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Key Documents

N0755

Sigma-Aldrich

Netilmicin sulfate salt

Sinônimo(s):

1-N-Ethylsisomicin

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About This Item

Fórmula linear:
C21H41N5O7 · 5/2H2SO4
Número CAS:
Peso molecular:
720.78
Número CE:
Número MDL:
Código UNSPSC:
51102829
NACRES:
NA.85

forma

powder

Nível de qualidade

cor

white to faint yellow

solubilidade

H2O: 10 mg/mL

espectro de atividade do antibiótico

Gram-negative bacteria
Gram-positive bacteria

Modo de ação

protein synthesis | interferes

temperatura de armazenamento

2-8°C

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

chave InChI

AGFWIZQEWFGATK-UNZHCMSXSA-N

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Descrição geral

Chemical structure: aminoglycoside

Aplicação

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 .

Ações bioquímicas/fisiológicas

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.

Pictogramas

Health hazard

Palavra indicadora

Danger

Frases de perigo

Classificações de perigo

Repr. 1B

Código de classe de armazenamento

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

Classe de risco de água (WGK)

WGK 3

Equipamento de proteção individual

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


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"Typhlitis" in rectum.
Unsal Ozgen et al.
Pediatrics international : official journal of the Japan Pediatric Society, 52(1), e32-e33 (2010-02-18)
Chengwei Liu et al.
Se pu = Chinese journal of chromatography, 29(2), 157-161 (2011-05-24)
A method was developed for the direct determination of netilmicin in rat serum using high performance liquid chromatography and resonance Rayleigh scattering (RRS). The separation was carried out on a C18 column with the isocratic elution of the mixture of
D W McEniry et al.
The Journal of antimicrobial chemotherapy, 21(2), 171-175 (1988-02-01)
Pseudomonas pseudomallei is resistant to many antimicrobial agents. We determined the susceptibility to twelve beta-lactams and six aminoglycosides of twelve isolates of P. pseudomallei. Imipenem (MIC range 0.5-1.0 mg/l; MIC90 1.0 mg/l), ceftazidime (MIC range 1-8 mg/l; MIC90 8.0 mg/l)
W E Siegenthaler et al.
The American journal of medicine, 80(6B), 2-14 (1986-06-30)
This article presents an overview of the aminoglycoside antibiotics used in clinical practice. Facts concerning the discovery and properties of the aminoglycosides are followed by information about spectrums of activity and mechanisms of action and resistance. Individual compounds are compared
J Patzer et al.
The Journal of antimicrobial chemotherapy, 18(1), 45-49 (1986-07-01)
Pseudomonas aeruginosa strains, 1285 in total, were isolated from hospitalized children in the period 1981-1984. Serotypes 011 and 06 and nontypable strains were the most frequently identified. 44.6% of serotype 011 strains and between 12.4 and 37.7% of other serotypes

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