Nitrocefin

Nitrocefin is a highly activated, chromogenic cephalosporin derivative. Nitrocefin is a chromogenic β-lactamase substrate. Nitrocefin undergoes a distinctive color change from yellow to red as the amide bond in the β-lactam ring is hydrolyzed by β-lactamase. Nitrocefin is used in competitive inhibition studies in developmental work on β-lactamase-resistant antibiotics[1][2][3][4].

Product Specifications

CAS Number

[41906-86-9]

UNSPSC

12352005

Hazard Statement

H302, H315, H319, H335

Target

Antibiotic; Bacterial; Beta-lactamase

Type

Reference compound

Related Pathways

Anti-infection

Applications

COVID-19-immunoregulation

Field of Research

Infection

Assay Protocol

https://www.medchemexpress.com/nitrocefin.html

Purity

98.11

Solubility

DMSO : 100 mg/mL (ultrasonic)

Smiles

O=C(C(N12)=C(/C=C/C3=CC=C([N+]([O-])=O)C=C3[N+]([O-])=O)CS[C@]2([H])[C@H](NC(CC4=CC=CS4)=O)C1=O)O

Molecular Formula

C21H16N4O8S2

Molecular Weight

516.50

Precautions

H302, H315, H319, H335

References & Citations

[1]Lee M, et al. A practical synthesis of nitrocefin. J Org Chem. 2005 Jan 7;70 (1) :367-9.|[2]Worthington RJ, et al. Overcoming resistance to β-lactam antibiotics. J Org Chem. 2013 May 3;78 (9) :4207-13.|[3]O'Callaghan CH, et al. Novel method for detection of beta-lactamases by using a chromogenic cephalosporin substrate. Antimicrob Agents Chemother. 1972 Apr;1 (4) :283-8.|[4]Chow C, et al. Blanchard JS. Kinetic characterization of hydrolysis of nitrocefin, cefoxitin, and meropenem by β-lactamase from Mycobacterium tuberculosis. Biochemistry. 2013 Jun 11;52 (23) :4097-104.