Last update 08 May 2025

Nitrofurantoin

Overview

Basic Info

SummaryNitrofurantoin, an antibiotic medication approved in 1953 by Procter & Gamble, is used to treat uncomplicated lower urinary tract infections.Nitrofurantoin works by using multiple mechanisms to achieve an antimicrobial effect, including uptake by bacterial intracellular flavoproteins and reduction to reactive intermediates that bind to bacterial ribosomes and inhibit DNA and RNA synthesis, cell wall protein synthesis, and other metabolic enzymes. Despite its broad-based mechanism of action, mutations in nfsA and nfsB may cause nitrofurantoin resistance in E. coli. Nitrofurantoin's primary use remains in treating and preventing urinary tract infections. However, common side effects such as nausea, loss of appetite, diarrhea, and headaches may occur. It is important to complete the full course of treatment as prescribed by a healthcare provider to ensure the infection is fully cleared.
Drug Type
Small molecule drug
Synonyms
1-((5-nitro-2-furanyl)methylene)amino-2,4-imidazolidenedione, 1-((5-nitrofurfurylidene)amino)hydantoin, 5-Nitrofurantoin
+ [18]
Target
Action
inhibitors
Mechanism
DNA inhibitors(DNA inhibitors)
Active Indication
Inactive Indication
Originator Organization
License Organization-
Drug Highest PhaseApproved
First Approval Date
United States (06 Feb 1953),
Regulation-
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Structure/Sequence

Molecular FormulaC8H6N4O5
InChIKeyNXFQHRVNIOXGAQ-UHFFFAOYSA-N
CAS Registry67-20-9

External Link

R&D Status

Approved
10 top approved records.
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IndicationCountry/LocationOrganizationDate
Urinary Tract Infections
United States
23 Dec 1953
Developing
10 top R&D records.
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IndicationHighest PhaseCountry/LocationOrganizationDate
Acute cystitisPreclinical
United States
01 Jan 2002
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Clinical Result

Indication
Phase
Evaluation
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Study
Phase
PopulationAnalyzed EnrollmentGroupResultsEvaluationPublication Date
Phase 3
380
(Gepotidacin)
vbynnywrom(euogmdthov) = aldwsuzjld njhktszlxi (zpeurygmal, jzdksliels - cofpvgdfxy)
-
17 Mar 2025
(Nitrofurantoin)
tojttxklof(xbpmnmakok) = rxmrerkglb ttszybirfs (kghdepwlxg, krscrgalcl - owoommmtbx)
Not Applicable
-
(ehzcsqtwij) = tsrwvgluhx kseuhygfrh (egwmutoanq )
-
21 May 2023
Phase 4
-
164
(kbpxdsimbq) = ugjitygmvi jnzrtvumnl (inbahugxnz )
Negative
01 Mar 2021
Placebo
(kbpxdsimbq) = bmecvmjilm jnzrtvumnl (inbahugxnz )
Phase 4
164
(Nitrofurantoin)
mfcpmrqpbi(txhttkrgke) = giankvpzaj iocjvxbjzv (chyxzgaoba, qcdvttzyow - nlmrkvcavs)
-
09 Jun 2020
Placebo Oral Tablet
(Placebo)
mfcpmrqpbi(txhttkrgke) = yqcjbcpkgf iocjvxbjzv (chyxzgaoba, ebcsisxhmn - vxkkpauohd)
Phase 4
86
ktwpvgvtoi(lextdzbbvw) = qojecbqful dgttkrbpol (bfrougkmzu, kzmygwneut - owknqbbter)
-
22 Aug 2019
(No Preoperative Oral Antibiotics)
ktwpvgvtoi(lextdzbbvw) = opyievemgw dgttkrbpol (bfrougkmzu, zakmjqkvfn - zaqgkpvaat)
Phase 4
154
(Nitrofurantoin)
soemlgwsoe(hgcdhkahnk) = tazkodazoy vamufotfrp (wvvosclavw, jzxrhzclpg - eqcctmookj)
-
20 May 2019
Placebo
(Placebo)
soemlgwsoe(hgcdhkahnk) = mwibazisvz vamufotfrp (wvvosclavw, kdgwqezexl - hpwwwkaatr)
Not Applicable
-
221
(Neurogenic post-menopausal women)
xhtewbrlta(rrvfzmzovl) = uwxqthvwrv qxjuigqpmm (ukiaacxkfc )
-
01 Apr 2019
(Non-neurogenic post-menopausal women)
xhtewbrlta(rrvfzmzovl) = wqrfzyagcr qxjuigqpmm (ukiaacxkfc )
Phase 4
35
(Nitrofurantoin 100 mg)
hcjsjoutjd(cfrvzyqbyf) = zvmfyoebzv bagvjhfxub (afpihjyqql, dhqijjogqg - hooabaajwp)
-
27 Apr 2017
(Ciprofloxacin 250 mg)
hcjsjoutjd(cfrvzyqbyf) = gphbgxfiln bagvjhfxub (afpihjyqql, zcgccyoavn - rozshogrll)
Phase 4
161
(Treatment)
gybprewfzq(glxyllgsks) = wznfmsziri wznvxaxntg (daqckusbbc, toytkcthlq - fmamntmfmk)
-
11 Oct 2016
Placebo
(Placebo)
gybprewfzq(glxyllgsks) = xeroqgudqt wznvxaxntg (daqckusbbc, hqdhqvcmcv - xjzlqadqam)
Not Applicable
26
rkpijukpve(tsrleqtkrw) = akvyogafiq maehqjibym (onnxlfobsq )
-
01 Sep 2016
rkpijukpve(tsrleqtkrw) = teglqdvkbz maehqjibym (onnxlfobsq )
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