nitrofurantoin

Trade name: furadantin

Small moleculeapproved

Approved

Feb 6, 1953

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. — NCATS

Clinical trial activity

53 trials · 94 clinical orgs · 39 marketing orgs

Phase 1
10
Phase 2
9
Phase 3
6
Phase 4
27

Earliest trial started Jan 1, 2002 (NCT00391651)

Timeline

1950s

  1. Feb 6, 1953

    Procter and Gamble — Earliest FDA Approval

  2. Feb 6, 1953

    Procter and Gamble — NDA Organization

  3. Feb 6, 1953

    Procter and Gamble — NDA Secondary Org

  4. Dec 23, 1953

    Casper Pharma LLC — NDA Secondary Org

1970s

  1. Jun 5, 1970

    Alvogen — NDA Secondary Org

  2. Sep 30, 1970

    Lannett Company, Inc. — Marketing Organization

  3. Sep 30, 1970

    Chartwell Pharmaceuticals — Marketing Organization

  4. Nov 25, 1970

    Sandoz — Marketing Organization

1990s

  1. Jan 28, 1993

    Impax Laboratories — Marketing Organization

  2. Jan 25, 1995

    Athem — Marketing Organization

  3. Jan 25, 1995

    Invatech — Marketing Organization

  4. Jan 25, 1995

    Pharmgen — Marketing Organization

  5. Jul 9, 1997

    Aurobindo Pharma — Marketing Organization

  6. Jul 9, 1997

    Mylan — Marketing Organization

2000s

  1. Jan 1, 2002

    Mylan — Earliest Phase 1 Sponsor(trial)

  2. Jan 1, 2002

    Earliest Phase 2 Sponsor(trial)

  3. Mar 30, 2005

    Ranbaxy — Marketing Organization

  4. Apr 5, 2005

    Novartis — Marketing Organization

2010s

  1. May 11, 2011

    Amneal Pharmaceuticals — Marketing Organization

  2. Jan 1, 2013

    Earliest Phase 3 Sponsor(trial)

  3. Aug 14, 2013

    Nostrum Laboratories — Marketing Organization

  4. Aug 14, 2013

    Strides Pharma Science — Marketing Organization

  5. Sep 8, 2014

    Novel Anti-Infective Technologies, LLC — Marketing Organization

  6. Jun 18, 2015

    Actavis — Marketing Organization

  7. Jun 18, 2015

    Allergan PLC (2015) — Marketing Organization

  8. Jul 8, 2015

    Watson Pharmaceuticals — Marketing Organization

  9. Feb 16, 2016

    Sun Pharmaceuticals — Marketing Organization

  10. Dec 12, 2017

    Zydus Discovery DMCC — Marketing Organization

  11. May 24, 2018

    Sunny Pharmtech Inc — Marketing Organization

2020s

  1. Jun 25, 2021

    Alembic — Marketing Organization

  2. Feb 18, 2022

    Inventia Hlthcare — Marketing Organization

  3. Jul 20, 2022

    Alvogen — Marketing Organization

  4. Mar 21, 2023

    Mankind Pharma — Marketing Organization

  5. Apr 14, 2023

    Novitium Pharma — Marketing Organization

  6. Apr 14, 2023

    Ani Pharmaceuticals — Marketing Organization

  7. Nov 3, 2023

    OMSAV PHARMA — Marketing Organization

  8. Nov 3, 2023

    Micro Labs Ltd India — Marketing Organization

  9. Oct 28, 2024

    Biocon Limited — Marketing Organization

  10. Jan 14, 2025

    Appco Pharma — Marketing Organization

  11. Jan 14, 2025

    Somerset Pharmaceuticals — Marketing Organization

  12. Jul 2, 2025

    Annora Pharma — Marketing Organization

  13. Apr 7, 2026

    CREEKWOOD PHARMS — Marketing Organization

Indications

Mechanism of action

  • DNAINHIBITOR

    DNA inhibitor

    Generates free radicals causing DNA damage.

Approval history

  • approvedPriority reviewFeb 6, 1953

Chemistry & pharmacology

Loading structure…

SMILES

O=C1CN(/N=C/c2ccc([N+](=O)[O-])o2)C(=O)N1
Mol. weight
238.16 g/mol
Lipinski Ro5
Pass
Rule of 3
No
Chirality
Achiral Molecule
Inorganic
No
Polymer
No
Delivery
Oral, Parenteral
Availability
Prescription Only

Oral

Yes

Parenteral

Yes

Topical

No

Sources

Also known as

  • 1-((5-nitro-2-furanyl)methylene)amino-2,4-imidazolidenedione
  • 1-((5-nitro-2-furanyl)methylene)amino-2,4-imidazolidenedione
  • 1-((5-nitrofurfurylidene)amino)hydantoin
  • 1-((5-nitrofurfurylidene)amino)hydantoin
  • 5-nitrofurantoin
  • 5-nitrofurantoin
  • berkfurin
  • berkfurin
  • ceduran
  • ceduran
  • dantafur
  • dantafur
  • furadantin
  • furadantin
  • furadantin
  • furadantin
  • furadantoin
  • furalan
  • furalan
  • genfura
  • ivadantin
  • ivadantin
  • macrobid
  • macrobid
  • macrodantin
  • macrodantin
  • macrodantin
  • n-(5-nitrofurfurylidene)-1-aminohydantoin
  • n-(5-nitrofurfurylidene)-1-aminohydantoin
  • nitrofurantoin
  • nitrofurantoin
  • nitrofurantoin
  • nitrofurantoin
  • nitrofurantoin
  • nitrofurantoin
  • nitrofurantoin
  • nitrofurantoin
  • nitrofurantoin
  • nitrofurantoina
  • nitrofurantoina
  • nitrofurantoin anhydrous
  • nitrofurantoin anhydrous
  • nitrofurantoine
  • nitrofurantoine
  • nitrofurantoin macrocrystal
  • nitrofurantoin macrocrystal
  • nitrofurantoin macrocrystalline
  • nitrofurantoin macrocrystalline
  • nitrofurantoin macrocrystalline
  • nitrofurantoin, macrocrystalline
  • nitrofurantoin, macrocrystalline
  • nitrofurantoin, macrocrystalline
  • nitrofurantoin, macrocrystalline
  • nitrofurantoin, macrocrystals
  • nitrofurantoin, macrocrystals
  • nitrofurantoin monohydrate
  • nitrofurantoin sodium
  • nitrofurantoin sodium
  • nitrofurantoin sodium
  • nitrofurantoin sodium
  • nitrofurantoin sodium
  • nitrofurantoin sodium
  • nitrofurantoin sodium
  • nitrofurantoinum
  • nitrofurantoinum
  • nitrofurantoinum anhydrous
  • nitrofurantoinum anhydrous

Clinical trials

NCT IDPhaseStart dateSponsor(s)
NCT06907199Phase 1Dec 1, 2025National Institute of Diabetes and Digestive and Kidney Diseases (NIDDK), National Institutes of Health (NIH), The University of Texas, Dallas, University of Texas, Galveston
NCT07202832N/AOct 15, 2025Assiut University
NCT07186465Phase 4Sep 11, 2025Mahidol University
NCT06723392Phase 1Jun 30, 2025Aga Khan University, Boston University, Columbia University, Institute of Nutrition of Central America and Panama, International Center for Diarrheal Disease Research, Jawaharlal Nehru Medical College, Lata Medical Research Foundation, Nagpur, India, National Institute of Child Health and Human Development (NICHD), RTI International, Thomas Jefferson University, University of Alabama, Birmingham, University of Colorado, Denver, University of Kinshasa, University of North Carolina at Chapel Hill, University of Virginia, University Teaching Hospital, Lusaka, Zambia
NCT07198919Phase 1/Phase 2 (Phase 2)May 20, 2025Altamash Institute of Dental Medicine
NCT06815549Phase 3Feb 17, 2025Government of Russia
NCT06518291Phase 4Jan 31, 2025Shalamar Institute of Health Sciences
NCT06332781Phase 4Aug 1, 2024Brown University
NCT06387329Phase 4Apr 4, 2024United States Army
NCT05630833Phase 3Dec 12, 2022GlaxoSmithKline
NCT05652374Phase 4Oct 20, 2022IBSA Institut Biochimique SA, Radboud University
NCT05519072Phase 4Aug 16, 2022Atlantic Health System, Columbia University
NCT05600023Phase 4Aug 1, 2022Altamash Institute of Dental Medicine
NCT05274672Phase 4Mar 1, 2022Baylor Scott and White, Baylor University, Yeshiva University
NCT05138822Phase 1Dec 7, 2021GlaxoSmithKline
NCT05074628Early Phase 1 (Phase 1)Dec 1, 2021Cairo University
NCT04959331Phase 4Nov 2, 2021Balearic Islands Health Service (Ibsalut), Gerencia de Atención Primaria, Madrid, Instituto de Investigación Sanitaria Aragón, Jordi Gol i Gurina Foundation
NCT05254808Phase 3Sep 6, 2021Utrecht University, ZonMw: The Netherlands Organisation for Health Research and Development
NCT04900571Phase 4Jan 1, 2021Altamash Institute of Dental Medicine
NCT04502095Phase 4Aug 4, 2020State University of New York, Buffalo
Showing 20 of 53 trials
Page 1 / 3

Organizations

Research & Development (94)

OrganizationOrg typeTrialsAs lead sponsorPhasesEarliest year
GlaxoSmithKlineFor profit4422019
Altamash Institute of Dental MedicineAcademic/Hospital3322021
Kendle International Inc.For profit3012002
MylanFor profit3312002
Atlantic Health SystemAcademic/Hospital2212020
Columbia UniversityAcademic/Hospital2022022
Duke UniversityAcademic/Hospital2112011
Emek Medical CenterAcademic/Hospital2222006
Mayo ClinicAcademic/Hospital2112015
University of British ColumbiaAcademic/Hospital2112015
University of California, San DiegoAcademic/Hospital2222015
University of GenoaAcademic/Hospital2022013
University of PittsburghAcademic/Hospital2222008
Aga Khan UniversityAcademic/Hospital1012025
Assiut UniversityAcademic/Hospital1112025
Balearic Islands Health Service (Ibsalut)Academic/Hospital1012021
Bangladesh Medical UniversityAcademic/Hospital1112018
Baskent UniversityAcademic/Hospital1012013
Baylor Scott and WhiteAcademic/Hospital1012022
Baylor UniversityAcademic/Hospital1112022
94 organizations
Page 1 / 5

Marketing (49)

OrganizationOrg typeRelationshipDate
ActavisFor profitMKTGJun 18, 2015
ActavisFor profitSYNMay 3, 2016
AlembicFor profitMKTGJun 25, 2021
AlembicFor profitSYNJun 25, 2021
Allergan PLC (2015)For profitMKTGJun 18, 2015
AlvogenFor profitNDA2Jun 5, 1970
AlvogenFor profitSYNJun 5, 1970
AlvogenFor profitSYNJun 5, 1970
AlvogenFor profitMKTGJul 20, 2022
Amneal PharmaceuticalsFor profitMKTGMay 11, 2011
Ani PharmaceuticalsFor profitMKTGApr 14, 2023
Annora PharmaFor profitMKTGJul 2, 2025
Appco PharmaFor profitMKTGJan 14, 2025
AthemFor profitMKTGJan 25, 1995
Aurobindo PharmaFor profitMKTGJul 9, 1997
Aurobindo PharmaFor profitSYNMar 30, 2023
Biocon LimitedFor profitMKTGOct 28, 2024
CREEKWOOD PHARMSFor profitMKTGApr 7, 2026
Casper Pharma LLCFor profitNDA2Dec 23, 1953
Chartwell PharmaceuticalsFor profitMKTGSep 30, 1970
Chartwell PharmaceuticalsFor profitSYNMar 22, 2004
Elkins SinnFor profitMKTG
Impax LaboratoriesFor profitMKTGJan 28, 1993
InvatechFor profitMKTGJan 25, 1995
Inventia HlthcareFor profitMKTGFeb 18, 2022
Lannett Company, Inc.For profitMKTGSep 30, 1970
Mankind PharmaFor profitMKTGMar 21, 2023
Micro Labs Ltd IndiaFor profitMKTGNov 3, 2023
MylanFor profitMKTGJul 9, 1997
Nostrum LaboratoriesFor profitMKTGAug 14, 2013
NovartisFor profitMKTGApr 5, 2005
Novel Anti-Infective Technologies, LLCFor profitMKTGSep 8, 2014
Novitium PharmaFor profitMKTGApr 14, 2023
OMSAV PHARMAFor profitMKTGNov 3, 2023
PharmgenFor profitMKTGJan 25, 1995
Procter and GambleFor profitNDAFeb 6, 1953
Procter and GambleFor profitNDA2Feb 6, 1953
RanbaxyFor profitMKTGMar 30, 2005
SandozFor profitMKTGNov 25, 1970
Somerset PharmaceuticalsFor profitMKTGJan 14, 2025
Strides Pharma ScienceFor profitMKTGAug 14, 2013
Sun PharmaceuticalsFor profitMKTGFeb 16, 2016
Sunny Pharmtech IncFor profitMKTGMay 24, 2018
Sunny Pharmtech IncFor profitMKTGMay 24, 2018
TevaFor profitMKTG
Watson PharmaceuticalsFor profitSYNNov 22, 1978
Watson PharmaceuticalsFor profitMKTGJul 8, 2015
Whiteworth Towne PaulsenFor profitMKTG
Zydus Discovery DMCCFor profitMKTGDec 12, 2017