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Details

Stereochemistry ACHIRAL
Molecular Formula C8H6N4O5.H2O
Molecular Weight 256.1727
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 1
Charge 0

SHOW SMILES / InChI
Structure of NITROFURANTOIN MONOHYDRATE

SMILES

c1cc(N(=O)=O)oc1/C(/[H])=N/N2CC(=NC2=O)O.O

InChI

InChIKey=NHBPVLAHAVEISO-JSGFVSQVSA-N
InChI=1S/C8H6N4O5.H2O/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);1H2/b9-3+;

HIDE SMILES / InChI

Molecular Formula C8H6N4O5
Molecular Weight 238.1574
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 1
Optical Activity NONE

Molecular Formula H2O
Molecular Weight 18.0153
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

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
[Nil nocere. Severe polyneuropathy during nitrofurantoin therapy of renal insufficiency].
1968 Mar 14
[Cardiomyopathy caused by nitrofurantoin].
1969 Nov 9
[Peculiarities of nitrofurantoin polyneuropathy].
1971 Apr 30
Furadantin neuropathy.
1971 Aug
[Nitrofurantoin-induced polyneuropathy].
1971 Nov-Dec
[Characteristics of nitrofurantoin-induced polyneuropathy].
1973
Anicteric liver damage during nitrofurantoin medication.
1975
Cholestatic hepatitis after administration of furan derivatives.
1975 May
Trigeminal neuralgia induced by nitrofurantoin treatment.
1977 Aug 18
The clinical significant of cystitis cystica in girls: results of a prospective study.
1978 May
Nitrofurantoin-induced chronic active hepatitis.
1980 Jan
Adverse reactions to nitrofurantoin. Analysis of 921 reports.
1980 Nov
Nitrofurantoin-induced granulomatous hepatitis.
1981 Aug
Nitrofurantoin unmasking peripheral neuropathy in a type 2 diabetic patient.
1984 Apr
Nitrofurantoin-induced cholestatic hepatitis from cow's milk in a teenaged boy.
1984 Feb
The effect of nitrofurantoin on bladder tumor cell lines: in vitro growth and implantation in the cauterized mouse bladder.
1985 Dec
Seventh-nerve palsy and hepatitis associated with nitrofurantoin.
1986 Dec
Broth microdilution testing of susceptibilities to 30 antimicrobial agents of Mycobacterium avium strains from patients with acquired immune deficiency syndrome.
1987 Oct
[Toxic pulmonary and neuronal reactions to nitrofurantoin].
1990 Jan-Mar
Glutathione-dependent detoxification of peroxide in bovine ciliary body.
1990 Jun
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
[Hemolytic anemia in a newborn after maternal treatment with nitrofurantoin at the end of pregnancy].
2000 Jul
Ocular myasthenia and nitrofurantoin.
2000 Oct
Adverse reactions of nitrofurantoin, trimethoprim and sulfamethoxazole in children.
2004 Aug
Drug-induced liver injury.
2004 Mar 1
Prediction of genotoxicity of chemical compounds by statistical learning methods.
2005 Jun
Inducers of oxidative stress block ciliary neurotrophic factor activation of Jak/STAT signaling in neurons.
2005 Mar
Breast cancer resistance protein 1 limits fetal distribution of nitrofurantoin in the pregnant mouse.
2007 Dec
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
Pharmacologic profiling of human and rat cytochrome P450 1A1 and 1A2 induction and competition.
2008 Dec
Dequalinium, a new inhibitor of Mycobacterium tuberculosis mycothiol ligase identified by high-throughput screening.
2009 Jul
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
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%)
Substance Class Chemical
Created
by admin
on Sat Jun 26 07:26:38 UTC 2021
Edited
by admin
on Sat Jun 26 07:26:38 UTC 2021
Record UNII
E1QI2CQQ1I
Record Status Validated (UNII)
Record Version
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Name Type Language
NITROFURANTOIN MONOHYDRATE
MI   WHO-DD   WHO-IP  
Common Name English
NITROFURANTOIN MONOHYDRATE [WHO-DD]
Common Name English
1-((5-NITROFURFURYLIDENE)AMINO)HYDANTOIN, MONOHYDRATE
Systematic Name English
NITROFURANTOIN MONOHYDRATE [MI]
Common Name English
NITROFURANTOINUM MONOHYDRATE [WHO-IP LATIN]
Common Name English
FURADANTIN MONOHYDRATE
Common Name English
2,4-IMIDAZOLIDINEDIONE, 1-(((5-NITRO-2-FURANYL)METHYLENE)AMINO)-, MONOHYDRATE
Systematic Name English
NITROFURANTOIN MONOHYDRATE [WHO-IP]
Common Name English
NITROFURANTOIN, MONOHYDRATE
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C255
Created by admin on Sat Jun 26 07:26:38 UTC 2021 , Edited by admin on Sat Jun 26 07:26:38 UTC 2021
Code System Code Type Description
PUBCHEM
9571008
Created by admin on Sat Jun 26 07:26:38 UTC 2021 , Edited by admin on Sat Jun 26 07:26:38 UTC 2021
PRIMARY
EVMPD
SUB16448MIG
Created by admin on Sat Jun 26 07:26:38 UTC 2021 , Edited by admin on Sat Jun 26 07:26:38 UTC 2021
PRIMARY
FDA UNII
E1QI2CQQ1I
Created by admin on Sat Jun 26 07:26:38 UTC 2021 , Edited by admin on Sat Jun 26 07:26:38 UTC 2021
PRIMARY
WHO INTERNATIONAL PHARMACOPEIA
NITROFURANTOIN MONOHYDRATE
Created by admin on Sat Jun 26 07:26:38 UTC 2021 , Edited by admin on Sat Jun 26 07:26:38 UTC 2021
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
221129
Created by admin on Sat Jun 26 07:26:38 UTC 2021 , Edited by admin on Sat Jun 26 07:26:38 UTC 2021
PRIMARY RxNorm
EPA CompTox
17140-81-7
Created by admin on Sat Jun 26 07:26:38 UTC 2021 , Edited by admin on Sat Jun 26 07:26:38 UTC 2021
PRIMARY
DRUG BANK
DBSALT001891
Created by admin on Sat Jun 26 07:26:38 UTC 2021 , Edited by admin on Sat Jun 26 07:26:38 UTC 2021
PRIMARY
NCI_THESAURUS
C77144
Created by admin on Sat Jun 26 07:26:38 UTC 2021 , Edited by admin on Sat Jun 26 07:26:38 UTC 2021
PRIMARY
CAS
17140-81-7
Created by admin on Sat Jun 26 07:26:38 UTC 2021 , Edited by admin on Sat Jun 26 07:26:38 UTC 2021
PRIMARY
MERCK INDEX
M7956
Created by admin on Sat Jun 26 07:26:38 UTC 2021 , Edited by admin on Sat Jun 26 07:26:38 UTC 2021
PRIMARY Merck Index
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