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Identification
NameKanamycin
Accession NumberDB01172  (APRD00026)
TypeSmall Molecule
GroupsApproved, Vet Approved
DescriptionKanamycin (also known as kanamycin A) is an aminoglycoside bacteriocidal antibiotic, available in oral, intravenous, and intramuscular forms, and used to treat a wide variety of infections. Kanamycin is isolated from the bacterium Streptomyces kanamyceticus and its most commonly used form is kanamycin sulfate.
Structure
Thumb
Synonyms
4,6-diamino-2-hydroxy-1,3-cyclohexane 3,6'diamino-3,6'-dideoxydi-α-D-glucoside
4,6-diamino-2-hydroxy-1,3-cyclohexylene 3,6'-diamino-3,6'-dideoxydi-D-glucopyranoside
Kanamycin A
External Identifiers
  • 8063-07-8
Approved Prescription ProductsNot Available
Approved Generic Prescription ProductsNot Available
Approved Over the Counter ProductsNot Available
Unapproved/Other Products Not Available
International Brands
NameCompany
EfficinLupin
KanamytrexAlcon
KancinAlembic
Kancin-LAtlantic
KantrexMerck
WinamycinWinston
Brand mixturesNot Available
Salts
Name/CASStructureProperties
Kanamycin sulfate
Thumb
  • InChI Key: OOYGSFOGFJDDHP-KMCOLRRFSA-N
  • Monoisotopic Mass: 582.205437256
  • Average Mass: 582.577
DBSALT000401
Categories
UNIIEQK9Q303C5
CAS number59-01-8
WeightAverage: 484.4986
Monoisotopic: 484.238058014
Chemical FormulaC18H36N4O11
InChI KeySBUJHOSQTJFQJX-LCMAVPODNA-N
InChI
InChI=1/C18H36N4O11/c19-2-6-10(25)12(27)13(28)18(30-6)33-16-5(21)1-4(20)15(14(16)29)32-17-11(26)8(22)9(24)7(3-23)31-17/h4-18,23-29H,1-3,19-22H2/t4-,5+,6-,7-,8+,9-,10-,11-,12+,13-,14-,15+,16-,17-,18-/s2
IUPAC Name
(2R,3S,4S,5R,6R)-2-(aminomethyl)-6-{[(1R,2R,3S,4R,6S)-4,6-diamino-3-{[(2S,3R,4S,5S,6R)-4-amino-3,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-2-hydroxycyclohexyl]oxy}oxane-3,4,5-triol
SMILES
NC[[email protected]]1O[[email protected]](O[C@@H]2[C@@H](N)C[C@@H](N)[[email protected]](O[[email protected]]3O[[email protected]](CO)[C@@H](O)[[email protected]](N)[[email protected]]3O)[[email protected]]2O)[[email protected]](O)[C@@H](O)[C@@H]1O
Pharmacology
IndicationFor treatment of infections where one or more of the following are the known or suspected pathogens: E. coli, Proteus species (both indole-positive and indole-negative), E. aerogenes, K. pneumoniae, S. marcescens, and Acinetobacter species.
Structured Indications Not Available
PharmacodynamicsKanamycin 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 kanamycin "irreversibly" bind to specific 30S-subunit proteins and 16S rRNA. Specifically Kanamycin 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.
TargetKindPharmacological actionActionsOrganismUniProt ID
30S ribosomal protein S12Proteinyes
inhibitor
Escherichia coli (strain K12)P0A7S3 details
16S rRNANucleotideyes
inhibitor
Enteric bacteria and other eubacterianot applicabledetails
Related Articles
AbsorptionKanamycin is rapidly absorbed after intramuscular injection and peak serum levels are generally reached within approximately one hour. Poor oral and topical absorption except with severe skin damage.
Volume of distributionNot Available
Protein bindingNot Available
MetabolismNot Available
Route of eliminationNot Available
Half life2.5 hours
ClearanceNot Available
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. Oral LD50 is 17500 mg/kg in mice, over 4 g/kg in rats, and over 3 g/kg in rabbits.
Affected organisms
  • Enteric bacteria and other eubacteria
Pathways
PathwayCategorySMPDB ID
Kanamycin Action PathwayDrug actionSMP00255
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
Interactions
Drug Interactions
DrugInteractionDrug group
AceclofenacAceclofenac may decrease the excretion rate of Kanamycin which could result in a higher serum level.Approved
AcetovanilloneAcetovanillone may decrease the excretion rate of Kanamycin which could result in a higher serum level.Investigational
AcetyldigitoxinThe serum concentration of Acetyldigitoxin can be decreased when it is combined with Kanamycin.Approved
Acetylsalicylic acidAcetylsalicylic acid may decrease the excretion rate of Kanamycin which could result in a higher serum level.Approved, Vet Approved
AdapaleneAdapalene may decrease the excretion rate of Kanamycin which could result in a higher serum level.Approved
Alendronic acidKanamycin may increase the hypocalcemic activities of Alendronic acid.Approved
AmdinocillinThe serum concentration of Kanamycin can be decreased when it is combined with Amdinocillin.Withdrawn
AmoxicillinThe serum concentration of Kanamycin can be decreased when it is combined with Amoxicillin.Approved, Vet Approved
Amphotericin BAmphotericin B may increase the nephrotoxic activities of Kanamycin.Approved, Investigational
AmpicillinThe serum concentration of Kanamycin can be decreased when it is combined with Ampicillin.Approved, Vet Approved
AnisodamineAnisodamine may decrease the excretion rate of Kanamycin which could result in a higher serum level.Investigational
AntipyrineAntipyrine may decrease the excretion rate of Kanamycin which could result in a higher serum level.Approved
AnvirzelThe serum concentration of Anvirzel can be decreased when it is combined with Kanamycin.Investigational
ApremilastApremilast may decrease the excretion rate of Kanamycin which could result in a higher serum level.Approved, Investigational
Atracurium besylateKanamycin may increase the respiratory depressant activities of Atracurium besylate.Approved
AzapropazoneAzapropazone may decrease the excretion rate of Kanamycin which could result in a higher serum level.Withdrawn
AzelastineAzelastine may decrease the excretion rate of Kanamycin which could result in a higher serum level.Approved
AzidocillinThe serum concentration of Kanamycin can be decreased when it is combined with Azidocillin.Approved
AzlocillinThe serum concentration of Kanamycin can be decreased when it is combined with Azlocillin.Approved
BacampicillinThe serum concentration of Kanamycin can be decreased when it is combined with Bacampicillin.Approved
BacitracinKanamycin may increase the nephrotoxic activities of Bacitracin.Approved, Vet Approved
BalsalazideBalsalazide may decrease the excretion rate of Kanamycin which could result in a higher serum level.Approved, Investigational
BcgThe therapeutic efficacy of Bcg can be decreased when used in combination with Kanamycin.Investigational
BenoxaprofenBenoxaprofen may decrease the excretion rate of Kanamycin which could result in a higher serum level.Withdrawn
Benzathine benzylpenicillinThe serum concentration of Kanamycin can be decreased when it is combined with Benzathine benzylpenicillin.Approved, Vet Approved
BenzylpenicillinThe serum concentration of Kanamycin can be decreased when it is combined with Benzylpenicillin.Approved, Vet Approved
Benzylpenicillin PotassiumThe serum concentration of Kanamycin can be decreased when it is combined with Benzylpenicillin Potassium.Approved
Benzylpenicilloyl PolylysineThe serum concentration of Kanamycin can be decreased when it is combined with Benzylpenicilloyl Polylysine.Approved
Betulinic AcidBetulinic Acid may decrease the excretion rate of Kanamycin which could result in a higher serum level.Investigational
Botulinum Toxin Type AKanamycin may increase the neuromuscular blocking activities of Botulinum Toxin Type A.Approved, Investigational
Botulinum Toxin Type BKanamycin may increase the neuromuscular blocking activities of Botulinum Toxin Type B.Approved
BromfenacBromfenac may decrease the excretion rate of Kanamycin which could result in a higher serum level.Approved
BucillamineBucillamine may decrease the excretion rate of Kanamycin which could result in a higher serum level.Investigational
BumetanideThe risk or severity of adverse effects can be increased when Bumetanide is combined with Kanamycin.Approved
CapreomycinCapreomycin may increase the neuromuscular blocking activities of Kanamycin.Approved
CarbenicillinThe serum concentration of Kanamycin can be decreased when it is combined with Carbenicillin.Approved
CarboplatinKanamycin may increase the ototoxic activities of Carboplatin.Approved
CarindacillinThe serum concentration of Kanamycin can be decreased when it is combined with Carindacillin.Approved
CarprofenCarprofen may decrease the excretion rate of Kanamycin which could result in a higher serum level.Approved, Vet Approved, Withdrawn
CastanospermineCastanospermine may decrease the excretion rate of Kanamycin which could result in a higher serum level.Experimental
CelecoxibCelecoxib may decrease the excretion rate of Kanamycin which could result in a higher serum level.Approved, Investigational
ChloroquineChloroquine may decrease the excretion rate of Kanamycin which could result in a higher serum level.Approved, Vet Approved
Cisatracurium besylateKanamycin may increase the respiratory depressant activities of Cisatracurium besylate.Approved
CisplatinCisplatin may increase the nephrotoxic activities of Kanamycin.Approved
ClodronateKanamycin may increase the hypocalcemic activities of Clodronate.Approved, Investigational, Vet Approved
ClonixinClonixin may decrease the excretion rate of Kanamycin which could result in a higher serum level.Approved
CloxacillinThe serum concentration of Kanamycin can be decreased when it is combined with Cloxacillin.Approved, Vet Approved
ColistimethateKanamycin may increase the nephrotoxic activities of Colistimethate.Approved, Vet Approved
CurcuminCurcumin may decrease the excretion rate of Kanamycin which could result in a higher serum level.Investigational
CyclacillinThe serum concentration of Kanamycin can be decreased when it is combined with Cyclacillin.Approved
CyclosporineKanamycin may increase the nephrotoxic activities of Cyclosporine.Approved, Investigational, Vet Approved
D-LimoneneD-Limonene may decrease the excretion rate of Kanamycin which could result in a higher serum level.Investigational
DecamethoniumKanamycin may increase the respiratory depressant activities of Decamethonium.Approved
DeslanosideThe serum concentration of Deslanoside can be decreased when it is combined with Kanamycin.Approved
DiclofenacDiclofenac may decrease the excretion rate of Kanamycin which could result in a higher serum level.Approved, Vet Approved
DicloxacillinThe serum concentration of Kanamycin can be decreased when it is combined with Dicloxacillin.Approved, Vet Approved
DiflunisalDiflunisal may decrease the excretion rate of Kanamycin which could result in a higher serum level.Approved
DigitoxinThe serum concentration of Digitoxin can be decreased when it is combined with Kanamycin.Approved
DigoxinThe serum concentration of Digoxin can be decreased when it is combined with Kanamycin.Approved
Domoic AcidKanamycin may increase the respiratory depressant activities of Domoic Acid.Experimental
Doxacurium chlorideKanamycin may increase the respiratory depressant activities of Doxacurium chloride.Approved
DroxicamDroxicam may decrease the excretion rate of Kanamycin which could result in a higher serum level.Approved
DuvelisibDuvelisib may decrease the excretion rate of Kanamycin which could result in a higher serum level.Investigational
E6201E6201 may decrease the excretion rate of Kanamycin which could result in a higher serum level.Investigational
EbselenEbselen may decrease the excretion rate of Kanamycin which could result in a higher serum level.Investigational
EpirizoleEpirizole may decrease the excretion rate of Kanamycin which could result in a higher serum level.Approved
Etacrynic acidThe risk or severity of adverse effects can be increased when Etacrynic acid is combined with Kanamycin.Approved
EtanerceptEtanercept may decrease the excretion rate of Kanamycin which could result in a higher serum level.Approved, Investigational
Etidronic acidKanamycin may increase the hypocalcemic activities of Etidronic acid.Approved
EtodolacEtodolac may decrease the excretion rate of Kanamycin which could result in a higher serum level.Approved, Investigational, Vet Approved
EtofenamateEtofenamate may decrease the excretion rate of Kanamycin which could result in a higher serum level.Approved
EtoricoxibEtoricoxib may decrease the excretion rate of Kanamycin which could result in a higher serum level.Approved, Investigational
Evening primrose oilEvening primrose oil may decrease the excretion rate of Kanamycin which could result in a higher serum level.Approved
exisulindexisulind may decrease the excretion rate of Kanamycin which could result in a higher serum level.Investigational
FenbufenFenbufen may decrease the excretion rate of Kanamycin which could result in a higher serum level.Approved
FenoprofenFenoprofen may decrease the excretion rate of Kanamycin which could result in a higher serum level.Approved
FloctafenineFloctafenine may decrease the excretion rate of Kanamycin which could result in a higher serum level.Approved, Withdrawn
FlucloxacillinThe serum concentration of Kanamycin can be decreased when it is combined with Flucloxacillin.Approved
FlunixinFlunixin may decrease the excretion rate of Kanamycin which could result in a higher serum level.Vet Approved
FlurbiprofenFlurbiprofen may decrease the excretion rate of Kanamycin which could result in a higher serum level.Approved, Investigational
FoscarnetFoscarnet may increase the nephrotoxic activities of Kanamycin.Approved
FurosemideThe risk or severity of adverse effects can be increased when Furosemide is combined with Kanamycin.Approved, Vet Approved
Gallamine TriethiodideKanamycin may increase the respiratory depressant activities of Gallamine Triethiodide.Approved
HigenamineHigenamine may decrease the excretion rate of Kanamycin which could result in a higher serum level.Investigational
HMPL-004HMPL-004 may decrease the excretion rate of Kanamycin which could result in a higher serum level.Investigational
IbandronateKanamycin may increase the hypocalcemic activities of Ibandronate.Approved, Investigational
IbuprofenIbuprofen may decrease the excretion rate of Kanamycin which could result in a higher serum level.Approved
IbuproxamIbuproxam may decrease the excretion rate of Kanamycin which could result in a higher serum level.Withdrawn
IcatibantIcatibant may decrease the excretion rate of Kanamycin which could result in a higher serum level.Approved
IndomethacinIndomethacin may decrease the excretion rate of Kanamycin which could result in a higher serum level.Approved, Investigational
IndoprofenIndoprofen may decrease the excretion rate of Kanamycin which could result in a higher serum level.Withdrawn
IsoxicamIsoxicam may decrease the excretion rate of Kanamycin which could result in a higher serum level.Withdrawn
KebuzoneKebuzone may decrease the excretion rate of Kanamycin which could result in a higher serum level.Experimental
KetoprofenKetoprofen may decrease the excretion rate of Kanamycin which could result in a higher serum level.Approved, Vet Approved
KetorolacKetorolac may decrease the excretion rate of Kanamycin which could result in a higher serum level.Approved
LeflunomideLeflunomide may decrease the excretion rate of Kanamycin which could result in a higher serum level.Approved, Investigational
LisofyllineLisofylline may decrease the excretion rate of Kanamycin which could result in a higher serum level.Investigational
LornoxicamLornoxicam may decrease the excretion rate of Kanamycin which could result in a higher serum level.Approved
LoxoprofenLoxoprofen may decrease the excretion rate of Kanamycin which could result in a higher serum level.Approved
LumiracoxibLumiracoxib may decrease the excretion rate of Kanamycin which could result in a higher serum level.Approved, Investigational
Magnesium salicylateMagnesium salicylate may decrease the excretion rate of Kanamycin which could result in a higher serum level.Approved
MannitolMannitol may increase the nephrotoxic activities of Kanamycin.Approved, Investigational
MasoprocolMasoprocol may decrease the excretion rate of Kanamycin which could result in a higher serum level.Approved
MecamylamineKanamycin may increase the neuromuscular blocking activities of Mecamylamine.Approved
Meclofenamic acidMeclofenamic acid may decrease the excretion rate of Kanamycin which could result in a higher serum level.Approved, Vet Approved
Mefenamic acidMefenamic acid may decrease the excretion rate of Kanamycin which could result in a higher serum level.Approved
MeloxicamMeloxicam may decrease the excretion rate of Kanamycin which could result in a higher serum level.Approved, Vet Approved
MesalazineMesalazine may decrease the excretion rate of Kanamycin which could result in a higher serum level.Approved
MetamizoleMetamizole may decrease the excretion rate of Kanamycin which could result in a higher serum level.Withdrawn
MeticillinThe serum concentration of Kanamycin can be decreased when it is combined with Meticillin.Approved
MetocurineKanamycin may increase the respiratory depressant activities of Metocurine.Approved
Metocurine IodideKanamycin may increase the respiratory depressant activities of Metocurine Iodide.Withdrawn
MezlocillinThe serum concentration of Kanamycin can be decreased when it is combined with Mezlocillin.Approved
MivacuriumKanamycin may increase the respiratory depressant activities of Mivacurium.Approved
MizoribineMizoribine may decrease the excretion rate of Kanamycin which could result in a higher serum level.Investigational
Mycophenolate mofetilMycophenolate mofetil may decrease the excretion rate of Kanamycin which could result in a higher serum level.Approved, Investigational
Mycophenolic acidMycophenolic acid may decrease the excretion rate of Kanamycin which could result in a higher serum level.Approved
NabumetoneNabumetone may decrease the excretion rate of Kanamycin which could result in a higher serum level.Approved
NafamostatNafamostat may decrease the excretion rate of Kanamycin which could result in a higher serum level.Investigational
NafcillinThe serum concentration of Kanamycin can be decreased when it is combined with Nafcillin.Approved
NaftifineNaftifine may decrease the excretion rate of Kanamycin which could result in a higher serum level.Approved
NaproxenNaproxen may decrease the excretion rate of Kanamycin which could result in a higher serum level.Approved, Vet Approved
NCX 4016NCX 4016 may decrease the excretion rate of Kanamycin which could result in a higher serum level.Investigational
NeosaxitoxinKanamycin may increase the respiratory depressant activities of Neosaxitoxin.Investigational
NepafenacNepafenac may decrease the excretion rate of Kanamycin which could result in a higher serum level.Approved
Niflumic AcidNiflumic Acid may decrease the excretion rate of Kanamycin which could result in a higher serum level.Approved
NimesulideNimesulide may decrease the excretion rate of Kanamycin which could result in a higher serum level.Approved, Withdrawn
NitroaspirinNitroaspirin may decrease the excretion rate of Kanamycin which could result in a higher serum level.Investigational
OlopatadineOlopatadine may decrease the excretion rate of Kanamycin which could result in a higher serum level.Approved
OlsalazineOlsalazine may decrease the excretion rate of Kanamycin which could result in a higher serum level.Approved
OrgoteinOrgotein may decrease the excretion rate of Kanamycin which could result in a higher serum level.Vet Approved
OuabainThe serum concentration of Ouabain can be decreased when it is combined with Kanamycin.Approved
OxacillinThe serum concentration of Kanamycin can be decreased when it is combined with Oxacillin.Approved
OxaprozinOxaprozin may decrease the excretion rate of Kanamycin which could result in a higher serum level.Approved
OxyphenbutazoneOxyphenbutazone may decrease the excretion rate of Kanamycin which could result in a higher serum level.Withdrawn
PamidronateKanamycin may increase the hypocalcemic activities of Pamidronate.Approved
PancuroniumKanamycin may increase the respiratory depressant activities of Pancuronium.Approved
ParecoxibParecoxib may decrease the excretion rate of Kanamycin which could result in a higher serum level.Approved
PhenoxymethylpenicillinThe serum concentration of Kanamycin can be decreased when it is combined with Phenoxymethylpenicillin.Approved, Vet Approved
PhenylbutazonePhenylbutazone may decrease the excretion rate of Kanamycin which could result in a higher serum level.Approved, Vet Approved
Picosulfuric acidThe therapeutic efficacy of Picosulfuric acid can be decreased when used in combination with Kanamycin.Approved
PimecrolimusPimecrolimus may decrease the excretion rate of Kanamycin which could result in a higher serum level.Approved, Investigational
PipecuroniumKanamycin may increase the respiratory depressant activities of Pipecuronium.Approved
PiperacillinThe serum concentration of Kanamycin can be decreased when it is combined with Piperacillin.Approved
PiretanideThe risk or severity of adverse effects can be increased when Piretanide is combined with Kanamycin.Experimental
PirfenidonePirfenidone may decrease the excretion rate of Kanamycin which could result in a higher serum level.Investigational
PiroxicamPiroxicam may decrease the excretion rate of Kanamycin which could result in a higher serum level.Approved, Investigational
PivampicillinThe serum concentration of Kanamycin can be decreased when it is combined with Pivampicillin.Approved
PivmecillinamThe serum concentration of Kanamycin can be decreased when it is combined with Pivmecillinam.Approved
Procaine benzylpenicillinThe serum concentration of Kanamycin can be decreased when it is combined with Procaine benzylpenicillin.Approved, Vet Approved
PropacetamolPropacetamol may decrease the excretion rate of Kanamycin which could result in a higher serum level.Approved
PTC299PTC299 may decrease the excretion rate of Kanamycin which could result in a higher serum level.Investigational
PyrantelKanamycin may increase the respiratory depressant activities of Pyrantel.Approved, Vet Approved
RapacuroniumKanamycin may increase the respiratory depressant activities of Rapacuronium.Withdrawn
ResveratrolResveratrol may decrease the excretion rate of Kanamycin which could result in a higher serum level.Experimental, Investigational
RisedronateKanamycin may increase the hypocalcemic activities of Risedronate.Approved, Investigational
RocuroniumKanamycin may increase the respiratory depressant activities of Rocuronium.Approved
RofecoxibRofecoxib may decrease the excretion rate of Kanamycin which could result in a higher serum level.Investigational, Withdrawn
SalicylamideSalicylamide may decrease the excretion rate of Kanamycin which could result in a higher serum level.Approved
Salicylic acidSalicylic acid may decrease the excretion rate of Kanamycin which could result in a higher serum level.Approved, Vet Approved
SalsalateSalsalate may decrease the excretion rate of Kanamycin which could result in a higher serum level.Approved
SeratrodastSeratrodast may decrease the excretion rate of Kanamycin which could result in a higher serum level.Approved, Investigational
SRT501SRT501 may decrease the excretion rate of Kanamycin which could result in a higher serum level.Investigational
SuccinylcholineKanamycin may increase the respiratory depressant activities of Succinylcholine.Approved
SulbactamThe serum concentration of Kanamycin can be decreased when it is combined with Sulbactam.Approved
SulfasalazineSulfasalazine may decrease the excretion rate of Kanamycin which could result in a higher serum level.Approved
SulindacSulindac may decrease the excretion rate of Kanamycin which could result in a higher serum level.Approved
SultamicillinThe serum concentration of Kanamycin can be decreased when it is combined with Sultamicillin.Investigational
SuprofenSuprofen may decrease the excretion rate of Kanamycin which could result in a higher serum level.Approved, Withdrawn
TazobactamThe serum concentration of Kanamycin can be decreased when it is combined with Tazobactam.Approved
Technetium tc 99m etidronateKanamycin may increase the hypocalcemic activities of Technetium tc 99m etidronate.Approved
Technetium Tc-99m MedronateKanamycin may increase the hypocalcemic activities of Technetium Tc-99m Medronate.Approved
TenofovirThe serum concentration of Kanamycin can be increased when it is combined with Tenofovir.Approved, Investigational
TenoxicamTenoxicam may decrease the excretion rate of Kanamycin which could result in a higher serum level.Approved
TepoxalinTepoxalin may decrease the excretion rate of Kanamycin which could result in a higher serum level.Vet Approved
TeriflunomideTeriflunomide may decrease the excretion rate of Kanamycin which could result in a higher serum level.Approved
Tiaprofenic acidTiaprofenic acid may decrease the excretion rate of Kanamycin which could result in a higher serum level.Approved
TicarcillinThe serum concentration of Kanamycin can be decreased when it is combined with Ticarcillin.Approved, Vet Approved
TiludronateKanamycin may increase the hypocalcemic activities of Tiludronate.Approved, Vet Approved
TinoridineTinoridine may decrease the excretion rate of Kanamycin which could result in a higher serum level.Investigational
Tolfenamic AcidTolfenamic Acid may decrease the excretion rate of Kanamycin which could result in a higher serum level.Approved
TolmetinTolmetin may decrease the excretion rate of Kanamycin which could result in a higher serum level.Approved
TorasemideThe risk or severity of adverse effects can be increased when Torasemide is combined with Kanamycin.Approved
TranilastTranilast may decrease the excretion rate of Kanamycin which could result in a higher serum level.Approved, Investigational
Trisalicylate-cholineTrisalicylate-choline may decrease the excretion rate of Kanamycin which could result in a higher serum level.Approved
TubocurarineKanamycin may increase the respiratory depressant activities of Tubocurarine.Approved
ValdecoxibValdecoxib may decrease the excretion rate of Kanamycin which could result in a higher serum level.Investigational, Withdrawn
VancomycinVancomycin may increase the nephrotoxic activities of Kanamycin.Approved
VecuroniumKanamycin may increase the respiratory depressant activities of Vecuronium.Approved
ZaltoprofenZaltoprofen may decrease the excretion rate of Kanamycin which could result in a higher serum level.Approved
ZileutonZileuton may decrease the excretion rate of Kanamycin which could result in a higher serum level.Approved, Investigational, Withdrawn
Zoledronic acidKanamycin may increase the hypocalcemic activities of Zoledronic acid.Approved
ZomepiracZomepirac may decrease the excretion rate of Kanamycin which could result in a higher serum level.Withdrawn
Food InteractionsNot Available
References
Synthesis Reference

Hamao Umezawa, Shinichi Kondo, “Method for production of kanamycin C and its derivatives.” U.S. Patent US4120955, issued December, 1975.

US4120955
General ReferencesNot Available
External Links
ATC CodesJ01GB04A07AA08S01AA24
AHFS CodesNot Available
PDB Entries
FDA labelNot Available
MSDSDownload (71.9 KB)
ADMET
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption-0.9351
Blood Brain Barrier-0.9815
Caco-2 permeable-0.7545
P-glycoprotein substrateSubstrate0.5281
P-glycoprotein inhibitor INon-inhibitor0.7592
P-glycoprotein inhibitor IINon-inhibitor0.904
Renal organic cation transporterNon-inhibitor0.8353
CYP450 2C9 substrateNon-substrate0.8325
CYP450 2D6 substrateNon-substrate0.8323
CYP450 3A4 substrateNon-substrate0.6719
CYP450 1A2 substrateNon-inhibitor0.9143
CYP450 2C9 inhibitorNon-inhibitor0.9259
CYP450 2D6 inhibitorNon-inhibitor0.9317
CYP450 2C19 inhibitorNon-inhibitor0.915
CYP450 3A4 inhibitorNon-inhibitor0.97
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9261
Ames testNon AMES toxic0.7406
CarcinogenicityNon-carcinogens0.9488
BiodegradationNot ready biodegradable0.849
Rat acute toxicity1.5431 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9772
hERG inhibition (predictor II)Non-inhibitor0.8151
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397 )
Pharmacoeconomics
ManufacturersNot Available
Packagers
Dosage formsNot Available
Prices
Unit descriptionCostUnit
Kanamycin sulfate powder25.2USD g
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
PatentsNot Available
Properties
StateSolid
Experimental Properties
PropertyValueSource
logP-6.3Not Available
Predicted Properties
PropertyValueSource
Water Solubility92.3 mg/mLALOGPS
logP-3.1ALOGPS
logP-7.1ChemAxon
logS-0.72ALOGPS
pKa (Strongest Acidic)12.11ChemAxon
pKa (Strongest Basic)9.75ChemAxon
Physiological Charge4ChemAxon
Hydrogen Acceptor Count15ChemAxon
Hydrogen Donor Count11ChemAxon
Polar Surface Area282.61 Å2ChemAxon
Rotatable Bond Count6ChemAxon
Refractivity106.13 m3·mol-1ChemAxon
Polarizability47.57 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
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
  • Glucosamine
  • Amino sugar
  • O-glycosyl compound
  • Glycosyl compound
  • Cyclohexylamine
  • Cyclohexanol
  • Oxane
  • Monosaccharide
  • Cyclic alcohol
  • Secondary alcohol
  • Polyol
  • 1,2-diol
  • 1,2-aminoalcohol
  • Oxacycle
  • Organoheterocyclic compound
  • Acetal
  • Hydrocarbon derivative
  • Primary amine
  • Primary alcohol
  • Organonitrogen compound
  • Primary aliphatic amine
  • Amine
  • Alcohol
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External Descriptors

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. Stavropoulos TA, Strathdee CA: Synergy between tetA and rpsL provides high-stringency positive and negative selection in bacterial artificial chromosome vectors. Genomics. 2001 Feb 15;72(1):99-104. [PubMed:11247671 ]
  4. Gondo Y, Shioyama Y, Nakao K, Katsuki M: A novel positive detection system of in vivo mutations in rpsL (strA) transgenic mice. Mutat Res. 1996 May 17;360(1):1-14. [PubMed:8657204 ]
  5. Amanuma K, Takeda H, Amanuma H, Aoki Y: Transgenic zebrafish for detecting mutations caused by compounds in aquatic environments. Nat Biotechnol. 2000 Jan;18(1):62-5. [PubMed:10625393 ]
2. 16S rRNA
Kind
Nucleotide
Organism
Enteric bacteria and other eubacteria
Pharmacological action
yes
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. Roy U, Nair D: Biodiversity of organotin resistant Pseudomonas from west coast of India. Ecotoxicology. 2007 Mar;16(2):253-61. Epub 2006 Nov 28. [PubMed:17131180 ]
  4. Pikuta EV, Hoover RB, Bej AK, Marsic D, Whitman WB, Krader PE, Tang J: Trichococcus patagoniensis sp. nov., a facultative anaerobe that grows at -5 degrees C, isolated from penguin guano in Chilean Patagonia. Int J Syst Evol Microbiol. 2006 Sep;56(Pt 9):2055-62. [PubMed:16957099 ]
  5. Chung JH, Park YS, Kim J, Shin GW, Nam MH, Oh MK, Kim CW, Jung GY, Hyun Park J: Parallel analysis of antimicrobial activities in microbial community by SSCP based on CE. Electrophoresis. 2007 Jul;28(14):2416-23. [PubMed:17577886 ]

Enzymes

Kind
Protein
Organism
Mycobacterium tuberculosis
Pharmacological action
unknown
General Function:
Involved in N-acetyltransferase activity
Specific Function:
Catalyzes the coenzyme A-dependent acetylation of the 2' hydroxyl or amino group of a broad spectrum of aminoglycosides. It confers resistance to aminoglycosides
Gene Name:
aac
Uniprot ID:
P0A5N0
Molecular Weight:
20038.0 Da
References
  1. Vetting MW, Hegde SS, Javid-Majd F, Blanchard JS, Roderick SL: Aminoglycoside 2'-N-acetyltransferase from Mycobacterium tuberculosis in complex with coenzyme A and aminoglycoside substrates. Nat Struct Biol. 2002 Sep;9(9):653-8. [PubMed:12161746 ]
Kind
Protein
Organism
Staphylococcus aureus
Pharmacological action
unknown
General Function:
Nucleotidyltransferase activity
Specific Function:
Inactivates the antibiotic kanamycin by catalyzing the transfer of a nucleotidyl group from nucleoside triphosphates such as ATP to the 4'-hydroxyl group of the aminoglycoside.
Gene Name:
knt
Uniprot ID:
P05057
Molecular Weight:
28797.38 Da
References
  1. Gates CA, Northrop DB: Substrate specificities and structure-activity relationships for the nucleotidylation of antibiotics catalyzed by aminoglycoside nucleotidyltransferase 2''-I. Biochemistry. 1988 May 17;27(10):3820-5. [PubMed:2841975 ]
Kind
Protein
Organism
Escherichia coli
Pharmacological action
unknown
General Function:
Kanamycin kinase activity
Specific Function:
Resistance to kanamycin and structurally-related aminoglycosides, including amikacin.
Gene Name:
aphA1
Uniprot ID:
P00551
Molecular Weight:
30960.85 Da
References
  1. Wieninger SA, Serpersu EH, Ullmann GM: ATP binding enables broad antibiotic selectivity of aminoglycoside phosphotransferase(3')-IIIa: an elastic network analysis. J Mol Biol. 2011 Jun 10;409(3):450-65. doi: 10.1016/j.jmb.2011.03.061. Epub 2011 Apr 6. [PubMed:21477597 ]
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Drug created on June 13, 2005 07:24 / Updated on August 17, 2016 12:23