519-28. [PubMed:10319086 ]
External Links
ATC CodesJ01GB06D06AX12J01RA06S01AA21
AHFS Codes
  • 08:12.02
PDB EntriesNot Available
FDA labelNot Available
MSDSDownload (73.4 KB)
Interactions
Drug Interactions
Drug
AceclofenacAceclofenac may decrease the excretion rate of Amikacin which could result in a lower serum level and potentially a reduction in efficacy.
AcetyldigitoxinThe serum concentration of Acetyldigitoxin can be decreased when it is combined with Amikacin.
Acetylsalicylic acidAcetylsalicylic acid may decrease the excretion rate of Amikacin which could result in a lower serum level and potentially a reduction in efficacy.
AdapaleneAdapalene may decrease the excretion rate of Amikacin which could result in a lower serum level and potentially a reduction in efficacy.
Alendronic acidAmikacin may increase the hypocalcemic activities of Alendronic acid.
AmdinocillinThe serum concentration of Amikacin can be decreased when it is combined with Amdinocillin.
AmoxicillinThe serum concentration of Amikacin can be decreased when it is combined with Amoxicillin.
Amphotericin BAmphotericin B may increase the nephrotoxic activities of Amikacin.
AmpicillinThe serum concentration of Amikacin can be decreased when it is combined with Ampicillin.
AntipyrineAntipyrine may decrease the excretion rate of Amikacin which could result in a lower serum level and potentially a reduction in efficacy.
ApremilastApremilast may decrease the excretion rate of Amikacin which could result in a lower serum level and potentially a reduction in efficacy.
AzapropazoneAzapropazone may decrease the excretion rate of Amikacin which could result in a lower serum level and potentially a reduction in efficacy.
AzelastineAzelastine may decrease the excretion rate of Amikacin which could result in a lower serum level and potentially a reduction in efficacy.
AzlocillinThe serum concentration of Amikacin can be decreased when it is combined with Azlocillin.
BalsalazideBalsalazide may decrease the excretion rate of Amikacin which could result in a lower serum level and potentially a reduction in efficacy.
BenoxaprofenBenoxaprofen may decrease the excretion rate of Amikacin which could result in a lower serum level and potentially a reduction in efficacy.
Benzathine benzylpenicillinThe serum concentration of Amikacin can be decreased when it is combined with Benzathine benzylpenicillin.
BenzylpenicillinThe serum concentration of Amikacin can be decreased when it is combined with Benzylpenicillin.
Benzylpenicillin PotassiumThe serum concentration of Amikacin can be decreased when it is combined with Benzylpenicillin Potassium.
Botulinum Toxin Type AAmikacin may increase the neuromuscular blocking activities of Botulinum Toxin Type A.
Botulinum Toxin Type BAmikacin may increase the neuromuscular blocking activities of Botulinum Toxin Type B.
BromfenacBromfenac may decrease the excretion rate of Amikacin which could result in a lower serum level and potentially a reduction in efficacy.
BumetanideThe risk or severity of adverse effects can be increased when Bumetanide is combined with Amikacin.
CapreomycinCapreomycin may increase the neuromuscular blocking activities of Amikacin.
CarbenicillinThe serum concentration of Amikacin can be decreased when it is combined with Carbenicillin.
CarboplatinAmikacin may increase the ototoxic activities of Carboplatin.
CarprofenCarprofen may decrease the excretion rate of Amikacin which could result in a lower serum level and potentially a reduction in efficacy.
CastanospermineCastanospermine may decrease the excretion rate of Amikacin which could result in a lower serum level and potentially a reduction in efficacy.
CelecoxibCelecoxib may decrease the excretion rate of Amikacin which could result in a lower serum level and potentially a reduction in efficacy.
ChloroquineChloroquine may decrease the excretion rate of Amikacin which could result in a lower serum level and potentially a reduction in efficacy.
CisplatinCisplatin may increase the nephrotoxic activities of Amikacin.
ClodronateAmikacin may increase the hypocalcemic activities of Clodronate.
ClonixinClonixin may decrease the excretion rate of Amikacin which could result in a lower serum level and potentially a reduction in efficacy.
CloxacillinThe serum concentration of Amikacin can be decreased when it is combined with Cloxacillin.
ColistimethateAmikacin may increase the nephrotoxic activities of Colistimethate.
CyclacillinThe serum concentration of Amikacin can be decreased when it is combined with Cyclacillin.
CyclosporineAmikacin may increase the nephrotoxic activities of Cyclosporine.
D-LimoneneD-Limonene may decrease the excretion rate of Amikacin which could result in a lower serum level and potentially a reduction in efficacy.
DeslanosideThe serum concentration of Deslanoside can be decreased when it is combined with Amikacin.
DiclofenacDiclofenac may decrease the excretion rate of Amikacin which could result in a lower serum level and potentially a reduction in efficacy.
DicloxacillinThe serum concentration of Amikacin can be decreased when it is combined with Dicloxacillin.
DiflunisalDiflunisal may decrease the excretion rate of Amikacin which could result in a lower serum level and potentially a reduction in efficacy.
DigitoxinThe serum concentration of Digitoxin can be decreased when it is combined with Amikacin.
DigoxinThe serum concentration of Digoxin can be decreased when it is combined with Amikacin.
DroxicamDroxicam may decrease the excretion rate of Amikacin which could result in a lower serum level and potentially a reduction in efficacy.
EpirizoleEpirizole may decrease the excretion rate of Amikacin which could result in a lower serum level and potentially a reduction in efficacy.
Etacrynic acidThe risk or severity of adverse effects can be increased when Etacrynic acid is combined with Amikacin.
EtanerceptEtanercept may decrease the excretion rate of Amikacin which could result in a lower serum level and potentially a reduction in efficacy.
Etidronic acidAmikacin may increase the hypocalcemic activities of Etidronic acid.
EtodolacEtodolac may decrease the excretion rate of Amikacin which could result in a lower serum level and potentially a reduction in efficacy.
EtofenamateEtofenamate may decrease the excretion rate of Amikacin which could result in a lower serum level and potentially a reduction in efficacy.
EtoricoxibEtoricoxib may decrease the excretion rate of Amikacin which could result in a lower serum level and potentially a reduction in efficacy.
Evening primrose oilEvening primrose oil may decrease the excretion rate of Amikacin which could result in a lower serum level and potentially a reduction in efficacy.
exisulindexisulind may decrease the excretion rate of Amikacin which could result in a lower serum level and potentially a reduction in efficacy.
FenbufenFenbufen may decrease the excretion rate of Amikacin which could result in a lower serum level and potentially a reduction in efficacy.
FenoprofenFenoprofen may decrease the excretion rate of Amikacin which could result in a lower serum level and potentially a reduction in efficacy.
FloctafenineFloctafenine may decrease the excretion rate of Amikacin which could result in a lower serum level and potentially a reduction in efficacy.
FlucloxacillinThe serum concentration of Amikacin can be decreased when it is combined with Flucloxacillin.
FlunixinFlunixin may decrease the excretion rate of Amikacin which could result in a lower serum level and potentially a reduction in efficacy.
FlurbiprofenFlurbiprofen may decrease the excretion rate of Amikacin which could result in a lower serum level and potentially a reduction in efficacy.
FoscarnetFoscarnet may increase the nephrotoxic activities of Amikacin.
FurosemideThe risk or severity of adverse effects can be increased when Furosemide is combined with Amikacin.
HMPL-004HMPL-004 may decrease the excretion rate of Amikacin which could result in a lower serum level and potentially a reduction in efficacy.
IbandronateAmikacin may increase the hypocalcemic activities of Ibandronate.
IbuprofenIbuprofen may decrease the excretion rate of Amikacin which could result in a lower serum level and potentially a reduction in efficacy.
IbuproxamIbuproxam may decrease the excretion rate of Amikacin which could result in a lower serum level and potentially a reduction in efficacy.
IcatibantIcatibant may decrease the excretion rate of Amikacin which could result in a lower serum level and potentially a reduction in efficacy.
IndomethacinIndomethacin may decrease the excretion rate of Amikacin which could result in a lower serum level and potentially a reduction in efficacy.
IndoprofenIndoprofen may decrease the excretion rate of Amikacin which could result in a lower serum level and potentially a reduction in efficacy.
IsoxicamIsoxicam may decrease the excretion rate of Amikacin which could result in a lower serum level and potentially a reduction in efficacy.
KebuzoneKebuzone may decrease the excretion rate of Amikacin which could result in a lower serum level and potentially a reduction in efficacy.
KetoprofenKetoprofen may decrease the excretion rate of Amikacin which could result in a lower serum level and potentially a reduction in efficacy.
KetorolacKetorolac may decrease the excretion rate of Amikacin which could result in a lower serum level and potentially a reduction in efficacy.
LeflunomideLeflunomide may decrease the excretion rate of Amikacin which could result in a lower serum level and potentially a reduction in efficacy.
LornoxicamLornoxicam may decrease the excretion rate of Amikacin which could result in a lower serum level and potentially a reduction in efficacy.
LoxoprofenLoxoprofen may decrease the excretion rate of Amikacin which could result in a lower serum level and potentially a reduction in efficacy.
LumiracoxibLumiracoxib may decrease the excretion rate of Amikacin which could result in a lower serum level and potentially a reduction in efficacy.
Magnesium salicylateMagnesium salicylate may decrease the excretion rate of Amikacin which could result in a lower serum level and potentially a reduction in efficacy.
MannitolMannitol may increase the nephrotoxic activities of Amikacin.
MasoprocolMasoprocol may decrease the excretion rate of Amikacin which could result in a lower serum level and potentially a reduction in efficacy.
MecamylamineAmikacin may increase the neuromuscular blocking activities of Mecamylamine.
Meclofenamic acidMeclofenamic acid may decrease the excretion rate of Amikacin which could result in a lower serum level and potentially a reduction in efficacy.
Mefenamic acidMefenamic acid may decrease the excretion rate of Amikacin which could result in a lower serum level and potentially a reduction in efficacy.
MeloxicamMeloxicam may decrease the excretion rate of Amikacin which could result in a lower serum level and potentially a reduction in efficacy.
MesalazineMesalazine may decrease the excretion rate of Amikacin which could result in a lower serum level and potentially a reduction in efficacy.
MetamizoleMetamizole may decrease the excretion rate of Amikacin which could result in a lower serum level and potentially a reduction in efficacy.
MeticillinThe serum concentration of Amikacin can be decreased when it is combined with Meticillin.
MezlocillinThe serum concentration of Amikacin can be decreased when it is combined with Mezlocillin.
Mycophenolate mofetilMycophenolate mofetil may decrease the excretion rate of Amikacin which could result in a lower serum level and potentially a reduction in efficacy.
Mycophenolic acidMycophenolic acid may decrease the excretion rate of Amikacin which could result in a lower serum level and potentially a reduction in efficacy.
NabumetoneNabumetone may decrease the excretion rate of Amikacin which could result in a lower serum level and potentially a reduction in efficacy.
NafcillinThe serum concentration of Amikacin can be decreased when it is combined with Nafcillin.
NaftifineNaftifine may decrease the excretion rate of Amikacin which could result in a lower serum level and potentially a reduction in efficacy.
NaproxenNaproxen may decrease the excretion rate of Amikacin which could result in a lower serum level and potentially a reduction in efficacy.
NCX 4016NCX 4016 may decrease the excretion rate of Amikacin which could result in a lower serum level and potentially a reduction in efficacy.
NepafenacNepafenac may decrease the excretion rate of Amikacin which could result in a lower serum level and potentially a reduction in efficacy.
Niflumic AcidNiflumic Acid may decrease the excretion rate of Amikacin which could result in a lower serum level and potentially a reduction in efficacy.
NimesulideNimesulide may decrease the excretion rate of Amikacin which could result in a lower serum level and potentially a reduction in efficacy.
OlopatadineOlopatadine may decrease the excretion rate of Amikacin which could result in a lower serum level and potentially a reduction in efficacy.
OlsalazineOlsalazine may decrease the excretion rate of Amikacin which could result in a lower serum level and potentially a reduction in efficacy.
OrgoteinOrgotein may decrease the excretion rate of Amikacin which could result in a lower serum level and potentially a reduction in efficacy.
OuabainThe serum concentration of Ouabain can be decreased when it is combined with Amikacin.
OxacillinThe serum concentration of Amikacin can be decreased when it is combined with Oxacillin.
OxaprozinOxaprozin may decrease the excretion rate of Amikacin which could result in a lower serum level and potentially a reduction in efficacy.
OxyphenbutazoneOxyphenbutazone may decrease the excretion rate of Amikacin which could result in a lower serum level and potentially a reduction in efficacy.
PamidronateAmikacin may increase the hypocalcemic activities of Pamidronate.
ParecoxibParecoxib may decrease the excretion rate of Amikacin which could result in a lower serum level and potentially a reduction in efficacy.
PhenoxymethylpenicillinThe serum concentration of Amikacin can be decreased when it is combined with Phenoxymethylpenicillin.
PhenylbutazonePhenylbutazone may decrease the excretion rate of Amikacin which could result in a lower serum level and potentially a reduction in efficacy.
Picosulfuric acidThe therapeutic efficacy of Picosulfuric acid can be decreased when used in combination with Amikacin.
PimecrolimusPimecrolimus may decrease the excretion rate of Amikacin which could result in a lower serum level and potentially a reduction in efficacy.
PiperacillinThe serum concentration of Amikacin can be decreased when it is combined with Piperacillin.
PiretanideThe risk or severity of adverse effects can be increased when Piretanide is combined with Amikacin.
PirfenidonePirfenidone may decrease the excretion rate of Amikacin which could result in a lower serum level and potentially a reduction in efficacy.
PiroxicamPiroxicam may decrease the excretion rate of Amikacin which could result in a lower serum level and potentially a reduction in efficacy.
PivampicillinThe serum concentration of Amikacin can be decreased when it is combined with Pivampicillin.
PivmecillinamThe serum concentration of Amikacin can be decreased when it is combined with Pivmecillinam.
Procaine benzylpenicillinThe serum concentration of Amikacin can be decreased when it is combined with Procaine benzylpenicillin.
PropacetamolPropacetamol may decrease the excretion rate of Amikacin which could result in a lower serum level and potentially a reduction in efficacy.
PTC299PTC299 may decrease the excretion rate of Amikacin which could result in a lower serum level and potentially a reduction in efficacy.
ResveratrolResveratrol may decrease the excretion rate of Amikacin which could result in a lower serum level and potentially a reduction in efficacy.
RisedronateAmikacin may increase the hypocalcemic activities of Risedronate.
RofecoxibRofecoxib may decrease the excretion rate of Amikacin which could result in a lower serum level and potentially a reduction in efficacy.
SalicylamideSalicylamide may decrease the excretion rate of Amikacin which could result in a lower serum level and potentially a reduction in efficacy.
Salicylic acidSalicylic acid may decrease the excretion rate of Amikacin which could result in a lower serum level and potentially a reduction in efficacy.
SalsalateSalsalate may decrease the excretion rate of Amikacin which could result in a lower serum level and potentially a reduction in efficacy.
SeratrodastSeratrodast may decrease the excretion rate of Amikacin which could result in a lower serum level and potentially a reduction in efficacy.
SRT501SRT501 may decrease the excretion rate of Amikacin which could result in a lower serum level and potentially a reduction in efficacy.
SulbactamThe serum concentration of Amikacin can be decreased when it is combined with Sulbactam.
SulfasalazineSulfasalazine may decrease the excretion rate of Amikacin which could result in a lower serum level and potentially a reduction in efficacy.
SulindacSulindac may decrease the excretion rate of Amikacin which could result in a lower serum level and potentially a reduction in efficacy.
SuprofenSuprofen may decrease the excretion rate of Amikacin which could result in a lower serum level and potentially a reduction in efficacy.
Technetium Tc-99m MedronateAmikacin may increase the hypocalcemic activities of Technetium Tc-99m Medronate.
TenofovirThe serum concentration of Amikacin can be increased when it is combined with Tenofovir.
TenoxicamTenoxicam may decrease the excretion rate of Amikacin which could result in a lower serum level and potentially a reduction in efficacy.
TepoxalinTepoxalin may decrease the excretion rate of Amikacin which could result in a lower serum level and potentially a reduction in efficacy.
TeriflunomideTeriflunomide may decrease the excretion rate of Amikacin which could result in a lower serum level and potentially a reduction in efficacy.
Tiaprofenic acidTiaprofenic acid may decrease the excretion rate of Amikacin which could result in a lower serum level and potentially a reduction in efficacy.
TicarcillinThe serum concentration of Amikacin can be decreased when it is combined with Ticarcillin.
TiludronateAmikacin may increase the hypocalcemic activities of Tiludronate.
Tolfenamic AcidTolfenamic Acid may decrease the excretion rate of Amikacin which could result in a lower serum level and potentially a reduction in efficacy.
TolmetinTolmetin may decrease the excretion rate of Amikacin which could result in a lower serum level and potentially a reduction in efficacy.
TorasemideThe risk or severity of adverse effects can be increased when Torasemide is combined with Amikacin.
TranilastTranilast may decrease the excretion rate of Amikacin which could result in a lower serum level and potentially a reduction in efficacy.
Trisalicylate-cholineTrisalicylate-choline may decrease the excretion rate of Amikacin which could result in a lower serum level and potentially a reduction in efficacy.
ValdecoxibValdecoxib may decrease the excretion rate of Amikacin which could result in a lower serum level and potentially a reduction in efficacy.
VancomycinVancomycin may increase the nephrotoxic activities of Amikacin.
ZaltoprofenZaltoprofen may decrease the excretion rate of Amikacin which could result in a lower serum level and potentially a reduction in efficacy.
ZileutonZileuton may decrease the excretion rate of Amikacin which could result in a lower serum level and potentially a reduction in efficacy.
Zoledronic acidAmikacin may increase the hypocalcemic activities of Zoledronic acid.
ZomepiracZomepirac may decrease the excretion rate of Amikacin which could result in a lower serum level and potentially a reduction in efficacy.
Food InteractionsNot Available

Targets

Kind
Protein
Organism
Escherichia coli (strain K12)
Pharmacological action
yes
Actions
inhibitor
General Function:
Trna binding
Specific Function:
With S4 and S5 plays an important role in translational accuracy.Interacts with and stabilizes bases of the 16S rRNA that are involved in tRNA selection in the A site and with the mRNA backbone. Located at the interface of the 30S and 50S subunits, it traverses the body of the 30S subunit contacting proteins on the other side and probably holding the rRNA structure together. The combined cluste...
Gene Name:
rpsL
Uniprot ID:
P0A7S3
Molecular Weight:
13736.995 Da
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284 ]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423 ]
  3. Tolmasky ME: Bacterial resistance to aminoglycosides and beta-lactams: the Tn1331 transposon paradigm. Front Biosci. 2000 Jan 1;5:D20-9. [PubMed:10702385 ]
2. 16S rRNA
Kind
Nucleotide
Organism
Enteric bacteria and other eubacteria
Pharmacological action
unknown
Actions
inhibitor
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284 ]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423 ]
  3. Doi Y, de Oliveira Garcia D, Adams J, Paterson DL: Coproduction of novel 16S rRNA methylase RmtD and metallo-beta-lactamase SPM-1 in a panresistant Pseudomonas aeruginosa isolate from Brazil. Antimicrob Agents Chemother. 2007 Mar;51(3):852-6. Epub 2006 Dec 11. [PubMed:17158944 ]
  4. Bogaerts P, Galimand M, Bauraing C, Deplano A, Vanhoof R, De Mendonca R, Rodriguez-Villalobos H, Struelens M, Glupczynski Y: Emergence of ArmA and RmtB aminoglycoside resistance 16S rRNA methylases in Belgium. J Antimicrob Chemother. 2007 Mar;59(3):459-64. Epub 2007 Jan 15. [PubMed:17224412 ]
  5. Possoz C, Newmark J, Sorto N, Sherratt DJ, Tolmasky ME: Sublethal concentrations of the aminoglycoside amikacin interfere with cell division without affecting chromosome dynamics. Antimicrob Agents Chemother. 2007 Jan;51(1):252-6. Epub 2006 Oct 16. [PubMed:17043119 ]
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Drug created on June 13, 2005 07:24 / Updated on August 17, 2016 12:23