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Namespace Prefixes

PrefixIRI
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n16http://linked.opendata.cz/resource/drugbank/drug/DB00955/identifier/drugbank/
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n13http://linked.opendata.cz/resource/drugbank/drug/DB00955/identifier/chebi/
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n8http://linked.opendata.cz/resource/drugbank/drug/DB00955/identifier/pharmgkb/
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n15http://linked.opendata.cz/resource/atc/
n14http://linked.opendata.cz/ontology/sukl/drug/

Statements

Subject Item
n2:DB00955
rdf:type
n3:Drug
n3: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. [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.
n3:generalReferences
# "Link":http://www.medsafe.govt.nz/profs/Datasheet/n/Netromycininj.htm # 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":http://www.ncbi.nlm.nih.gov/pubmed/16028643 # 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":http://www.ncbi.nlm.nih.gov/pubmed/15307571 # 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":http://www.ncbi.nlm.nih.gov/pubmed/15237240
n3:group
approved
n3:halfLife
2.5 hours
n3: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.
n3:manufacturer
n19:271B4209-363D-11E5-9242-09173F13E4C5
owl:sameAs
n10:DB00955 n11:DB00955
dcterms:title
Netilmicin
adms:identifier
n7:Netilmicin n8:PA164754913 n12:C07657 n13:7528 n16:DB00955
n3:mechanismOfAction
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.
n3:synonym
1-N-Ethylsisomicin 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 Netilmicin Netilmycin
n3: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.
n3:proteinBinding
Protein-binding of is low and depends on the test conditions (mainly the concentration of cations in the test medium).
n3:synthesisReference
Chou-Hong Tann, Tiruvettipuram K. Thiruvengadam, John S. Chiu, Cesar Colon, "Process for preparing netilmicin." U.S. Patent US4831123, issued June, 1966.
n17:hasConcept
n18:M0014673
n3:IUPAC-Name
n4:271B420E-363D-11E5-9242-09173F13E4C5
n3:InChI
n4:271B4214-363D-11E5-9242-09173F13E4C5
n3:Molecular-Formula
n4:271B4213-363D-11E5-9242-09173F13E4C5
n3:Molecular-Weight
n4:271B4210-363D-11E5-9242-09173F13E4C5
n3:Monoisotopic-Weight
n4:271B4211-363D-11E5-9242-09173F13E4C5
n3:SMILES
n4:271B4212-363D-11E5-9242-09173F13E4C5
n3:Water-Solubility
n4:271B4224-363D-11E5-9242-09173F13E4C5 n4:271B420C-363D-11E5-9242-09173F13E4C5
n3:logP
n4:271B4225-363D-11E5-9242-09173F13E4C5 n4:271B420D-363D-11E5-9242-09173F13E4C5 n4:271B420A-363D-11E5-9242-09173F13E4C5
n3:logS
n4:271B420B-363D-11E5-9242-09173F13E4C5
n14:hasATCCode
n15:S01AA23 n15:J01GB07
n3:H-Bond-Acceptor-Count
n4:271B421A-363D-11E5-9242-09173F13E4C5
n3:H-Bond-Donor-Count
n4:271B421B-363D-11E5-9242-09173F13E4C5
n3:InChIKey
n4:271B4215-363D-11E5-9242-09173F13E4C5
n3:Polar-Surface-Area--PSA-
n4:271B4216-363D-11E5-9242-09173F13E4C5
n3:Polarizability
n4:271B4218-363D-11E5-9242-09173F13E4C5
n3:Refractivity
n4:271B4217-363D-11E5-9242-09173F13E4C5
n3:Rotatable-Bond-Count
n4:271B4219-363D-11E5-9242-09173F13E4C5
n3: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.
n3:affectedOrganism
Enteric bacteria and other eubacteria
n3:casRegistryNumber
56391-56-1
n3:category
n3:Bioavailability
n4:271B4220-363D-11E5-9242-09173F13E4C5
n3:Ghose-Filter
n4:271B4222-363D-11E5-9242-09173F13E4C5
n3:MDDR-Like-Rule
n4:271B4223-363D-11E5-9242-09173F13E4C5
n3:Number-of-Rings
n4:271B421F-363D-11E5-9242-09173F13E4C5
n3:Physiological-Charge
n4:271B421E-363D-11E5-9242-09173F13E4C5
n3:Rule-of-Five
n4:271B4221-363D-11E5-9242-09173F13E4C5
n3:Traditional-IUPAC-Name
n4:271B420F-363D-11E5-9242-09173F13E4C5
n3:pKa--strongest-acidic-
n4:271B421C-363D-11E5-9242-09173F13E4C5
n3:pKa--strongest-basic-
n4:271B421D-363D-11E5-9242-09173F13E4C5