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N0755

Sigma-Aldrich

Netilmicin sulfate salt

Synonyme(s) :

1-N-Ethylsisomicin

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About This Item

Formule linéaire :
C21H41N5O7 · 5/2H2SO4
Numéro CAS:
56391-57-2
Poids moléculaire :
720.78
Numéro CE :
260-147-3
Numéro MDL:
MFCD01311715
Code UNSPSC :
51102829
Nomenclature NACRES :
NA.85

Forme

powder

Niveau de qualité

200

Couleur

white to faint yellow

Solubilité

H2O: 10 mg/mL

Spectre d'activité de l'antibiotique

Gram-negative bacteria
Gram-positive bacteria

Mode d’action

protein synthesis | interferes

Température de stockage

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

Clé InChI

AGFWIZQEWFGATK-UNZHCMSXSA-N

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Catégories apparentées

Description générale

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 .

Actions biochimiques/physiologiques

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.

Pictogrammes

Health hazard
GHS08

Mention d'avertissement

Danger

Mentions de danger

H360

Classification des risques

Repr. 1B

Code de la classe de stockage

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

Classe de danger pour l'eau (WGK)

WGK 3

Équipement de protection individuelle

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

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Consulter la Bibliothèque de documents

Dorota Wrześniok et al.
Acta poloniae pharmaceutica, 69(1), 41-45 (2012-05-12)
Netilmicin, which is mainly used as the sulfate, is a semisynthetic, water soluble aminoglycoside antibiotic obtained by chemical modification of sisomicin. It is active against both Gram-positive and Gram-negative bacteria, including strains which are resistant to other aminoglycosides. Netilmicin form
George Samonis et al.
PloS one, 7(5), e37375-e37375 (2012-05-25)
Stenotrophomonas maltophilia is acquiring increasing importance as a nosocomial pathogen. We retrospectively studied the characteristics and outcome of patients with any type of S. maltophilia infection at the University Hospital of Heraklion, Crete, Greece, between 1/2005-12/2010. S. maltophilia antimicrobial susceptibility
Veronica Pianini et al.
Journal of ocular pharmacology and therapeutics : the official journal of the Association for Ocular Pharmacology and Therapeutics, 26(6), 617-621 (2010-11-03)
To compare the efficacy and safety of preservative-free Netilmycin/Dexamethasone with that of preserved Tobramycin/Dexamethasone, postcataract surgery. Prospective, randomized, single-blind study on patients submitted to phacoemulsification. During preoperatory visits, at 7 and 21 days conjunctival hyperemia, corneal edema, Tyndall, Shirmer I
Adriano Magli et al.
International ophthalmology, 32(1), 47-49 (2012-01-05)
To report clinical manifestations of a female patient with bilateral bacterial keratitis following photorefractive keratectomy (PRK). Bilateral PRK was performed for moderate hyperopia. Bandage contact lenses were fitted at the conclusion of the surgery. Bilateral infectious keratitis with hypopion was
Bilateral punctum atresia and lacrimal sac fistula in a child with CHARGE syndrome.
Zafer Onaran et al.
Clinical & experimental ophthalmology, 37(9), 894-895 (2010-01-23)
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