PZ0014

Sigma-Aldrich

Linezolid

≥98% (HPLC)

Synonym(s):
N-[[(5S)-3-[3-Fluoro-4-(4-morpholinyl)phenyl]-2-oxo-5-oxazolidinyl]methyl]acetamide, U-100766, PNU-100766
Empirical Formula (Hill Notation):
C16H20FN3O4
CAS Number:
Molecular Weight:
337.35
MDL number:
PubChem Substance ID:
NACRES:
NA.77

Quality Level

assay

≥98% (HPLC)

form

powder

manufacturer/tradename

Pfizer®

color

white to off-white

solubility

DMSO: >20 mg/mL

originator

Pfizer

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 is the first member of the oxazolidinones antibiotic class which shows wide activity against Gram-positive bacteria, including drug resistant strains.

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.

Packaging

5, 25 mg in glass bottle

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.

Features and Benefits

This compound is also offered as part of Sigma′s Library of Pharmacologically Active Compounds (LOPAC®1280), a biologically annotated collection of high-quality, ready-to-screen compounds. Click here to learn more.
This compound is also offered as part of Sigma′s Library of Pharmacologically Active Compounds (LOPAC®Pfizer), a collection of 90 Pfizer-developed drugs and research tools. Click here to learn more.

Other Notes

This compound was developed by Pfizer for Immunology research. To learn more about Sigma′s partnership with Pfizer and view other authentic, high-quality Pfizer compounds, visit sigma.com/bsm-pfizer.

To browse the list of other pharma-developed compounds and Approved Drugs/Drug Candidates, click here.

Legal Information

Sold for research purposes under agreement from Pfizer Inc.
LOPAC is a registered trademark of Sigma-Aldrich Co. LLC
Pfizer is a registered trademark of Pfizer, Inc.

Pictograms

Health hazard

Signal Word

Danger

Hazard Statements

Precautionary Statements

Target Organs

Bone

RIDADR

NONH for all modes of transport

WGK Germany

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificate of Analysis
Certificate of Origin
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...
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....
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...
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...
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...
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