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Key Documents

N0755

Sigma-Aldrich

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
EC Number:
260-147-3
MDL number:
MFCD01311715
UNSPSC Code:
51102829
NACRES:
NA.85

form

powder

Quality Level

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

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

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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

Signal Word

Danger

Hazard Statements

H360

Hazard Classifications

Repr. 1B

Storage Class Code

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

WGK

WGK 3

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

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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
R Vanhoof et al.
The Journal of antimicrobial chemotherapy, 44(4), 483-488 (1999-12-10)
A total of 1102 consecutive clinical blood isolates, including 897 Enterobacteriaceae and 205 non-fermenting bacilli, were obtained from 13 university and university-affiliated hospitals, which were divided into a Northern and a Southern group. Resistance to gentamicin, tobramycin, netilmicin, amikacin and
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
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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