Details
Stereochemistry | ACHIRAL |
Molecular Formula | C8H6N4O5 |
Molecular Weight | 238.1574 |
Optical Activity | NONE |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 1 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
c1cc(N(=O)=O)oc1/C(/[H])=N/N2CC(=NC2=O)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+
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.
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: P52647 Gene ID: 946587.0 Gene Symbol: ydbK Target Organism: Escherichia coli (strain K12) Sources: https://www.ncbi.nlm.nih.gov/pubmed/12069963 |
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Target ID: CHEMBL2364041 |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
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Curative | FURADANTIN Approved UseNitrofurantoin macrocrystals is specifically indicated for the treatment of urinary tract infections when due to susceptible strains of Escherichia coli, enterococci, Staphylococcus aureus, and certain susceptible strains of Klebsiella and Enterobacter species. Nitrofurantoin is not indicated for the treatment of pyelonephritis or perinephric abscesses. To reduce the development of drug-resistant bacteria and maintain the effectiveness of nitrofurantoin macrocrystals and other antibacterial drugs, nitrofurantoin macrocrystals should be used only to treat or prevent infections that are proven or strongly suspected to be caused by susceptible bacteria. When culture and susceptibility information are available, they should be considered in selecting or modifying antibacterial therapy. In the absence of such data, local epidemiology and susceptibility patterns may contribute to the empiric selection of therapy. Nitrofurantoins lack the broader tissue distribution of other therapeutic agents approved for urinary tract infections. Consequently, many patients who are treated with nitrofurantoin macrocrystals are predisposed to persistence or reappearance of bacteriuria. Urine specimens for culture and susceptibility testing should be obtained before and after completion of therapy. If persistence or reappearance of bacteriuria occurs after treatment with nitrofurantoin macrocrystals, other therapeutic agents with broader tissue distribution should be selected. In considering the use of nitrofurantoin macrocrystals, lower eradication rates should be balanced against the increased potential for systemic toxicity and for the development of antimicrobial resistance when agents with broader tissue distribution are utilized. Launch Date-5.33347205E11 |
Cmax
Value | Dose | Co-administered | Analyte | Population |
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0.326 mg/L EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/30859184 |
50 mg 4 times / day steady-state, oral dose: 50 mg route of administration: Oral experiment type: STEADY-STATE co-administered: |
NITROFURANTOIN plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE food status: UNKNOWN |
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0.69 mg/L EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/30859184 |
100 mg 3 times / day steady-state, oral dose: 100 mg route of administration: Oral experiment type: STEADY-STATE co-administered: |
NITROFURANTOIN plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE food status: UNKNOWN |
AUC
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
4.43 mg × h/L EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/30859184 |
50 mg 4 times / day steady-state, oral dose: 50 mg route of administration: Oral experiment type: STEADY-STATE co-administered: |
NITROFURANTOIN plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE food status: UNKNOWN |
|
6.49 mg × h/L EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/30859184 |
100 mg 3 times / day steady-state, oral dose: 100 mg route of administration: Oral experiment type: STEADY-STATE co-administered: |
NITROFURANTOIN plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE food status: UNKNOWN |
T1/2
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
2.3 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/30859184 |
50 mg 4 times / day steady-state, oral dose: 50 mg route of administration: Oral experiment type: STEADY-STATE co-administered: |
NITROFURANTOIN plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE food status: UNKNOWN |
|
1.7 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/30859184 |
100 mg 3 times / day steady-state, oral dose: 100 mg route of administration: Oral experiment type: STEADY-STATE co-administered: |
NITROFURANTOIN plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE food status: UNKNOWN |
Funbound
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
10% EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/7085535 |
unknown, unknown |
NITROFURANTOIN plasma | Homo sapiens population: UNKNOWN age: UNKNOWN sex: UNKNOWN food status: UNKNOWN |
Doses
Dose | Population | Adverse events |
---|---|---|
100 mg 1 times / day multiple, oral Recommended Dose: 100 mg, 1 times / day Route: oral Route: multiple Dose: 100 mg, 1 times / day Sources: |
healthy, 50 years n = 1 Health Status: healthy Age Group: 50 years Sex: F Population Size: 1 Sources: |
Disc. AE: Pneumonia... AEs leading to discontinuation/dose reduction: Pneumonia Sources: |
125 mg multiple, oral (mean) Recommended |
unhealthy, 62-75 years n = 5 Health Status: unhealthy Condition: urinary infections Age Group: 62-75 years Sex: M+F Population Size: 5 Sources: |
Disc. AE: Interstitial pneumonitis... AEs leading to discontinuation/dose reduction: Interstitial pneumonitis Sources: |
50 mg 2 times / day multiple, oral Studied dose Dose: 50 mg, 2 times / day Route: oral Route: multiple Dose: 50 mg, 2 times / day Sources: |
unhealthy, mean age 31.3 years n = 48 Health Status: unhealthy Condition: urinary infections Age Group: mean age 31.3 years Sex: F Population Size: 48 Sources: |
Disc. AE: Nausea... AEs leading to discontinuation/dose reduction: Nausea (28%) Sources: |
AEs
AE | Significance | Dose | Population |
---|---|---|---|
Pneumonia | Disc. AE | 100 mg 1 times / day multiple, oral Recommended Dose: 100 mg, 1 times / day Route: oral Route: multiple Dose: 100 mg, 1 times / day Sources: |
healthy, 50 years n = 1 Health Status: healthy Age Group: 50 years Sex: F Population Size: 1 Sources: |
Interstitial pneumonitis | Disc. AE | 125 mg multiple, oral (mean) Recommended |
unhealthy, 62-75 years n = 5 Health Status: unhealthy Condition: urinary infections Age Group: 62-75 years Sex: M+F Population Size: 5 Sources: |
Nausea | 28% Disc. AE |
50 mg 2 times / day multiple, oral Studied dose Dose: 50 mg, 2 times / day Route: oral Route: multiple Dose: 50 mg, 2 times / day Sources: |
unhealthy, mean age 31.3 years n = 48 Health Status: unhealthy Condition: urinary infections Age Group: mean age 31.3 years Sex: F Population Size: 48 Sources: |
PubMed
Title | Date | PubMed |
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[Toxic polyneuritis in a female patient with chronic pyelonephritis after long-term treatment with nitrofurantoin]. | 1966 Dec 8 |
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[Nil nocere. Severe polyneuropathy during nitrofurantoin therapy of renal insufficiency]. | 1968 Mar 14 |
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[Peculiarities of nitrofurantoin polyneuropathy]. | 1971 Apr 30 |
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Furadantin neuropathy. | 1971 Aug |
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[Characteristics of nitrofurantoin-induced polyneuropathy]. | 1973 |
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Nitrofurantoin polyneuropathy. | 1973 May |
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[Polyneuropathy due to nitrofurantoin]. | 1975 |
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Cholestatic hepatitis after administration of furan derivatives. | 1975 May |
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The clinical significant of cystitis cystica in girls: results of a prospective study. | 1978 May |
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Nitrofurantoin-induced granulomatous hepatitis. | 1981 Aug |
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Nitrofurantoin neuropathy. | 1981 Aug |
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Lateral rectus muscle palsy associated with nitrofurantoin (Macrodantin) | 1982 Dec |
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Activation of misonidazole by rat liver microsomes and purified NADPH-cytochrome c reductase. | 1982 Feb 15 |
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Enhancement by electron-affinic agents of the therapeutic effects of cytotoxic agents against the KHT tumor: structure-activity relationships. | 1982 Mar-Apr |
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Nitrofurantoin unmasking peripheral neuropathy in a type 2 diabetic patient. | 1984 Apr |
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Nitrofurantoin-induced cholestatic hepatitis from cow's milk in a teenaged boy. | 1984 Feb |
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The effect of nitrofurantoin on bladder tumor cell lines: in vitro growth and implantation in the cauterized mouse bladder. | 1985 Dec |
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[Chronic active hepatitis caused by nitrofurantoin: a case report]. | 1985 Jan 26 |
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Glutathione-dependent detoxification of peroxide in bovine ciliary body. | 1990 Jun |
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Nitrofurantoin-induced pulmonary toxicity. In vivo evidence for oxidative stress-mediated mechanisms. | 1992 Mar 3 |
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Treatment of experimental pneumocystosis: review of 7 years of experience and development of a new system for classifying antimicrobial drugs. | 1992 Sep |
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Bactericidal activity of nitrofurans against growing and dormant Mycobacterium bovis BCG. | 2000 Dec |
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Ocular myasthenia and nitrofurantoin. | 2000 Oct |
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Activation of transcription factors by drugs inducing oxidative stress in rat liver. | 2002 Jan 15 |
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Nitrofurantoin-induced chronic active hepatitis. | 2002 Mar |
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[Liver cirrhosis due to chronic use of nitrofurantoin]. | 2004 Jan 31 |
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Prediction of genotoxicity of chemical compounds by statistical learning methods. | 2005 Jun |
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Inducers of oxidative stress block ciliary neurotrophic factor activation of Jak/STAT signaling in neurons. | 2005 Mar |
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Sex-dependent expression and activity of the ATP-binding cassette transporter breast cancer resistance protein (BCRP/ABCG2) in liver. | 2005 May |
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Accidental intravenous administration of racemic adrenaline: two cases associated with adverse cardiac effects. | 2005 Oct |
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Breast cancer resistance protein 1 limits fetal distribution of nitrofurantoin in the pregnant mouse. | 2007 Dec |
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Effects of the flavonoid chrysin on nitrofurantoin pharmacokinetics in rats: potential involvement of ABCG2. | 2007 Feb |
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Drug-induced interstitial pneumonia. | 2008 Apr |
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Nitrofurantoin-induced peripheral neuropathy: a lesson to be re-learnt. | 2008 Jan-Mar |
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Role of cytochrome P450 reductase in nitrofurantoin-induced redox cycling and cytotoxicity. | 2008 Mar 15 |
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Nitroreductive metabolic activation of some carcinogenic nitro heterocyclic food contaminants in rat mammary tissue cellular fractions. | 2009 Jan |
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Knocking down breast cancer resistance protein (Bcrp) by adenoviral vector-mediated RNA interference (RNAi) in sandwich-cultured rat hepatocytes: a novel tool to assess the contribution of Bcrp to drug biliary excretion. | 2009 Jan-Feb |
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Dequalinium, a new inhibitor of Mycobacterium tuberculosis mycothiol ligase identified by high-throughput screening. | 2009 Jul |
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Identification of genomic biomarkers for concurrent diagnosis of drug-induced renal tubular injury using a large-scale toxicogenomics database. | 2009 Nov 9 |
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Milk secretion of nitrofurantoin, as a specific BCRP/ABCG2 substrate, in assaf sheep: modulation by isoflavones. | 2009 Oct |
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Acute renal failure from nitrofurantoin-induced acute granulomatous interstitial nephritis. | 2010 Jan |
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Early identification of clinically relevant drug interactions with the human bile salt export pump (BSEP/ABCB11). | 2013 Dec |
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A correlation between the in vitro drug toxicity of drugs to cell lines that express human P450s and their propensity to cause liver injury in humans. | 2014 Jan |
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Systems pharmacological analysis of drugs inducing stevens-johnson syndrome and toxic epidermal necrolysis. | 2015 May 18 |
|
Chemical structure-related mechanisms underlying in vivo genotoxicity induced by nitrofurantoin and its constituent moieties in gpt delta rats. | 2015 May 4 |
Sample Use Guides
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
Sources: https://www.ncbi.nlm.nih.gov/pubmed/23377809
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%)
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Classification Tree | Code System | Code | ||
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LIVERTOX |
690
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NDF-RT |
N0000007658
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WHO-ESSENTIAL MEDICINES LIST |
6.2.2
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WHO-ATC |
J01XE01
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IARC | Nitrofurantoin | ||
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NCI_THESAURUS |
C255
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NDF-RT |
N0000175494
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WHO-ATC |
J01XE51
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WHO-VATC |
QJ01XE01
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NDF-RT |
N0000007658
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Code System | Code | Type | Description | ||
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C29293
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DB00698
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CHEMBL572
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D009582
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1464001
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PRIMARY | USP-RS | ||
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1949
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NITROFURANTOIN
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PRIMARY | Description: Lemon-yellow crystals or a yellow, crystalline powder; odourless or almost odourless. Solubility: Practically insoluble in water; very slightly soluble in ethanol (~750 g/l) TS; soluble in dimethylformamide R. Category: Antibacterial drug. Storage: Nitrofurantoin should be kept in a well-closed container, protected from light, and stored at a temperature not exceeding25?C. Labelling: The designation on the container of Nitrofurantoin should state whether the substance is the monohydrate or is in theanhydrous form. Additional information: Nitrofurantoin melts at about 271?C with decomposition. Nitrofurantoin and its solutions are discoloured byalkali and by exposure to light and are decomposed upon contact with metals other than stainless steel and aluminium. Definition: Nitrofurantoin contains not less than 98.0% and not more than 102.0% of C8H6N4O5, calculated with reference to thedried substance. | ||
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7454
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927AH8112L
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SUB129837
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NITROFURANTOIN
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Nitrofurantoin
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M7956
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67-20-9
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488
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200-646-5
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6604200
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SUB09326MIG
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ACTIVE MOIETY
METABOLITE (PARENT)
SALT/SOLVATE (PARENT)