369-24-4

Basic information

• Product Name: 2-Fluoroisoniazide
• Synonyms: 2-FLUOROISONICOTINIC ACID HYDRAZIDE;2-Fluoroisoniazide;2-Fluoropyridine-4-carbohydrazide;2-fluoroisonicotinohydrazide;4-Pyridinecarboxylicacid, 2-fluoro-, hydrazide
• CAS NO: 369-24-4
• Molecular Formula: C6H6FN3O
• Molecular Weight: 155.13
• Mol File: 369-24-4.mol
• Article Data: 4

Chemical Properties

• Boiling Point: °Cat760mmHg
• Flash Point: °C
• Appearance: off white powder
• Density: 1.356 g/cm³
• Vapor Pressure: 5.31E-07mmHg at 25°C
• Refractive Index: 1.541
• CAS DataBase Reference: 2-Fluoroisoniazide(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Fluoroisoniazide(369-24-4)
• EPA Substance Registry System: 2-Fluoroisoniazide(369-24-4)

Safety Data

• Hazardous Substances Data: 369-24-4(Hazardous Substances Data)

Usage

General Description

2-Fluoroisoniazide is a modified form of the antibiotic isoniazid that has been developed to improve its efficacy against drug-resistant strains of tuberculosis. This chemical compound contains a fluorine atom, which enhances its bioavailability and antimicrobial activity. 2-Fluoroisoniazide works by inhibiting the biosynthesis of mycolic acids, a critical component of the bacterial cell wall, leading to the disruption of cell wall integrity and ultimately the death of the tuberculosis bacteria. This modification of isoniazid addresses some of the limitations of the original drug, making it a promising candidate for the treatment of drug-resistant tuberculosis infections. Ongoing research and clinical trials continue to evaluate the efficacy and safety of 2-Fluoroisoniazide as a potential treatment for drug-resistant tuberculosis.

InChI:InChI=1/C6H4FNO2/c7-5-3-4(6(9)10)1-2-8-5/h1-3H,(H,9,10)

Upstream product

• 455-69-6 2-fluoro-isonicotinic acid methyl ester 
• 402-65-3 2-fluoropyridine-4-carboxylic acid 
• 123412-95-3 ethyl 2-fluoroisonicotinate 

Downstream Products

• 1412405-56-1 2-((4-ethyl-5-(2-fluoropyridin-4-yl)-4H-1,2,4-triazol-3-yl)thio)-N-(4-isopropylphenyl)acetamide 

Relevant articles and documents

Reinvestigation of the structure-activity relationships of isoniazid

Isoniazid (INH) remains a cornerstone for treatment of drug susceptible tuberculosis (TB), yet the quantitative structure-activity relationships for INH are not well documented in the literature. In this paper, we have evaluated a systematic series of INH analogs against contemporary Mycobacterium tuberculosis strains from different lineages and a few non-tuberculous mycobacteria (NTM). Deletion of the pyridyl nitrogen atom, isomerization of the pyridine nitrogen to other positions, replacement of the pyridine ring with isosteric heterocycles, and modification of the hydrazide moiety of INH abolishes antitubercular activity. Similarly, substitution of the pyridine ring at the 3-position is not tolerated while substitution at the 2-position is permitted with 2-methyl-INH 9 displaying antimycobacterial activity comparable to INH. To assess the specific activity of this series of INH analogs against mycobacteria, we assayed them against a panel of gram-positive and gram-negative bacteria, as well as a few fungi. As expected INH and its analogs display a narrow spectrum of activity and are inactive against all non-mycobacterial strains evaluated, except for 4, which has modest inhibitory activity against Cryptococcus neoformans. Our findings provide an updated analysis of the structure-activity relationship of INH that we hope will serve as useful resource for the community.

Narrow SAR in odorant sensing Orco receptor agonists

The systematic exploration of a series of triazole-based agonists of the cation channel insect odorant receptor is reported. The structure-activity relationships of independent sections of the molecules are examined. Very small changes to the compound structure were found to exert a large impact on compound activity. Optimal substitutions were combined using a 'mix-and-match' strategy to produce best-in-class compounds that are capable of potently agonizing odorant receptor activity and may form the basis for the identification of a new mode of insect behavior modification.