Toggle Nav
Close
  • Menu
  • Setting

Linezolid

Catalog No.
A5181
Antibacterial reagent
Grouped product items
SizePriceStock Qty
10mM (in 1mL DMSO)
$60.00
In stock
10mg
$58.00
In stock
25mg
$105.00
In stock
100mg
$285.00
In stock

Tel: +1-832-696-8203

Email: [email protected]

Worldwide Distributors

Background

Linezolid, a synthetic oxazolidinone antimicrobial, shows a wide spectrum against Gram-positive bacteria andmultidrug-resistant bacteria such as anaerobes, methicillin-resistant Staphylococcus aureus (MRSA), vancomycin-resistant enterococci, penicillin-resistant pneumococci and streptococcus [1,2].

Oxazolidinones could inhibit protein synthesis by binding to a site on the bacterial 23S ribosomal RNA of the 50S subunit and prevent the formation of a functional 70S-initiation complex. Linezolid is also a weak, nonselective and reversible inhibitor of monoamine oxidase [2].

In Vitro: Linezolid was a potent inhibitor of cell-free transcription-translation in E. coli. IC50 was 1.8 mM[3]. linezolid MICs vary slightly owing to the different test method and laboratory. The MIC values were between 0.5 and 4 mg/L for streptococci, enterococci and staphylococci [4].

Clinical Trials: Linezolid is fully bioavailable following oral administration, with maximum plasma linezolid concentrations achieved between 1 and 2 hours after oral administration. The elimination half-life of linezolid is 5–7 hours, and twice-daily administration of 400–600mg provides steady-state concentrations in the therapeutic range[5].

In clinical trials involving hospitalised patients with skin/soft tissue infections (predominantly S. aureus), intravenous/oral administration of linezolid (up to 1250 mg/day) produced clinical success in > 83% of individuals. In patients with community-acquired pneumonia, success rates were > 94%[6]. Linezolid could also be used in patients with nosocomial pneumonia[7].Linezolid appears to be well tolerated and the most common side effects is gastrointestinal disturbances [6].

References:
[1] Tsiodras S, Gold H S, Sakoulas G, et al.  Linezolid resistance in a clinical isolate of Staphylococcus aureus[J]. The Lancet, 2001, 358(9277): 207-208.
[2] Swaney S M, Aoki H, Ganoza M C, et al.  The oxazolidinone linezolid inhibits initiation of protein synthesis in bacteria[J]. Antimicrobial agents and chemotherapy, 1998, 42(12): 3251-3255.
[3] Shinabarger D L, Marotti K R, Murray R W, et al.  Mechanism of action of oxazolidinones: effects of linezolid and eperezolid on translation reactions[J]. Antimicrobial agents and chemotherapy, 1997, 41(10): 2132-2136.
[4] Livermore D M.  Linezolid in vitro: mechanism and antibacterial spectrum[J]. Journal of antimicrobial chemotherapy, 2003, 51(suppl 2): ii9-ii16.
[5] Stalker D J, Jungbluth G L.  Clinical pharmacokinetics of linezolid, a novel oxazolidinoneantibacterial[J]. Clinical pharmacokinetics, 2003, 42(13): 1129-1140.
[6] Clemett D, Markham A.  Linezolid[J]. Drugs, 2000, 59(4): 815-827.
[7] Wunderink R G, Cammarata S K, Oliphant T H, et al.  Continuation of a randomized, double-blind, multicenter study of linezolid versus vancomycin in the treatment of patients with nosocomial pneumonia[J]. Clinical therapeutics, 2003, 25(3): 980-992.

Chemical Properties

Physical AppearanceA solid
StorageStore at -20°C
M.Wt337.35
Cas No.165800-03-3
FormulaC16H20FN3O4
Solubility≥16.85 mg/mL in DMSO; ≥2.48 mg/mL in H2O with gentle warming and ultrasonic; ≥9.5 mg/mL in EtOH with ultrasonic
Chemical NameN-[[(5S)-3-(3-fluoro-4-morpholin-4-ylphenyl)-2-oxo-1,3-oxazolidin-5-yl]methyl]acetamide
SDFDownload SDF
Canonical SMILESCC(=O)NCC1CN(C(=O)O1)C2=CC(=C(C=C2)N3CCOCC3)F
Shipping ConditionEvaluation sample solution: ship with blue ice. All other available sizes: ship with RT, or blue ice upon request.
General tipsFor obtaining a higher solubility, please warm the tube at 37°C and shake it in the ultrasonic bath for a while. Stock solution can be stored below -20°C for several months.

Protocol

Antibacterial test [1]:

Bacteria

E. coli UC6782

Preparation method

The solubility of this compound in DMSO is > 16.9 mg/mL. General tips for obtaining a higher concentration: Please warm the tube at 37 °C for 10 minutes and/or shake it in the ultrasonic bath for a while. Stock solution can be stored below - 20 °C for several months.

Reacting condition

0.01 ~ 1000 μM; 60 mins

Applications

Linezolid potently inhibited protein synthesis in E. coli UC6782, with the IC90 value of 30 μM. Linezolid was at least 2.5 times more potent than DuP-721 and about twice as potent as streptomycin.

References:

[1]. Shinabarger D L, Marotti K R, Murray R W, et al. Mechanism of action of oxazolidinones: effects of linezolid and eperezolid on translation reactions[J]. Antimicrobial agents and chemotherapy, 1997, 41(10): 2132-2136.

Quality Control