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PZ0014

Sigma-Aldrich

Linezolid

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

Synonym(e):

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

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About This Item

Empirische Formel (Hill-System):
C16H20FN3O4
CAS-Nummer:
165800-03-3
Molekulargewicht:
337.35
MDL-Nummer:
MFCD00937825
UNSPSC-Code:
12352200
PubChem Substanz-ID:
329823683
NACRES:
NA.77

product name

Linezolid, ≥98% (HPLC)

Qualitätsniveau

100

Assay

≥98% (HPLC)

Form

powder

Farbe

white to off-white

Löslichkeit

DMSO: >20 mg/mL

Lagertemp.

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

InChIKey

TYZROVQLWOKYKF-ZDUSSCGKSA-N

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Allgemeine Beschreibung

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.

Anwendung

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. Wirkung

Linezolid ist ein Oxazolidinonantimikrobiotikum. Es bindet an eine Stelle der bakteriellen 23S-ribsomalen RNA der 50S-Untereinheit und verhindert die Bildung eines funktionellen 70S-Initiationskomplexes, wodurch es die bakterielle mRNA-Translation hemmt. Linezolid ist auch ein schwacher, reversibler, nicht selektiver Inhibitor von Monoaminoxidase.

Piktogramme

Health hazard
GHS08

Signalwort

Danger

H-Sätze

H372

Gefahreneinstufungen

STOT RE 1 Oral

Zielorgane

Bone

Lagerklassenschlüssel

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

WGK

WGK 3

Flammpunkt (°F)

Not applicable

Flammpunkt (°C)

Not applicable

Analysenzertifikate (COA)

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Die Dokumentenbibliothek aufrufen

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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