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N0755

Netilmicin sulfate salt

Synonym(s):

1-N-Ethylsisomicin

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About This Item

Linear Formula:
C21H41N5O7 · 5/2H2SO4
CAS Number:
56391-57-2
Molecular Weight:
720.78
UNSPSC Code:
51102829
NACRES:
NA.85
EC Number:
260-147-3
MDL number:
MFCD01311715
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form

powder

Quality Segment

200

color

white to faint yellow

solubility

H2O: 10 mg/mL

antibiotic activity spectrum

Gram-negative bacteria, Gram-positive bacteria

mode of action

protein synthesis | interferes

storage temp.

2-8°C

SMILES string

[S](=O)(=O)(O)O.[S](=O)(=O)(O)O.[S](=O)(=O)(O)O.[S](=O)(=O)(O)O.[S](=O)(=O)(O)O.N([C@@H]4[C@H]([C@H](OC[C@@]4(O)C)O[C@@H]5[C@H]([C@@H]([C@H](C[C@H]5NCC)N)O[C@H]6OC(=CC[C@H]6N)CN)O)O)C.N([C@@H]1[C@H]([C@H](OC[C@@]1(O)C)O[C@@H]2[C@H]([C@@H]([C@H](C[C@H]2NCC

InChI

1S/2C21H41N5O7.5H2O4S/c2*1-4-26-13-7-12(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;5*1-5(2,3)4/h2*5,11-20,25-29H,4,6-9,22-24H2,1-3H3;5*(H2,1,2,3,4)/t2*11-,12+,13-,14+,15-,16-,17+,18-,19-,20-,21+;;;;;/m11...../s1

InChI key

AGFWIZQEWFGATK-UNZHCMSXSA-N

General description

Chemical structure: aminoglycoside

Application

Netilmicin is an aminoglycoside antibiotic active against most Gram-negative and some Gram-positive bacteria. It is a semisynthetic 1-N-ethyl derivative of sisomycin, an aminoglycoside antibiotic with action similar to gentamicin, but has less ear and kidney toxicity. It is used in aminoglycoside resistance studies and in susceptibility studies of Pseudomonas aeruginosa and Pseudomonas pseudomallei .

Biochem/physiol Actions

An aminoglycoside antibiotic active against most Gram-negative and some Gram-positive bacteria, including many gentamycin-resistant strains. The antibiotic enters the cell through a porin channel and binds to the 30S ribosomal subunit, causing misreading of mRNA.
Netilmicin irreversibly binds to specific 30S-subunit proteins and 16S rRNA. Netilmicin binds to four nucleotides of 16S rRNA and a single amino acid of protein S12. This interferes with the 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. This results in nonfunctional and toxic peptides and the bacterium is unable to synthesize crucial proteins.

pictograms

Health hazard
GHS08

signalword

Danger

hcodes

H360

Hazard Classifications

Repr. 1B

Storage Class

6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects

wgk

WGK 3

ppe

Eyeshields, Gloves, type P3 (EN 143) respirator cartridges

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