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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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Katherine S Long et al.
Antimicrobial agents and chemotherapy, 56(2), 603-612 (2011-12-07)
Linezolid is an oxazolidinone antibiotic in clinical use for the treatment of serious infections of resistant Gram-positive bacteria. It inhibits protein synthesis by binding to the peptidyl transferase center on the ribosome. Almost all known resistance mechanisms involve small alterations
Jansy Sarathy et al.
Antimicrobial agents and chemotherapy, 57(4), 1648-1653 (2013-01-22)
During active tuberculosis a spectrum of physiologically different Mycobacterium tuberculosis bacilli reside in human tissues. Subpopulations of the pathogen survive antibiotic treatment for a prolonged time in a dormant state of phenotypic drug resistance, a phenomenon independent of genetic mutations.
Lanqing Cui et al.
PloS one, 8(2), e57096-e57096 (2013-02-26)
Four methicillin-resistant coagulase-negative staphylococci (MRCoNS), one Staphylococcus haemolyticus and three Staphylococcus cohnii, from infections of humans collected via the Ministry of Health National Antimicrobial Resistance Surveillance Net (Mohnarin) program in China were identified as linezolid-resistant. These four isolates were negative
Binh An Diep et al.
The Journal of infectious diseases, 208(1), 75-82 (2013-03-28)
Linezolid is recommended for treatment of pneumonia and other invasive infections caused by methicillin-resistant Staphylococcus aureus (MRSA). The premise underlying this recommendation is that linezolid inhibits in vivo production of potent staphylococcal exotoxins, including Panton-Valentine leukocidin (PVL) and α-hemolysin (Hla)
Laura Morata et al.
Antimicrobial agents and chemotherapy, 57(4), 1913-1917 (2013-02-14)
Linezolid is an antibiotic with time-dependent activity, and both the percentage of time that plasma concentrations exceed the MIC and the area under the concentration-time curve over 24 h in the steady state divided by the MIC (AUC24/MIC ratio) are
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