Nitrofurantoin

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Nitrofurantoin

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Catalog Number	PR67209
CAS	67-20-9
Structure
Description	Nitrofurantoin is a nitrofuran antibiotic used to treat uncomplicated urinary tract infections. Nitrofurantoin is converted by bacterial nitroreductases to electrophilic intermediates which inhibit the citric acid cycle as well as synthesis of DNA, RNA, and protein. This drug is more resistant to the development of bacterial resistance because it acts on many targets at once.
Synonyms	Macrodantin; Furadantin; 5-Nitrofurantoin
IUPAC Name	1-[(E)-(5-nitrofuran-2-yl)methylideneamino]imidazolidine-2,4-dione
Molecular Weight	238.16
Molecular Formula	C8H6N4O5
InChI	NXFQHRVNIOXGAQ-YCRREMRBSA-N
InChI Key	InChI=1S/C8H6N4O5/c13-6-4-11(8(14)10-6)9-3-5-1-2-7(17-5)12(15)16/h1-3H,4H2,(H,10,13,14)/b9-3+
Drug Categories	Agents causing hyperkalemia; Anti-Bacterial Agents; Anti-Infective Agents; Anti-Infective Agents, Urinary; Antibacterials for Systemic Use; Antiinfectives for Systemic Use; BCRP/ABCG2 Substrates; BSEP/ABCB11 Substrates; Drugs that are Mainly Renally Excreted; Furans; Methemoglobinemia Associated Agents; Nitro Compounds; Nitrofuran Antibacterial; Nitrofuran Derivatives; Nitrofurans; P-glycoprotein substrates; Renal Agents; Thyroxine-binding globulin substrates
Drug Interactions	Abacavir-Nitrofurantoin may decrease the excretion rate of Abacavir which could result in a higher serum level. Abemaciclib-Abemaciclib may decrease the excretion rate of Nitrofurantoin which could result in a higher serum level. Acebutolol-The risk or severity of hyperkalemia can be increased when Nitrofurantoin is combined with Acebutolol. Aceclofenac-The risk or severity of hyperkalemia can be increased when Nitrofurantoin is combined with Aceclofenac. Acemetacin-The risk or severity of hyperkalemia can be increased when Nitrofurantoin is combined with Acemetacin.
Half-Life	The half life of nitrofurantoin is 0.72-0.78h.
Isomeric SMILES	C1C(=O)NC(=O)N1/N=C/C2=CC=C(O2)[N+](=O)[O-]
Type	Small Molecule
Therapeutic Category	Antibacterials

Pharmacology

Indications

Nitrofurantoin is primarily indicated for the treatment of acute uncomplicated urinary tract infections. It is prescribed to combat infections specifically within the urinary tract, offering·herapeutic approach in managing·hese conditions.

Pharmacodynamics

The pharmacodynamic action of nitrofurantoin involves interference with essential bacterial processes that result in bacterial cell death. This antibiotic achieves rapid attainment of therapeutic concentrations within the urine, ensuring·hogen eradication. Additionally, it is cleared from the body swiftly, further enhancing·hieves a peak plasma concentration (Cmax) rang·h an area under the curve (AUC) of 2.21 to 2.42 mg*h/L. The bioavailability of nitrofurantoin falls between 38.8% and 44.3%. Notably, consuming·h food significantly enhances its absorption and prolong·he duration of effective therapeutic concentrations in the urine.

Metabolism

Following·h 0.8% to 1.8% of the dose being·han or equal to 0.9% of the dose undergoes transformation into other metabolites. This limited metabolism underscores the drug's primary urinary excretion pathway, emphasizing·he importance of renal function in its clearance.

Mechanism of Action

Nitrofurantoin is metabolized by bacterial nitroreductases into electrophilic intermediates. These intermediates play a crucial role in inhibiting the citric acid cycle and interfering with the synthesis of DNA, RNA, and proteins. This multifaceted mechanism effectively hampers bacterial growth and proliferation.

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