| Size | Price | Stock | Qty |
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| 1mg |
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| 5mg |
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| 10mg |
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| 50mg |
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| 100mg |
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| Other Sizes |
| Targets |
Antibacterial agent
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| ln Vitro |
DuP-721 (1.5-4 μg/ml) suppresses Mycobacterium TB strains that are both susceptible to and resistant to traditional antituberculosis medications. Furthermore, it exhibits no cross resistance to any of the studied anti-tuberculosis medications[1]. At 250 μg/ml, DuP-721 is ineffective against M. avium and M. intracellulare. M. kansassi and M. scrofulaceum are inhibited at 1.95 μg/ml and 15.6 μg/ml, respectively, and M. gordonoe and M. fortuitum at 3.9 μg/ml[1].
DL-S-n-(3-(4-acetyl)-2-oxo-5-oxazolidynyl methyl) acetamide (DuP-721) is an orally active representative of the oxazolidinone series of antimicrobials. At concentrations ranging from 1.5 to 4 micrograms/ml, DuP-721 inhibited equally the strains of Mycobacterium tuberculosis susceptible and resistant to conventional antituberculosis drugs. DuP-721 inhibited M. gordonae and M. fortuitum at 3.9 micrograms/ml, M. kansasii at 1.95, and M. scrofulaceum at 15.6 micrograms/ml. It was not active against M. avium and M. intracellulare at concentrations of 250 micrograms/ml. The inhibition of the metabolism of M. tuberculosis as indicated by the liquid scintillation radiometric method was 56% at fourfold the minimum inhibitory concentration (MIC) of DuP-721 that compared well to that of the fourfold MIC concentrations of rifampicin and isoniazid. The in vitro activity of DuP-721 was not affected by reducing the pH from 6.8 to 5.5 [2]. |
| ln Vivo |
Oral gavage of DuP-721 (50-160 mg/kg) provides protection against M. mouse infection with TB. When given daily for 17 days at a dose of 50 mg/kg po, DuP-721 completely protects all infected animals. When the drug is only given on days 11 and 12, post-infection, the same result is seen at a dose of 160 mg/kg[1].
In mice infected with M. tuberculosis, the 50% effective dose (ED50) for DuP-721 was 13.2 mg/kg when administered daily beginning 4 hr postinfection for 17 days. The ED50 was 71.8 mg/kg when DuP-721 was administered only on days 11 and 12 postinfection. A 100% survival rate was obtained at 50 and 160 mg/kg when DuP-721 was administered daily for 17 days, and only on days 11 and 12 after the infection, respectively. The increase in the survival time by DuP-721 at 100 mg/kg (eightfold the ED50 dose) when administered daily for 17 days beginning 4 hr after infection was inferior to that by eightfold the ED50 dose of rifampicin and isoniazid administered on days 11 and 12 postinfection [2]. |
| References |
[1]. Antimycobacterial activities of oxazolidinones: a review. Infect Disord Drug Targets. 2006 Dec;6(4):343-54.
[2]. Oxazolidinones, a new class of synthetic antituberculosis agent. In vitro and in vivo activities of DuP-721 against Mycobacterium tuberculosis. Diagn Microbiol Infect Dis. 1991 Nov-Dec;14(6):465-71. |
| Additional Infomation |
Oxazolidinones are a novel class of fully synthetic antibacterial drugs with broad-spectrum antibacterial activity against a variety of clinically significant susceptible and resistant bacteria. These compounds have been shown to inhibit translation, the initial stage of protein synthesis. The first oxazolidinone compound, DuP-721, showed good anti-tuberculosis activity in experimental animals after oral or parenteral administration, but was not further developed due to lethal toxicity in animal models. Subsequently, two oxazolidinone compounds, PNU-100480 and linezolid, showed good anti-mycobacterial activity in mouse models. Linezolid has been approved for clinical use, while PNU-100480 has not been further developed. DA-7867 showed good antibacterial activity in vitro and superior in vivo antibacterial activity compared to linezolid, but was poorly tolerated in rat toxicology studies. The anti-mycobacterial activity of AZD-2563 has not been investigated. RBx 7644 has weak antibacterial activity against mycobacteria, while RBx 8700 has strong antibacterial activity against all slow-growing mycobacteria, and the activity is concentration-dependent. RBx 8700 has better activity against multidrug-resistant Mycobacterium tuberculosis strains than RBx 7644 and has intracellular activity. Toxicity, especially bone marrow suppression, has always been an important limiting factor in the development of oxazolidinone drugs. GM-CSF detection helps to screen molecules with less potential for bone marrow suppression. This article reviews the great potential of oxazolidinone drugs in the fight against tuberculosis. [1]
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| Molecular Formula |
C14H16N2O4
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|---|---|
| Molecular Weight |
276.29
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| Exact Mass |
276.111
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| Elemental Analysis |
C, 60.86; H, 5.84; N, 10.14; O, 23.16
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| CAS # |
104421-21-8
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| PubChem CID |
9882056
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| Appearance |
White to off-white Solid powder
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| LogP |
1.806
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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 |
4
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| Heavy Atom Count |
20
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| Complexity |
402
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| Defined Atom Stereocenter Count |
1
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| SMILES |
C(C1C=CC(N2CC(CNC(=O)C)OC2=O)=CC=1)(=O)C
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| InChi Key |
POXUJOYUVLWPQN-ZDUSSCGKSA-N
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| InChi Code |
InChI=1S/C14H16N2O4/c1-9(17)11-3-5-12(6-4-11)16-8-13(20-14(16)19)7-15-10(2)18/h3-6,13H,7-8H2,1-2H3,(H,15,18)/t13-/m0/s1
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| Chemical Name |
(S)-N-((3-(4-acetylphenyl)-2-oxooxazolidin-5-yl)methyl)acetamide
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| Synonyms |
Dup-721; Dup721; 4-Acetylphenyloxooxazolidinylmethylacetamide; N-[[3-(4-acetylphenyl)-2-oxo-1,3-oxazolidin-5-yl]methyl]acetamide; 104421-21-8; Acetamide, N-((3-(4-acetylphenyl)-2-oxo-5-oxazolidinyl)methyl)-, (S)-; N-((3-(4-acetylphenyl)-2-oxo-1,3-oxazolidin-5-yl)methyl)acetamide; 3-(4-Acetylphenyl)-5-acetamidomethyl-2-oxazolidinone; SCHEMBL9521400; Dup 721;
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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) |
DMSO : 100 mg/mL (361.94 mM)
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|---|---|
| Solubility (In Vivo) |
Solubility in Formulation 1: ≥ 2.5 mg/mL (9.05 mM) (saturation unknown) in 10% DMSO + 40% PEG300 + 5% Tween80 + 45% Saline (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 400 μL PEG300 and mix evenly; then add 50 μL Tween-80 to the above solution and mix evenly; then add 450 μL normal saline to adjust the volume to 1 mL. Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH₂ O to obtain a clear solution. Solubility in Formulation 2: ≥ 2.5 mg/mL (9.05 mM) (saturation unknown) in 10% DMSO + 90% (20% SBE-β-CD in Saline) (add these co-solvents sequentially from left to right, and one by one), clear solution. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 900 μL of 20% SBE-β-CD physiological saline solution and mix evenly. Preparation of 20% SBE-β-CD in Saline (4°C，1 week): Dissolve 2 g SBE-β-CD in 10 mL saline to obtain a clear solution. View More
Solubility in Formulation 3: ≥ 2.5 mg/mL (9.05 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (add these co-solvents sequentially from left to right, and one by one), clear solution. |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 3.6194 mL | 18.0969 mL | 36.1939 mL | |
| 5 mM | 0.7239 mL | 3.6194 mL | 7.2388 mL | |
| 10 mM | 0.3619 mL | 1.8097 mL | 3.6194 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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