6594. Nitrocefin

Nomenclature

CAS number: 41906-86-9
(6R,7R)-3-[(1E)-2-(2,4-Dinitrophenyl)ethenyl]-8-oxo-7-[(2-thienylacetyl)amino]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid; 3-(2,4-dinitrostyryl)-(6R,7R)-7-(2-thienylacetamido)-ceph-3-em-4-carboxylic acid, E-isomer; 87/312.
C21H16N4O8S2; mol wt 516.50.
C 48.83%, H 3.12%, N 10.85%, O 24.78%, S 12.42%.

Description and references

Chromogenic cephalosporin. Prepd (not claimed): C. H. O'Callaghan et al., US 3830700 (1974 to Glaxo). Characterization and use in detection of β-lactamases: idem et al., Antimicrob. Agents Chemother. 1, 283 (1972). Synthesis: N. C. M. Barendse et al., Synthesis 1998, 145. Improved synthesis: M. Lee et al., J. Org. Chem. 70, 367 (2005). Review of commercially available nitrocefin-based β-lactamase tests: A. T. Meszaros et al., Am. Clin. Lab. 14, 20-22 (1995).

Chemical structure

Properties

Orange solid, mp 103-113° (dec) (O'Callaghan, 1974); also reported as crystals from methanol, mp 167-169° (dec) (Lee). [α]D20 -224° (c = 1.0 in dioxane). Absorption max (ethanol): 231, 289, 386 nm (ε 24300, 10300, 18000). Absorption max (0.1M pH 6 phosphate buffer): 233, 290, 391 nm (ε 22200, 12200, 17400). Undergoes a color change from yellow to pink or red upon exposure to β-lactamases.

Use

In determn of β-lactamase activity in biological samples.