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Substance Name: Nitrofurantoin [USP:INN:BAN:JAN]
RN: 67-20-9
UNII: 927AH8112L
InChIKey: NXFQHRVNIOXGAQ-YCRREMRBSA-N
Note
- A urinary anti-infective agent effective against most gram-positive and gram-negative organisms. Although sulfonamides and antibiotics are usually the agents of choice for urinary tract infections, nitrofurantoin is widely used for prophylaxis and long-term suppression.
Molecular Formula
- C8-H6-N4-O5
Molecular Weight
- 238.1584
- All
- Classifications
- Links to Resources
- Names & Synonyms
- Registry Numbers
- Structure Descriptors
- Toxicity
- Physical Properties
Classification Codes
Classification Codes
- Anti-Bacterial Agents
- Anti-Infective Agents
- Anti-Infective Agents, Urinary
- Antibacterial (Urinary)
- Drug / Therapeutic Agent
- Human Data
- Mutation Data
- Renal Agents
- Reproductive Effect
- Tumor Data
Superlist Classification Code
- Overall Carcinogenic Evaluation: Group 3
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Regulatory Agencies (Superlist Locators)
Other Resources (Internet Locators)
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Names and Synonyms
Name of Substance
- Nitrofurantoin
- Nitrofurantoin [USP:INN:BAN:JAN]
MeSH Heading
- Nitrofurantoin
Synonyms
- 1-((5-Nitrofurfurylidene)amino)hydantoin
- 1-(5-Nitro-2-furfurylidenamino)hydantoin
- 1-(5-Nitro-2-furfurylideneamino)hydantoin
- 2,4-Imidazolidinedione, 1-(((5-nitro-2-furanyl)methylene)amino)-
- 5-Nitrofurantoin
- AI3-26388
- Alfuran
- Benkfuran
- Berkfuran
- Berkfurin
- CCRIS 1192
- Ceduran
- Chemiofuran
- Cistofuran
- Cyantin
- Cystit
- Dantafur
- EINECS 200-646-5
- Fua Med
- Fur-ren
- Furabid
- Furachel
- Furadantin
- Furadantin Retard
- Furadantina MC
- Furadantine
- Furadantine mc
- Furadantine-MC
- Furadantoin
- Furadoine
- Furadonin
- Furadonine
- Furadoninum
- Furadontin
- Furagin
- Furalan
- Furaloid
- Furantoin
- Furatoin
- Furazidin
- Furedan
- Furina
- Furobactina
- Furophen T
- Gerofuran
- HSDB 3135
- Hydantoin, 1-((5-nitrofurfurylidene)amino)-
- Ituran
- Macpac
- Macrobid
- Macrodantin
- Macrodantina
- Macrofuran
- Macrofurin
- N-(5-Nitro-2-furfurylidene)-1-aminohydantoin
- N-(5-Nitro-2-furfurylideno)-1-aminohydantoina
- N-(5-Nitro-2-furfurylideno)-1-aminohydantoina [Polish]
- N-(5-Nitrofurfurylidene)-1-aminohydantoin
- N-Toin
- NCI-C55196
- Nierofu
- Nifurantin
- Nifuretten
- Nitoin
- Nitrex
- Nitrofur-C
- Nitrofuradantin
- Nitrofurantoin
- Nitrofurantoin, macrocrystalline
- Nitrofurantoina
- Nitrofurantoina [DCIT]
- Nitrofurantoine
- Nitrofurantoine [INN-French]
- Nitrofurantoinum
- Nitrofurantoinum [INN-Latin]
- Novofuran
- NSC 2107
- NSC 44150
- Orafuran
- Parfuran
- Phenurin
- PiyEloseptyl
- Ro-Antoin
- Siraliden
- Trantoin
- Uerineks
- UNII-927AH8112L
- Urantoin
- Urizept
- Uro-Selz
- Uro-Tablinen
- Urodin
- Urofuran
- Urofurin
- Urolisa
- Urolong
- USAF EA-2
- Welfurin
- Zoofurin
Systematic Names
- 2,4-Imidazolidenedione, 1-(((5-nitro-2-furanyl)methylene)amino)-
- 2,4-Imidazolidinedione, 1-(((5-nitro-2-furanyl)methylene)amino)-
- Hydantoin, 1-((5-nitrofurfurylidene)amino)-
- Nitrofurantoin
Superlist Name
- Nitrofurantoin
Registry Numbers
CAS Registry Number
- 67-20-9
FDA UNII
- 927AH8112L
Related Registry Numbers
- 17140-81-7 (mono-hydrate)
- 54-87-5 (hydrochloride salt)
System Generated Number
- 0000067209
Structure Descriptors
InChI
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+InChIKey
NXFQHRVNIOXGAQ-YCRREMRBSA-NSmiles
[O-][N+](=O)Toxicity
Organism | Test Type | Route | Reported Dose (Normalized Dose) | Effect | Source |
---|---|---|---|---|---|
chicken | LD50 | oral | 53mg/kg (53mg/kg) | Journal of Nutrition. Vol. 112, Pg. 1741, 1982. | |
human | TDLo | oral | 80mg/kg (80mg/kg) | BEHAVIORAL: ATAXIA PERIPHERAL NERVE AND SENSATION: RECORDING FROM PERIPHERAL MOTOR NERVE | Archives of Neurology Vol. 18, Pg. 680, 1968. |
human | TDLo | unreported | 60mg/kg (60mg/kg) | KIDNEY, URETER, AND BLADDER: OTHER CHANGES IN URINE COMPOSITION | British Medical Journal. Vol. 2, Pg. 1044, 1976. |
mammal (species unspecified) | LDLo | oral | 250mg/kg (250mg/kg) | Bollettino Chimico Farmaceutico. Vol. 102, Pg. 505, 1963. | |
man | TDLo | oral | 29mg/kg/20D-I (29mg/kg) | BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY) SENSE ORGANS AND SPECIAL SENSES: VISUAL FIELD CHANGES: EYE BRAIN AND COVERINGS: INCREASED INTRACRANIAL PRESSURE | Drug Intelligence and Clinical Pharmacy. Vol. 22, Pg. 345, 1988. |
man | TDLo | oral | 40mg/kg/2W-I (40mg/kg) | KIDNEY, URETER, AND BLADDER: INTERSTITIAL NEPHRITIS KIDNEY, URETER, AND BLADDER: PROTEINURIS BLOOD: CHANGES IN LEUCOCYTE (WBC) COUNT | Lancet. Vol. 348, Pg. 1177, 1996. |
mouse | LD50 | intraperitoneal | 100mg/kg (100mg/kg) | National Technical Information Service. Vol. AD277-689, | |
mouse | LD50 | oral | 360mg/kg (360mg/kg) | Journal of Medicinal Chemistry. Vol. 16, Pg. 312, 1973. | |
rat | LD50 | intraperitoneal | 112mg/kg (112mg/kg) | Research Progress in Organic-Biological and Medicinal Chemistry. Vol. 2, Pg. 303, 1970. | |
rat | LD50 | oral | 604mg/kg (604mg/kg) | Research Progress in Organic-Biological and Medicinal Chemistry. Vol. 2, Pg. 303, 1970. | |
women | TDLo | oral | 24mg/kg (24mg/kg) | BLOOD: OTHER HEMOLYSIS WITH OR WITHOUT ANEMIA | American Journal of Clinical Pathology. Vol. 58, Pg. 408, 1972. |
women | TDLo | oral | 42mg/kg/6W-I (42mg/kg) | LIVER: "JAUNDICE, OTHER OR UNCLASSIFIED" LIVER: "HEPATITIS (HEPATOCELLULAR NECROSIS), DIFFUSE" LIVER: LIVER FUNCTION TESTS IMPAIRED | Medical Journal of Australia. Vol. 156, Pg. 347, 1992. |
women | TDLo | oral | 365mg/kg/1Y-I (365mg/kg) | LIVER: LIVER FUNCTION TESTS IMPAIRED LUNGS, THORAX, OR RESPIRATION: FIBROSIS (INTERSTITIAL) LUNGS, THORAX, OR RESPIRATION: DYSPNEA | Postgraduate Medical Journal. Vol. 73, Pg. 519, 1997. |
Physical Properties
Physical Property | Value | Units | Temp (deg C) | Source |
---|---|---|---|---|
Melting Point | 263 | deg C | EXP | |
pKa Dissociation Constant | 7.2 | (none) | EXP | |
log P (octanol-water) | -0.47 | (none) | EXP | |
Water Solubility | 79.5 | mg/L | 24 | EXP |
Vapor Pressure | 2.78E-10 | mm Hg | 25 | EST |
Henry's Law Constant | 1.33E-12 | atm-m3/mole | 25 | EST |
Atmospheric OH Rate Constant | 1.78E-11 | cm3/molecule-sec | 25 | EST |
Physical property data is provided to ChemIDplus by SRC, Inc.