Oxazolidinones are a novel class of synthetic, orally-active antibacterial agents. DuP 105, which is representative of this class of compounds, is synthesized as a racemic mixture of two diastereoisomers. To ensure lot-to-lot consistency, separation and quantitation of these diastereoisomers is essential. Separation by reverse phase LC has not been achieved. This paper presents a supercritical fluid chromatography method using a Chiralcel OD column to resolve these diastereoisomers. A retention mechanism is briefly elaborated, based on the effects of temperature, pressure, percent modifier and type of modifier on resolution.

01 Sep 1993·Biochemical and Biophysical Research CommunicationsQ3 · BIOLOGY

The Oxazolidinone Antibacterial Agent DuP 105 Does Not Act on Cell Wall Biosynthesis or on a β-Lactamase

Q3 · BIOLOGY

Article

Author: Richard B. Silverman ; Rabindra K. Sinha ; Nam Tran ; Francis C. Neuhaus

(S)-3-(4-Methylsulfinylphenyl)-5-(acetamidomethyl)oxazolidinone (DuP 105; 1, R = CH3SO, R' = Ac), one of a new class of antibacterial agents, is shown to be devoid of inactivation and inhibitory properties toward bacterial cell wall biosynthesis and toward a beta-lactamase. This is consistent with the idea that this class of compounds acts by a route different from that of the beta-lactam antibiotics.

01 Jan 1990·Drugs under experimental and clinical research

An automated pulse labelling method for structure-activity relationship studies with antibacterial oxazolidinones.

Article

Author: Feldman, P A ; Eustice, D C ; Brown, L J ; Brittelli, D R ; Slee, A M ; Borkowski, J J

The 3-aryl-2-oxooxazolidinones are a new class of synthetic antibacterial agents that potently inhibit protein synthesis. An automated pulse labelling method with [3H]-lysine was developed with Bacillus subtilis to obtain additional quantitative activity data for structure-activity relationship studies with the oxazolidinones. Inhibition constants were calculated after a Logit fit of the data into the formula: % of control = 100/(1 + e[-B(X - A)]), where B is the slope of the model, X is the natural log of the inhibitor concentration and A is the natural log of the inhibitor concentration required to inhibit protein synthesis by 50% (ln IC50). When substituents at the 5-methyl position of the heterocyclic ring (B-substituent) were NHCOCH3, OH or Cl, the correlation coefficient was 0.87 between the MIC and IC50 values (for all compounds with MICs less than or equal to 16 micrograms/ml). The D-isomers of DuP 721 (A-substituent = CH3CO) and DuP 105 (A-substituent = CH3SO) gave MICs of 128 micrograms/ml and IC50s of greater than or equal to 50 micrograms/ml for protein synthesis, showing that only the L-isomers were active. By MIC testing, oxazolidinones with the B-substituent of NHCOCH3 and the A-substituent of CH3CO, NO2, CH3S, CH3SO2 or (CH3)2CH had comparable antibacterial potency; however, pulse labelling analysis showed that compounds with an A-substituent of CH3CO or NO2 were more potent inhibitors of protein synthesis.

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Indication	Highest Phase	Country/Location	Organization	Date
Anaerobic bacterial infection	Phase 1	US	Bristol Myers Squibb Co.	-
Gram-Positive Bacterial Infections	Phase 1	US	Bristol Myers Squibb Co.	-

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