NITROFURANTOIN

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 Search

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

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	1
Optical Activity	NONE

Description
Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2013/009175s036lbl.pdf

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 Target	Pharmacology	Condition	Potency
Probable pyruvate-flavodoxin oxidoreductase 3 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	Substrate 661
DNA 282 Target ID: CHEMBL2364041 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2013/009175s036lbl.pdf	Inhibitor 8504

Conditions

Condition	Modality	Targets	Highest Phase	Product
Urinary tract infections 207 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2013/009175s036lbl.pdf	Curative		Approved 8583	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 1953

C_max

Value	Dose	Co-administered	Analyte	Population
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
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

T_1/2

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

F_unbound

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: https://pubmed.ncbi.nlm.nih.gov/16718946/	healthy, 50 years Health Status: healthy Age Group: 50 years Sex: F Sources: https://pubmed.ncbi.nlm.nih.gov/16718946/	Disc. AE: Pneumonia... AEs leading to discontinuation/dose reduction: Pneumonia Sources: https://pubmed.ncbi.nlm.nih.gov/16718946/
125 mg multiple, oral Recommended Dose: 125 mg Route: oral Route: multiple Dose: 125 mg Sources: https://pubmed.ncbi.nlm.nih.gov/5700010/	unhealthy, 62-75 years Health Status: unhealthy Age Group: 62-75 years Sex: M+F Sources: https://pubmed.ncbi.nlm.nih.gov/5700010/	Disc. AE: Interstitial pneumonitis... AEs leading to discontinuation/dose reduction: Interstitial pneumonitis Sources: https://pubmed.ncbi.nlm.nih.gov/5700010/
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: https://pubmed.ncbi.nlm.nih.gov/7019458/	unhealthy, mean age 31.3 years Health Status: unhealthy Age Group: mean age 31.3 years Sex: F Sources: https://pubmed.ncbi.nlm.nih.gov/7019458/	Disc. AE: Nausea... AEs leading to discontinuation/dose reduction: Nausea (28%) Sources: https://pubmed.ncbi.nlm.nih.gov/7019458/

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: https://pubmed.ncbi.nlm.nih.gov/16718946/	healthy, 50 years Health Status: healthy Age Group: 50 years Sex: F Sources: https://pubmed.ncbi.nlm.nih.gov/16718946/
Interstitial pneumonitis	Disc. AE	125 mg multiple, oral Recommended Dose: 125 mg Route: oral Route: multiple Dose: 125 mg Sources: https://pubmed.ncbi.nlm.nih.gov/5700010/	unhealthy, 62-75 years Health Status: unhealthy Age Group: 62-75 years Sex: M+F Sources: https://pubmed.ncbi.nlm.nih.gov/5700010/
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: https://pubmed.ncbi.nlm.nih.gov/7019458/	unhealthy, mean age 31.3 years Health Status: unhealthy Age Group: mean age 31.3 years Sex: F Sources: https://pubmed.ncbi.nlm.nih.gov/7019458/

Sourcing

Vendor/Aggregator	ID	URL
ChEBI	CHEBI:71415	https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:71415
eMolecules	886566	https://www.emolecules.com/cgi-bin/more?vid=886566
MolPort	MolPort-001-018-217	https://www.molport.com/shop/molecule-link/MolPort-001-018-217
ZINC	ZINC000003875368	http://zinc15.docking.org/substances/ZINC000003875368

PubMed

Title	Date	PubMed
Systems pharmacological analysis of drugs inducing stevens-johnson syndrome and toxic epidermal necrolysis.	2015-05-18	25811541
Chemical structure-related mechanisms underlying in vivo genotoxicity induced by nitrofurantoin and its constituent moieties in gpt delta rats.	2015-05-04	25772432
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.	2014-01	24085192
Early identification of clinically relevant drug interactions with the human bile salt export pump (BSEP/ABCB11).	2013-12	24014644
Genomic biomarkers for cardiotoxicity in rats as a sensitive tool in preclinical studies.	2013-10	23558518
Acute renal failure from nitrofurantoin-induced acute granulomatous interstitial nephritis.	2010-01	19828642
Identification of genomic biomarkers for concurrent diagnosis of drug-induced renal tubular injury using a large-scale toxicogenomics database.	2009-11-09	19761811
Antibacterial medication use during pregnancy and risk of birth defects: National Birth Defects Prevention Study.	2009-11	19884587
Milk secretion of nitrofurantoin, as a specific BCRP/ABCG2 substrate, in assaf sheep: modulation by isoflavones.	2009-10	19754918
Nitrofurantoin-induced acute liver damage in pregnancy.	2009-09	19789166
Furazolidone and nitrofurantoin in the treatment of experimental Pneumocystis carinii pneumonia.	1991-01	2014971
Glutathione-dependent detoxification of peroxide in bovine ciliary body.	1990-06	2373173
[Toxic pulmonary and neuronal reactions to nitrofurantoin].	1990-01-01	2223723
Broth microdilution testing of susceptibilities to 30 antimicrobial agents of Mycobacterium avium strains from patients with acquired immune deficiency syndrome.	1987-10	3501698
Seventh-nerve palsy and hepatitis associated with nitrofurantoin.	1986-12	3804357
The effect of nitrofurantoin on bladder tumor cell lines: in vitro growth and implantation in the cauterized mouse bladder.	1985-12	4057424
[Chronic active hepatitis caused by nitrofurantoin: a case report].	1985-01-26	3969597
Nitrofurantoin unmasking peripheral neuropathy in a type 2 diabetic patient.	1984-04	6712378
Nitrofurantoin-induced cholestatic hepatitis from cow's milk in a teenaged boy.	1984-02	6730475
Lateral rectus muscle palsy associated with nitrofurantoin (Macrodantin)	1982-12	7180920
Adverse reactions to nitrofurantoin in the United Kingdom, Sweden, and Holland.	1982-05-15	6282377
Enhancement by electron-affinic agents of the therapeutic effects of cytotoxic agents against the KHT tumor: structure-activity relationships.	1982-03-01	7107385
Activation of misonidazole by rat liver microsomes and purified NADPH-cytochrome c reductase.	1982-02-15	6802140
Nitrofurantoin-induced granulomatous hepatitis.	1981-08	7269024
Nitrofurantoin neuropathy.	1981-08	6272676
Adverse reactions to nitrofurantoin. Analysis of 921 reports.	1980-11	7435512
[Protection against experimental neuritis caused by nitrofurantoin].	1980-03	7459038
Nitrofurantoin-induced chronic active hepatitis.	1980-01	7350873
Nitrofurantoin-induced chronic liver disease. Clinical course and outcome of five cases.	1979	482863
The clinical significant of cystitis cystica in girls: results of a prospective study.	1978-05	660739
[Possibility of limitation and prevention of functional damage in experimental neuritis due to nitrofurantoin].	1977-12	610729
Trigeminal neuralgia induced by nitrofurantoin treatment.	1977-08-18	72798
Letter: Benign intracranial hypertension associated with nitrofurantoin therapy.	1974-12-28	4441887
Acute pulmonary reaction to nitrofurantoin.	1974-09	4428461
[Tetraplegia after nitrofurantoin treatment (author's transl)].	1974-05-24	4210548
Cerebellar toxic effects from nitrofurantoin.	1973-09	4360418
Nitrofurantoin polyneuropathy.	1973-05	4349239
[Characteristics of nitrofurantoin-induced polyneuropathy].	1973	4727524
[A case of curable hepatonephritis induced by prolonged treatment with nitrofurantoin].	1972-01-08	5010743
[Nitrofurantoin-induced polyneuropathy].	1971-11-01	4333216
Furadantin neuropathy.	1971-08	4331903
[Peculiarities of nitrofurantoin polyneuropathy].	1971-04-30	5574121
[Cardiomyopathy caused by nitrofurantoin].	1969-11-09	5362072
[Apropos of a new case of polyneuritis due to nitrofurantoin].	1968-10-20	5742624
[Neurotoxicity of nitrofurantoin: a case of polyneuritis and acute confusional psychosis].	1968-04-15	5734898
[Nil nocere. Severe polyneuropathy during nitrofurantoin therapy of renal insufficiency].	1968-03-14	5682390
[Nitrofurantoin polyneuritis].	1968-02	5185289
Electrodiagnostic study of a patient with peripheral neuropathy after nitrofurantoin therapy.	1967-04	4290180
[Toxic polyneuritis in a female patient with chronic pyelonephritis after long-term treatment with nitrofurantoin].	1966-12-08	5980645
Polyneuropathy due to nitrofurantoin.	1966-02	4379323

Patents

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 Created by `admin` on `Mon Mar 31 18:21:05 GMT 2025` Edited by `admin` on `Mon Mar 31 18:21:05 GMT 2025`
Record UNII	927AH8112L
Record Status	`Validated (UNII)`
Record Version

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Related Record	Type

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Classification Tree Code System Code

LIVERTOX

NBK548318