nitrofurantoin
Trade name: furadantin
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
Earliest trial started Jan 1, 2002 (NCT00391651)
Timeline
1950s
- Feb 6, 1953
Procter and Gamble — Earliest FDA Approval
- Feb 6, 1953
Procter and Gamble — NDA Organization
- Feb 6, 1953
Procter and Gamble — NDA Secondary Org
- Dec 23, 1953
Casper Pharma LLC — NDA Secondary Org
1970s
- Jun 5, 1970
Alvogen — NDA Secondary Org
- Sep 30, 1970
Lannett Company, Inc. — Marketing Organization
- Sep 30, 1970
Chartwell Pharmaceuticals — Marketing Organization
- Nov 25, 1970
Sandoz — Marketing Organization
1990s
- Jan 28, 1993
Impax Laboratories — Marketing Organization
- Jan 25, 1995
Athem — Marketing Organization
- Jan 25, 1995
Invatech — Marketing Organization
- Jan 25, 1995
Pharmgen — Marketing Organization
- Jul 9, 1997
Aurobindo Pharma — Marketing Organization
- Jul 9, 1997
Mylan — Marketing Organization
2000s
2010s
- May 11, 2011
Amneal Pharmaceuticals — Marketing Organization
- Jan 1, 2013
Earliest Phase 3 Sponsor(trial)
- Aug 14, 2013
Nostrum Laboratories — Marketing Organization
- Aug 14, 2013
Strides Pharma Science — Marketing Organization
- Sep 8, 2014
Novel Anti-Infective Technologies, LLC — Marketing Organization
- Jun 18, 2015
Actavis — Marketing Organization
- Jun 18, 2015
Allergan PLC (2015) — Marketing Organization
- Jul 8, 2015
Watson Pharmaceuticals — Marketing Organization
- Feb 16, 2016
Sun Pharmaceuticals — Marketing Organization
- Dec 12, 2017
Zydus Discovery DMCC — Marketing Organization
- May 24, 2018
Sunny Pharmtech Inc — Marketing Organization
2020s
- Jun 25, 2021
Alembic — Marketing Organization
- Feb 18, 2022
Inventia Hlthcare — Marketing Organization
- Jul 20, 2022
Alvogen — Marketing Organization
- Mar 21, 2023
Mankind Pharma — Marketing Organization
- Apr 14, 2023
Novitium Pharma — Marketing Organization
- Apr 14, 2023
Ani Pharmaceuticals — Marketing Organization
- Nov 3, 2023
OMSAV PHARMA — Marketing Organization
- Nov 3, 2023
Micro Labs Ltd India — Marketing Organization
- Oct 28, 2024
Biocon Limited — Marketing Organization
- Jan 14, 2025
Appco Pharma — Marketing Organization
- Jan 14, 2025
Somerset Pharmaceuticals — Marketing Organization
- Jul 2, 2025
Annora Pharma — Marketing Organization
- Apr 7, 2026
CREEKWOOD PHARMS — Marketing Organization
Indications
Approved for
Studied for
- Antibiotic Prophylaxis · Phase 4
- Bacterial Infections · Phase 4
- Bacteriuria · Phase 1
- Catheter-Related Infections · Phase 4
- Cystitis · Phase 4
- Cystitis, Interstitial · Phase 4
- Depression · Phase 1
- Drug Delivery Systems · Phase 1/Phase 2
- Enterococcus faecalis · Phase 3
- Escherichia coli Infections · Phase 3
- General Surgery · Early Phase 1
- Gestational Age · Phase 1
- Healthy Volunteers · Phase 1
- Kidney Calculi · Phase 4
- Kidney Diseases · Phase 3
- Methicillin-Resistant Staphylococcus aureus · Phase 4
- Nephrolithiasis · Phase 4
- Pain · Phase 4
- Pelvic Organ Prolapse · Phase 4
- Postoperative Pain · Phase 4
- Premature Birth · Phase 1
- Prostatic Hyperplasia · Phase 4
- Pulpitis · Phase 4
- Renal Insufficiency, Chronic · Phase 3
- Stillbirth · Phase 1
- Urinary Bladder Neoplasms · Phase 4
- Urinary Bladder, Overactive · Phase 4
- Urinary Incontinence, Stress · Phase 4
- Vesico-Ureteral Reflux · Phase 3
Mechanism of action
- DNAINHIBITOR
DNA inhibitor
Generates free radicals causing DNA damage.
Approval history
- approvedPriority reviewFeb 6, 1953
Chemistry & pharmacology
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
- ChEMBLCHEMBL572 ↗
- WikipediaNitrofurantoin ↗
- NCATS927AH8112L ↗
- ChEMBLCHEMBL1201000 ↗
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 ID | Phase | Start date | Sponsor(s) |
|---|---|---|---|
| NCT06907199 | Phase 1 | Dec 1, 2025 | National Institute of Diabetes and Digestive and Kidney Diseases (NIDDK), National Institutes of Health (NIH), The University of Texas, Dallas, University of Texas, Galveston |
| NCT07202832 | N/A | Oct 15, 2025 | Assiut University |
| NCT07186465 | Phase 4 | Sep 11, 2025 | Mahidol University |
| NCT06723392 | Phase 1 | Jun 30, 2025 | Aga 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 |
| NCT07198919 | Phase 1/Phase 2 (Phase 2) | May 20, 2025 | Altamash Institute of Dental Medicine |
| NCT06815549 | Phase 3 | Feb 17, 2025 | Government of Russia |
| NCT06518291 | Phase 4 | Jan 31, 2025 | Shalamar Institute of Health Sciences |
| NCT06332781 | Phase 4 | Aug 1, 2024 | Brown University |
| NCT06387329 | Phase 4 | Apr 4, 2024 | United States Army |
| NCT05630833 | Phase 3 | Dec 12, 2022 | GlaxoSmithKline |
| NCT05652374 | Phase 4 | Oct 20, 2022 | IBSA Institut Biochimique SA, Radboud University |
| NCT05519072 | Phase 4 | Aug 16, 2022 | Atlantic Health System, Columbia University |
| NCT05600023 | Phase 4 | Aug 1, 2022 | Altamash Institute of Dental Medicine |
| NCT05274672 | Phase 4 | Mar 1, 2022 | Baylor Scott and White, Baylor University, Yeshiva University |
| NCT05138822 | Phase 1 | Dec 7, 2021 | GlaxoSmithKline |
| NCT05074628 | Early Phase 1 (Phase 1) | Dec 1, 2021 | Cairo University |
| NCT04959331 | Phase 4 | Nov 2, 2021 | Balearic Islands Health Service (Ibsalut), Gerencia de Atención Primaria, Madrid, Instituto de Investigación Sanitaria Aragón, Jordi Gol i Gurina Foundation |
| NCT05254808 | Phase 3 | Sep 6, 2021 | Utrecht University, ZonMw: The Netherlands Organisation for Health Research and Development |
| NCT04900571 | Phase 4 | Jan 1, 2021 | Altamash Institute of Dental Medicine |
| NCT04502095 | Phase 4 | Aug 4, 2020 | State University of New York, Buffalo |
Organizations
Research & Development (94)
| Organization | Org type | Trials | As lead sponsor | Phases | Earliest year |
|---|---|---|---|---|---|
| GlaxoSmithKline | For profit | 4 | 4 | 2 | 2019 |
| Altamash Institute of Dental Medicine | Academic/Hospital | 3 | 3 | 2 | 2021 |
| Kendle International Inc. | For profit | 3 | 0 | 1 | 2002 |
| Mylan | For profit | 3 | 3 | 1 | 2002 |
| Atlantic Health System | Academic/Hospital | 2 | 2 | 1 | 2020 |
| Columbia University | Academic/Hospital | 2 | 0 | 2 | 2022 |
| Duke University | Academic/Hospital | 2 | 1 | 1 | 2011 |
| Emek Medical Center | Academic/Hospital | 2 | 2 | 2 | 2006 |
| Mayo Clinic | Academic/Hospital | 2 | 1 | 1 | 2015 |
| University of British Columbia | Academic/Hospital | 2 | 1 | 1 | 2015 |
| University of California, San Diego | Academic/Hospital | 2 | 2 | 2 | 2015 |
| University of Genoa | Academic/Hospital | 2 | 0 | 2 | 2013 |
| University of Pittsburgh | Academic/Hospital | 2 | 2 | 2 | 2008 |
| Aga Khan University | Academic/Hospital | 1 | 0 | 1 | 2025 |
| Assiut University | Academic/Hospital | 1 | 1 | 1 | 2025 |
| Balearic Islands Health Service (Ibsalut) | Academic/Hospital | 1 | 0 | 1 | 2021 |
| Bangladesh Medical University | Academic/Hospital | 1 | 1 | 1 | 2018 |
| Baskent University | Academic/Hospital | 1 | 0 | 1 | 2013 |
| Baylor Scott and White | Academic/Hospital | 1 | 0 | 1 | 2022 |
| Baylor University | Academic/Hospital | 1 | 1 | 1 | 2022 |
Marketing (49)
| Organization | Org type | Relationship | Date |
|---|---|---|---|
| Actavis | For profit | MKTG | Jun 18, 2015 |
| Actavis | For profit | SYN | May 3, 2016 |
| Alembic | For profit | MKTG | Jun 25, 2021 |
| Alembic | For profit | SYN | Jun 25, 2021 |
| Allergan PLC (2015) | For profit | MKTG | Jun 18, 2015 |
| Alvogen | For profit | NDA2 | Jun 5, 1970 |
| Alvogen | For profit | SYN | Jun 5, 1970 |
| Alvogen | For profit | SYN | Jun 5, 1970 |
| Alvogen | For profit | MKTG | Jul 20, 2022 |
| Amneal Pharmaceuticals | For profit | MKTG | May 11, 2011 |
| Ani Pharmaceuticals | For profit | MKTG | Apr 14, 2023 |
| Annora Pharma | For profit | MKTG | Jul 2, 2025 |
| Appco Pharma | For profit | MKTG | Jan 14, 2025 |
| Athem | For profit | MKTG | Jan 25, 1995 |
| Aurobindo Pharma | For profit | MKTG | Jul 9, 1997 |
| Aurobindo Pharma | For profit | SYN | Mar 30, 2023 |
| Biocon Limited | For profit | MKTG | Oct 28, 2024 |
| CREEKWOOD PHARMS | For profit | MKTG | Apr 7, 2026 |
| Casper Pharma LLC | For profit | NDA2 | Dec 23, 1953 |
| Chartwell Pharmaceuticals | For profit | MKTG | Sep 30, 1970 |
| Chartwell Pharmaceuticals | For profit | SYN | Mar 22, 2004 |
| Elkins Sinn | For profit | MKTG | — |
| Impax Laboratories | For profit | MKTG | Jan 28, 1993 |
| Invatech | For profit | MKTG | Jan 25, 1995 |
| Inventia Hlthcare | For profit | MKTG | Feb 18, 2022 |
| Lannett Company, Inc. | For profit | MKTG | Sep 30, 1970 |
| Mankind Pharma | For profit | MKTG | Mar 21, 2023 |
| Micro Labs Ltd India | For profit | MKTG | Nov 3, 2023 |
| Mylan | For profit | MKTG | Jul 9, 1997 |
| Nostrum Laboratories | For profit | MKTG | Aug 14, 2013 |
| Novartis | For profit | MKTG | Apr 5, 2005 |
| Novel Anti-Infective Technologies, LLC | For profit | MKTG | Sep 8, 2014 |
| Novitium Pharma | For profit | MKTG | Apr 14, 2023 |
| OMSAV PHARMA | For profit | MKTG | Nov 3, 2023 |
| Pharmgen | For profit | MKTG | Jan 25, 1995 |
| Procter and Gamble | For profit | NDA | Feb 6, 1953 |
| Procter and Gamble | For profit | NDA2 | Feb 6, 1953 |
| Ranbaxy | For profit | MKTG | Mar 30, 2005 |
| Sandoz | For profit | MKTG | Nov 25, 1970 |
| Somerset Pharmaceuticals | For profit | MKTG | Jan 14, 2025 |
| Strides Pharma Science | For profit | MKTG | Aug 14, 2013 |
| Sun Pharmaceuticals | For profit | MKTG | Feb 16, 2016 |
| Sunny Pharmtech Inc | For profit | MKTG | May 24, 2018 |
| Sunny Pharmtech Inc | For profit | MKTG | May 24, 2018 |
| Teva | For profit | MKTG | — |
| Watson Pharmaceuticals | For profit | SYN | Nov 22, 1978 |
| Watson Pharmaceuticals | For profit | MKTG | Jul 8, 2015 |
| Whiteworth Towne Paulsen | For profit | MKTG | — |
| Zydus Discovery DMCC | For profit | MKTG | Dec 12, 2017 |