U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

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
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

Sources: Transactions. American Urological Association. Southeastern Section (1952), 2-5, (2-5), 26-34.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Target ID: P52647
Gene ID: 946587.0
Gene Symbol: ydbK
Target Organism: Escherichia coli (strain K12)
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Curative
FURADANTIN

Approved Use

Nitrofurantoin 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

Cmax

ValueDoseCo-administeredAnalytePopulation
0.326 mg/L
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
0.69 mg/L
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

AUC

ValueDoseCo-administeredAnalytePopulation
4.43 mg × h/L
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
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

T1/2

ValueDoseCo-administeredAnalytePopulation
2.3 h
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
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

Funbound

ValueDoseCo-administeredAnalytePopulation
10%
unknown, unknown
NITROFURANTOIN plasma
Homo sapiens
population: UNKNOWN
age: UNKNOWN
sex: UNKNOWN
food status: UNKNOWN
Doses

Doses

DosePopulationAdverse 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
Dose: 125 mg
Route: oral
Route: multiple
Dose: 125 mg
Sources:
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

AEs

AESignificanceDosePopulation
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
Dose: 125 mg
Route: oral
Route: multiple
Dose: 125 mg
Sources:
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

PubMed

TitleDatePubMed
[Cardiomyopathy caused by nitrofurantoin].
1969 Nov 9
[Peculiarities of nitrofurantoin polyneuropathy].
1971 Apr 30
Furadantin neuropathy.
1971 Aug
[Tetraplegia after nitrofurantoin treatment (author's transl)].
1974 May 24
[Polyneuropathy due to nitrofurantoin].
1975
Trigeminal neuralgia induced by nitrofurantoin treatment.
1977 Aug 18
Nitrofurantoin-induced chronic active hepatitis.
1980 Jan
[Protection against experimental neuritis caused by nitrofurantoin].
1980 Mar
Nitrofurantoin neuropathy.
1981 Aug
Activation of misonidazole by rat liver microsomes and purified NADPH-cytochrome c reductase.
1982 Feb 15
Enhancement by electron-affinic agents of the therapeutic effects of cytotoxic agents against the KHT tumor: structure-activity relationships.
1982 Mar-Apr
Adverse reactions to nitrofurantoin in the United Kingdom, Sweden, and Holland.
1982 May 15
[Chronic active hepatitis caused by nitrofurantoin: a case report].
1985 Jan 26
Seventh-nerve palsy and hepatitis associated with nitrofurantoin.
1986 Dec
Defenses against oxidation in human erythrocytes: role of glutathione reductase in the activation of glucose decarboxylation by hemolytic drugs.
1991 Apr
Furazolidone and nitrofurantoin in the treatment of experimental Pneumocystis carinii pneumonia.
1991 Jan
Treatment of experimental pneumocystosis: review of 7 years of experience and development of a new system for classifying antimicrobial drugs.
1992 Sep
Bactericidal activity of nitrofurans against growing and dormant Mycobacterium bovis BCG.
2000 Dec
Pulmonary and hepatic toxicity due to nitrofurantoin and fluconazole treatment.
2004 Apr
Antitumor activity of common antibiotics against superficial bladder cancer.
2004 Mar
Drug-induced liver injury.
2004 Mar 1
Prediction of genotoxicity of chemical compounds by statistical learning methods.
2005 Jun
[Unwanted side effects of antibacterials--a diagnostic challenge].
2008
Pharmacologic profiling of human and rat cytochrome P450 1A1 and 1A2 induction and competition.
2008 Dec
Acute kidney injury, hepatitis, and CPK elevation associated with nitrofurantoin therapy.
2009 Feb
Antibacterial medication use during pregnancy and risk of birth defects: National Birth Defects Prevention Study.
2009 Nov
Early identification of clinically relevant drug interactions with the human bile salt export pump (BSEP/ABCB11).
2013 Dec
Systems pharmacological analysis of drugs inducing stevens-johnson syndrome and toxic epidermal necrolysis.
2015 May 18
Patents

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 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%)
Name Type Language
NITROFURANTOIN
EP   GREEN BOOK   HSDB   INN   JAN   MART.   MI   ORANGE BOOK   USP   USP-RS   VANDF   WHO-DD  
INN  
Official Name English
MACROBID COMPONENT NITROFURANTOIN, MACROCRYSTALLINE
Common Name English
NITROFURANTOIN [IARC]
Common Name English
nitrofurantoin [INN]
Common Name English
NITROFURANTOIN MACROCRYSTALLINE [VANDF]
Common Name English
NITROFURANTOIN [MART.]
Common Name English
NITROFURANTOIN [USP-RS]
Common Name English
NITROFURANTOIN [USP MONOGRAPH]
Common Name English
NSC-44150
Code English
NITROFURANTOIN, MACROCRYSTALLINE COMPONENT OF MACROBID
Common Name English
NITROFURANTOINUM ANHYDROUS [WHO-IP LATIN]
Common Name English
FURADANTIN
Brand Name English
NITROFURANTOIN MACROCRYSTALLINE
VANDF  
Common Name English
NITROFURANTOIN ANHYDROUS [WHO-IP]
Common Name English
NITROFURANTOIN [ORANGE BOOK]
Common Name English
NITROFURANTOIN [VANDF]
Common Name English
NITROFURANTOIN [GREEN BOOK]
Common Name English
FURALAN
Brand Name English
NITROFURANTOIN COMPONENT OF MACROBID
Common Name English
1-[(5-Nitrofurfurylidene)amino]hydantoin
Systematic Name English
1-((5-NITRO-2-FURANYL)METHYLENE)AMINO-2,4-IMIDAZOLIDENEDIONE
Common Name English
NITROFURANTOIN [HSDB]
Common Name English
NITROFURANTOIN ANHYDROUS
WHO-IP  
Common Name English
NSC-2107
Code English
Nitrofurantoin [WHO-DD]
Common Name English
NITROFURANTOIN [EP MONOGRAPH]
Common Name English
MACRODANTIN
Brand Name English
MACROBID COMPONENT NITROFURANTOIN
Common Name English
NITROFURANTOIN [MI]
Common Name English
NITROFURANTOIN [JAN]
Common Name English
Classification Tree Code System Code
LIVERTOX NBK548318
Created by admin on Wed Jul 05 23:38:35 UTC 2023 , Edited by admin on Wed Jul 05 23:38:35 UTC 2023
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
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
DAILYMED
927AH8112L
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PRIMARY
NSC
2107
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PRIMARY
SMS_ID
100000092406
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PRIMARY
NCI_THESAURUS
C29293
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PRIMARY
DRUG BANK
DB00698
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PRIMARY
ChEMBL
CHEMBL572
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PRIMARY
MESH
D009582
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PRIMARY
DRUG CENTRAL
1949
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PRIMARY
WHO INTERNATIONAL PHARMACOPEIA
NITROFURANTOIN
Created by admin on Wed Jul 05 23:38:35 UTC 2023 , Edited by admin on Wed Jul 05 23:38:35 UTC 2023
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.
RXCUI
7454
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PRIMARY
FDA UNII
927AH8112L
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PRIMARY
EVMPD
SUB129837
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PRIMARY
WIKIPEDIA
NITROFURANTOIN
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PRIMARY
LACTMED
Nitrofurantoin
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PRIMARY
MERCK INDEX
M7956
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PRIMARY Merck Index
CAS
67-20-9
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PRIMARY
RS_ITEM_NUM
1464001
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PRIMARY
NSC
44150
Created by admin on Wed Jul 05 23:38:35 UTC 2023 , Edited by admin on Wed Jul 05 23:38:35 UTC 2023
PRIMARY
INN
488
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PRIMARY
ECHA (EC/EINECS)
200-646-5
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PRIMARY
CHEBI
71415
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PRIMARY
PUBCHEM
6604200
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PRIMARY
EVMPD
SUB09326MIG
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PRIMARY