Nitrofurantoin NEW

Nitrofurantoin Cas 67-20-9

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Nitrofurantoin is a synthetic nitrofuran-class antibiotic. Chemically, it is a derivative of furan with a nitro group at the 5-position and a hydantoin side chain. Its primary medical use is the treatment and prevention of urinary tract infections (UTIs).

Key Uses in Chemical & Pharmaceutical Contexts:

1. Organic Synthesis & Medicinal Chemistry: Serves as a key example in the design of prodrugs and targeted antibiotics. Its structure is studied for structure-activity relationships (SAR), particularly how its nitro group is selectively reduced by bacterial enzymes in the low-oxygen environment of the urinary tract to generate reactive, bactericidal intermediates.

2. Analytical Reference Standard: High-purity nitrofurantoin is used as a calibrant and reference material in analytical chemistry (e.g., HPLC, UV-Vis spectroscopy) to quantify the drug in pharmaceutical formulations, biological samples, and for quality control during manufacturing.

3. Solid-State Chemistry & Polymorphism: It is a well-known case study in pharmaceutical polymorphism. It exists in multiple crystalline forms (notably anhydrous and monohydrate), which have different solubilities and dissolution rates. Controlling the polymorph is a critical chemical and engineering challenge for ensuring consistent drug performance.

4. Photochemistry & Stability Studies: Its photodegradation is a subject of study. The nitroaromatic moiety can decompose under light, making it a model for investigating drug stability, degradation pathways, and the development of protective formulations.

5. Research into Bacterial Resistance Mechanisms: In biochemical research, it is used as a tool to study bacterial nitroreductase activity and the evolution of resistance to nitroheterocyclic compounds.

In summary, beyond its clinical role, nitrofurantoin is a model compound in pharmaceutical chemistry for studying polymorphism, targeted drug activation, analytical methods, and solid-state properties.

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