Identification

Name
Netilmicin
Accession Number
DB00955  (APRD00232)
Type
Small Molecule
Groups
Approved, Investigational
Description

Netilmicin is a semisynthetic 1-N-ethyl derivative of sisomycin, an aminoglycoside antibiotic with action similar to gentamicin, but less ear and kidney toxicity. 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
  • Netilmycin
Product Ingredients
IngredientUNIICASInChI Key
Netilmicin sulfateS741ZJS97U56391-57-2Not applicable
Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Netromycin Inj 100mg/mlSolution100 mgIntramuscular; IntravenousSchering Plough1981-12-312004-07-21Canada
Netromycin Inj 50mg/mlSolution50 mgIntramuscular; IntravenousSchering Plough1981-12-312004-07-21Canada
International/Other Brands
Netromycin
Categories
UNII
4O5J85GJJB
CAS number
56391-56-1
Weight
Average: 475.587
Monoisotopic: 475.30059868
Chemical Formula
C21H41N5O7
InChI Key
CIDUJQMULVCIBT-MQDUPKMGSA-N
InChI
InChI=1S/C21H41N5O7/c1-4-26-13-7-12(24)16(32-19-11(23)6-5-10(8-22)31-19)14(27)17(13)33-20-15(28)18(25-3)21(2,29)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}-5-methyl-4-(methylamino)oxane-3,5-diol
SMILES

Pharmacology

Indication

For 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
Pharmacodynamics

Netilmicin 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 action

Aminoglycosides 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.

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

Rapidly 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 distribution
Not Available
Protein binding

Protein-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 elimination
Not Available
Half life

2.5 hours

Clearance
Not Available
Toxicity

Netilmicin 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
PathwayCategory
Netilmicin Action PathwayDrug action
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
DrugInteractionDrug group
AceclofenacAceclofenac may decrease the excretion rate of Netilmicin which could result in a higher serum level.Approved, Investigational
AcemetacinAcemetacin may decrease the excretion rate of Netilmicin which could result in a higher serum level.Approved, Experimental, Investigational
AcetyldigitoxinThe serum concentration of Acetyldigitoxin can be decreased when it is combined with Netilmicin.Approved
AcetyldigoxinThe serum concentration of Acetyldigoxin can be decreased when it is combined with Netilmicin.Experimental
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
AlclofenacAlclofenac may decrease the excretion rate of Netilmicin which could result in a higher serum level.Approved, Withdrawn
AlcuroniumNetilmicin may increase the respiratory depressant activities of Alcuronium.Experimental
Alendronic acidNetilmicin may increase the hypocalcemic activities of Alendronic acid.Approved
AlminoprofenAlminoprofen may decrease the excretion rate of Netilmicin which could result in a higher serum level.Experimental
AmdinocillinThe serum concentration of Netilmicin can be decreased when it is combined with Amdinocillin.Investigational, 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
AndrographolideAndrographolide may decrease the excretion rate of Netilmicin which could result in a higher serum level.Investigational
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
ApocyninApocynin may decrease the excretion rate of Netilmicin which could result in a higher serum level.Investigational
ApremilastApremilast may decrease the excretion rate of Netilmicin which could result in a higher serum level.Approved, Investigational
AspoxicillinThe serum concentration of Netilmicin can be decreased when it is combined with Aspoxicillin.Experimental
AtracuriumNetilmicin may increase the respiratory depressant activities of Atracurium.Experimental, 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, Investigational
BalsalazideBalsalazide may decrease the excretion rate of Netilmicin 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 Netilmicin.Investigational
BendazacBendazac may decrease the excretion rate of Netilmicin which could result in a higher serum level.Experimental
BenorilateBenorilate may decrease the excretion rate of Netilmicin which could result in a higher serum level.Experimental
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
BenzydamineBenzydamine may decrease the excretion rate of Netilmicin which could result in a higher serum level.Approved
BenzylpenicillinThe serum concentration of Netilmicin can be decreased when it is combined with Benzylpenicillin.Approved, Vet Approved
Benzylpenicilloyl PolylysineThe serum concentration of Netilmicin can be decreased when it is combined with Benzylpenicilloyl Polylysine.Approved
BevoniumBevonium may decrease the excretion rate of Netilmicin which could result in a higher serum level.Experimental
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
BufexamacBufexamac may decrease the excretion rate of Netilmicin which could result in a higher serum level.Experimental
BumadizoneBumadizone may decrease the excretion rate of Netilmicin which could result in a higher serum level.Experimental
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, Investigational
Carbenicillin indanylThe serum concentration of Netilmicin can be decreased when it is combined with Carbenicillin indanyl.Approved, Investigational
CarboplatinNetilmicin may increase the ototoxic activities of Carboplatin.Approved
CarfecillinThe serum concentration of Netilmicin can be decreased when it is combined with Carfecillin.Experimental
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
Choline magnesium trisalicylateCholine magnesium trisalicylate may decrease the excretion rate of Netilmicin which could result in a higher serum level.Approved
CisatracuriumNetilmicin may increase the respiratory depressant activities of Cisatracurium.Approved, Experimental
Cisatracurium besylateNetilmicin may increase the respiratory depressant activities of Cisatracurium besylate.Approved
CisplatinCisplatin may increase the nephrotoxic activities of Netilmicin.Approved
Clodronic AcidNetilmicin may increase the hypocalcemic activities of Clodronic Acid.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
CymarinThe serum concentration of Cymarin can be decreased when it is combined with Netilmicin.Experimental
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
DifenpiramideDifenpiramide may decrease the excretion rate of Netilmicin which could result in a higher serum level.Experimental
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, Investigational
DigoxinThe serum concentration of Digoxin can be decreased when it is combined with Netilmicin.Approved
Digoxin Immune Fab (Ovine)The serum concentration of Digoxin Immune Fab (Ovine) 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
E-6201E-6201 may decrease the excretion rate of Netilmicin which could result in a higher serum level.Investigational
EpicillinThe serum concentration of Netilmicin can be decreased when it is combined with Epicillin.Experimental
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
EthenzamideEthenzamide may decrease the excretion rate of Netilmicin which could result in a higher serum level.Experimental
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, Investigational
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, Investigational
exisulindexisulind may decrease the excretion rate of Netilmicin which could result in a higher serum level.Investigational
FelbinacFelbinac may decrease the excretion rate of Netilmicin which could result in a higher serum level.Experimental
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
FentiazacFentiazac may decrease the excretion rate of Netilmicin which could result in a higher serum level.Experimental
FeprazoneFeprazone may decrease the excretion rate of Netilmicin which could result in a higher serum level.Experimental
Ferulic acidFerulic acid may decrease the excretion rate of Netilmicin which could result in a higher serum level.Experimental
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, Investigational
FlunixinFlunixin may decrease the excretion rate of Netilmicin which could result in a higher serum level.Vet Approved
FlunoxaprofenFlunoxaprofen may decrease the excretion rate of Netilmicin which could result in a higher serum level.Experimental
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
GallamineNetilmicin may increase the respiratory depressant activities of Gallamine.Experimental
Gallamine TriethiodideNetilmicin may increase the respiratory depressant activities of Gallamine Triethiodide.Approved
GitoformateThe serum concentration of Gitoformate can be decreased when it is combined with Netilmicin.Experimental
GuacetisalGuacetisal may decrease the excretion rate of Netilmicin which could result in a higher serum level.Experimental
HigenamineHigenamine 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
Imidazole salicylateImidazole salicylate may decrease the excretion rate of Netilmicin which could result in a higher serum level.Experimental
IndobufenIndobufen may decrease the excretion rate of Netilmicin which could result in a higher serum level.Investigational
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
Lanatoside CThe serum concentration of Lanatoside C can be decreased when it is combined with Netilmicin.Experimental
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
LonazolacLonazolac may decrease the excretion rate of Netilmicin which could result in a higher serum level.Experimental
LornoxicamLornoxicam may decrease the excretion rate of Netilmicin which could result in a higher serum level.Approved, Investigational
LoxoprofenLoxoprofen may decrease the excretion rate of Netilmicin which could result in a higher serum level.Approved, Investigational
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, Investigational
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.Investigational, Withdrawn
MetampicillinThe serum concentration of Netilmicin can be decreased when it is combined with Metampicillin.Experimental
MeticillinThe serum concentration of Netilmicin can be decreased when it is combined with Meticillin.Approved, Investigational
MetildigoxinThe serum concentration of Metildigoxin can be decreased when it is combined with Netilmicin.Experimental
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, Investigational
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
MofebutazoneMofebutazone may decrease the excretion rate of Netilmicin which could result in a higher serum level.Experimental
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.Approved, 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
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
NifenazoneNifenazone may decrease the excretion rate of Netilmicin which could result in a higher serum level.Experimental
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, Investigational, Withdrawn
NitroaspirinNitroaspirin may decrease the excretion rate of Netilmicin which could result in a higher serum level.Investigational
OleandrinThe serum concentration of Oleandrin can be decreased when it is combined with Netilmicin.Experimental, 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.Approved, 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
ParthenolideParthenolide may decrease the excretion rate of Netilmicin which could result in a higher serum level.Investigational
PenamecillinThe serum concentration of Netilmicin can be decreased when it is combined with Penamecillin.Experimental
PenimepicyclineThe serum concentration of Netilmicin can be decreased when it is combined with Penimepicycline.Experimental
PeruvosideThe serum concentration of Peruvoside can be decreased when it is combined with Netilmicin.Experimental
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.Approved, Investigational
PiroxicamPiroxicam may decrease the excretion rate of Netilmicin which could result in a higher serum level.Approved, Investigational
PirprofenPirprofen may decrease the excretion rate of Netilmicin which could result in a higher serum level.Experimental
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
PranoprofenPranoprofen may decrease the excretion rate of Netilmicin which could result in a higher serum level.Experimental, Investigational
Procaine benzylpenicillinThe serum concentration of Netilmicin can be decreased when it is combined with Procaine benzylpenicillin.Approved, Vet Approved
ProglumetacinProglumetacin may decrease the excretion rate of Netilmicin which could result in a higher serum level.Experimental
PropacetamolPropacetamol may decrease the excretion rate of Netilmicin which could result in a higher serum level.Approved, Investigational
PropicillinThe serum concentration of Netilmicin can be decreased when it is combined with Propicillin.Experimental
PropyphenazonePropyphenazone may decrease the excretion rate of Netilmicin which could result in a higher serum level.Experimental
ProquazoneProquazone may decrease the excretion rate of Netilmicin which could result in a higher serum level.Experimental
ProscillaridinThe serum concentration of Proscillaridin can be decreased when it is combined with Netilmicin.Experimental
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.Approved, 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
SemapimodSemapimod may decrease the excretion rate of Netilmicin which could result in a higher serum level.Investigational
SeratrodastSeratrodast may decrease the excretion rate of Netilmicin which could result in a higher serum level.Approved
SerrapeptaseSerrapeptase may decrease the excretion rate of Netilmicin which could result in a higher serum level.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
SulbenicillinThe serum concentration of Netilmicin can be decreased when it is combined with Sulbenicillin.Experimental
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
SuxibuzoneSuxibuzone may decrease the excretion rate of Netilmicin which could result in a higher serum level.Experimental
TalampicillinThe serum concentration of Netilmicin can be decreased when it is combined with Talampicillin.Experimental
TarenflurbilTarenflurbil may decrease the excretion rate of Netilmicin which could result in a higher serum level.Investigational
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
TenidapTenidap may decrease the excretion rate of Netilmicin which could result in a higher serum level.Experimental
Tenofovir disoproxilThe serum concentration of Netilmicin can be increased when it is combined with Tenofovir disoproxil.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, Investigational, Vet Approved
Tiludronic acidNetilmicin may increase the hypocalcemic activities of Tiludronic acid.Approved, Investigational, 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
TribenosideTribenoside may decrease the excretion rate of Netilmicin which could result in a higher serum level.Experimental
TriptolideTriptolide may decrease the excretion rate of Netilmicin which could result in a higher serum level.Investigational
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, Investigational
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 Interactions
Not 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
Human Metabolome Database
HMDB15090
KEGG Drug
D08268
KEGG Compound
C07657
PubChem Compound
441306
PubChem Substance
46507404
ChemSpider
20152952
ChEBI
7528
ChEMBL
CHEMBL1572
Therapeutic Targets Database
DAP000404
PharmGKB
PA164754913
Wikipedia
Netilmicin
ATC Codes
S01AA23 — NetilmicinJ01GB07 — Netilmicin
MSDS
Download (57 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
0RecruitingTreatmentOsteomyelitis1
4CompletedTreatmentPneumonia Ventilator Associated1

Pharmacoeconomics

Manufacturers
  • Schering corp sub schering plough corp
Packagers
Not Available
Dosage forms
FormRouteStrength
SolutionIntramuscular; Intravenous100 mg
SolutionIntramuscular; Intravenous50 mg
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
PropertyValueSource
water solubility100 mg/mLNot Available
logP-3Not Available
Predicted Properties
PropertyValueSource
Water Solubility9.2 mg/mLALOGPS
logP-1.4ALOGPS
logP-3.5ChemAxon
logS-1.7ALOGPS
pKa (Strongest Acidic)12.55ChemAxon
pKa (Strongest Basic)9.8ChemAxon
Physiological Charge5ChemAxon
Hydrogen Acceptor Count12ChemAxon
Hydrogen Donor Count8ChemAxon
Polar Surface Area199.73 Å2ChemAxon
Rotatable Bond Count8ChemAxon
Refractivity119.84 m3·mol-1ChemAxon
Polarizability50.76 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability0ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
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)

Spectra

Mass Spec (NIST)
Not Available
Spectra
Not Available

Taxonomy

Description
This compound belongs to the class of organic compounds known as aminocyclitol glycosides. These are organic compounds containing an amicocyclitol moiety glycosidically linked to a carbohydrate moiety. There are two major classes of aminoglycosides containing a 2-streptamine core. They are called 4,5- and 4,6-disubstituted 2-deoxystreptamines.
Kingdom
Organic compounds
Super Class
Organic oxygen compounds
Class
Organooxygen compounds
Sub Class
Carbohydrates and carbohydrate conjugates
Direct Parent
Aminocyclitol glycosides
Alternative Parents
O-glycosyl compounds / Aminocyclitols and derivatives / Cyclohexylamines / Cyclohexanols / Oxanes / Monosaccharides / Tertiary alcohols / 1,2-aminoalcohols / Oxacyclic compounds / Dialkylamines
show 4 more
Substituents
Amino cyclitol glycoside / Glycosyl compound / O-glycosyl compound / Aminocyclitol or derivatives / Cyclohexanol / Cyclohexylamine / Cyclitol or derivatives / Monosaccharide / Oxane / Cyclic alcohol
show 17 more
Molecular Framework
Aliphatic heteromonocyclic compounds
External Descriptors
Not Available

Targets

Kind
Protein
Organism
Escherichia coli (strain K12)
Pharmacological action
Yes
Actions
Inhibitor
General Function
Trna binding
Specific Function
With S4 and S5 plays an important role in translational accuracy.Interacts with and stabilizes bases of the 16S rRNA that are involved in tRNA selection in the A site and with the mRNA backbone. 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]
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]

Drug created on June 13, 2005 07:24 / Updated on December 01, 2017 14:36