371914-92-0

Basic information

• Product Name: (6R,7R)-3-[5-Chloro-2-(2,4-dichlorophenoxy)phenoxymethyl]-7-[2-(2-thienyl)acetamido]-3-cephem-4-carboxylic acid
• Synonyms: Lamectacin; NB-2001
• CAS NO: 371914-92-0
• Molecular Formula: C₂₆H₁₉Cl₃N₂O₆S₂
• Molecular Weight: 625.93813
• Mol File: 371914-92-0.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: (6R,7R)-3-[5-Chloro-2-(2,4-dichlorophenoxy)phenoxymethyl]-7-[2-(2-thienyl)acetamido]-3-cephem-4-carboxylic acid(CAS DataBase Reference)
• NIST Chemistry Reference: (6R,7R)-3-[5-Chloro-2-(2,4-dichlorophenoxy)phenoxymethyl]-7-[2-(2-thienyl)acetamido]-3-cephem-4-carboxylic acid(371914-92-0)
• EPA Substance Registry System: (6R,7R)-3-[5-Chloro-2-(2,4-dichlorophenoxy)phenoxymethyl]-7-[2-(2-thienyl)acetamido]-3-cephem-4-carboxylic acid(371914-92-0)

Safety Data

• Hazardous Substances Data: 371914-92-0(Hazardous Substances Data)

Upstream product

• 29126-13-4 3-hydroxymethyl-8-oxo-7-[(2-thienylacetyl)amino]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid diphenylmethyl ester 
• 3380-34-5 triclosan 

Downstream Products

• 3380-34-5 triclosan 

Relevant articles and documents

NB2001, a novel antibacterial agent with broad-spectrum activity and enhanced potency against β-lactamase-producing strains

Enzyme-catalyzed therapeutic activation (ECTA) is a novel prodrug strategy to overcome drug resistance resulting from enzyme overexpression. β-Lactamase overexpression is a common mechanism of bacterial resistance to β-lactam antibiotics. We present here the results for one of the β-lactamase ECTA compounds, NB2001, which consists of the antibacterial agent triclosan in a prodrug form with a cephalosporin scaffold. Unlike conventional β-lactam antibiotics, where hydrolysis of the β-lactam ring inactivates the antibiotic, hydrolysis of NB2001 by β-lactamase releases triclosan. Evidence supporting the proposed mechanism is as follows. (i) NB2001 is a substrate for TEM-1 β-lactamase, forming triclosan with a second-order rate constant (kcat/Km) of greater than 77,000 M-1 s-1. (ii) Triclosan is detected in NB2001-treated, β-lactamase-producing Escherichia coli but not in E. coli that does not express β-lactamase. (iii) NB2001 activity against β-lactamase-producing E. coli is decreased in the presence of the β-lactamase inhibitor clavulanic acid. NB2001 was similar to or more potent than reference antibiotics against clinical isolates of Staphylococcus aureus (including MRSA), Staphylococcus epidermidis, Streptococcus pneumoniae, vancomycin-resistant Enterococcus faecalis, Moraxella catarrhalis and Haemophilus influenzae. NB2001 is also active against Klebsiella pneumoniae, Enterobacter aerogenes, and Enterobacter cloacae. The results indicate that NB2001 is a potent, broad-spectrum antibacterial agent and demonstrate the potential of ECTA in overcoming β-lactamase-mediated resistance.