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PZ0014

Sigma-Aldrich

Linezolid

≥98% (HPLC), powder, bacterial mRNA translation inhibitor

Synonyme(s) :

N-[[(5S)-3-[3-Fluoro-4-(4-morpholinyl)phenyl]-2-oxo-5-oxazolidinyl]methyl]acetamide, PNU-100766, U-100766

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About This Item

Formule empirique (notation de Hill):
C16H20FN3O4
Numéro CAS:
165800-03-3
Poids moléculaire :
337.35
Numéro MDL:
MFCD00937825
Code UNSPSC :
12352200
ID de substance PubChem :
329823683
Nomenclature NACRES :
NA.77

product name

Linezolid, ≥98% (HPLC)

Niveau de qualité

100

Pureté

≥98% (HPLC)

Forme

powder

Couleur

white to off-white

Solubilité

DMSO: >20 mg/mL

Température de stockage

room temp

Chaîne SMILES 

CC(=O)NC[C@H]1CN(C(=O)O1)c2ccc(N3CCOCC3)c(F)c2

InChI

1S/C16H20FN3O4/c1-11(21)18-9-13-10-20(16(22)24-13)12-2-3-15(14(17)8-12)19-4-6-23-7-5-19/h2-3,8,13H,4-7,9-10H2,1H3,(H,18,21)/t13-/m0/s1

Clé InChI

TYZROVQLWOKYKF-ZDUSSCGKSA-N

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Description générale

Linezolid exhibits its activity against several Gram-positive bacteria including penicillin-resistant, methicillin-resistant, and vancomycin- resistant. Linezolid can decrease the rate of translation reaction by inhibiting the formation of initiation complex thereby reducing the length of the newly formed peptidechain. Additionally, it may also play a role in reducing the virulence leading to reduced toxins produced by Gram-positive bacteria.

Application

Linezolid has been used in checkerboard-type drug combination MIC (minimum inhibitory concentrations) assay to determine whether ivacaftor shows positive interaction with linezolid. It has been used for the determination of minimum biofilm inhibitory concentration and for the treatment of Mycobacterium abscessus-infected Drosophila melanogaster w1118 flies.Linezolid has been used as an antibiotic to study its effects on the development of malaria-associated acute respiratory distress syndrome (MAARDS) in rat lungs. It has been used as an antibiotic to study its effects in combination with baicalein on methicillin-resistant Staphylococcus aureus strains. It has been used as an antibiotic to study its effects on planktonic growth and formation of biofilms by Enterococcus faecalis.

Actions biochimiques/physiologiques

Linezolid is an oxazolidinone antimicrobial. It binds to a site on the bacterial 23S ribosomal RNA of the 50S subunit and prevents the formation of a functional 70S initiation complex, thus inhibiting bacterial mRNA translation. Linezolid is also a weak, reversible, nonselective inhibitor of monoamine oxidase.

Pictogrammes

Health hazard
GHS08

Mention d'avertissement

Danger

Mentions de danger

H372

Classification des risques

STOT RE 1 Oral

Organes cibles

Bone

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

Point d'éclair (°F)

Not applicable

Point d'éclair (°C)

Not applicable

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Matthew S Dryden
The Journal of antimicrobial chemotherapy, 66 Suppl 4, iv7-iv15 (2011-05-06)
Linezolid has been widely used in the treatment of Gram-positive infections for more than a decade. It is unique amongst antibiotics active against most multiply-resistant Gram-positive bacteria in that there is an oral preparation with 100% bioavailability and an extensive
Giovanni Sotgiu et al.
The European respiratory journal, 40(6), 1430-1442 (2012-04-13)
Linezolid is used off-label to treat multidrug-resistant tuberculosis (MDR-TB) in absence of systematic evidence. We performed a systematic review and meta-analysis on efficacy, safety and tolerability of linezolid-containing regimes based on individual data analysis. 12 studies (11 countries from three
Gregory J Moran et al.
The Lancet. Infectious diseases, 14(8), 696-705 (2014-06-10)
New antibiotics are needed to treat infections caused by drug-resistant bacteria. Tedizolid is a novel oxazolidinone antibacterial drug designed to provide enhanced activity against Gram-positive pathogens. We aimed to assess the efficacy and safety of intravenous to oral tedizolid for
Sanjay Chhibber et al.
PloS one, 8(2), e56022-e56022 (2013-02-19)
Staphylococcus aureus remains the predominant pathogen in diabetic foot infections and prevalence of methicillin resistant S.aureus (MRSA) strains further complicates the situation. The incidence of MRSA in infected foot ulcers is 15-30% and there is an alarming trend for its
Bing Gu et al.
The Journal of antimicrobial chemotherapy, 68(1), 4-11 (2012-09-06)
The oxazolidinone antibiotic linezolid has demonstrated potent antimicrobial activity against Gram-positive bacterial pathogens, including methicillin-resistant staphylococci. This article systematically reviews the published literature for reports of linezolid-resistant Staphylococcus (LRS) infections to identify epidemiological, microbiological and clinical features for these infections.
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