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PZ0014

Sigma-Aldrich

Linezolid

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

Synonym(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

Empirical Formula (Hill Notation):
C16H20FN3O4
CAS Number:
165800-03-3
Molecular Weight:
337.35
MDL number:
MFCD00937825
UNSPSC Code:
12352200
PubChem Substance ID:
329823683
NACRES:
NA.77

product name

Linezolid, ≥98% (HPLC)

Quality Level

100

assay

≥98% (HPLC)

form

powder

color

white to off-white

solubility

DMSO: >20 mg/mL

storage temp.

room temp

SMILES string

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

InChI key

TYZROVQLWOKYKF-ZDUSSCGKSA-N

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General description

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.

Biochem/physiol Actions

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.

pictograms

Health hazard
GHS08

signalword

Danger

hcodes

H372

Hazard Classifications

STOT RE 1 Oral

target_organs

Bone

Storage Class

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

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

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Zhong Chen et al.
Journal of medicinal chemistry, 64(20), 15037-15052 (2021-10-19)
YycFG, one of the two-component systems involved in the regulation of biofilm formation, has attracted increasing interest as a potential target of antibacterial and antibiofilm agents. YycG inhibitors for Staphylococcus aureus and Staphylococcus epidermidis have been developed, but Enterococcus faecalis
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
Seyed Mohammad Reza Hashemian et al.
Drug design, development and therapy, 12, 1759-1767 (2018-06-29)
Linezolid can be considered as the first member of the class of oxazolidinone antibiotics. The compound is a synthetic antibiotic that inhibits bacterial protein synthesis through binding to rRNA. It also inhibits the creation of the initiation complex during protein
D Clemett et al.
Drugs, 59(4), 815-827 (2000-05-10)
Linezolid is an oxazolidinone antibacterial agent that acts by inhibiting the initiation of bacterial protein synthesis. Cross-resistance between linezolid and other inhibitors of protein synthesis has not been demonstrated. Linezolid has a wide spectrum of activity against gram-positive organisms including
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
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