Nitrocefin

• CAT Number: R039865
• CAS Number: 41906-86-9
• Molecular Formula: C21H16N4O8S2
• Molecular Weight: 516.499
• Purity: ≥95%
• Storage: -20°C
• IUPAC Name: (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
• InChI: InChI=1S/C21H16N4O8S2/c26-16(9-14-2-1-7-34-14)22-17-19(27)23-18(21(28)29)12(10-35-20(17)23)4-3-11-5-6-13(24(30)31)8-15(11)25(32)33/h1-8,17,20H,9-10H2,(H,22,26)(H,28,29)/b4-3+/t17-,20-/m1/s1
• InChIKey: LHNIIDJCEODSHA-OQRUQETBSA-N
• SMILES: C(O)(=O)C=1N2[C@@]([C@H](NC(CC3=CC=CS3)=O)C2=O)(SCC1/C=C/C4=C(N(=O)=O)C=C(N(=O)=O)C=C4)[H]

Nitrocefin is a cephalosporin with chromogenic properties and is routinely used to detect beta-lactamase enzymes produced by beta-lactam resistant bacteria. Nitrocefin is soluble in DMSO and is commonly used at a 1.0 mg/mL concentration.Essentially all beta-lactamase enzymes hydrolyze the amide bond between the carbonyl carbon and the nitrogen in the beta-lactam ring of nitrocefin. Macroscopic detection of this process is made possible because a ultraviolet absorption shift from intact versus hydrolyzed nitrocefin occurs within the visible light spectrum (~380 nm to ~500 nm, or yellow to red).

Reference

O/’Callaghan, Cynthia H. et. al. /Novel Method for Detection of B-Lactamases by Using a Chromogenic Cephalosporin Substrate./ Antimicrobial Agents and Chemotherapy 1.4 (1972): 283-88. Ncbi.gov Web. 10 Oct. 2012.Parr, T. R., Jr. /Simple Screening Method for Beta-lactamase-positive and -negative Ampicillin-resistant Haemophilus Influenzae Isolates./ Journal of Clinical Microbiology 20.1 (1984): 131-32. Ncbi.gov. Web. 10 Oct. 2012.