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Dup-721

Alias: 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;
Cat No.:V52150 Purity: ≥98%
DuP-721 is a broad-spectrum orally bioactive antibacterial agent that is effective against a variety of clinically sensitive and drug-resistant bacteria, especially M. tuberculosis.
Dup-721
Dup-721 Chemical Structure CAS No.: 104421-21-8
Product category: Bacterial
This product is for research use only, not for human use. We do not sell to patients.
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Product Description
DuP-721 is a broad-spectrum orally bioactive antibacterial agent that is effective against a variety of clinically sensitive and drug-resistant bacteria, especially M. tuberculosis.
Biological Activity I Assay Protocols (From Reference)
Targets
Antibacterial agent
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 new class of totally synthetic antibacterial agents with wide spectrum of activity against a variety of clinically significant susceptible and resistant bacteria. These compounds have been shown to inhibit translation at the initiation phase of protein synthesis. DuP-721, the first oxazolidinone showed good activity against M. tuberculosis when given orally or parenterally to experimental animals but was not developed further due to lethal toxicity in animal models. Later two oxazolidinones, PNU-100480 and Linezolid, demonstrated promising antimycobacterial activities in the murine model. While Linezolid has been approved for clinical use, PNU-100480 was not been developed further. DA-7867 showed good in vitro and better in vivo efficacy than Linezolid but was poorly tolerated in rat toxicology studies. The antimycobacterial activity of AZD-2563 has not been explored. RBx 7644 had modest antimycobacterial activity while RBx 8700 has potent antibacterial and concentration dependent activity against all slow growing mycobacteria. It demonstrated better activity than RBx 7644 against MDR strains of M. tuberculosis along with intracellular activity. Toxicity, especially myelosuppression, has been an important limiting factor for development of an oxazolidinones. The GM-CSF assay has helped in selecting molecules with less myleosuppressive potential. We report, a review on the promising antituberculosis activities of the class oxazolidinones. [1]
These protocols are for reference only. InvivoChem does not independently validate these methods.
Physicochemical Properties
Molecular Formula
C14H16N2O4
Molecular Weight
276.29
Exact Mass
276.111
Elemental Analysis
C, 60.86; H, 5.84; N, 10.14; O, 23.16
CAS #
104421-21-8
PubChem CID
9882056
Appearance
White to off-white Solid powder
LogP
1.806
Hydrogen Bond Donor Count
1
Hydrogen Bond Acceptor Count
4
Rotatable Bond Count
4
Heavy Atom Count
20
Complexity
402
Defined Atom Stereocenter Count
1
SMILES
C(C1C=CC(N2CC(CNC(=O)C)OC2=O)=CC=1)(=O)C
InChi Key
POXUJOYUVLWPQN-ZDUSSCGKSA-N
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
Chemical Name
(S)-N-((3-(4-acetylphenyl)-2-oxooxazolidin-5-yl)methyl)acetamide
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;
HS Tariff Code
2934.99.9001
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)
Solubility Data
Solubility (In Vitro)
DMSO : 100 mg/mL (361.94 mM)
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.

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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.
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 corn oil and mix evenly.


 (Please use freshly prepared in vivo formulations for optimal results.)
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.

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What is the mass of compound required to make a 10 mM stock solution in 5 ml of DMSO given that the molecular weight of the compound is 350.26 g/mol?
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Dilution Calculator allows you to calculate how to dilute a stock solution of known concentrations. For example, you may Enter C1, C2 & V2 to calculate V1, as detailed below:

What volume of a given 10 mM stock solution is required to make 25 ml of a 25 μM solution?
Using the equation C1V1 = C2V2, where C1=10 mM, C2=25 μM, V2=25 ml and V1 is the unknown:
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  • The answer of 62.5 μL (0.1 ml) appears in the Volume (Start) box
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Molecular Weight Calculator allows you to calculate the molar mass and elemental composition of a compound, as detailed below:

Note: Chemical formula is case sensitive: C12H18N3O4  c12h18n3o4
Instructions to calculate molar mass (molecular weight) of a chemical compound:
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Definitions of molecular mass, molecular weight, molar mass and molar weight:
  • Molecular mass (or molecular weight) is the mass of one molecule of a substance and is expressed in the unified atomic mass units (u). (1 u is equal to 1/12 the mass of one atom of carbon-12)
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In vivo Formulation Calculator (Clear solution)
Step 1: Enter information below (Recommended: An additional animal to make allowance for loss during the experiment)
Step 2: Enter in vivo formulation (This is only a calculator, not the exact formulation for a specific product. Please contact us first if there is no in vivo formulation in the solubility section.)
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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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