Identification

Name
Arbekacin
Accession Number
DB06696
Type
Small Molecule
Groups
Approved, Investigational
Description

An semisynthetic aminoglycoside antibiotic. Often used for treatment of multi-resistant bacterial infection such as methicillin-resistant Staphylococcus aureus (MRSA). Amikacin is also nephrotoxic and ototoxic.

Structure
Thumb
Synonyms
  • ABK
  • Arbekacina
  • Arbekacine
  • Arbekacinum
  • Habekacin
  • Haberacin
External IDs
1665-RB / AHB-DBK / HABA-Dibekacin / HABA-DKB / HBK / ME-1100 / ME1100
Product Ingredients
IngredientUNIICASInChI Key
Arbekacin SulfateG7395HZ992104931-87-5UTUVRPOLEMRKQC-XDJMXTNXSA-N
Categories
UNII
G7V6SLI20L
CAS number
51025-85-5
Weight
Average: 552.619
Monoisotopic: 552.311891658
Chemical Formula
C22H44N6O10
InChI Key
MKKYBZZTJQGVCD-XTCKQBCOSA-N
InChI
InChI=1S/C22H44N6O10/c23-4-3-12(30)20(34)28-11-5-10(26)18(37-21-9(25)2-1-8(6-24)35-21)17(33)19(11)38-22-16(32)14(27)15(31)13(7-29)36-22/h8-19,21-22,29-33H,1-7,23-27H2,(H,28,34)/t8-,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,6S)-3-amino-6-(aminomethyl)oxan-2-yl]oxy}-3-hydroxycyclohexyl]-2-hydroxybutanamide
SMILES

Pharmacology

Indication

Arbekacin is used for the short term treatment of multi-resistant bacterial infections, such as methicillin-resistant Staphylococcus aureus (MRSA).

Structured Indications
Not Available
Pharmacodynamics

Aminoglycosides, such as Arbekacin, work by binding to the bacterial 30S ribosomal subunit, causing misreading of t-RNA which consequently, leaves the bacterium unable to synthesize proteins vital to its growth. Energy is needed for aminoglycoside uptake into the bacterial cell. Anaerobes have less energy available for this uptake, so aminoglycosides are less active against anaerobes. Aminoglycosides are useful primarily in infections involving aerobic, gram-negative bacteria, such as Pseudomonas, Acinetobacter, and Enterobacter.

Mechanism of action

Aminoglycosides, such as Arbekacin, inhibit protein synthesis in susceptible bacteria by irreversibly binding to bacterial 30S and 16S ribosomal subunits. Specifically Arbekacin 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 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)
Absorption

Aminoglycosides are not well absorbed from the gastrointestinal tract. Their absorption is markedly improved by parenteral administration.

Volume of distribution
Not Available
Protein binding

3-12%

Metabolism
Not Available
Route of elimination
Not Available
Half life

3 hours

Clearance
Not Available
Toxicity

Ototoxicity and nephrotoxicity are the most serious adverse effects of aminoglycoside therapy and are more likely to occur in patients with a history of renal impairment or who are receiving other ototoxic and/or nephrotoxic drugs. Normal duration of IM or IV aminoglycoside therapy is 7-10 days. Although a longer duration may be necessary in some cases, toxicity is more likely to occur when aminoglycoside treatment is continued for longer than 10 days.

Affected organisms
  • Enteric bacteria and other eubacteria
  • Escherichia coli
  • Staphylococcus aureus
  • Acinetobacter
Pathways
PathwayCategory
Arbekacin Action PathwayDrug action
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
DrugInteractionDrug group
AceclofenacAceclofenac may decrease the excretion rate of Arbekacin which could result in a higher serum level.Approved, Investigational
AcemetacinAcemetacin may decrease the excretion rate of Arbekacin which could result in a higher serum level.Approved, Experimental, Investigational
AcetyldigitoxinThe serum concentration of Acetyldigitoxin can be decreased when it is combined with Arbekacin.Approved
AcetyldigoxinThe serum concentration of Acetyldigoxin can be decreased when it is combined with Arbekacin.Experimental
Acetylsalicylic acidAcetylsalicylic acid may decrease the excretion rate of Arbekacin which could result in a higher serum level.Approved, Vet Approved
AdapaleneAdapalene may decrease the excretion rate of Arbekacin which could result in a higher serum level.Approved
AlclofenacAlclofenac may decrease the excretion rate of Arbekacin which could result in a higher serum level.Approved, Withdrawn
AlcuroniumArbekacin may increase the respiratory depressant activities of Alcuronium.Experimental
Alendronic acidArbekacin may increase the hypocalcemic activities of Alendronic acid.Approved
AlminoprofenAlminoprofen may decrease the excretion rate of Arbekacin which could result in a higher serum level.Experimental
AmdinocillinThe serum concentration of Arbekacin can be decreased when it is combined with Amdinocillin.Investigational, Withdrawn
AmoxicillinThe serum concentration of Arbekacin can be decreased when it is combined with Amoxicillin.Approved, Vet Approved
Amphotericin BAmphotericin B may increase the nephrotoxic activities of Arbekacin.Approved, Investigational
AmpicillinThe serum concentration of Arbekacin can be decreased when it is combined with Ampicillin.Approved, Vet Approved
AndrographolideAndrographolide may decrease the excretion rate of Arbekacin which could result in a higher serum level.Investigational
AnisodamineAnisodamine may decrease the excretion rate of Arbekacin which could result in a higher serum level.Investigational
AntipyrineAntipyrine may decrease the excretion rate of Arbekacin which could result in a higher serum level.Approved
ApocyninApocynin may decrease the excretion rate of Arbekacin which could result in a higher serum level.Investigational
ApremilastApremilast may decrease the excretion rate of Arbekacin which could result in a higher serum level.Approved, Investigational
AspoxicillinThe serum concentration of Arbekacin can be decreased when it is combined with Aspoxicillin.Experimental
AtracuriumArbekacin may increase the respiratory depressant activities of Atracurium.Experimental, Investigational
Atracurium besylateArbekacin may increase the respiratory depressant activities of Atracurium besylate.Approved
AzapropazoneAzapropazone may decrease the excretion rate of Arbekacin which could result in a higher serum level.Withdrawn
AzelastineAzelastine may decrease the excretion rate of Arbekacin which could result in a higher serum level.Approved
AzidocillinThe serum concentration of Arbekacin can be decreased when it is combined with Azidocillin.Approved
AzlocillinThe serum concentration of Arbekacin can be decreased when it is combined with Azlocillin.Approved
BacampicillinThe serum concentration of Arbekacin can be decreased when it is combined with Bacampicillin.Approved, Investigational
BalsalazideBalsalazide may decrease the excretion rate of Arbekacin which could result in a higher serum level.Approved, Investigational
BendazacBendazac may decrease the excretion rate of Arbekacin which could result in a higher serum level.Experimental
BenorilateBenorilate may decrease the excretion rate of Arbekacin which could result in a higher serum level.Experimental
BenoxaprofenBenoxaprofen may decrease the excretion rate of Arbekacin which could result in a higher serum level.Withdrawn
Benzathine benzylpenicillinThe serum concentration of Arbekacin can be decreased when it is combined with Benzathine benzylpenicillin.Approved, Vet Approved
BenzydamineBenzydamine may decrease the excretion rate of Arbekacin which could result in a higher serum level.Approved
BenzylpenicillinThe serum concentration of Arbekacin can be decreased when it is combined with Benzylpenicillin.Approved, Vet Approved
Benzylpenicilloyl PolylysineThe serum concentration of Arbekacin can be decreased when it is combined with Benzylpenicilloyl Polylysine.Approved
BevoniumBevonium may decrease the excretion rate of Arbekacin which could result in a higher serum level.Experimental
Botulinum Toxin Type AArbekacin may increase the neuromuscular blocking activities of Botulinum Toxin Type A.Approved, Investigational
Botulinum Toxin Type BArbekacin may increase the neuromuscular blocking activities of Botulinum Toxin Type B.Approved
BromfenacBromfenac may decrease the excretion rate of Arbekacin which could result in a higher serum level.Approved
BucillamineBucillamine may decrease the excretion rate of Arbekacin which could result in a higher serum level.Investigational
BufexamacBufexamac may decrease the excretion rate of Arbekacin which could result in a higher serum level.Experimental
BumadizoneBumadizone may decrease the excretion rate of Arbekacin which could result in a higher serum level.Experimental
BumetanideThe risk or severity of adverse effects can be increased when Bumetanide is combined with Arbekacin.Approved
CapreomycinCapreomycin may increase the neuromuscular blocking activities of Arbekacin.Approved
CarbenicillinThe serum concentration of Arbekacin can be decreased when it is combined with Carbenicillin.Approved, Investigational
Carbenicillin indanylThe serum concentration of Arbekacin can be decreased when it is combined with Carbenicillin indanyl.Approved, Investigational
CarboplatinArbekacin may increase the ototoxic activities of Carboplatin.Approved
CarfecillinThe serum concentration of Arbekacin can be decreased when it is combined with Carfecillin.Experimental
CarprofenCarprofen may decrease the excretion rate of Arbekacin which could result in a higher serum level.Approved, Vet Approved, Withdrawn
CastanospermineCastanospermine may decrease the excretion rate of Arbekacin which could result in a higher serum level.Experimental
CelecoxibCelecoxib may decrease the excretion rate of Arbekacin which could result in a higher serum level.Approved, Investigational
ChloroquineChloroquine may decrease the excretion rate of Arbekacin which could result in a higher serum level.Approved, Vet Approved
Choline magnesium trisalicylateCholine magnesium trisalicylate may decrease the excretion rate of Arbekacin which could result in a higher serum level.Approved
CisatracuriumArbekacin may increase the respiratory depressant activities of Cisatracurium.Approved, Experimental
Cisatracurium besylateArbekacin may increase the respiratory depressant activities of Cisatracurium besylate.Approved
CisplatinCisplatin may increase the nephrotoxic activities of Arbekacin.Approved
Clodronic AcidArbekacin may increase the hypocalcemic activities of Clodronic Acid.Approved, Investigational, Vet Approved
ClonixinClonixin may decrease the excretion rate of Arbekacin which could result in a higher serum level.Approved
CloxacillinThe serum concentration of Arbekacin can be decreased when it is combined with Cloxacillin.Approved, Vet Approved
ColistimethateArbekacin may increase the nephrotoxic activities of Colistimethate.Approved, Vet Approved
CurcuminCurcumin may decrease the excretion rate of Arbekacin which could result in a higher serum level.Investigational
CyclacillinThe serum concentration of Arbekacin can be decreased when it is combined with Cyclacillin.Approved
CyclosporineArbekacin may increase the nephrotoxic activities of Cyclosporine.Approved, Investigational, Vet Approved
CymarinThe serum concentration of Cymarin can be decreased when it is combined with Arbekacin.Experimental
D-LimoneneD-Limonene may decrease the excretion rate of Arbekacin which could result in a higher serum level.Investigational
DecamethoniumArbekacin may increase the respiratory depressant activities of Decamethonium.Approved
DeslanosideThe serum concentration of Deslanoside can be decreased when it is combined with Arbekacin.Approved
DiclofenacDiclofenac may decrease the excretion rate of Arbekacin which could result in a higher serum level.Approved, Vet Approved
DicloxacillinThe serum concentration of Arbekacin can be decreased when it is combined with Dicloxacillin.Approved, Vet Approved
DifenpiramideDifenpiramide may decrease the excretion rate of Arbekacin which could result in a higher serum level.Experimental
DiflunisalDiflunisal may decrease the excretion rate of Arbekacin which could result in a higher serum level.Approved
DigitoxinThe serum concentration of Digitoxin can be decreased when it is combined with Arbekacin.Approved, Investigational
DigoxinThe serum concentration of Digoxin can be decreased when it is combined with Arbekacin.Approved
Digoxin Immune Fab (Ovine)The serum concentration of Digoxin Immune Fab (Ovine) can be decreased when it is combined with Arbekacin.Approved
Domoic AcidArbekacin may increase the respiratory depressant activities of Domoic Acid.Experimental
Doxacurium chlorideArbekacin may increase the respiratory depressant activities of Doxacurium chloride.Approved
DroxicamDroxicam may decrease the excretion rate of Arbekacin which could result in a higher serum level.Approved
DuvelisibDuvelisib may decrease the excretion rate of Arbekacin which could result in a higher serum level.Investigational
E-6201E-6201 may decrease the excretion rate of Arbekacin which could result in a higher serum level.Investigational
EpicillinThe serum concentration of Arbekacin can be decreased when it is combined with Epicillin.Experimental
EpirizoleEpirizole may decrease the excretion rate of Arbekacin 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 Arbekacin.Approved
EtanerceptEtanercept may decrease the excretion rate of Arbekacin which could result in a higher serum level.Approved, Investigational
EthenzamideEthenzamide may decrease the excretion rate of Arbekacin which could result in a higher serum level.Experimental
Etidronic acidArbekacin may increase the hypocalcemic activities of Etidronic acid.Approved
EtodolacEtodolac may decrease the excretion rate of Arbekacin which could result in a higher serum level.Approved, Investigational, Vet Approved
EtofenamateEtofenamate may decrease the excretion rate of Arbekacin which could result in a higher serum level.Approved, Investigational
EtoricoxibEtoricoxib may decrease the excretion rate of Arbekacin which could result in a higher serum level.Approved, Investigational
Evening primrose oilEvening primrose oil may decrease the excretion rate of Arbekacin which could result in a higher serum level.Approved, Investigational
exisulindexisulind may decrease the excretion rate of Arbekacin which could result in a higher serum level.Investigational
FelbinacFelbinac may decrease the excretion rate of Arbekacin which could result in a higher serum level.Experimental
FenbufenFenbufen may decrease the excretion rate of Arbekacin which could result in a higher serum level.Approved
FenoprofenFenoprofen may decrease the excretion rate of Arbekacin which could result in a higher serum level.Approved
FentiazacFentiazac may decrease the excretion rate of Arbekacin which could result in a higher serum level.Experimental
FeprazoneFeprazone may decrease the excretion rate of Arbekacin which could result in a higher serum level.Experimental
Ferulic acidFerulic acid may decrease the excretion rate of Arbekacin which could result in a higher serum level.Experimental
FloctafenineFloctafenine may decrease the excretion rate of Arbekacin which could result in a higher serum level.Approved, Withdrawn
FlucloxacillinThe serum concentration of Arbekacin can be decreased when it is combined with Flucloxacillin.Approved, Investigational
FlunixinFlunixin may decrease the excretion rate of Arbekacin which could result in a higher serum level.Vet Approved
FlunoxaprofenFlunoxaprofen may decrease the excretion rate of Arbekacin which could result in a higher serum level.Experimental
FlurbiprofenFlurbiprofen may decrease the excretion rate of Arbekacin which could result in a higher serum level.Approved, Investigational
FoscarnetFoscarnet may increase the nephrotoxic activities of Arbekacin.Approved
FurosemideThe risk or severity of adverse effects can be increased when Furosemide is combined with Arbekacin.Approved, Vet Approved
GallamineArbekacin may increase the respiratory depressant activities of Gallamine.Experimental
Gallamine TriethiodideArbekacin may increase the respiratory depressant activities of Gallamine Triethiodide.Approved
GitoformateThe serum concentration of Gitoformate can be decreased when it is combined with Arbekacin.Experimental
GuacetisalGuacetisal may decrease the excretion rate of Arbekacin which could result in a higher serum level.Experimental
HigenamineHigenamine may decrease the excretion rate of Arbekacin which could result in a higher serum level.Investigational
IbandronateArbekacin may increase the hypocalcemic activities of Ibandronate.Approved, Investigational
IbuprofenIbuprofen may decrease the excretion rate of Arbekacin which could result in a higher serum level.Approved
IbuproxamIbuproxam may decrease the excretion rate of Arbekacin which could result in a higher serum level.Withdrawn
IcatibantIcatibant may decrease the excretion rate of Arbekacin which could result in a higher serum level.Approved
Imidazole salicylateImidazole salicylate may decrease the excretion rate of Arbekacin which could result in a higher serum level.Experimental
IndobufenIndobufen may decrease the excretion rate of Arbekacin which could result in a higher serum level.Investigational
IndomethacinIndomethacin may decrease the excretion rate of Arbekacin which could result in a higher serum level.Approved, Investigational
IndoprofenIndoprofen may decrease the excretion rate of Arbekacin which could result in a higher serum level.Withdrawn
IsoxicamIsoxicam may decrease the excretion rate of Arbekacin which could result in a higher serum level.Withdrawn
KebuzoneKebuzone may decrease the excretion rate of Arbekacin which could result in a higher serum level.Experimental
KetoprofenKetoprofen may decrease the excretion rate of Arbekacin which could result in a higher serum level.Approved, Vet Approved
KetorolacKetorolac may decrease the excretion rate of Arbekacin which could result in a higher serum level.Approved
Lanatoside CThe serum concentration of Lanatoside C can be decreased when it is combined with Arbekacin.Experimental
LeflunomideLeflunomide may decrease the excretion rate of Arbekacin which could result in a higher serum level.Approved, Investigational
LisofyllineLisofylline may decrease the excretion rate of Arbekacin which could result in a higher serum level.Investigational
LonazolacLonazolac may decrease the excretion rate of Arbekacin which could result in a higher serum level.Experimental
LornoxicamLornoxicam may decrease the excretion rate of Arbekacin which could result in a higher serum level.Approved, Investigational
LoxoprofenLoxoprofen may decrease the excretion rate of Arbekacin which could result in a higher serum level.Approved, Investigational
LumiracoxibLumiracoxib may decrease the excretion rate of Arbekacin which could result in a higher serum level.Approved, Investigational
Magnesium salicylateMagnesium salicylate may decrease the excretion rate of Arbekacin which could result in a higher serum level.Approved
MannitolMannitol may increase the nephrotoxic activities of Arbekacin.Approved, Investigational
MasoprocolMasoprocol may decrease the excretion rate of Arbekacin which could result in a higher serum level.Approved, Investigational
MecamylamineArbekacin may increase the neuromuscular blocking activities of Mecamylamine.Approved
Meclofenamic acidMeclofenamic acid may decrease the excretion rate of Arbekacin which could result in a higher serum level.Approved, Vet Approved
Mefenamic acidMefenamic acid may decrease the excretion rate of Arbekacin which could result in a higher serum level.Approved
MeloxicamMeloxicam may decrease the excretion rate of Arbekacin which could result in a higher serum level.Approved, Vet Approved
MesalazineMesalazine may decrease the excretion rate of Arbekacin which could result in a higher serum level.Approved
MetamizoleMetamizole may decrease the excretion rate of Arbekacin which could result in a higher serum level.Investigational, Withdrawn
MetampicillinThe serum concentration of Arbekacin can be decreased when it is combined with Metampicillin.Experimental
MeticillinThe serum concentration of Arbekacin can be decreased when it is combined with Meticillin.Approved, Investigational
MetildigoxinThe serum concentration of Metildigoxin can be decreased when it is combined with Arbekacin.Experimental
MetocurineArbekacin may increase the respiratory depressant activities of Metocurine.Approved
Metocurine IodideArbekacin may increase the respiratory depressant activities of Metocurine Iodide.Withdrawn
MezlocillinThe serum concentration of Arbekacin can be decreased when it is combined with Mezlocillin.Approved, Investigational
MivacuriumArbekacin may increase the respiratory depressant activities of Mivacurium.Approved
MizoribineMizoribine may decrease the excretion rate of Arbekacin which could result in a higher serum level.Investigational
MofebutazoneMofebutazone may decrease the excretion rate of Arbekacin which could result in a higher serum level.Experimental
Mycophenolate mofetilMycophenolate mofetil may decrease the excretion rate of Arbekacin which could result in a higher serum level.Approved, Investigational
Mycophenolic acidMycophenolic acid may decrease the excretion rate of Arbekacin which could result in a higher serum level.Approved
NabumetoneNabumetone may decrease the excretion rate of Arbekacin which could result in a higher serum level.Approved
NafamostatNafamostat may decrease the excretion rate of Arbekacin which could result in a higher serum level.Approved, Investigational
NafcillinThe serum concentration of Arbekacin can be decreased when it is combined with Nafcillin.Approved
NaftifineNaftifine may decrease the excretion rate of Arbekacin which could result in a higher serum level.Approved
NaproxenNaproxen may decrease the excretion rate of Arbekacin which could result in a higher serum level.Approved, Vet Approved
NeosaxitoxinArbekacin may increase the respiratory depressant activities of Neosaxitoxin.Investigational
NepafenacNepafenac may decrease the excretion rate of Arbekacin which could result in a higher serum level.Approved
NifenazoneNifenazone may decrease the excretion rate of Arbekacin which could result in a higher serum level.Experimental
Niflumic AcidNiflumic Acid may decrease the excretion rate of Arbekacin which could result in a higher serum level.Approved
NimesulideNimesulide may decrease the excretion rate of Arbekacin which could result in a higher serum level.Approved, Investigational, Withdrawn
NitroaspirinNitroaspirin may decrease the excretion rate of Arbekacin which could result in a higher serum level.Investigational
OleandrinThe serum concentration of Oleandrin can be decreased when it is combined with Arbekacin.Experimental, Investigational
OlopatadineOlopatadine may decrease the excretion rate of Arbekacin which could result in a higher serum level.Approved
OlsalazineOlsalazine may decrease the excretion rate of Arbekacin which could result in a higher serum level.Approved
OrgoteinOrgotein may decrease the excretion rate of Arbekacin which could result in a higher serum level.Vet Approved
OuabainThe serum concentration of Ouabain can be decreased when it is combined with Arbekacin.Approved
OxacillinThe serum concentration of Arbekacin can be decreased when it is combined with Oxacillin.Approved
OxaprozinOxaprozin may decrease the excretion rate of Arbekacin which could result in a higher serum level.Approved
OxyphenbutazoneOxyphenbutazone may decrease the excretion rate of Arbekacin which could result in a higher serum level.Approved, Withdrawn
PamidronateArbekacin may increase the hypocalcemic activities of Pamidronate.Approved
PancuroniumArbekacin may increase the respiratory depressant activities of Pancuronium.Approved
ParecoxibParecoxib may decrease the excretion rate of Arbekacin which could result in a higher serum level.Approved
ParthenolideParthenolide may decrease the excretion rate of Arbekacin which could result in a higher serum level.Investigational
PenamecillinThe serum concentration of Arbekacin can be decreased when it is combined with Penamecillin.Experimental
PenimepicyclineThe serum concentration of Arbekacin can be decreased when it is combined with Penimepicycline.Experimental
PeruvosideThe serum concentration of Peruvoside can be decreased when it is combined with Arbekacin.Experimental
PhenoxymethylpenicillinThe serum concentration of Arbekacin can be decreased when it is combined with Phenoxymethylpenicillin.Approved, Vet Approved
PhenylbutazonePhenylbutazone may decrease the excretion rate of Arbekacin which could result in a higher serum level.Approved, Vet Approved
PimecrolimusPimecrolimus may decrease the excretion rate of Arbekacin which could result in a higher serum level.Approved, Investigational
PipecuroniumArbekacin may increase the respiratory depressant activities of Pipecuronium.Approved
PiperacillinThe serum concentration of Arbekacin 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 Arbekacin.Experimental
PirfenidonePirfenidone may decrease the excretion rate of Arbekacin which could result in a higher serum level.Approved, Investigational
PiroxicamPiroxicam may decrease the excretion rate of Arbekacin which could result in a higher serum level.Approved, Investigational
PirprofenPirprofen may decrease the excretion rate of Arbekacin which could result in a higher serum level.Experimental
PivampicillinThe serum concentration of Arbekacin can be decreased when it is combined with Pivampicillin.Approved
PivmecillinamThe serum concentration of Arbekacin can be decreased when it is combined with Pivmecillinam.Approved
PranoprofenPranoprofen may decrease the excretion rate of Arbekacin which could result in a higher serum level.Experimental, Investigational
Procaine benzylpenicillinThe serum concentration of Arbekacin can be decreased when it is combined with Procaine benzylpenicillin.Approved, Vet Approved
ProglumetacinProglumetacin may decrease the excretion rate of Arbekacin which could result in a higher serum level.Experimental
PropacetamolPropacetamol may decrease the excretion rate of Arbekacin which could result in a higher serum level.Approved, Investigational
PropicillinThe serum concentration of Arbekacin can be decreased when it is combined with Propicillin.Experimental
PropyphenazonePropyphenazone may decrease the excretion rate of Arbekacin which could result in a higher serum level.Experimental
ProquazoneProquazone may decrease the excretion rate of Arbekacin which could result in a higher serum level.Experimental
ProscillaridinThe serum concentration of Proscillaridin can be decreased when it is combined with Arbekacin.Experimental
PTC299PTC299 may decrease the excretion rate of Arbekacin which could result in a higher serum level.Investigational
PyrantelArbekacin may increase the respiratory depressant activities of Pyrantel.Approved, Vet Approved
RapacuroniumArbekacin may increase the respiratory depressant activities of Rapacuronium.Withdrawn
ResveratrolResveratrol may decrease the excretion rate of Arbekacin which could result in a higher serum level.Approved, Experimental, Investigational
RisedronateArbekacin may increase the hypocalcemic activities of Risedronate.Approved, Investigational
RocuroniumArbekacin may increase the respiratory depressant activities of Rocuronium.Approved
RofecoxibRofecoxib may decrease the excretion rate of Arbekacin which could result in a higher serum level.Investigational, Withdrawn
SalicylamideSalicylamide may decrease the excretion rate of Arbekacin which could result in a higher serum level.Approved
Salicylic acidSalicylic acid may decrease the excretion rate of Arbekacin which could result in a higher serum level.Approved, Vet Approved
SalsalateSalsalate may decrease the excretion rate of Arbekacin which could result in a higher serum level.Approved
SemapimodSemapimod may decrease the excretion rate of Arbekacin which could result in a higher serum level.Investigational
SeratrodastSeratrodast may decrease the excretion rate of Arbekacin which could result in a higher serum level.Approved
SerrapeptaseSerrapeptase may decrease the excretion rate of Arbekacin which could result in a higher serum level.Investigational
SRT501SRT501 may decrease the excretion rate of Arbekacin which could result in a higher serum level.Investigational
SuccinylcholineArbekacin may increase the respiratory depressant activities of Succinylcholine.Approved
SulbactamThe serum concentration of Arbekacin can be decreased when it is combined with Sulbactam.Approved
SulbenicillinThe serum concentration of Arbekacin can be decreased when it is combined with Sulbenicillin.Experimental
SulfasalazineSulfasalazine may decrease the excretion rate of Arbekacin which could result in a higher serum level.Approved
SulindacSulindac may decrease the excretion rate of Arbekacin which could result in a higher serum level.Approved
SultamicillinThe serum concentration of Arbekacin can be decreased when it is combined with Sultamicillin.Investigational
SuprofenSuprofen may decrease the excretion rate of Arbekacin which could result in a higher serum level.Approved, Withdrawn
SuxibuzoneSuxibuzone may decrease the excretion rate of Arbekacin which could result in a higher serum level.Experimental
TalampicillinThe serum concentration of Arbekacin can be decreased when it is combined with Talampicillin.Experimental
TarenflurbilTarenflurbil may decrease the excretion rate of Arbekacin which could result in a higher serum level.Investigational
TazobactamThe serum concentration of Arbekacin can be decreased when it is combined with Tazobactam.Approved
Technetium Tc-99m etidronateArbekacin may increase the hypocalcemic activities of Technetium Tc-99m etidronate.Approved
Technetium Tc-99m medronateArbekacin may increase the hypocalcemic activities of Technetium Tc-99m medronate.Approved
TenidapTenidap may decrease the excretion rate of Arbekacin which could result in a higher serum level.Experimental
Tenofovir disoproxilThe serum concentration of Arbekacin can be increased when it is combined with Tenofovir disoproxil.Approved, Investigational
TenoxicamTenoxicam may decrease the excretion rate of Arbekacin which could result in a higher serum level.Approved
TepoxalinTepoxalin may decrease the excretion rate of Arbekacin which could result in a higher serum level.Vet Approved
TeriflunomideTeriflunomide may decrease the excretion rate of Arbekacin which could result in a higher serum level.Approved
Tiaprofenic acidTiaprofenic acid may decrease the excretion rate of Arbekacin which could result in a higher serum level.Approved
TicarcillinThe serum concentration of Arbekacin can be decreased when it is combined with Ticarcillin.Approved, Investigational, Vet Approved
Tiludronic acidArbekacin may increase the hypocalcemic activities of Tiludronic acid.Approved, Investigational, Vet Approved
TinoridineTinoridine may decrease the excretion rate of Arbekacin which could result in a higher serum level.Investigational
Tolfenamic AcidTolfenamic Acid may decrease the excretion rate of Arbekacin which could result in a higher serum level.Approved
TolmetinTolmetin may decrease the excretion rate of Arbekacin which could result in a higher serum level.Approved
TorasemideThe risk or severity of adverse effects can be increased when Torasemide is combined with Arbekacin.Approved
TranilastTranilast may decrease the excretion rate of Arbekacin which could result in a higher serum level.Approved, Investigational
TribenosideTribenoside may decrease the excretion rate of Arbekacin which could result in a higher serum level.Experimental
TriptolideTriptolide may decrease the excretion rate of Arbekacin which could result in a higher serum level.Investigational
TubocurarineArbekacin may increase the respiratory depressant activities of Tubocurarine.Approved
ValdecoxibValdecoxib may decrease the excretion rate of Arbekacin which could result in a higher serum level.Investigational, Withdrawn
VancomycinVancomycin may increase the nephrotoxic activities of Arbekacin.Approved
VecuroniumArbekacin may increase the respiratory depressant activities of Vecuronium.Approved
ZaltoprofenZaltoprofen may decrease the excretion rate of Arbekacin which could result in a higher serum level.Approved, Investigational
ZileutonZileuton may decrease the excretion rate of Arbekacin which could result in a higher serum level.Approved, Investigational, Withdrawn
Zoledronic acidArbekacin may increase the hypocalcemic activities of Zoledronic acid.Approved
ZomepiracZomepirac may decrease the excretion rate of Arbekacin which could result in a higher serum level.Withdrawn
Food Interactions
Not Available

References

Synthesis Reference

Shinichi Kondo, Seiji Shibahara, Takayuki Usui, Toshiaki Kudo, Shuichi Gomi, Atsushi Tamura, Yoko Ikeda, Daishiro Ikeda, Tomio Takeuchi, "Dibekacin derivatives and arbekacin derivatives active against resistant bacteria, and the production thereof." U.S. Patent US5618795, issued October, 1989.

US5618795
General References
  1. Inoue M, Nonoyama M, Okamoto R, Ida T: Antimicrobial activity of arbekacin, a new aminoglycoside antibiotic, against methicillin-resistant Staphylococcus aureus. Drugs Exp Clin Res. 1994;20(6):233-9. [PubMed:7758395]
  2. Morikawa K, Nonaka M, Yoshikawa Y, Torii I: Synergistic effect of fosfomycin and arbekacin on a methicillin-resistant Staphylococcus aureus-induced biofilm in a rat model. Int J Antimicrob Agents. 2005 Jan;25(1):44-50. [PubMed:15620825]
  3. Doi Y, Yokoyama K, Yamane K, Wachino J, Shibata N, Yagi T, Shibayama K, Kato H, Arakawa Y: Plasmid-mediated 16S rRNA methylase in Serratia marcescens conferring high-level resistance to aminoglycosides. Antimicrob Agents Chemother. 2004 Feb;48(2):491-6. [PubMed:14742200]
  4. Antimicrobial agents and Chemotherapy [Link]
External Links
Human Metabolome Database
HMDB15642
KEGG Drug
D07462
PubChem Compound
68682
PubChem Substance
99443250
ChemSpider
61936
ChEBI
37922
ChEMBL
CHEMBL426926
PharmGKB
PA165958370
Drugs.com
Drugs.com Drug Page
Wikipedia
Arbekacin
ATC Codes
J01GB12 — Arbekacin

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
1CompletedTreatmentHealthy Volunteers2
2Active Not RecruitingTreatmentMuscular Dystrophy, Duchenne1
Not AvailableAvailableNot AvailableInfection Due to Resistant Organism1

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage forms
Not Available
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)178Not Available
Predicted Properties
PropertyValueSource
Water Solubility41.0 mg/mLALOGPS
logP-2.9ALOGPS
logP-6.9ChemAxon
logS-1.1ALOGPS
pKa (Strongest Acidic)12.49ChemAxon
pKa (Strongest Basic)9.99ChemAxon
Physiological Charge5ChemAxon
Hydrogen Acceptor Count15ChemAxon
Hydrogen Donor Count11ChemAxon
Polar Surface Area297.27 Å2ChemAxon
Rotatable Bond Count10ChemAxon
Refractivity129.08 m3·mol-1ChemAxon
Polarizability56.65 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability0ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption-0.9365
Blood Brain Barrier-0.9659
Caco-2 permeable-0.7588
P-glycoprotein substrateSubstrate0.5786
P-glycoprotein inhibitor INon-inhibitor0.7254
P-glycoprotein inhibitor IINon-inhibitor0.8424
Renal organic cation transporterNon-inhibitor0.8676
CYP450 2C9 substrateNon-substrate0.8204
CYP450 2D6 substrateNon-substrate0.8289
CYP450 3A4 substrateNon-substrate0.559
CYP450 1A2 substrateNon-inhibitor0.933
CYP450 2C9 inhibitorNon-inhibitor0.9392
CYP450 2D6 inhibitorNon-inhibitor0.909
CYP450 2C19 inhibitorNon-inhibitor0.9122
CYP450 3A4 inhibitorNon-inhibitor0.9564
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9002
Ames testNon AMES toxic0.7048
CarcinogenicityNon-carcinogens0.9617
BiodegradationNot ready biodegradable0.6627
Rat acute toxicity1.8593 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9902
hERG inhibition (predictor II)Non-inhibitor0.5444
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

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 / Cyclohexanols / Cyclohexylamines / Oxanes / Monosaccharides / 1,3-aminoalcohols / 1,2-aminoalcohols / Propargyl-type 1,3-dipolar organic compounds / Acetals
show 6 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 20 more
Molecular Framework
Aliphatic heteromonocyclic compounds
External Descriptors
aminoglycoside, kanamycins (CHEBI:37922)

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. Funatsu G, Yaguchi M, Wittmann-Liebold B: Primary stucture of protein S12 from the small Escherichia coli ribosomal subunit. FEBS Lett. 1977 Jan 15;73(1):12-7. [PubMed:320034]
  4. Carter AP, Clemons WM, Brodersen DE, Morgan-Warren RJ, Wimberly BT, Ramakrishnan V: Functional insights from the structure of the 30S ribosomal subunit and its interactions with antibiotics. Nature. 2000 Sep 21;407(6802):340-8. [PubMed:11014183]

Drug created on May 05, 2010 10:31 / Updated on December 01, 2017 17:20