Dup-721
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MedKoo CAT#: 464747

CAS#: 104421-21-8

Description: Dup-721 is a new antimicrobial agent belonging to the oxazolidinone series, a new class of synthetic antibacterial agents.

Chemical Structure

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Dup-721
CAS# 104421-21-8
Product data Instruction

Theoretical Analysis

MedKoo Cat#: 464747
Name: Dup-721
CAS#: 104421-21-8
Chemical Formula: C14H16N2O4
Exact Mass: 276.11
Molecular Weight: 276.292
Elemental Analysis: C, 60.86; H, 5.84; N, 10.14; O, 23.16

Price and Availability

Size Price Availability Quantity
5mg USD 150 Ready to ship
10mg USD 250 Ready to ship
25mg USD 550 Ready to ship
50mg USD 950 Ready to ship
100mg USD 1650 Ready to ship
200mg USD 2650 Ready to ship
Bulk inquiry

Synonym: Dup-721; Dup721; Dup 721;

IUPAC/Chemical Name: (S)-N-((3-(4-acetylphenyl)-2-oxooxazolidin-5-yl)methyl)acetamide

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

SMILES Code: CC(C1=CC=C(N2C[C@H](CNC(C)=O)OC2=O)C=C1)=O

Appearance: Solid powder

Purity: >98% (or refer to the Certificate of Analysis)

Shipping Condition: Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition: Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility: To be determined

Shelf Life: >2 years if stored properly

Drug Formulation: To be determined

Stock Solution Storage: 0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code: 2934.99.9001

More Info:

Biological target: DuP-721 is a broad spectrum and orally active antibacterial agent against a variety of clinically susceptible and resistant bacteria, especially M. tuberculosis.
In vitro activity: 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. Reference: Diagn Microbiol Infect Dis. Nov-Dec 1991;14(6):465-71. https://pubmed.ncbi.nlm.nih.gov/1802533/
In vivo activity: 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. These results indicate that DuP-721 is protective against M. tuberculosis infection in mice. Reference: Diagn Microbiol Infect Dis. Nov-Dec 1991;14(6):465-71. https://pubmed.ncbi.nlm.nih.gov/1802533/

Solubility Data

Solvent Max Conc. mg/mL Max Conc. mM
Solubility
DMSO 100.0 361.94

Preparing Stock Solutions

The following data is based on the product molecular weight 276.29 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
Formulation protocol: 1. Slee AM, Wuonola MA, McRipley RJ, Zajac I, Zawada MJ, Bartholomew PT, Gregory WA, Forbes M. Oxazolidinones, a new class of synthetic antibacterial agents: in vitro and in vivo activities of DuP 105 and DuP 721. Antimicrob Agents Chemother. 1987 Nov;31(11):1791-7. doi: 10.1128/AAC.31.11.1791. PMID: 3435127; PMCID: PMC175041. 2. Ashtekar DR, Costa-Periera R, Shrinivasan T, Iyyer R, Vishvanathan N, Rittel W. 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. doi: 10.1016/0732-8893(91)90002-w. PMID: 1802533.
In vitro protocol: 1. Slee AM, Wuonola MA, McRipley RJ, Zajac I, Zawada MJ, Bartholomew PT, Gregory WA, Forbes M. Oxazolidinones, a new class of synthetic antibacterial agents: in vitro and in vivo activities of DuP 105 and DuP 721. Antimicrob Agents Chemother. 1987 Nov;31(11):1791-7. doi: 10.1128/AAC.31.11.1791. PMID: 3435127; PMCID: PMC175041. 2. Ashtekar DR, Costa-Periera R, Shrinivasan T, Iyyer R, Vishvanathan N, Rittel W. 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. doi: 10.1016/0732-8893(91)90002-w. PMID: 1802533.
In vivo protocol: 1. Slee AM, Wuonola MA, McRipley RJ, Zajac I, Zawada MJ, Bartholomew PT, Gregory WA, Forbes M. Oxazolidinones, a new class of synthetic antibacterial agents: in vitro and in vivo activities of DuP 105 and DuP 721. Antimicrob Agents Chemother. 1987 Nov;31(11):1791-7. doi: 10.1128/AAC.31.11.1791. PMID: 3435127; PMCID: PMC175041. 2. Ashtekar DR, Costa-Periera R, Shrinivasan T, Iyyer R, Vishvanathan N, Rittel W. 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. doi: 10.1016/0732-8893(91)90002-w. PMID: 1802533.

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1: Jadhavar PS, Vaja MD, Dhameliya TM, Chakraborti AK. Oxazolidinones as Anti- tubercular Agents: Discovery, Development and Future Perspectives. Curr Med Chem. 2015;22(38):4379-97. doi: 10.2174/0929867323666151106125759. PMID: 26549430.

2: Sood R, Bhadauriya T, Rao M, Gautam R, Malhotra S, Barman TK, Upadhyay DJ, Rattan A. Antimycobacterial activities of oxazolidinones: a review. Infect Disord Drug Targets. 2006 Dec;6(4):343-54. doi: 10.2174/187152606779025860. PMID: 17168800.

3: Ford CW, Zurenko GE, Barbachyn MR. The discovery of linezolid, the first oxazolidinone antibacterial agent. Curr Drug Targets Infect Disord. 2001 Aug;1(2):181-99. doi: 10.2174/1568005014606099. PMID: 12455414.

4: Burghardt H, Schimz KL, Müller M. On the target of a novel class of antibiotics, oxazolidinones, active against multidrug-resistant Gram-positive bacteria. FEBS Lett. 1998 Mar 20;425(1):40-4. doi: 10.1016/s0014-5793(98)00194-x. PMID: 9541003.

5: Ford CW, Hamel JC, Stapert D, Moerman JK, Hutchinson DK, Barbachyn MR, Zurenko GE. Oxazolidinones: new antibacterial agents. Trends Microbiol. 1997 May;5(5):196-200. doi: 10.1016/S0966-842X(97)01032-9. PMID: 9160508.

6: Gleave DM, Brickner SJ. Oxazolidinone Antibacterial Agents. An Enantioselective Synthesis of the [6,5,5] Tricyclic Fused Oxazolidinone Ring System and Application to the Synthesis of a Rigid DuP 721 Analogue. J Org Chem. 1996 Sep 6;61(18):6470-6474. doi: 10.1021/jo960945s. PMID: 11667499.

7: Ashtekar DR, Costa-Perira R, Nagrajan K, Vishvanathan N, Bhatt AD, Rittel W. In vitro and in vivo activities of the nitroimidazole CGI 17341 against Mycobacterium tuberculosis. Antimicrob Agents Chemother. 1993 Feb;37(2):183-6. doi: 10.1128/AAC.37.2.183. PMID: 8452346; PMCID: PMC187635.

8: Brumfitt W, Hamilton-Miller JM. Antibacterial oxazolidinones. In vitro activity of a new analogue, E3709. Diagn Microbiol Infect Dis. 1992 Sep- Oct;15(7):621-5. doi: 10.1016/0732-8893(90)90040-3. PMID: 1424519.

9: Ashtekar DR, Costa-Periera R, Shrinivasan T, Iyyer R, Vishvanathan N, Rittel W. 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. doi: 10.1016/0732-8893(91)90002-w. PMID: 1802533.

10: Eustice DC, Brittelli DR, Feldman PA, Brown LJ, Borkowski JJ, Slee AM. An automated pulse labelling method for structure-activity relationship studies with antibacterial oxazolidinones. Drugs Exp Clin Res. 1990;16(4):149-55. PMID: 2127566.

11: Brumfitt W, Hamilton-Miller JM, Gargan RA. Variation in response of gram- positive cocci to the combination DuP 721 and ciprofloxacin. J Antimicrob Chemother. 1989 Sep;24(3):465-7. doi: 10.1093/jac/24.3.465. PMID: 2808200.

12: Maple PA, Hamilton-Miller JM, Brumfitt W. Comparative in-vitro activity of vancomycin, teicoplanin, ramoplanin (formerly A16686), paldimycin, DuP 721 and DuP 105 against methicillin and gentamicin resistant Staphylococcus aureus. J Antimicrob Chemother. 1989 Apr;23(4):517-25. doi: 10.1093/jac/23.4.517. PMID: 2526111.

13: Mini E, Novelli A, Mazzei T, Periti P. Comparative in vitro activity of the new oxazolidinones DuP 721 and DuP 105 against staphylococci and streptococci. Eur J Clin Microbiol Infect Dis. 1989 Mar;8(3):256-60. doi: 10.1007/BF01965273. PMID: 2523807.

14: Eustice DC, Feldman PA, Zajac I, Slee AM. Mechanism of action of DuP 721: inhibition of an early event during initiation of protein synthesis. Antimicrob Agents Chemother. 1988 Aug;32(8):1218-22. doi: 10.1128/AAC.32.8.1218. PMID: 2461163; PMCID: PMC172380.

15: Daly JS, Eliopoulos GM, Reiszner E, Moellering RC Jr. Activity and mechanism of action of DuP 105 and DuP 721, new oxazolidinone compounds. J Antimicrob Chemother. 1988 Jun;21(6):721-30. doi: 10.1093/jac/21.6.721. PMID: 3410799.

16: Brumfitt W, Hamilton-Miller JM. In-vitro microbiological activities of DuP 105 and DuP 721, novel synthetic oxazolidinones. J Antimicrob Chemother. 1988 Jun;21(6):711-20. doi: 10.1093/jac/21.6.711. PMID: 3137206.

17: Neu HC, Novelli A, Saha G, Chin NX. In vitro activities of two oxazolidinone antimicrobial agents, DuP 721 and DuP 105. Antimicrob Agents Chemother. 1988 Apr;32(4):580-3. doi: 10.1128/AAC.32.4.580. PMID: 3377467; PMCID: PMC172224.

18: Eustice DC, Feldman PA, Slee AM. The mechanism of action of DuP 721, a new antibacterial agent: effects on macromolecular synthesis. Biochem Biophys Res Commun. 1988 Feb 15;150(3):965-71. doi: 10.1016/0006-291x(88)90723-1. PMID: 2449210.

19: Barry AL. In vitro evaluation of DuP 105 and DuP 721, two new oxazolidinone antimicrobial agents. Antimicrob Agents Chemother. 1988 Jan;32(1):150-2. doi: 10.1128/AAC.32.1.150. PMID: 3348606; PMCID: PMC172119.

20: Slee AM, Wuonola MA, McRipley RJ, Zajac I, Zawada MJ, Bartholomew PT, Gregory WA, Forbes M. Oxazolidinones, a new class of synthetic antibacterial agents: in vitro and in vivo activities of DuP 105 and DuP 721. Antimicrob Agents Chemother. 1987 Nov;31(11):1791-7. doi: 10.1128/AAC.31.11.1791. PMID: 3435127; PMCID: PMC175041.