Description

Nitrocefin (CAS No. 41906-86-9) is a highly sensitive chromogenic cephalosporin substrate widely utilized in microbiology and biochemical research for the detection of β-lactamase activity. With the molecular formula C₂₁H₁₆N₄O₈S₂, Nitrocefin undergoes a striking color change from yellow to red upon hydrolysis by β-lactamases, making it an essential tool for studying antibiotic resistance mechanisms. This compound is particularly valued for its rapid reaction kinetics and high specificity, enabling real-time monitoring of enzymatic activity in bacterial cultures and purified enzyme preparations.

Our Nitrocefin is supplied as a high-purity reagent, rigorously tested for performance in both research and clinical diagnostics. Ideal for use in assays such as the Cefinase™ test, it is compatible with a wide range of bacterial species and β-lactamase variants, including extended-spectrum β-lactamases (ESBLs). Each batch is quality-controlled to ensure consistent sensitivity and reliability, meeting the stringent requirements of academic, pharmaceutical, and diagnostic laboratories.

Properties

• CAS Number: 41906-86-9
• Complexity: 991
• IUPAC Name: (6R,7R)-3-[(E)-2-(2,4-dinitrophenyl)vinyl]-8-oxo-7-[[2-(2-thienyl)acetyl]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
• InChI Key: LHNIIDJCEODSHA-OQRUQETBSA-N
• Exact Mass: 516.04095583
• Molecular Formula: C21H16N4O8S2
• Molecular Weight: 516.5
• SMILES: C1C(=C(N2[C@H](S1)[C@@H](C2=O)NC(=O)CC3=CC=CS3)C(=O)O)/C=C/C4=C(C=C(C=C4)[N+](=O)[O-])[N+](=O)[O-]
• Topological: 232
• Monoisotopic Mass: 516.04095583
• Synonyms: Nitrocefin, 41906-86-9, EWP54G0J8F, Nitrocefin [BAN], NITROCEFIN [MI], UNII-EWP54G0J8F, (7R)-3-((E)-2,4-Dinitrostyryl)-7-(2-thienylacetamido)-3-cephem-4-carboxylic acid, 3-(2,4-Dinitrostyryl)-(6R, 7R)-7-(2-thienylacetamido)-ceph-3-em-4-carboxylic Acid, (6R-(3(E),6alpha,7beta))-3-(2-(2,4-Dinitrophenyl)ethenyl)-8-oxo-7-((2-thienylacetyl)amino)-5-thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylic acid, Cefinase, (6R,7R)-3-((E)-2-(2,4-dinitrophenyl)ethenyl)-8-oxo-7-(2-(thiophen-2-yl)acetamido)-5-thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylic acid, (6R,7R)-3-[(E)-2-(2,4-dinitrophenyl)ethenyl]-8-oxo-7-[2-(thiophen-2-yl)acetamido]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid, glaxo 87-312, (6R-(3(E),6 alpha,7 beta))-3-(2-(2,4-dinitrophenyl)ethenyl)-8-oxo-7-((2-thienylacetyl)amino)-5-thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylic acid, (6R,7R)-7-[[(E)-4-(2,4-Dinitrophenyl)-2-(2-thienyl)but-3-enoyl]amino]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid, (6R,7R)-3-[(E)-2-(2,4-dinitrophenyl)ethenyl]-8-oxo-7-[(2-thiophen-2-ylacetyl)amino]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid, Nitrocefin (Standard), SCHEMBL132936, CHEMBL480517, DTXSID401318525, BCP20283, EX-A7930, BDBM50557068, AKOS040744420, DB11592, EN46644, HY-108913R, AS-76556, HY-108913, CS-0031509, NS00072437, Q1993962

Nitrocefin is primarily used as a chromogenic substrate for detecting β-lactamase activity in bacterial isolates, aiding in the identification of antibiotic-resistant strains. It is widely employed in clinical microbiology for rapid screening of β-lactamase-producing organisms, including Staphylococcus aureus and Enterobacteriaceae. Researchers also utilize Nitrocefin in kinetic assays to characterize novel β-lactamase inhibitors and study enzyme mechanisms. Its high sensitivity makes it suitable for low-volume microplate assays and point-of-care diagnostic applications.

Safety and Hazards

GHS Hazard Statements

• H315 (100%): Causes skin irritation [Warning Skin corrosion/irritation]
• H317 (100%): May cause an allergic skin reaction [Warning Sensitization, Skin]
• H318 (100%): Causes serious eye damage [Danger Serious eye damage/eye irritation]

Precautionary Statements

• P261, P264, P264+P265, P272, P280, P302+P352, P305+P354+P338, P317, P321, P332+P317, P333+P317, P362+P364, and P501

Hazard Classes and Categories

• Skin Irrit. 2 (100%)
• Skin Sens. 1A (100%)
• Eye Dam. 1 (100%)

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Disclaimer: Sold exclusively for laboratory research. Prohibited for commercial use, diagnostics, or human/animal applications. Buyers assume all compliance liability.