Details
Stereochemistry | ACHIRAL |
Molecular Formula | C8H5N4O5.Na |
Molecular Weight | 260.1389 |
Optical Activity | NONE |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 1 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
[Na+].[O-][N+](=O)C1=CC=C(O1)\C=N\N2CC(=O)[N-]C2=O
InChI
InChIKey=AFDJQFFKYDCYIG-JSGFVSQVSA-M
InChI=1S/C8H6N4O5.Na/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);/q;+1/p-1/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 |
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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 Date1953 |
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 |
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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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Electrodiagnostic study of a patient with peripheral neuropathy after nitrofurantoin therapy. | 1967 Apr |
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[Neurotoxicity of nitrofurantoin: a case of polyneuritis and acute confusional psychosis]. | 1968 Apr 15 |
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[Nitrofurantoin polyneuritis]. | 1968 Feb |
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[Nil nocere. Severe polyneuropathy during nitrofurantoin therapy of renal insufficiency]. | 1968 Mar 14 |
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[Apropos of a new case of polyneuritis due to nitrofurantoin]. | 1968 Oct 20 |
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[Peculiarities of nitrofurantoin polyneuropathy]. | 1971 Apr 30 |
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Furadantin neuropathy. | 1971 Aug |
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[A case of curable hepatonephritis induced by prolonged treatment with nitrofurantoin]. | 1972 Jan 8 |
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[Characteristics of nitrofurantoin-induced polyneuropathy]. | 1973 |
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Nitrofurantoin polyneuropathy. | 1973 May |
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Cerebellar toxic effects from nitrofurantoin. | 1973 Sep |
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Letter: Benign intracranial hypertension associated with nitrofurantoin therapy. | 1974 Dec 28 |
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[Tetraplegia after nitrofurantoin treatment (author's transl)]. | 1974 May 24 |
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Acute pulmonary reaction to nitrofurantoin. | 1974 Sep |
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Trigeminal neuralgia induced by nitrofurantoin treatment. | 1977 Aug 18 |
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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 chronic liver disease. Clinical course and outcome of five cases. | 1979 |
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Nitrofurantoin-induced chronic active hepatitis. | 1980 Jan |
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[Protection against experimental neuritis caused by nitrofurantoin]. | 1980 Mar |
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Adverse reactions to nitrofurantoin. Analysis of 921 reports. | 1980 Nov |
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Nitrofurantoin-induced granulomatous hepatitis. | 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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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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Seventh-nerve palsy and hepatitis associated with nitrofurantoin. | 1986 Dec |
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Broth microdilution testing of susceptibilities to 30 antimicrobial agents of Mycobacterium avium strains from patients with acquired immune deficiency syndrome. | 1987 Oct |
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[Toxic pulmonary and neuronal reactions to nitrofurantoin]. | 1990 Jan-Mar |
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Defenses against oxidation in human erythrocytes: role of glutathione reductase in the activation of glucose decarboxylation by hemolytic drugs. | 1991 Apr |
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[Unwanted side effects of antibacterials--a diagnostic challenge]. | 2008 |
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Drug-induced interstitial pneumonia. | 2008 Apr |
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N-(4-[2-(1,2,3,4-tetrahydro-6,7-dimethoxy-2-isoquinolinyl)ethyl]-phenyl)-9,10-dihydro-5-methoxy-9-oxo-4-acridine carboxamide (GF120918) as a chemical ATP-binding cassette transporter family G member 2 (Abcg2) knockout model to study nitrofurantoin transfer into milk. | 2008 Dec |
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Pharmacologic profiling of human and rat cytochrome P450 1A1 and 1A2 induction and competition. | 2008 Dec |
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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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Differential effects of chrysin on nitrofurantoin pharmacokinetics mediated by intestinal breast cancer resistance protein in rats and mice. | 2009 |
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DRESS syndrome caused by nitrofurantoin. | 2009 Apr |
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Acute kidney injury, hepatitis, and CPK elevation associated with nitrofurantoin therapy. | 2009 Feb |
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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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Antibacterial medication use during pregnancy and risk of birth defects: National Birth Defects Prevention Study. | 2009 Nov |
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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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Nitrofurantoin-induced acute liver damage in pregnancy. | 2009 Sep |
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Acute renal failure from nitrofurantoin-induced acute granulomatous interstitial nephritis. | 2010 Jan |
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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 |
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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NCI_THESAURUS |
C255
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54-87-5
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C66241
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DTXSID80202308
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DBSALT001418
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SUB03441MIG
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100000085739
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9562058
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Nitrofurantoin sodium
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MAL9M0T5LV
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200-216-7
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CHEMBL572
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ACTIVE MOIETY
SUBSTANCE RECORD