| Size | Price | Stock | Qty |
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| Targets |
23S rRNA of the 50S Ribosomal Subunit. (R)-Linezolid exerts its antibacterial effects by binding to the 23S rRNA of the 50S ribosomal subunit, a site near the peptidyl transferase center (PTC). This binding prevents the formation of the initiation complex for bacterial protein synthesis, effectively blocking the translation of messenger RNA (mRNA) into proteins. By inhibiting the initiation stage specifically, it disrupts bacterial growth (bacteriostatic action against most susceptible Gram-positive organisms).
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| ln Vitro |
Linezolid (the racemate or S-enantiomer) inhibits cell-free protein synthesis with an IC50 of approximately 1-2 microM. Linezolid exhibits MIC values of 1-4 microg/mL against susceptible Gram-positive cocci, including MRSA, VRE, and Streptococcus pneumoniae. The (R)-enantiomer, as the biologically less active form, is used as an impurity standard. The (S)-enantiomer is the clinically active form; the exact IC50 for the pure (R)-enantiomer is significantly higher (less potent).
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| ln Vivo |
In a murine model of systemic infection caused by S. aureus, Linezolid (the S-enantiomer or racemate) (25-100 mg/kg p.o. or i.v.) produces dose-dependent bactericidal activity and improves survival. The (R)-enantiomer is not evaluated for in vivo efficacy due to its low potency and role as an impurity standard. In pharmacokinetic studies, the (R)-enantiomer may have different plasma exposure and clearance rates than the (S)-enantiomer in animals, influencing the safety profile.
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| Enzyme Assay |
Ribosomal binding assays: The 50S ribosomal subunits are isolated from E. coli or S. aureus. The purified 50S subunit (20-50 pmol) is incubated with [3H]-linezolid (or [3H]-chloramphenicol, a known reference ligand) and varying concentrations of (R)-Linezolid (0.1-1000 nM) in binding buffer (50 mM Tris-HCl pH 7.5, 10 mM MgCl2, 50 mM NH4Cl, 6 mM beta-mercaptoethanol) for 60-90 minutes at 37degC. Bound and free radioligands are separated by filtration through nitrocellulose filters, and bound radioactivity is measured by liquid scintillation. IC50 is calculated and converted to Ki.
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| Cell Assay |
S. aureus ATCC 29213 or E. faecium ATCC 51559 are cultured in cation-adjusted Mueller-Hinton broth. A bacterial suspension (0.5 McFarland standard, ~1 × 10⁵ CFU/mL) is added to 96-well plates containing serial two-fold dilutions of (R)-Linezolid (0.03-64 microg/mL) and the reference linezolid. Plates are incubated at 35degC for 18-24 hours. The Minimum Inhibitory Concentration (MIC) is defined as the lowest concentration of the compound that inhibits visible growth (OD600 measured via spectrophotometer). The MIC is determined in triplicate. The (R)-enantiomer is expected to have significantly higher MIC (>32 microg/mL) than the active (S)-enantiomer (MIC 1-4 microg/mL).
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| ADME/Pharmacokinetics |
Not applicable for efficacy studies (impurity standard). In a general PK study, male Sprague-Dawley rats (200-250 g) are dosed orally with racemic linezolid (20 mg/kg). Blood samples are collected at 0, 0.5, 1, 2, 4, 6, 8, 12, 24 h post-dose. Plasma is analyzed by chiral LC-MS/MS to quantify the individual (R) and (S) enantiomers separately using (R)-Linezolid as the reference standard for the (R)-enantiomer peak. PK parameters (Cmax, Tmax, AUC, t½, clearance) for the (R)-enantiomer are calculated.
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| Toxicity/Toxicokinetics |
(R)-Linezolid is not used as a therapeutic drug. The clinically used drug linezolid (Zyvox) has a favorable safety profile. Common adverse effects include diarrhea, nausea, headache, and myelosuppression (thrombocytopenia, anemia, leukopenia) with prolonged use (>2 weeks). Rare but serious side effects include serotonin syndrome (if co-administered with serotonergic drugs), optic/peripheral neuropathy, and lactic acidosis. The (R)-enantiomer's toxicity profile is not separately characterized but is considered an impurity.
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| Additional Infomation |
Linezolid (Zyvox) was FDA-approved in 2000 as the first clinically available oxazolidinone antibiotic for treating infections caused by Gram-positive bacteria, including VRE, MRSA, and nosocomial pneumonia. (R)-Linezolid is used exclusively as an analytical reference standard in pharmaceutical quality control (QC). Its primary application is the detection and quantification of the R-enantiomer impurity in Linezolid API (Active Pharmaceutical Ingredient) and finished drug products to ensure enantiomeric purity, as dictated by pharmacopeial standards (e.g., USP, EP).
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| Molecular Formula |
C₁₆H₂₀FN₃O₄
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|---|---|
| Molecular Weight |
337.35
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| Exact Mass |
337.143
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| CAS # |
872992-20-6
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| PubChem CID |
73180
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| Appearance |
White to off-white solid powder
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| Density |
1.3±0.1 g/cm3
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| Boiling Point |
585.5±50.0 °C at 760 mmHg
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| Flash Point |
307.9±30.1 °C
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| Vapour Pressure |
0.0±1.6 mmHg at 25°C
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| Index of Refraction |
1.554
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| LogP |
0.3
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| Hydrogen Bond Donor Count |
1
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| Hydrogen Bond Acceptor Count |
6
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| Rotatable Bond Count |
4
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| Heavy Atom Count |
24
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| Complexity |
472
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| Defined Atom Stereocenter Count |
1
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| SMILES |
O=C1O[C@H](CNC(=O)C)CN1C1C=CC(N2CCOCC2)=C(F)C=1
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| InChi Key |
TYZROVQLWOKYKF-CYBMUJFWSA-N
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| InChi Code |
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-/m1/s1
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| Chemical Name |
N-[[(5R)-3-(3-fluoro-4-morpholin-4-ylphenyl)-2-oxo-1,3-oxazolidin-5-yl]methyl]acetamide
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| Synonyms |
(R)Linezolid; (R) Linezolid
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| HS Tariff Code |
2934.99.9001
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| Storage |
Powder -20°C 3 years 4°C 2 years In solvent -80°C 6 months -20°C 1 month |
| Shipping Condition |
Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)
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| Solubility (In Vitro) |
May dissolve in DMSO (in most cases), if not, try other solvents such as H2O, Ethanol, or DMF with a minute amount of products to avoid loss of samples
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| Solubility (In Vivo) |
Note: Listed below are some common formulations that may be used to formulate products with low water solubility (e.g. < 1 mg/mL), you may test these formulations using a minute amount of products to avoid loss of samples.
Injection Formulations
Injection Formulation 1: DMSO : Tween 80： Saline = 10 : 5 : 85 (i.e. 100 μL DMSO stock solution → 50 μL Tween 80 → 850 μL Saline)(e.g. IP/IV/IM/SC) *Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH ₂ O to obtain a clear solution. Injection Formulation 2: DMSO : PEG300 ：Tween 80 : Saline = 10 : 40 : 5 : 45 (i.e. 100 μL DMSO → 400 μLPEG300 → 50 μL Tween 80 → 450 μL Saline) Injection Formulation 3: DMSO : Corn oil = 10 : 90 (i.e. 100 μL DMSO → 900 μL Corn oil) Example: Take the Injection Formulation 3 (DMSO : Corn oil = 10 : 90) as an example, if 1 mL of 2.5 mg/mL working solution is to be prepared, you can take 100 μL 25 mg/mL DMSO stock solution and add to 900 μL corn oil, mix well to obtain a clear or suspension solution (2.5 mg/mL, ready for use in animals). View More
Injection Formulation 4: DMSO : 20% SBE-β-CD in saline = 10 : 90 [i.e. 100 μL DMSO → 900 μL (20% SBE-β-CD in saline)] Oral Formulations
Oral Formulation 1: Suspend in 0.5% CMC Na (carboxymethylcellulose sodium) Oral Formulation 2: Suspend in 0.5% Carboxymethyl cellulose Example: Take the Oral Formulation 1 (Suspend in 0.5% CMC Na) as an example, if 100 mL of 2.5 mg/mL working solution is to be prepared, you can first prepare 0.5% CMC Na solution by measuring 0.5 g CMC Na and dissolve it in 100 mL ddH2O to obtain a clear solution; then add 250 mg of the product to 100 mL 0.5% CMC Na solution, to make the suspension solution (2.5 mg/mL, ready for use in animals). View More
Oral Formulation 3: Dissolved in PEG400 (Please use freshly prepared in vivo formulations for optimal results.) |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 2.9643 mL | 14.8214 mL | 29.6428 mL | |
| 5 mM | 0.5929 mL | 2.9643 mL | 5.9286 mL | |
| 10 mM | 0.2964 mL | 1.4821 mL | 2.9643 mL |
*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.
Calculation results
Working concentration： mg/mL；
Method for preparing DMSO stock solution： mg drug pre-dissolved in μL DMSO (stock solution concentration mg/mL). Please contact us first if the concentration exceeds the DMSO solubility of the batch of drug.
Method for preparing in vivo formulation:：Take μL DMSO stock solution, next add μL PEG300, mix and clarify, next addμL Tween 80, mix and clarify, next add μL ddH2O，mix and clarify.
(1) Please be sure that the solution is clear before the addition of next solvent. Dissolution methods like vortex, ultrasound or warming and heat may be used to aid dissolving.
(2) Be sure to add the solvent(s) in order.
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