| Size | Price | Stock | Qty |
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| 50mg |
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| 100mg |
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| Other Sizes |
| Targets |
The compound itself does not have a specific biological target. However, oxazolidinone derivatives are a well-established class of antibacterial agents that target the bacterial 50S ribosomal subunit. They inhibit protein synthesis by binding to the peptidyl transferase center, preventing the formation of the initiation complex. Examples include linezolid and tedizolid. (S)-Methyl 2-oxooxazolidine-4-carboxylate is a synthetic precursor that can be elaborated into such active antibacterial compounds through further chemical transformations.
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| ln Vitro |
The parent compound is not directly tested for antibacterial activity; rather, its derivatives are. Oxazolidinone antibiotics derived from such intermediates exhibit potent in vitro activity against Gram-positive pathogens, including methicillin-resistant Staphylococcus aureus (MRSA), vancomycin-resistant Enterococci (VRE), and multidrug-resistant Streptococcus pneumoniae. Minimum inhibitory concentration (MIC) values for clinically used oxazolidinones like linezolid are typically 1-4 microg/mL against susceptible strains. These compounds inhibit protein synthesis by binding to the 23S rRNA of the 50S ribosomal subunit.
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| ln Vivo |
No specific in vivo activity data for the parent compound (S)-Methyl 2-oxooxazolidine-4-carboxylate is available. However, oxazolidinone antibiotics synthesized from this building block have well-established in vivo activity. For example, linezolid shows excellent bioavailability (>90% oral) and tissue penetration in animal models of infection. In murine thigh infection models, linezolid produces dose-dependent bacterial killing with a pharmacokinetic/pharmacodynamic (PK/PD) index target of AUC/MIC ratio > 80. Tedizolid, a newer oxazolidinone, demonstrates once-daily dosing and enhanced potency in animal models.
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| Enzyme Assay |
Non-cellular assays for measuring the antibacterial activity of oxazolidinone derivatives include ribosomal binding assays. A standard protocol uses purified 50S ribosomal subunits from S. aureus. The test compound is incubated with 50S subunits at 37degC for 10 minutes in binding buffer (20 mM Tris-HCl pH 7.6, 100 mM NH4Cl, 10 mM MgCl2). A radiolabeled probe (e.g., 3H-labeled linezolid) is added, followed by a 30-minute incubation. Unbound compound is removed by rapid filtration through nitrocellulose filters, and bound radioactivity is measured by liquid scintillation counting. Specific binding is determined by subtracting non-specific binding in the presence of an excess of unlabeled compound.
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| Cell Assay |
Cells for testing antibacterial activity include a panel of Gram-positive bacterial strains. A standard broth microdilution assay follows CLSI guidelines M07. Bacterial cultures are grown overnight in Mueller-Hinton broth at 37degC. The cultures are diluted to approximately 5 × 10⁵ CFU/mL. The test compound (S)-Methyl 2-oxooxazolidine-4-carboxylate or its derivatives are serially diluted 2-fold (0.03-64 microg/mL) in 96-well plates. Bacterial suspension (100 microL) is added to each well, and plates are incubated at 37degC for 18-24 hours. MIC is read as the lowest concentration with no visible growth, using a microplate reader at 600 nm or visual inspection.
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| Animal Protocol |
In vivo experiments for oxazolidinone antibiotics typically use a murine model of systemic infection. Female BALB/c mice (6-8 weeks) are inoculated intraperitoneally with a lethal dose of S. aureus (approx. 1 × 10⁷ CFU/mouse) suspended in 5% mucin. Test compound, (S)-Methyl 2-oxooxazolidine-4-carboxylate derivative, is administered orally or intravenously 1 hour post-infection. Doses typically range from 1-50 mg/kg. Survival is monitored for 7 days. For pharmacokinetic/pharmacodynamic studies, neutropenic mouse thigh infection models involve subcutaneous administration every 4-8 hours, with bacterial burden measured by homogenizing and plating thigh tissues.
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| ADME/Pharmacokinetics |
(S)-Methyl 2-oxooxazolidine-4-carboxylate has a molecular weight of 145.11 g/mol and a molecular formula of C₅H₇NO4. It is a white to off-white solid at room temperature. The compound is soluble in organic solvents such as methanol, ethanol, DMSO, and dichloromethane but has limited solubility in water. As an ester, it is susceptible to hydrolysis under basic conditions. It should be stored at -20degC in a tightly sealed container under anhydrous conditions to maintain stability. Chiral purity is typically >99% enantiomeric excess (ee) due to the (S) configuration at the 4-position.
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| Toxicity/Toxicokinetics |
Detailed toxicological data for the parent compound is not publicly available. However, based on its oxazolidinone core structure and ester functional group, it is expected to have moderate acute toxicity. The compound may cause skin and eye irritation upon contact. As an ester, it may be metabolized by plasma esterases to the corresponding carboxylic acid, which may have reduced biological activity. For structurally related oxazolidinones, chronic toxicity includes reversible myelosuppression (thrombocytopenia and anemia) associated with prolonged use. Standard laboratory precautions should be followed during handling.
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| Additional Infomation |
(S)-Methyl 2-oxooxazolidine-4-carboxylate is a key chiral building block used in the pharmaceutical industry for the synthesis of antibacterial agents, particularly oxazolidinone antibiotics. It is not an approved drug and has not undergone clinical trials. The compound enables the introduction of the essential 4-(S)-stereochemistry required for oxazolidinone antibacterial activity. It is used in drug discovery programs for optimizing potency, pharmacokinetics, and safety profiles. Additionally, it serves as a precursor for synthesizing chiral amines, amino alcohols, and other heterocyclic scaffolds for medicinal chemistry.
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| Molecular Formula |
C5H7NO4
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|---|---|
| Molecular Weight |
145.11
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| Exact Mass |
145.038
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| CAS # |
132682-22-5
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| PubChem CID |
385463
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| Appearance |
Liquid
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| Density |
1.3±0.1 g/cm3
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| Boiling Point |
357.8±31.0 °C at 760 mmHg
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| Flash Point |
170.2±24.8 °C
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| Vapour Pressure |
0.0±0.8 mmHg at 25°C
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| Index of Refraction |
1.456
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| LogP |
-0.32
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| Hydrogen Bond Donor Count |
1
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| Hydrogen Bond Acceptor Count |
4
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| Rotatable Bond Count |
2
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| Heavy Atom Count |
10
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| Complexity |
167
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| Defined Atom Stereocenter Count |
1
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| SMILES |
O=C1OC[C@@H](C(OC)=O)N1
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| InChi Key |
PZIWTVKXOORXAZ-VKHMYHEASA-N
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| InChi Code |
InChI=1S/C5H7NO4/c1-9-4(7)3-2-10-5(8)6-3/h3H,2H2,1H3,(H,6,8)/t3-/m0/s1
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| Chemical Name |
methyl (4S)-2-oxo-1,3-oxazolidine-4-carboxylate
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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 Note: This product requires protection from light (avoid light exposure) during transportation and storage. |
| 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 | 6.8913 mL | 34.4566 mL | 68.9132 mL | |
| 5 mM | 1.3783 mL | 6.8913 mL | 13.7826 mL | |
| 10 mM | 0.6891 mL | 3.4457 mL | 6.8913 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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