Identification

Name
Kanamycin
Accession Number
DB01172  (APRD00026)
Type
Small Molecule
Groups
Approved, Investigational, Vet Approved
Description

Kanamycin (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 IDs
8063-07-8
Product Ingredients
IngredientUNIICASInChI Key
Kanamycin sulfateJ80EX28SMQ25389-94-0OOYGSFOGFJDDHP-KMCOLRRFSA-N
International/Other Brands
Efficin (Lupin) / Kanamytrex (Alcon) / Kancin (Alembic) / Kancin-L (Atlantic) / Kantrex (Merck) / Winamycin (Winston)
Categories
UNII
EQK9Q303C5
CAS number
59-01-8
Weight
Average: 484.4986
Monoisotopic: 484.238058014
Chemical Formula
C18H36N4O11
InChI Key
SBUJHOSQTJFQJX-NOAMYHISSA-N
InChI
InChI=1S/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-/m1/s1
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

Pharmacology

Indication

For 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
Pharmacodynamics

Kanamycin 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 action

Aminoglycosides 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.

TargetActionsOrganism
A30S ribosomal protein S12
inhibitor
Escherichia coli (strain K12)
A16S rRNA
inhibitor
Enteric bacteria and other eubacteria
Absorption

Kanamycin 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 distribution
Not Available
Protein binding
Not Available
Metabolism
Not Available
Route of elimination
Not Available
Half life

2.5 hours

Clearance
Not Available
Toxicity

Mild 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
PathwayCategory
Kanamycin Action PathwayDrug action
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
DrugInteractionDrug group
AceclofenacAceclofenac may decrease the excretion rate of Kanamycin which could result in a higher serum level.Approved, Investigational
AcemetacinAcemetacin may decrease the excretion rate of Kanamycin which could result in a higher serum level.Approved, Experimental, Investigational
AcetyldigitoxinThe serum concentration of Acetyldigitoxin can be decreased when it is combined with Kanamycin.Approved
AcetyldigoxinThe serum concentration of Acetyldigoxin can be decreased when it is combined with Kanamycin.Experimental
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
AlclofenacAlclofenac may decrease the excretion rate of Kanamycin which could result in a higher serum level.Approved, Withdrawn
AlcuroniumKanamycin may increase the respiratory depressant activities of Alcuronium.Experimental
Alendronic acidKanamycin may increase the hypocalcemic activities of Alendronic acid.Approved
AlminoprofenAlminoprofen may decrease the excretion rate of Kanamycin which could result in a higher serum level.Experimental
AmdinocillinThe serum concentration of Kanamycin can be decreased when it is combined with Amdinocillin.Investigational, 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
AndrographolideAndrographolide may decrease the excretion rate of Kanamycin which could result in a higher serum level.Investigational
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
ApocyninApocynin may decrease the excretion rate of Kanamycin which could result in a higher serum level.Investigational
ApremilastApremilast may decrease the excretion rate of Kanamycin which could result in a higher serum level.Approved, Investigational
AspoxicillinThe serum concentration of Kanamycin can be decreased when it is combined with Aspoxicillin.Experimental
AtracuriumKanamycin may increase the respiratory depressant activities of Atracurium.Experimental, 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, Investigational
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
BCG vaccineThe therapeutic efficacy of BCG vaccine can be decreased when used in combination with Kanamycin.Investigational
BendazacBendazac may decrease the excretion rate of Kanamycin which could result in a higher serum level.Experimental
BenorilateBenorilate may decrease the excretion rate of Kanamycin which could result in a higher serum level.Experimental
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
BenzydamineBenzydamine may decrease the excretion rate of Kanamycin which could result in a higher serum level.Approved
BenzylpenicillinThe serum concentration of Kanamycin can be decreased when it is combined with Benzylpenicillin.Approved, Vet Approved
Benzylpenicilloyl PolylysineThe serum concentration of Kanamycin can be decreased when it is combined with Benzylpenicilloyl Polylysine.Approved
BevoniumBevonium may decrease the excretion rate of Kanamycin which could result in a higher serum level.Experimental
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
BufexamacBufexamac may decrease the excretion rate of Kanamycin which could result in a higher serum level.Experimental
BumadizoneBumadizone may decrease the excretion rate of Kanamycin which could result in a higher serum level.Experimental
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
Carbaspirin calciumCarbaspirin calcium may decrease the excretion rate of Kanamycin which could result in a higher serum level.Experimental, Investigational
CarbenicillinThe serum concentration of Kanamycin can be decreased when it is combined with Carbenicillin.Approved, Investigational
Carbenicillin indanylThe serum concentration of Kanamycin can be decreased when it is combined with Carbenicillin indanyl.Approved, Investigational
CarboplatinKanamycin may increase the ototoxic activities of Carboplatin.Approved
CarfecillinThe serum concentration of Kanamycin can be decreased when it is combined with Carfecillin.Experimental
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
Choline magnesium trisalicylateCholine magnesium trisalicylate may decrease the excretion rate of Kanamycin which could result in a higher serum level.Approved
CisatracuriumKanamycin may increase the respiratory depressant activities of Cisatracurium.Approved, Experimental
Cisatracurium besylateKanamycin may increase the respiratory depressant activities of Cisatracurium besylate.Approved
CisplatinCisplatin may increase the nephrotoxic activities of Kanamycin.Approved
Clodronic AcidKanamycin may increase the hypocalcemic activities of Clodronic Acid.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
CymarinThe serum concentration of Cymarin can be decreased when it is combined with Kanamycin.Experimental
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
DifenpiramideDifenpiramide may decrease the excretion rate of Kanamycin which could result in a higher serum level.Experimental
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, Investigational
DigoxinThe serum concentration of Digoxin can be decreased when it is combined with Kanamycin.Approved
Digoxin Immune Fab (Ovine)The serum concentration of Digoxin Immune Fab (Ovine) 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
E-6201E-6201 may decrease the excretion rate of Kanamycin which could result in a higher serum level.Investigational
EpicillinThe serum concentration of Kanamycin can be decreased when it is combined with Epicillin.Experimental
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
EthenzamideEthenzamide may decrease the excretion rate of Kanamycin which could result in a higher serum level.Experimental
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, Investigational
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, Investigational
exisulindexisulind may decrease the excretion rate of Kanamycin which could result in a higher serum level.Investigational
FelbinacFelbinac may decrease the excretion rate of Kanamycin which could result in a higher serum level.Experimental
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
FentiazacFentiazac may decrease the excretion rate of Kanamycin which could result in a higher serum level.Experimental
FeprazoneFeprazone may decrease the excretion rate of Kanamycin which could result in a higher serum level.Experimental
Ferulic acidFerulic acid may decrease the excretion rate of Kanamycin which could result in a higher serum level.Experimental
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, Investigational
FlunixinFlunixin may decrease the excretion rate of Kanamycin which could result in a higher serum level.Vet Approved
FlunoxaprofenFlunoxaprofen may decrease the excretion rate of Kanamycin which could result in a higher serum level.Experimental
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
GallamineKanamycin may increase the respiratory depressant activities of Gallamine.Experimental
Gallamine TriethiodideKanamycin may increase the respiratory depressant activities of Gallamine Triethiodide.Approved
GitoformateThe serum concentration of Gitoformate can be decreased when it is combined with Kanamycin.Experimental
GuacetisalGuacetisal may decrease the excretion rate of Kanamycin which could result in a higher serum level.Experimental
HigenamineHigenamine 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
Imidazole salicylateImidazole salicylate may decrease the excretion rate of Kanamycin which could result in a higher serum level.Experimental
IndobufenIndobufen may decrease the excretion rate of Kanamycin which could result in a higher serum level.Investigational
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
Lanatoside CThe serum concentration of Lanatoside C can be decreased when it is combined with Kanamycin.Experimental
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
LonazolacLonazolac may decrease the excretion rate of Kanamycin which could result in a higher serum level.Experimental
LornoxicamLornoxicam may decrease the excretion rate of Kanamycin which could result in a higher serum level.Approved, Investigational
LoxoprofenLoxoprofen may decrease the excretion rate of Kanamycin which could result in a higher serum level.Approved, Investigational
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, Investigational
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.Investigational, Withdrawn
MetampicillinThe serum concentration of Kanamycin can be decreased when it is combined with Metampicillin.Experimental
MeticillinThe serum concentration of Kanamycin can be decreased when it is combined with Meticillin.Approved, Investigational
MetildigoxinThe serum concentration of Metildigoxin can be decreased when it is combined with Kanamycin.Experimental
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, Investigational
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
MofebutazoneMofebutazone may decrease the excretion rate of Kanamycin which could result in a higher serum level.Experimental
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.Approved, 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
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
NifenazoneNifenazone may decrease the excretion rate of Kanamycin which could result in a higher serum level.Experimental
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, Investigational, Withdrawn
NitroaspirinNitroaspirin may decrease the excretion rate of Kanamycin which could result in a higher serum level.Investigational
OleandrinThe serum concentration of Oleandrin can be decreased when it is combined with Kanamycin.Experimental, 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.Approved, 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
ParthenolideParthenolide may decrease the excretion rate of Kanamycin which could result in a higher serum level.Investigational
PenamecillinThe serum concentration of Kanamycin can be decreased when it is combined with Penamecillin.Experimental
PenimepicyclineThe serum concentration of Kanamycin can be decreased when it is combined with Penimepicycline.Experimental
PeruvosideThe serum concentration of Peruvoside can be decreased when it is combined with Kanamycin.Experimental
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.Approved, Investigational
PiroxicamPiroxicam may decrease the excretion rate of Kanamycin which could result in a higher serum level.Approved, Investigational
PirprofenPirprofen may decrease the excretion rate of Kanamycin which could result in a higher serum level.Experimental
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
PranoprofenPranoprofen may decrease the excretion rate of Kanamycin which could result in a higher serum level.Experimental, Investigational
Procaine benzylpenicillinThe serum concentration of Kanamycin can be decreased when it is combined with Procaine benzylpenicillin.Approved, Vet Approved
ProglumetacinProglumetacin may decrease the excretion rate of Kanamycin which could result in a higher serum level.Experimental
PropacetamolPropacetamol may decrease the excretion rate of Kanamycin which could result in a higher serum level.Approved, Investigational
PropicillinThe serum concentration of Kanamycin can be decreased when it is combined with Propicillin.Experimental
PropyphenazonePropyphenazone may decrease the excretion rate of Kanamycin which could result in a higher serum level.Experimental
ProquazoneProquazone may decrease the excretion rate of Kanamycin which could result in a higher serum level.Experimental
ProscillaridinThe serum concentration of Proscillaridin can be decreased when it is combined with Kanamycin.Experimental
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.Approved, 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
SemapimodSemapimod may decrease the excretion rate of Kanamycin which could result in a higher serum level.Investigational
SeratrodastSeratrodast may decrease the excretion rate of Kanamycin which could result in a higher serum level.Approved
SerrapeptaseSerrapeptase may decrease the excretion rate of Kanamycin which could result in a higher serum level.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
SulbenicillinThe serum concentration of Kanamycin can be decreased when it is combined with Sulbenicillin.Experimental
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
SuxibuzoneSuxibuzone may decrease the excretion rate of Kanamycin which could result in a higher serum level.Experimental
TalampicillinThe serum concentration of Kanamycin can be decreased when it is combined with Talampicillin.Experimental
TarenflurbilTarenflurbil may decrease the excretion rate of Kanamycin which could result in a higher serum level.Investigational
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
TenidapTenidap may decrease the excretion rate of Kanamycin which could result in a higher serum level.Experimental
Tenofovir disoproxilThe serum concentration of Kanamycin can be increased when it is combined with Tenofovir disoproxil.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, Investigational, Vet Approved
Tiludronic acidKanamycin may increase the hypocalcemic activities of Tiludronic acid.Approved, Investigational, 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
TribenosideTribenoside may decrease the excretion rate of Kanamycin which could result in a higher serum level.Experimental
TriptolideTriptolide may decrease the excretion rate of Kanamycin which could result in a higher serum level.Investigational
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, Investigational
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 Interactions
Not 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 References
Not Available
External Links
Human Metabolome Database
HMDB15303
KEGG Compound
C01822
PubChem Compound
6032
PubChem Substance
46508178
ChemSpider
5810
ChEBI
17630
ChEMBL
CHEMBL1384
Therapeutic Targets Database
DNC000201
PharmGKB
PA450137
HET
KAN
RxList
RxList Drug Page
Drugs.com
Drugs.com Drug Page
Wikipedia
Kanamycin
ATC Codes
A07AA08 — KanamycinS01AA24 — KanamycinJ01GB04 — Kanamycin
PDB Entries
1kny / 1l8t / 1m4i / 1nd4 / 2esi / 3kp5 / 3q5r / 3sg9 / 3u6t / 4dfb
show 13 more
MSDS
Download (71.9 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
0RecruitingTreatmentOsteomyelitis1
1CompletedOtherTuberculosis1
1CompletedTreatmentHealthy Volunteers1
2, 3RecruitingTreatmentExtensively-drug Resistant Tuberculosis / Tuberculosis / Tuberculosis, Multidrug Resistant1
3CompletedPreventionNeoplasms, Colorectal1
3RecruitingTreatmentMDR-TB1
4RecruitingTreatmentHuman Immunodeficiency Virus (HIV) Infections1

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Dosage forms
Not Available
Prices
Unit descriptionCostUnit
Kanamycin sulfate powder25.2USD g
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents
Not Available

Properties

State
Solid
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 FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
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)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available
MS/MS Spectrum - DI-ESI-Ion Trap , PositiveLC-MS/MSNot Available
MS/MS Spectrum - DI-ESI-Hybrid FT , PositiveLC-MS/MSNot Available

Taxonomy

Description
This compound belongs to the class of organic compounds known as 4,6-disubstituted 2-deoxystreptamines. These are 2-deoxystreptamine aminoglycosides that a glycosidically linked to a pyranose of furanose unit at the C4- and C6-positions.
Kingdom
Organic compounds
Super Class
Organic oxygen compounds
Class
Organooxygen compounds
Sub Class
Carbohydrates and carbohydrate conjugates
Direct Parent
4,6-disubstituted 2-deoxystreptamines
Alternative Parents
O-glycosyl compounds / Aminocyclitols and derivatives / Cyclohexylamines / Cyclohexanols / Oxanes / Monosaccharides / 1,2-aminoalcohols / Polyols / Oxacyclic compounds / Acetals
show 4 more
Substituents
4,6-disubstituted 2-deoxystreptamine / Glycosyl compound / O-glycosyl compound / Aminocyclitol or derivatives / Cyclohexanol / Cyclohexylamine / Cyclitol or derivatives / Monosaccharide / Oxane / Cyclic alcohol
show 16 more
Molecular Framework
Aliphatic heteromonocyclic compounds
External Descriptors
kanamycins (CHEBI:17630)

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. Lo...
Gene Name
rpsL
Uniprot ID
P0A7S3
Uniprot Name
30S ribosomal protein S12
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
May catalyze the coenzyme A-dependent acetylation of the 2' hydroxyl or amino group of a broad spectrum of aminoglycosides and confer resistance to aminoglycosides (By similarity). In vitro assays show no significant increase of resistance to aminoglycosides, possibly due to low expression in a heterologous system (PubMed:9159528).
Specific Function
Aminoglycoside 2'-n-acetyltransferase activity
Gene Name
aac
Uniprot ID
P9WQG9
Uniprot Name
Aminoglycoside 2'-N-acetyltransferase
Molecular Weight
20037.53 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
Uniprot Name
Kanamycin nucleotidyltransferase
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
Uniprot Name
Aminoglycoside 3'-phosphotransferase
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]

Drug created on June 13, 2005 07:24 / Updated on December 01, 2017 17:14