Nitrofurantoin molecular structure

Nitrofurantoin

Also known as: Macrobid, Macrodantin, Furadantin, Nitrofurantin, Uvamin

CAS Number: 67-20-9

Nitrofuran urinary antibacterial

Pharmacopeia Standards

USPBPIPEPJP

Mechanism of Action

Nitrofurantoin is a prodrug reduced inside bacterial cells by flavoproteins and nitroreductases to highly reactive electrophilic intermediates. These intermediates attack ribosomal proteins, DNA, respiratory enzymes and pyruvate metabolism simultaneously, which explains the very low rate of acquired resistance after decades of use. Because it concentrates in urine and achieves little systemic tissue exposure, activity is confined to the urinary tract.

Technical Specifications

Generic / INN NameNitrofurantoin
CAS Registry Number67-20-9
Molecular FormulaC8H6N4O5
Molecular Weight238.16 g/mol g/mol
Typical Purity98.0-102.0% on dried basis (USP); related compounds within monograph limits
Storage ConditionsStore in well-closed, light-resistant containers at 15-30 C; avoid contact with metals other than stainless steel or aluminium
Shelf Life60 months from date of manufacture
CategoryNitrofurans

Specifications are indicative and intended for sourcing reference only. Always confirm against the supplier's Certificate of Analysis and the applicable pharmacopeial monograph before issuing a purchase specification.

Typical Applications

Oral capsules and tablets for uncomplicated lower urinary tract infection, macrocrystal and monohydrate/macrocrystal modified-release capsules, and paediatric oral suspensions.

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