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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
 

Classification Codes

Classification Codes

  • 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

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

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-N

Smiles

N1(CC(=O)NC1=O)\N=C\c1oc([N+](=O)[O-])cc1

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.