| Common Name |
Netilmicin
| 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 flily understood.
| Structure |
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
| Synonyms |
| Value |
Source |
1-N-EthylsisomicinChEBI
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-streptamineChEBI
O-3-Deoxy-4-C-methyl-3-(methylamino)-b-L-arabinopyranosyl-(1-6)-O-(2,6-diamino-2,3,4,6-tetradeoxy-a-D-glycero-hex-4-enopyranosyl-(1-4))-2-deoxy-N(1)-ethyl-D-streptamineGenerator
O-3-Deoxy-4-C-methyl-3-(methylamino)-β-L-arabinopyranosyl-(1-6)-O-(2,6-diamino-2,3,4,6-tetradeoxy-α-D-glycero-hex-4-enopyranosyl-(1-4))-2-deoxy-N(1)-ethyl-D-streptamineGenerator
NetilmycinHMDB
| Chemical Formlia |
C21H41N5O7
| Average Molecliar Weight |
475.5795
| Monoisotopic Molecliar Weight |
475.300598691
| 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
| Traditional Name |
netilmicin slifate
| CAS Registry Number |
56391-56-1
| SMILES |
CCN[C@@H]1C[C@H](N)[C@@H](O[C@H]2OC(CN)=CC[C@H]2N)[C@H](O)[C@H]1O[C@H]1OC[C@H](O)[C@@H](NC)[C@@]1(C)O
| InChI Identifier |
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
| InChI Key |
ZBGPYVZLYBDXKO-HILBYHGXSA-N
| Chemical 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
Acetals
Organopnictogen compounds
Monoalkylamines
Hydrocarbon derivatives
| Substituents |
Amino cyclitol glycoside
Glycosyl compound
O-glycosyl compound
Aminocyclitol or derivatives
Cyclohexanol
Cyclohexylamine
Cyclitol or derivatives
Monosaccharide
Oxane
Cyclic alcohol
Tertiary alcohol
1,2-aminoalcohol
Secondary alcohol
Acetal
Secondary aliphatic amine
Secondary amine
Organoheterocyclic compound
Oxacycle
Primary aliphatic amine
Hydrocarbon derivative
Organopnictogen compound
Organic nitrogen compound
Amine
Alcohol
Primary amine
Organonitrogen compound
Aliphatic heteromonocyclic compound
| Molecliar Framework |
Aliphatic heteromonocyclic compounds
| External Descriptors |
monosaccharide derivative (CHEBI:7528 )
aminoglycoside antibiotic (CHEBI:7528 )
amino cyclitol glycoside (CHEBI:7528 )
beta-L-arabinoside (CHEBI:7528 )
| Ontology |
| Status |
Expected but not Quantified
| Origin |
Drug
| Biofunction |
Aminoglycosides
Anti-Bacterial Agents
Protein Synthesis Inhibitors
| Application |
Pharmaceutical
| Cellliar locations |
Cytoplasm
| Physical Properties |
| State |
Solid
| Experimental Properties |
| Property |
Value |
Reference |
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water Solubility8.43e+00 g/LNot Available
LogP-3Not Available
| Predicted Properties |
| Property |
Value |
Source |
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
Rlie of FiveYesChemAxon
Ghose FilterYesChemAxon
Vebers RlieYesChemAxon
MDDR-like RlieYesChemAxon
| Spectra |
| Spectra |
| Spectrum Type |
Description |
Splash Key |
|
| Predicted LC-MS/MS |
Predicted LC-MS/MS Spectrum – 10V, PositiveNot Available
| Predicted LC-MS/MS |
Predicted LC-MS/MS Spectrum – 20V, PositiveNot Available
| Predicted LC-MS/MS |
Predicted LC-MS/MS Spectrum – 40V, PositiveNot Available
| Predicted LC-MS/MS |
Predicted LC-MS/MS Spectrum – 10V, NegativeNot Available
| Predicted LC-MS/MS |
Predicted LC-MS/MS Spectrum – 20V, NegativeNot Available
| Predicted LC-MS/MS |
Predicted LC-MS/MS Spectrum – 40V, NegativeNot Available
| Biological Properties |
| Cellliar Locations |
Cytoplasm
| Biofluid Locations |
Blood
Urine
| Tissue Location |
Not Available
| Pathways |
| Name |
SMPDB Link |
KEGG Link |
Netilmicin PathwaySMP00257Not Available
| Normal Concentrations |
| Biofluid |
Status |
Age |
Condition |
Reference |
Details |
BloodExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB00955
21059682
details
UrineExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB00955
21059682
details
|
| Abnormal Concentrations |
|
Not Available
| Associated Disorders and Diseases |
| Disease References |
None
| Associated OMIM IDs |
None
| External Links |
| DrugBank ID |
DB00955
| DrugBank Metabolite ID |
Not Available
| Phenol Explorer Compound ID |
Not Available
| Phenol Explorer Metabolite ID |
Not Available
| FoodDB ID |
Not Available
| KNApSAcK ID |
Not Available
| Chemspider ID |
5256761
| KEGG Compound ID |
C07657
| BioCyc ID |
Not Available
| BiGG ID |
Not Available
| Wikipedia Link |
Netilmicin
| NuGOwiki Link |
HMDB15090
| Metagene Link |
HMDB15090
| METLIN ID |
Not Available
| PubChem Compound |
6857423
| PDB ID |
Not Available
| ChEBI ID |
7528
Product: Vidofludimus
References |
| Synthesis Reference |
Not Available |
| Material Safety Data Sheet (MSDS) |
Not Available |
| General References |
- 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 ]
- 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 ]
- 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 ]
|
PMID: 22208561
