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Details

Stereochemistry ACHIRAL
Molecular Formula C8H6N4O5
Molecular Weight 238.157
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 1
Charge 0

SHOW SMILES / InChI
Structure of NITROFURANTOIN

SMILES

[O-][N+](=O)C1=CC=C(O1)\C=N\N2CC(=O)NC2=O

InChI

InChIKey=NXFQHRVNIOXGAQ-YCRREMRBSA-N
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+

HIDE SMILES / InChI

Molecular Formula C8H6N4O5
Molecular Weight 238.157
Charge 0
Count
MOL RATIO 1 MOL RATIO (average)
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 1
Optical Activity NONE

Description

Furadantin (nitrofurantoin), a synthetic chemical, is a stable, yellow, crystalline compound. Furadantin is an antibacterial agent for specific urinary tract infections. Orally administered Furadantin is readily absorbed and rapidly excreted in urine. Blood concentrations at therapeutic dosage are usually low. Unlike many drugs, the presence of food or agents delaying gastric emptying can increase the bioavailability of Furadantin, presumably by allowing better dissolution in gastric juices. Nitrofurantoin is active against some gram positive organisms such as S. aureus, S. epidermidis, S. saprophyticus, Enterococcus faecalis, S. agalactiae, group D streptococci, viridians streptococci and Corynebacterium. Its spectrum of activity against gram negative organisms includes E. coli, Enterobacter, Neisseria, Salmonella and Shigella. It may be used as an alternative to trimethoprim/sulfamethoxazole for treating urinary tract infections though it may be less effective at eradicating vaginal bacteria. May also be used in females as prophylaxis against recurrent cystitis related to coitus. Nitrofurantoin is highly stable to the development of bacterial resistance, a property thought to be due to its multiplicity of mechanisms of action. Nitrofurantoin is activated by bacterial flavoproteins (nitrofuran reductase) to active reduced reactive intermediates that are thought to modulate and damage ribosomal proteins or other macromolecules, especially DNA, causing inhibition of DNA, RNA, protein, and cell wall synthesis. The overall effect is inhibition of bacterial growth or cell death.

Originator

Approval Year

Targets

Primary TargetPharmacologyConditionPotency

Conditions

ConditionModalityTargetsHighest PhaseProduct
Curative
FURADANTIN

Cmax

ValueDoseCo-administeredAnalytePopulation
0.326 mg/L
50 mg 4 times / day steady-state, oral
NITROFURANTOIN plasma
Homo sapiens
0.69 mg/L
100 mg 3 times / day steady-state, oral
NITROFURANTOIN plasma
Homo sapiens

AUC

ValueDoseCo-administeredAnalytePopulation
4.43 mg × h/L
50 mg 4 times / day steady-state, oral
NITROFURANTOIN plasma
Homo sapiens
6.49 mg × h/L
100 mg 3 times / day steady-state, oral
NITROFURANTOIN plasma
Homo sapiens

T1/2

ValueDoseCo-administeredAnalytePopulation
2.3 h
50 mg 4 times / day steady-state, oral
NITROFURANTOIN plasma
Homo sapiens
1.7 h
100 mg 3 times / day steady-state, oral
NITROFURANTOIN plasma
Homo sapiens

Funbound

ValueDoseCo-administeredAnalytePopulation
10%
unknown, unknown
NITROFURANTOIN plasma
Homo sapiens

Doses

AEs

PubMed

Sample Use Guides

In Vivo Use Guide
Adults: 50-100 mg four times a day -- the lower dosage level is recommended for uncomplicated urinary tract infections. Pediatric Patients: 5-7 mg/kg of body weight per 24 hours, given in four divided doses (contraindicated under one month of age).
Route of Administration: Oral
In Vitro Use Guide
In vitro nitrofurantoin has the best sensitivity in community-acquired urinary tract infections (UTIs). Nitrofurantoin has showed a low MIC distribution and high sensitivity percentage (93.3%)
Substance Class Chemical
Record UNII
927AH8112L
Record Status Validated (UNII)
Record Version