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Identification
NameNetilmicin
Accession NumberDB00955  (APRD00232)
TypeSmall Molecule
GroupsApproved
DescriptionNetilmicin is a semisynthetic 1-N-ethyl derivative of sisomycin, an aminoglycoside antibiotic with action similar to gentamicin, but less ear and kidney toxicity. [PubChem] Netilmicin inhibits protein synthesis in susceptible organisms by binding to the bacterial 30S ribosomal subunit and interfering with mRNA binding and the acceptor tRNA site. The bactericidal effect of netilmiicin is not fully understood.
Structure
Thumb
Synonyms
1-N-Ethylsisomicin
Netilmicin
Netilmycin
O-3-Deoxy-4-C-methyl-3-(methylamino)-beta-L-arabinopyranosyl-(1-6)-O-(2,6-diamino-2,3,4,6-tetradeoxy-alpha-D-glycero-hex-4-enopyranosyl-(1-4))-2-deoxy-N(1)-ethyl-D-streptamine
External Identifiers Not Available
Approved Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Netromycin Inj 100mg/mlSolution100 mgIntramuscular; IntravenousSchering Plough Canada Inc1981-12-312004-07-21Canada
Netromycin Inj 50mg/mlSolution50 mgIntramuscular; IntravenousSchering Plough Canada Inc1981-12-312004-07-21Canada
Approved Generic Prescription ProductsNot Available
Approved Over the Counter ProductsNot Available
Unapproved/Other Products Not Available
International Brands
NameCompany
NetromycinNot Available
Brand mixturesNot Available
Salts
Name/CASStructureProperties
Netilmicin sulfate
56391-57-2
ThumbNot applicableDBSALT001164
Categories
UNII4O5J85GJJB
CAS number56391-56-1
WeightAverage: 475.5795
Monoisotopic: 475.300598691
Chemical FormulaC21H41N5O7
InChI KeyZBGPYVZLYBDXKO-HILBYHGXSA-N
InChI
InChI=1S/C21H41N5O7/c1-4-26-13-7-12(24)16(32-19-11(23)6-5-10(8-22)31-19)15(28)17(13)33-20-21(2,29)18(25-3)14(27)9-30-20/h5,11-20,25-29H,4,6-9,22-24H2,1-3H3/t11-,12+,13-,14+,15+,16-,17+,18-,19-,20-,21-/m1/s1
IUPAC Name
(2R,3R,4R,5R)-2-{[(1S,2S,3R,4S,6R)-4-amino-3-{[(2S,3R)-3-amino-6-(aminomethyl)-3,4-dihydro-2H-pyran-2-yl]oxy}-6-(ethylamino)-2-hydroxycyclohexyl]oxy}-3-methyl-4-(methylamino)oxane-3,5-diol
SMILES
CCN[C@@H]1C[[email protected]](N)[C@@H](O[[email protected]]2OC(CN)=CC[[email protected]]2N)[[email protected]](O)[[email protected]]1O[[email protected]]1OC[[email protected]](O)[C@@H](NC)[C@@]1(C)O
Pharmacology
IndicationFor the treatment of bacteremia, septicaemia, respiratory tract infections, skin and soft-tissue infection, burns, wounds, and peri-operative infections caused by susceptible strains.
Structured Indications Not Available
PharmacodynamicsNetilmicin is a semisynthetic, water soluble antibiotic of the aminoglycoside group, produced by the fermentation of Micromonospora inyoensis, a species of actinomycete. Aminoglycosides are useful primarily in infections involving aerobic, Gram-negative bacteria, such as Pseudomonas, Acinetobacter, and Enterobacter. It is active at low concentrations against a wide variety of pathogenic bacteria including Escherichia coli, bacteria of the Klebsiella-Enterobacter-Serratia group, Citrobacter sp., Proteus sp. (indole-positive and indole-negative), including Proteus mirabilis, P. morganii, P. rettgrei, P. vulgaris, Pseudomonas aeruginosa and Neisseria gonorrhoea. Netilmicin is also active in vitro against isolates of Hemophilus influenzae, Salmonella sp., Shigella sp. and against penicillinase and non-penicillinase-producing Staphylococcus including methicillin-resistant strains. Some strains of Providencia sp., Acinetobacter sp. and Aeromonas sp. are also sensitive to netilmicin. Many strains of the above organisms which are found to be resistant to other aminoglycosides, such as kanamycin, gentamicin, tobramycin and sisomicin, are susceptible to netilmicin in vitro. Occasionally, strains have been identified which are resistant to amikacin but susceptible to netilmicin. The combination of netilmicin and penicillin G has a synergistic bactericidal effect against most strains of Streptococcus faecalis (enterococcus). The combined effect of netilmicin and carbenicillin or ticarcillin is synergistic for many strains of Pseudomonas aeruginosa. In addition, many isolates of Serratia, which are resistant to multiple antibiotics, are inhibited by synergistic combinations of netilmicin with carbenicillin, azlocillin, mezlocillin, cefamandole, cefotaxime or moxalactam. Aminoglycosides are mostly ineffective against anaerobic bacteria, fungi and viruses.
Mechanism of actionAminoglycosides like netilmicin "irreversibly" bind to specific 30S-subunit proteins and 16S rRNA. Specifically netilmicin 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, leaving the bacterium unable to synthesize proteins vital to its growth.
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
AbsorptionRapidly and completely absorbed after IM administration, peak serum levels were achieved within 30-60 minutes. Aminoglycosides are poorly absorbed orally. Topical absorption is also poor unless severe skin damage is present.
Volume of distributionNot Available
Protein bindingProtein-binding of is low and depends on the test conditions (mainly the concentration of cations in the test medium).
Metabolism

No evidence of metabolic transformation, typically 80% is recoverable in the urine within 24 hours

Route of eliminationNot Available
Half life2.5 hours
ClearanceNot Available
ToxicityNetilmicin has nephrotoxic and ototoxic potential. Nephrotoxicity occurs via drug accumulation in renal proximal tubular cells resulting in cellular damage. Tubular cells may regenerate despite continued exposure and nephrotoxicity is usually mild and reversible. Netilmicin is less nephrotoxic than neomycin, gentamicin, tobramycin, and amikacin, likely due to a reduced number of cationic amino groups in its structure. Otoxicity occurs as a result of irreversible damage to hair cells of the cochlea and/or summit of the ampullar cristae in the vestibular complex caused drug accumulation in the endolymph and perilymph of the inner ear. Otoxicity appears to be correlated to total exposure and may be cumulative with further doses of aminoglycosides or other ototoxic drugs (e.g. cisplatin, furosemide). High frequency hearing loss is followed by low frequency hearing loss, which may be followed by retrograde degeneration of the auditory nerve. Vestibular toxicity may cause vertigo, nausea and vomiting, dizziness and loss of balance.
Affected organisms
  • Enteric bacteria and other eubacteria
Pathways
PathwayCategorySMPDB ID
Netilmicin Action PathwayDrug actionSMP00257
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
Interactions
Drug Interactions
DrugInteractionDrug group
AceclofenacAceclofenac may decrease the excretion rate of Netilmicin which could result in a higher serum level.Approved
AcetovanilloneAcetovanillone may decrease the excretion rate of Netilmicin which could result in a higher serum level.Investigational
AcetyldigitoxinThe serum concentration of Acetyldigitoxin can be decreased when it is combined with Netilmicin.Approved
Acetylsalicylic acidAcetylsalicylic acid may decrease the excretion rate of Netilmicin which could result in a higher serum level.Approved, Vet Approved
AdapaleneAdapalene may decrease the excretion rate of Netilmicin which could result in a higher serum level.Approved
Alendronic acidNetilmicin may increase the hypocalcemic activities of Alendronic acid.Approved
AmdinocillinThe serum concentration of Netilmicin can be decreased when it is combined with Amdinocillin.Withdrawn
AmoxicillinThe serum concentration of Netilmicin can be decreased when it is combined with Amoxicillin.Approved, Vet Approved
Amphotericin BAmphotericin B may increase the nephrotoxic activities of Netilmicin.Approved, Investigational
AmpicillinThe serum concentration of Netilmicin can be decreased when it is combined with Ampicillin.Approved, Vet Approved
AnisodamineAnisodamine may decrease the excretion rate of Netilmicin which could result in a higher serum level.Investigational
AntipyrineAntipyrine may decrease the excretion rate of Netilmicin which could result in a higher serum level.Approved
AnvirzelThe serum concentration of Anvirzel can be decreased when it is combined with Netilmicin.Investigational
ApremilastApremilast may decrease the excretion rate of Netilmicin which could result in a higher serum level.Approved, Investigational
Atracurium besylateNetilmicin may increase the respiratory depressant activities of Atracurium besylate.Approved
AzapropazoneAzapropazone may decrease the excretion rate of Netilmicin which could result in a higher serum level.Withdrawn
AzelastineAzelastine may decrease the excretion rate of Netilmicin which could result in a higher serum level.Approved
AzidocillinThe serum concentration of Netilmicin can be decreased when it is combined with Azidocillin.Approved
AzlocillinThe serum concentration of Netilmicin can be decreased when it is combined with Azlocillin.Approved
BacampicillinThe serum concentration of Netilmicin can be decreased when it is combined with Bacampicillin.Approved
BalsalazideBalsalazide may decrease the excretion rate of Netilmicin which could result in a higher serum level.Approved, Investigational
BcgThe therapeutic efficacy of Bcg can be decreased when used in combination with Netilmicin.Investigational
BenoxaprofenBenoxaprofen may decrease the excretion rate of Netilmicin which could result in a higher serum level.Withdrawn
Benzathine benzylpenicillinThe serum concentration of Netilmicin can be decreased when it is combined with Benzathine benzylpenicillin.Approved, Vet Approved
BenzylpenicillinThe serum concentration of Netilmicin can be decreased when it is combined with Benzylpenicillin.Approved, Vet Approved
Benzylpenicillin PotassiumThe serum concentration of Netilmicin can be decreased when it is combined with Benzylpenicillin Potassium.Approved
Benzylpenicilloyl PolylysineThe serum concentration of Netilmicin can be decreased when it is combined with Benzylpenicilloyl Polylysine.Approved
Betulinic AcidBetulinic Acid may decrease the excretion rate of Netilmicin which could result in a higher serum level.Investigational
Botulinum Toxin Type ANetilmicin may increase the neuromuscular blocking activities of Botulinum Toxin Type A.Approved, Investigational
Botulinum Toxin Type BNetilmicin may increase the neuromuscular blocking activities of Botulinum Toxin Type B.Approved
BromfenacBromfenac may decrease the excretion rate of Netilmicin which could result in a higher serum level.Approved
BucillamineBucillamine may decrease the excretion rate of Netilmicin which could result in a higher serum level.Investigational
BumetanideThe risk or severity of adverse effects can be increased when Bumetanide is combined with Netilmicin.Approved
CapreomycinCapreomycin may increase the neuromuscular blocking activities of Netilmicin.Approved
CarbenicillinThe serum concentration of Netilmicin can be decreased when it is combined with Carbenicillin.Approved
CarboplatinNetilmicin may increase the ototoxic activities of Carboplatin.Approved
CarindacillinThe serum concentration of Netilmicin can be decreased when it is combined with Carindacillin.Approved
CarprofenCarprofen may decrease the excretion rate of Netilmicin which could result in a higher serum level.Approved, Vet Approved, Withdrawn
CastanospermineCastanospermine may decrease the excretion rate of Netilmicin which could result in a higher serum level.Experimental
CelecoxibCelecoxib may decrease the excretion rate of Netilmicin which could result in a higher serum level.Approved, Investigational
ChloroquineChloroquine may decrease the excretion rate of Netilmicin which could result in a higher serum level.Approved, Vet Approved
Cisatracurium besylateNetilmicin may increase the respiratory depressant activities of Cisatracurium besylate.Approved
CisplatinCisplatin may increase the nephrotoxic activities of Netilmicin.Approved
ClodronateNetilmicin may increase the hypocalcemic activities of Clodronate.Approved, Investigational, Vet Approved
ClonixinClonixin may decrease the excretion rate of Netilmicin which could result in a higher serum level.Approved
CloxacillinThe serum concentration of Netilmicin can be decreased when it is combined with Cloxacillin.Approved, Vet Approved
ColistimethateNetilmicin may increase the nephrotoxic activities of Colistimethate.Approved, Vet Approved
CurcuminCurcumin may decrease the excretion rate of Netilmicin which could result in a higher serum level.Investigational
CyclacillinThe serum concentration of Netilmicin can be decreased when it is combined with Cyclacillin.Approved
CyclosporineNetilmicin may increase the nephrotoxic activities of Cyclosporine.Approved, Investigational, Vet Approved
D-LimoneneD-Limonene may decrease the excretion rate of Netilmicin which could result in a higher serum level.Investigational
DecamethoniumNetilmicin may increase the respiratory depressant activities of Decamethonium.Approved
DeslanosideThe serum concentration of Deslanoside can be decreased when it is combined with Netilmicin.Approved
DiclofenacDiclofenac may decrease the excretion rate of Netilmicin which could result in a higher serum level.Approved, Vet Approved
DicloxacillinThe serum concentration of Netilmicin can be decreased when it is combined with Dicloxacillin.Approved, Vet Approved
DiflunisalDiflunisal may decrease the excretion rate of Netilmicin which could result in a higher serum level.Approved
DigitoxinThe serum concentration of Digitoxin can be decreased when it is combined with Netilmicin.Approved
DigoxinThe serum concentration of Digoxin can be decreased when it is combined with Netilmicin.Approved
Domoic AcidNetilmicin may increase the respiratory depressant activities of Domoic Acid.Experimental
Doxacurium chlorideNetilmicin may increase the respiratory depressant activities of Doxacurium chloride.Approved
DroxicamDroxicam may decrease the excretion rate of Netilmicin which could result in a higher serum level.Approved
DuvelisibDuvelisib may decrease the excretion rate of Netilmicin which could result in a higher serum level.Investigational
E6201E6201 may decrease the excretion rate of Netilmicin which could result in a higher serum level.Investigational
EbselenEbselen may decrease the excretion rate of Netilmicin which could result in a higher serum level.Investigational
EpirizoleEpirizole may decrease the excretion rate of Netilmicin 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 Netilmicin.Approved
EtanerceptEtanercept may decrease the excretion rate of Netilmicin which could result in a higher serum level.Approved, Investigational
Etidronic acidNetilmicin may increase the hypocalcemic activities of Etidronic acid.Approved
EtodolacEtodolac may decrease the excretion rate of Netilmicin which could result in a higher serum level.Approved, Investigational, Vet Approved
EtofenamateEtofenamate may decrease the excretion rate of Netilmicin which could result in a higher serum level.Approved
EtoricoxibEtoricoxib may decrease the excretion rate of Netilmicin which could result in a higher serum level.Approved, Investigational
Evening primrose oilEvening primrose oil may decrease the excretion rate of Netilmicin which could result in a higher serum level.Approved
exisulindexisulind may decrease the excretion rate of Netilmicin which could result in a higher serum level.Investigational
FenbufenFenbufen may decrease the excretion rate of Netilmicin which could result in a higher serum level.Approved
FenoprofenFenoprofen may decrease the excretion rate of Netilmicin which could result in a higher serum level.Approved
FloctafenineFloctafenine may decrease the excretion rate of Netilmicin which could result in a higher serum level.Approved, Withdrawn
FlucloxacillinThe serum concentration of Netilmicin can be decreased when it is combined with Flucloxacillin.Approved
FlunixinFlunixin may decrease the excretion rate of Netilmicin which could result in a higher serum level.Vet Approved
FlurbiprofenFlurbiprofen may decrease the excretion rate of Netilmicin which could result in a higher serum level.Approved, Investigational
FoscarnetFoscarnet may increase the nephrotoxic activities of Netilmicin.Approved
FurosemideThe risk or severity of adverse effects can be increased when Furosemide is combined with Netilmicin.Approved, Vet Approved
Gallamine TriethiodideNetilmicin may increase the respiratory depressant activities of Gallamine Triethiodide.Approved
HigenamineHigenamine may decrease the excretion rate of Netilmicin which could result in a higher serum level.Investigational
HMPL-004HMPL-004 may decrease the excretion rate of Netilmicin which could result in a higher serum level.Investigational
IbandronateNetilmicin may increase the hypocalcemic activities of Ibandronate.Approved, Investigational
IbuprofenIbuprofen may decrease the excretion rate of Netilmicin which could result in a higher serum level.Approved
IbuproxamIbuproxam may decrease the excretion rate of Netilmicin which could result in a higher serum level.Withdrawn
IcatibantIcatibant may decrease the excretion rate of Netilmicin which could result in a higher serum level.Approved
IndomethacinIndomethacin may decrease the excretion rate of Netilmicin which could result in a higher serum level.Approved, Investigational
IndoprofenIndoprofen may decrease the excretion rate of Netilmicin which could result in a higher serum level.Withdrawn
IsoxicamIsoxicam may decrease the excretion rate of Netilmicin which could result in a higher serum level.Withdrawn
KebuzoneKebuzone may decrease the excretion rate of Netilmicin which could result in a higher serum level.Experimental
KetoprofenKetoprofen may decrease the excretion rate of Netilmicin which could result in a higher serum level.Approved, Vet Approved
KetorolacKetorolac may decrease the excretion rate of Netilmicin which could result in a higher serum level.Approved
LeflunomideLeflunomide may decrease the excretion rate of Netilmicin which could result in a higher serum level.Approved, Investigational
LisofyllineLisofylline may decrease the excretion rate of Netilmicin which could result in a higher serum level.Investigational
LornoxicamLornoxicam may decrease the excretion rate of Netilmicin which could result in a higher serum level.Approved
LoxoprofenLoxoprofen may decrease the excretion rate of Netilmicin which could result in a higher serum level.Approved
LumiracoxibLumiracoxib may decrease the excretion rate of Netilmicin which could result in a higher serum level.Approved, Investigational
Magnesium salicylateMagnesium salicylate may decrease the excretion rate of Netilmicin which could result in a higher serum level.Approved
MannitolMannitol may increase the nephrotoxic activities of Netilmicin.Approved, Investigational
MasoprocolMasoprocol may decrease the excretion rate of Netilmicin which could result in a higher serum level.Approved
MecamylamineNetilmicin may increase the neuromuscular blocking activities of Mecamylamine.Approved
Meclofenamic acidMeclofenamic acid may decrease the excretion rate of Netilmicin which could result in a higher serum level.Approved, Vet Approved
Mefenamic acidMefenamic acid may decrease the excretion rate of Netilmicin which could result in a higher serum level.Approved
MeloxicamMeloxicam may decrease the excretion rate of Netilmicin which could result in a higher serum level.Approved, Vet Approved
MesalazineMesalazine may decrease the excretion rate of Netilmicin which could result in a higher serum level.Approved
MetamizoleMetamizole may decrease the excretion rate of Netilmicin which could result in a higher serum level.Withdrawn
MeticillinThe serum concentration of Netilmicin can be decreased when it is combined with Meticillin.Approved
MetocurineNetilmicin may increase the respiratory depressant activities of Metocurine.Approved
Metocurine IodideNetilmicin may increase the respiratory depressant activities of Metocurine Iodide.Withdrawn
MezlocillinThe serum concentration of Netilmicin can be decreased when it is combined with Mezlocillin.Approved
MivacuriumNetilmicin may increase the respiratory depressant activities of Mivacurium.Approved
MizoribineMizoribine may decrease the excretion rate of Netilmicin which could result in a higher serum level.Investigational
Mycophenolate mofetilMycophenolate mofetil may decrease the excretion rate of Netilmicin which could result in a higher serum level.Approved, Investigational
Mycophenolic acidMycophenolic acid may decrease the excretion rate of Netilmicin which could result in a higher serum level.Approved
NabumetoneNabumetone may decrease the excretion rate of Netilmicin which could result in a higher serum level.Approved
NafamostatNafamostat may decrease the excretion rate of Netilmicin which could result in a higher serum level.Investigational
NafcillinThe serum concentration of Netilmicin can be decreased when it is combined with Nafcillin.Approved
NaftifineNaftifine may decrease the excretion rate of Netilmicin which could result in a higher serum level.Approved
NaproxenNaproxen may decrease the excretion rate of Netilmicin which could result in a higher serum level.Approved, Vet Approved
NCX 4016NCX 4016 may decrease the excretion rate of Netilmicin which could result in a higher serum level.Investigational
NeosaxitoxinNetilmicin may increase the respiratory depressant activities of Neosaxitoxin.Investigational
NepafenacNepafenac may decrease the excretion rate of Netilmicin which could result in a higher serum level.Approved
Niflumic AcidNiflumic Acid may decrease the excretion rate of Netilmicin which could result in a higher serum level.Approved
NimesulideNimesulide may decrease the excretion rate of Netilmicin which could result in a higher serum level.Approved, Withdrawn
NitroaspirinNitroaspirin may decrease the excretion rate of Netilmicin which could result in a higher serum level.Investigational
OlopatadineOlopatadine may decrease the excretion rate of Netilmicin which could result in a higher serum level.Approved
OlsalazineOlsalazine may decrease the excretion rate of Netilmicin which could result in a higher serum level.Approved
OrgoteinOrgotein may decrease the excretion rate of Netilmicin which could result in a higher serum level.Vet Approved
OuabainThe serum concentration of Ouabain can be decreased when it is combined with Netilmicin.Approved
OxacillinThe serum concentration of Netilmicin can be decreased when it is combined with Oxacillin.Approved
OxaprozinOxaprozin may decrease the excretion rate of Netilmicin which could result in a higher serum level.Approved
OxyphenbutazoneOxyphenbutazone may decrease the excretion rate of Netilmicin which could result in a higher serum level.Withdrawn
PamidronateNetilmicin may increase the hypocalcemic activities of Pamidronate.Approved
PancuroniumNetilmicin may increase the respiratory depressant activities of Pancuronium.Approved
ParecoxibParecoxib may decrease the excretion rate of Netilmicin which could result in a higher serum level.Approved
PhenoxymethylpenicillinThe serum concentration of Netilmicin can be decreased when it is combined with Phenoxymethylpenicillin.Approved, Vet Approved
PhenylbutazonePhenylbutazone may decrease the excretion rate of Netilmicin 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 Netilmicin.Approved
PimecrolimusPimecrolimus may decrease the excretion rate of Netilmicin which could result in a higher serum level.Approved, Investigational
PipecuroniumNetilmicin may increase the respiratory depressant activities of Pipecuronium.Approved
PiperacillinThe serum concentration of Netilmicin 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 Netilmicin.Experimental
PirfenidonePirfenidone may decrease the excretion rate of Netilmicin which could result in a higher serum level.Investigational
PiroxicamPiroxicam may decrease the excretion rate of Netilmicin which could result in a higher serum level.Approved, Investigational
PivampicillinThe serum concentration of Netilmicin can be decreased when it is combined with Pivampicillin.Approved
PivmecillinamThe serum concentration of Netilmicin can be decreased when it is combined with Pivmecillinam.Approved
Procaine benzylpenicillinThe serum concentration of Netilmicin can be decreased when it is combined with Procaine benzylpenicillin.Approved, Vet Approved
PropacetamolPropacetamol may decrease the excretion rate of Netilmicin which could result in a higher serum level.Approved
PTC299PTC299 may decrease the excretion rate of Netilmicin which could result in a higher serum level.Investigational
PyrantelNetilmicin may increase the respiratory depressant activities of Pyrantel.Approved, Vet Approved
RapacuroniumNetilmicin may increase the respiratory depressant activities of Rapacuronium.Withdrawn
ResveratrolResveratrol may decrease the excretion rate of Netilmicin which could result in a higher serum level.Experimental, Investigational
RisedronateNetilmicin may increase the hypocalcemic activities of Risedronate.Approved, Investigational
RocuroniumNetilmicin may increase the respiratory depressant activities of Rocuronium.Approved
RofecoxibRofecoxib may decrease the excretion rate of Netilmicin which could result in a higher serum level.Investigational, Withdrawn
SalicylamideSalicylamide may decrease the excretion rate of Netilmicin which could result in a higher serum level.Approved
Salicylic acidSalicylic acid may decrease the excretion rate of Netilmicin which could result in a higher serum level.Approved, Vet Approved
SalsalateSalsalate may decrease the excretion rate of Netilmicin which could result in a higher serum level.Approved
SeratrodastSeratrodast may decrease the excretion rate of Netilmicin which could result in a higher serum level.Approved, Investigational
SRT501SRT501 may decrease the excretion rate of Netilmicin which could result in a higher serum level.Investigational
SuccinylcholineNetilmicin may increase the respiratory depressant activities of Succinylcholine.Approved
SulbactamThe serum concentration of Netilmicin can be decreased when it is combined with Sulbactam.Approved
SulfasalazineSulfasalazine may decrease the excretion rate of Netilmicin which could result in a higher serum level.Approved
SulindacSulindac may decrease the excretion rate of Netilmicin which could result in a higher serum level.Approved
SultamicillinThe serum concentration of Netilmicin can be decreased when it is combined with Sultamicillin.Investigational
SuprofenSuprofen may decrease the excretion rate of Netilmicin which could result in a higher serum level.Approved, Withdrawn
TazobactamThe serum concentration of Netilmicin can be decreased when it is combined with Tazobactam.Approved
Technetium tc 99m etidronateNetilmicin may increase the hypocalcemic activities of Technetium tc 99m etidronate.Approved
Technetium Tc-99m MedronateNetilmicin may increase the hypocalcemic activities of Technetium Tc-99m Medronate.Approved
TenofovirThe serum concentration of Netilmicin can be increased when it is combined with Tenofovir.Approved, Investigational
TenoxicamTenoxicam may decrease the excretion rate of Netilmicin which could result in a higher serum level.Approved
TepoxalinTepoxalin may decrease the excretion rate of Netilmicin which could result in a higher serum level.Vet Approved
TeriflunomideTeriflunomide may decrease the excretion rate of Netilmicin which could result in a higher serum level.Approved
Tiaprofenic acidTiaprofenic acid may decrease the excretion rate of Netilmicin which could result in a higher serum level.Approved
TicarcillinThe serum concentration of Netilmicin can be decreased when it is combined with Ticarcillin.Approved, Vet Approved
TiludronateNetilmicin may increase the hypocalcemic activities of Tiludronate.Approved, Vet Approved
TinoridineTinoridine may decrease the excretion rate of Netilmicin which could result in a higher serum level.Investigational
Tolfenamic AcidTolfenamic Acid may decrease the excretion rate of Netilmicin which could result in a higher serum level.Approved
TolmetinTolmetin may decrease the excretion rate of Netilmicin which could result in a higher serum level.Approved
TorasemideThe risk or severity of adverse effects can be increased when Torasemide is combined with Netilmicin.Approved
TranilastTranilast may decrease the excretion rate of Netilmicin which could result in a higher serum level.Approved, Investigational
Trisalicylate-cholineTrisalicylate-choline may decrease the excretion rate of Netilmicin which could result in a higher serum level.Approved
TubocurarineNetilmicin may increase the respiratory depressant activities of Tubocurarine.Approved
ValdecoxibValdecoxib may decrease the excretion rate of Netilmicin which could result in a higher serum level.Investigational, Withdrawn
VancomycinVancomycin may increase the nephrotoxic activities of Netilmicin.Approved
VecuroniumNetilmicin may increase the respiratory depressant activities of Vecuronium.Approved
ZaltoprofenZaltoprofen may decrease the excretion rate of Netilmicin which could result in a higher serum level.Approved
ZileutonZileuton may decrease the excretion rate of Netilmicin which could result in a higher serum level.Approved, Investigational, Withdrawn
Zoledronic acidNetilmicin may increase the hypocalcemic activities of Zoledronic acid.Approved
ZomepiracZomepirac may decrease the excretion rate of Netilmicin which could result in a higher serum level.Withdrawn
Food InteractionsNot Available
References
Synthesis Reference

Chou-Hong Tann, Tiruvettipuram K. Thiruvengadam, John S. Chiu, Cesar Colon, “Process for preparing netilmicin.” U.S. Patent US4831123, issued June, 1966.

US4831123
General References
  1. Hemsworth S, Nunn AJ, Selwood K, Osborne C, Jones A, Pizer B: Once-daily netilmicin for neutropenic pyrexia in paediatric oncology. Acta Paediatr. 2005 Mar;94(3):268-74. [PubMed:16028643 ]
  2. Klingenberg C, Smabrekke L, Lier T, Flaegstad T: Validation of a simplified netilmicin dosage regimen in infants. Scand J Infect Dis. 2004;36(6-7):474-9. [PubMed:15307571 ]
  3. Brooks JR, Marlow N, Reeves BC, Millar MR: Use of once-daily netilmicin to treat infants with suspected sepsis in a neonatal intensive care unit. Biol Neonate. 2004;86(3):170-5. Epub 2004 Jun 29. [PubMed:15237240 ]
External Links
ATC CodesS01AA23J01GB07
AHFS CodesNot Available
PDB Entries
FDA labelNot Available
MSDSDownload (57 KB)
ADMET
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption-0.9129
Blood Brain Barrier-0.9912
Caco-2 permeable-0.7057
P-glycoprotein substrateSubstrate0.8191
P-glycoprotein inhibitor IInhibitor0.5133
P-glycoprotein inhibitor IINon-inhibitor0.9479
Renal organic cation transporterNon-inhibitor0.8985
CYP450 2C9 substrateNon-substrate0.8475
CYP450 2D6 substrateNon-substrate0.837
CYP450 3A4 substrateSubstrate0.5494
CYP450 1A2 substrateNon-inhibitor0.8995
CYP450 2C9 inhibitorNon-inhibitor0.9098
CYP450 2D6 inhibitorNon-inhibitor0.9237
CYP450 2C19 inhibitorNon-inhibitor0.9033
CYP450 3A4 inhibitorNon-inhibitor0.9691
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.8932
Ames testNon AMES toxic0.7193
CarcinogenicityNon-carcinogens0.9266
BiodegradationNot ready biodegradable0.9944
Rat acute toxicity2.0963 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.981
hERG inhibition (predictor II)Non-inhibitor0.6924
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397 )
Pharmacoeconomics
Manufacturers
  • Schering corp sub schering plough corp
PackagersNot Available
Dosage forms
FormRouteStrength
SolutionIntramuscular; Intravenous100 mg
SolutionIntramuscular; Intravenous50 mg
PricesNot Available
PatentsNot Available
Properties
StateSolid
Experimental Properties
PropertyValueSource
water solubility100 mg/mLNot Available
logP-3Not Available
Predicted Properties
PropertyValueSource
Water Solubility8.43 mg/mLALOGPS
logP-1.4ALOGPS
logP-3.5ChemAxon
logS-1.8ALOGPS
pKa (Strongest Acidic)12.49ChemAxon
pKa (Strongest Basic)9.97ChemAxon
Physiological Charge5ChemAxon
Hydrogen Acceptor Count12ChemAxon
Hydrogen Donor Count8ChemAxon
Polar Surface Area199.73 Å2ChemAxon
Rotatable Bond Count8ChemAxon
Refractivity119.84 m3·mol-1ChemAxon
Polarizability50.89 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 aminoglycosides. These are molecules or a portion of a molecule composed of amino-modified sugars.
KingdomOrganic compounds
Super ClassOrganooxygen compounds
ClassCarbohydrates and carbohydrate conjugates
Sub ClassAminosaccharides
Direct ParentAminoglycosides
Alternative Parents
Substituents
  • Aminoglycoside core
  • Glucosamine
  • Amino sugar
  • O-glycosyl compound
  • Glycosyl compound
  • Cyclohexylamine
  • Cyclohexanol
  • Oxane
  • Monosaccharide
  • Tertiary alcohol
  • Cyclic alcohol
  • Secondary alcohol
  • 1,2-aminoalcohol
  • Oxacycle
  • Organoheterocyclic compound
  • Secondary amine
  • Secondary aliphatic amine
  • Acetal
  • Hydrocarbon derivative
  • Primary amine
  • 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 ]
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. Tuuminen T, Heinasmaki T, Kerttula T: First report of bacteremia by Asaia bogorensis, in a patient with a history of intravenous-drug abuse. J Clin Microbiol. 2006 Aug;44(8):3048-50. [PubMed:16891542 ]
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Drug created on June 13, 2005 07:24 / Updated on December 08, 2016 11:46