Nifurtoinol is a synthetic nitrofuran antibacterial active pharmaceutical ingredient (API). Also known as hydroxymethylnitrofurantoin, Nifurtoinol is a nitrofuran derivative associated with antibacterial activity and has historically been used in the treatment of urinary tract infections.
Nifurtoinol is chemically classified as a substituted hydantoin nitrofuran derivative. It contains a 5-nitrofuran moiety linked to a hydroxymethyl-substituted imidazolidine-2,4-dione structure.
Nifurtoinol is a specialized antibacterial pharmaceutical API relevant to nitrofuran research, urinary-tract-infection formulations and pharmaceutical analytical applications.
The compound is recognized in pharmaceutical and pharmacological databases under CAS 1088-92-2 and ATC code J01XE02.
CAS Number: 1088-92-2
Molecular Formula: C₉H₈N₄O₆
Molecular Weight: 268.18 g/mol
Chemical Name: 3-(Hydroxymethyl)-1-[[(5-nitro-2-furanyl)methylene]amino]-2,4-imidazolidinedione
IUPAC Name: 3-(Hydroxymethyl)-1-[(5-nitrofuran-2-yl)methylideneamino]imidazolidine-2,4-dione
Synonym: Hydroxymethylnitrofurantoin
Drug Class: Nitrofuran Antibacterial
Therapeutic Class: Antibacterial
Therapeutic Area: Infectious Diseases / Urinary Tract Infections
Molecule Type: Synthetic Small Molecule
ATC Code: J01XE02
IUPHAR/BPS and NCATS support the CAS number, molecular formula, molecular weight and chemical identity of Nifurtoinol.
Nifurtoinol belongs to the nitrofuran class of antibacterial compounds. Its antibacterial activity is associated with metabolic reduction of the nitro group and formation of reactive intermediates.
Its activity may involve:
The precise molecular mechanisms of nitrofuran antibacterial activity can vary according to the organism and experimental conditions.
Nifurtoinol API is relevant to:
Nifurtoinol has historically been used as an antibacterial medicine for urinary tract infections. NCATS identifies Nifurtoinol as an antibacterial drug used for urinary tract infections.
Its historical pharmaceutical application is associated with the urinary tract, although current clinical use depends on the regulatory status and approved indications in the relevant market.
The nitrofuran group is a key structural feature of Nifurtoinol.
Nitrofuran antibacterial compounds can undergo enzymatic reduction inside susceptible microorganisms, producing reactive intermediates that contribute to antimicrobial activity.
Nifurtoinol is therefore relevant to research involving nitrofuran chemistry, antimicrobial activity and bacterial susceptibility.
Nifurtoinol is a synthetic organic compound with molecular weight approximately 268.18 g/mol. IUPHAR/BPS reports a topological polar surface area of approximately 129.49 Ų and XLogP of approximately 0.33.
Reference chemical data describe Nifurtoinol as forming yellow crystals and report decomposition around 258°C.
Published reference data indicate that Nifurtoinol has limited water solubility. One chemical reference reports water solubility of approximately 0.33 g/L at 22°C.
Because solubility can vary with temperature, pH, particle size and experimental methodology, this research value should not automatically be treated as a pharmaceutical release specification.
A controlled Nifurtoinol API manufacturing process may involve:
Typical Nifurtoinol API quality control may include:
Exact acceptance criteria should be taken from the current approved API specification or applicable pharmacopoeial monograph.
Store Nifurtoinol API in a tightly closed container under controlled pharmaceutical storage conditions, protected from excessive moisture, heat and direct light.
Commercial storage conditions should be established from validated stability data and the applicable API specification.
| Parameter | Specification |
|---|---|
| Appearance | White crystalline powder or crystals |
| Identification | IR & HPLC compliant |
| Assay (HPLC) | 98.0% – 102.0% |
| Loss on Drying | NMT 1.0% |
| Residue on Ignition | NMT 0.5% |
| Individual Impurity | NMT 0.5% |
| Total Impurities | NMT 2.0% |
| Water Content | NMT 1.0% |
| Melting Point | Approximately 258°C |