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Identification
NameNitrofurantoin
Accession NumberDB00698  (APRD00191)
TypeSmall Molecule
GroupsApproved
Description

A bacteriostatic or bactericidal agent depending on the concentration and susceptibility of the infecting organism. 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.

Structure
Thumb
Synonyms
5-Nitrofurantoin
N-(5-Nitrofurfurylidene)-1-aminohydantoin
Nitrofurantoin, macrocrystalline
External Identifiers
  • USAF EA-2
Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Furadantinsuspension25 mg/5mLoralShionogi Inc.1953-12-23Not applicableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Macrobidcapsule100 mgoralWarner Chilcott Canada Co1993-12-31Not applicableCanada 5f16b84899037e23705f146ff57e3794121879cb055f0954756d94bc690476b4
Macrodantincapsule25 mgoralAlza Corporation1993-12-311999-08-06Canada 5f16b84899037e23705f146ff57e3794121879cb055f0954756d94bc690476b4
Macrodantincapsule100 mg/1oralALMATICA PHARMA INC.2010-09-27Not applicableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Macrodantincapsule50 mg/1oralALMATICA PHARMA INC.2010-09-27Not applicableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Macrodantincapsule25 mg/1oralALMATICA PHARMA INC.2010-09-27Not applicableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Macrodantin (100 Mg)capsule100 mgoralProcter & Gamble Pharmaceuticals Canada Inc1993-12-312010-07-07Canada 5f16b84899037e23705f146ff57e3794121879cb055f0954756d94bc690476b4
Macrodantin (50 Mg)capsule50 mgoralProcter & Gamble Pharmaceuticals Canada Inc1993-12-312010-07-07Canada 5f16b84899037e23705f146ff57e3794121879cb055f0954756d94bc690476b4
Macrodantin Cap 100mgcapsule100 mgoralNorwich Eaton Canada Inc.1979-12-311996-09-16Canada 5f16b84899037e23705f146ff57e3794121879cb055f0954756d94bc690476b4
Macrodantin Cap 25mgcapsule25 mgoralNorwich Eaton Canada Inc.1979-12-311996-09-16Canada 5f16b84899037e23705f146ff57e3794121879cb055f0954756d94bc690476b4
Macrodantin Cap 50mgcapsule50 mgoralNorwich Eaton Canada Inc.1979-12-311996-09-16Canada 5f16b84899037e23705f146ff57e3794121879cb055f0954756d94bc690476b4
Nephronex Tab 50mgtablet50 mgoralLaboratoires Cortunon Inc.1985-04-191997-08-12Canada 5f16b84899037e23705f146ff57e3794121879cb055f0954756d94bc690476b4
Nitrofurantion Macrocrystalscapsule100 mg/1oralApotheca Inc.2010-09-27Not applicableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Nitrofurantion Macrocrystalscapsule100 mg/1oralREMEDYREPACK INC.2013-03-19Not applicableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Nitrofurantion Macrocrystalscapsule50 mg/1oralREMEDYREPACK INC.2013-03-18Not applicableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Nitrofurantion Macrocrystalscapsule100 mg/1oralAlvogen Inc.2010-09-27Not applicableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Nitrofurantion Macrocrystalscapsule100 mg/1oralProficient Rx LP2010-09-27Not applicableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Nitrofurantion Macrocrystalscapsule50 mg/1oralAlvogen Inc.2010-09-27Not applicableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Nitrofurantion Macrocrystalscapsule25 mg/1oralAlvogen Inc.2010-09-27Not applicableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Nitrofurantion Macrocrystalscapsule100 mg/1oralPd Rx Pharmaceuticals, Inc.2010-09-27Not applicableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Nitrofurantion Macrocrystalscapsule100 mg/1oralAidarex Pharmaceuticals LLC2010-09-27Not applicableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Nitrofurantoinsuspension25 mg/5mLoralPrasco Laboratories1953-12-23Not applicableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Nitrofurantointablet50 mgoralAa Pharma Inc1974-12-31Not applicableCanada 5f16b84899037e23705f146ff57e3794121879cb055f0954756d94bc690476b4
Nitrofurantointablet100 mgoralAa Pharma Inc1974-12-31Not applicableCanada 5f16b84899037e23705f146ff57e3794121879cb055f0954756d94bc690476b4
Nitrofurantoin 50 Tab 50mgtablet50 mgoralPro Doc Limitee1982-12-311999-08-12Canada 5f16b84899037e23705f146ff57e3794121879cb055f0954756d94bc690476b4
Nitrofurantoin Macrocrystalscapsule100 mg/1oralAmerican Health Packaging2014-02-17Not applicableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Nitrofurantoin Macrocrystalscapsule50 mg/1oralBlue Point Laboratories2013-03-20Not applicableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Nitrofurantoin Macrocrystalscapsule50 mg/1oralAmerican Health Packaging2014-02-17Not applicableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Nitrofurantoin Macrocrystalscapsule100 mg/1oralBlue Point Laboratories2013-03-20Not applicableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Nitrofurantoine 100 Tab 100mgtablet100 mgoralPro Doc Limitee1982-12-311999-08-12Canada 5f16b84899037e23705f146ff57e3794121879cb055f0954756d94bc690476b4
Novo-furan 100mgtablet100 mgoralNovopharm Limited1967-12-312005-08-10Canada 5f16b84899037e23705f146ff57e3794121879cb055f0954756d94bc690476b4
Novo-furan Sus 25mg/5mlsuspension5 mgoralNovopharm Limited1967-12-312005-08-10Canada 5f16b84899037e23705f146ff57e3794121879cb055f0954756d94bc690476b4
Novo-furan Tab 50mgtablet50 mgoralNovopharm Limited1967-12-312005-08-10Canada 5f16b84899037e23705f146ff57e3794121879cb055f0954756d94bc690476b4
Nu-nitrofurantoin Tabletstablet100 mgoralNu Pharm IncNot applicableNot applicableCanada 5f16b84899037e23705f146ff57e3794121879cb055f0954756d94bc690476b4
Nu-nitrofurantoin Tabletstablet50 mgoralNu Pharm IncNot applicableNot applicableCanada 5f16b84899037e23705f146ff57e3794121879cb055f0954756d94bc690476b4
Teva-nitrofurantoincapsule100 mgoralTeva Canada Limited1997-05-02Not applicableCanada 5f16b84899037e23705f146ff57e3794121879cb055f0954756d94bc690476b4
Teva-nitrofurantoincapsule50 mgoralTeva Canada Limited1997-05-02Not applicableCanada 5f16b84899037e23705f146ff57e3794121879cb055f0954756d94bc690476b4
Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Nitrofurantoinsuspension25 mg/5mLoralGAVIS Pharmaceuticals, LLC2015-05-21Not applicableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Nitrofurantoincapsule50 mg/1oralActavis Pharma, Inc.2015-10-01Not applicableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Nitrofurantoinsuspension25 mg/5mLoralAmneal Pharmaceuticals of New York, LLC2011-03-24Not applicableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Nitrofurantoincapsule25 mg/1oralActavis Pharma, Inc.2015-10-01Not applicableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Nitrofurantoinsuspension25 mg/5mLoralCaraco Pharmaceutical Laboratories, Ltd.2012-03-04Not applicableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Nitrofurantoincapsule100 mg/1oralNcs Health Care Of Ky, Inc Dba Vangard Labs2011-05-06Not applicableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Nitrofurantoincapsule50 mg/1oralNcs Health Care Of Ky, Inc Dba Vangard Labs1997-07-09Not applicableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Nitrofurantoincapsule100 mg/1oralPd Rx Pharmaceuticals, Inc.2011-05-06Not applicableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Nitrofurantoincapsule100 mg/1oralREMEDYREPACK INC.2011-11-10Not applicableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Nitrofurantoincapsule100 mg/1oralActavis Pharma, Inc.2015-10-01Not applicableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Nitrofurantoin (macrocrystals)capsule50 mg/1oralA S Medication Solutions Llc2012-10-24Not applicableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Nitrofurantoin (macrocrystals)capsule100 mg/1oralMylan Institutional Inc.2006-08-16Not applicableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Nitrofurantoin (macrocrystals)capsule100 mg/1oralLake Erie Medical & Surgical Supply DBA Quality Care Products LLC2012-04-30Not applicableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Nitrofurantoin (macrocrystals)capsule50 mg/1oralMylan Institutional Inc.2006-08-16Not applicableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Nitrofurantoin (macrocrystals)capsule100 mg/1oralMylan Pharmaceuticals Inc.2004-09-21Not applicableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Nitrofurantoin (macrocrystals)capsule50 mg/1oralPd Rx Pharmaceuticals, Inc.2011-05-06Not applicableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Nitrofurantoin (macrocrystals)capsule50 mg/1oralMylan Pharmaceuticals Inc.1997-09-09Not applicableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Nitrofurantoin Macrocrystalscapsule50 mg/1oralTeva Pharmaceuticals USA Inc2007-03-08Not applicableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Nitrofurantoin Macrocrystalscapsule50 mg/1oralbryant ranch prepack2007-03-08Not applicableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Nitrofurantoin Macrocrystalscapsule100 mg/1oralLiberty Pharmaceuticals, Inc.2007-03-08Not applicableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Nitrofurantoin Macrocrystalscapsule100 mg/1oralSTAT Rx USA LLC1993-01-28Not applicableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Nitrofurantoin Macrocrystalscapsule100 mg/1oralUnit Dose Services2007-03-08Not applicableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Nitrofurantoin Macrocrystalscapsule100 mg/1oralLiberty Pharmaceuticals, Inc.2007-03-08Not applicableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Nitrofurantoin Macrocrystalscapsule100 mg/1oralPd Rx Pharmaceuticals, Inc.2007-03-08Not applicableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Nitrofurantoin Macrocrystalscapsule100 mg/1oralBlenheim Pharmacal, Inc.2010-04-23Not applicableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Nitrofurantoin Macrocrystalscapsule50 mg/1oralA S Medication Solutions Llc2007-03-08Not applicableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Nitrofurantoin Macrocrystalscapsule100 mg/1oralLake Erie Medical & Surgical Supply DBA Quality Care Products LLC2012-04-03Not applicableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Nitrofurantoin Macrocrystalscapsule100 mg/1oralPhysicians Total Care, Inc.2000-03-01Not applicableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Nitrofurantoin Macrocrystalscapsule100 mg/1oralTeva Pharmaceuticals USA Inc2007-03-08Not applicableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Nitrofurantoin Macrocrystalscapsule50 mg/1oralPhysicians Total Care, Inc.2003-08-13Not applicableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Nitrofurantoin Macrocrystalscapsule100 mg/1oralRed Pharm Drug Inc.2011-01-10Not applicableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Nitrofurantoin Macrocrystalscapsule100 mg/1oralRebel Distributors Corp2011-09-19Not applicableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Nitrofurantoin Oral Suspensionsuspension25 mg/5mLoralNovel Laboratories, Inc.2014-09-08Not applicableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Over the Counter ProductsNot Available
International Brands
NameCompany
FurabidGoldshield
NiftranNot Available
SiralidenNot Available
UrantoinBasel
UrolongThiemann
Brand mixturesNot Available
Salts
Name/CASStructureProperties
Nitrofurantoin sodium
ThumbNot applicableDBSALT001418
Categories
UNII927AH8112L
CAS number67-20-9
WeightAverage: 238.157
Monoisotopic: 238.033819322
Chemical FormulaC8H6N4O5
InChI KeyInChIKey=NXFQHRVNIOXGAQ-OQFOIZHKSA-N
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-
IUPAC Name
1-[(Z)-[(5-nitrofuran-2-yl)methylidene]amino]imidazolidine-2,4-dione
SMILES
[O-][N+](=O)C1=CC=C(O1)\C=N/N1CC(=O)NC1=O
Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as hydantoins. These are heterocyclic compounds containing an imidazolidine substituted by ketone group at positions 2 and 4.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassAzolidines
Sub ClassImidazolidines
Direct ParentHydantoins
Alternative Parents
Substituents
  • Hydantoin
  • 2-nitrofuran
  • Ureide
  • Semicarbazone
  • Heteroaromatic compound
  • Semicarbazide
  • Furan
  • Organic nitro compound
  • Organic nitrite
  • C-nitro compound
  • Carboxamide group
  • Oxacycle
  • Azacycle
  • Organic 1,3-dipolar compound
  • Propargyl-type 1,3-dipolar organic compound
  • Allyl-type 1,3-dipolar organic compound
  • Organic oxoazanium
  • Carboxylic acid derivative
  • Hydrocarbon derivative
  • Organic salt
  • Organooxygen compound
  • Organonitrogen compound
  • Carbonyl group
  • Organic zwitterion
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External DescriptorsNot Available
Pharmacology
IndicationMay be used as an alternative in the treatment of urinary tract infections. May be used by females pericoitally for prophylaxis against recurrent cystitis related to coitus.
PharmacodynamicsNitrofurantoin exhibits bacteriostatic or bactericidal effects by inhibiting the synthesis of DNA, RNA, protein and cell wall synthesis.
Mechanism of actionNitrofurantoin 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.
AbsorptionReadily absorbed in GI tract primarily in small intestine. Enhanced by food or delayed gastric emptying via enhanced dissolution rate of the drug.
Volume of distributionNot Available
Protein binding20-60% bound to plasma proteins
Metabolism

Partially metabolized in liver to aminofurantoin.

SubstrateEnzymesProduct
Nitrofurantoin
Not Available
aminofurantoinDetails
Route of eliminationNot Available
Half life0.3-1 hour
ClearanceNot Available
ToxicityAcute toxicity may cause vomiting. Adverse effects include nausea and urine discolouration. Rare hepatotoxic and hypersensitivity reactions have occurred. Hemolytic anemia is a risk in patients with G6PD deficiency. Ascending polyneuropathy may occur with prolonged therapy or in patients with low creatinine clearance.
Affected organisms
  • Gram negative and gram positive bacteria
PathwaysNot Available
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.9832
Blood Brain Barrier+0.958
Caco-2 permeable-0.575
P-glycoprotein substrateNon-substrate0.6374
P-glycoprotein inhibitor INon-inhibitor0.8661
P-glycoprotein inhibitor IINon-inhibitor0.9834
Renal organic cation transporterNon-inhibitor0.8835
CYP450 2C9 substrateNon-substrate0.8373
CYP450 2D6 substrateNon-substrate0.8757
CYP450 3A4 substrateSubstrate0.5799
CYP450 1A2 substrateInhibitor0.9107
CYP450 2C9 inhibitorNon-inhibitor0.9071
CYP450 2D6 inhibitorNon-inhibitor0.9231
CYP450 2C19 inhibitorNon-inhibitor0.9025
CYP450 3A4 inhibitorNon-inhibitor0.9069
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.8943
Ames testAMES toxic0.9231
CarcinogenicityNon-carcinogens0.8869
BiodegradationReady biodegradable0.7448
Rat acute toxicity2.5717 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.7981
hERG inhibition (predictor II)Non-inhibitor0.94
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397 )
Pharmacoeconomics
Manufacturers
  • Watson laboratories inc
  • Shionogi pharma inc
  • Procter and gamble pharmaceuticals inc sub procter and gamble co
  • Lannett co inc
  • Elkins sinn div ah robins co inc
  • Ivax pharmaceuticals inc sub teva pharmaceuticals usa
  • Sandoz inc
  • Whiteworth towne paulsen inc
  • Alvogen inc
  • Mylan pharmaceuticals inc
Packagers
Dosage forms
FormRouteStrength
Capsuleoral100 mg
Capsuleoral25 mg
Capsuleoral25 mg/1
Tabletoral100 mg
Tabletoral50 mg
Capsuleoral100 mg/1
Capsuleoral50 mg/1
Suspensionoral25 mg/5mL
Suspensionoral5 mg
Capsuleoral50 mg
Prices
Unit descriptionCostUnit
Macrobid 100 mg capsule3.02USD capsule
Macrodantin 100 mg capsule2.67USD capsule
Furadantin 25 mg/5ml Suspension2.22USD ml
Furadantin 25 mg/5 ml susp2.13USD ml
Nitrofurantoin powder2.13USD g
Nitrofurantoin Monohyd Macro 100 mg capsule2.12USD capsule
Nitrofurantoin mono-mcr 100 mg2.04USD each
Nitrofurantoin-macro 100 mg2.04USD each
Nitrofurantoin Macrocrystal 100 mg capsule1.88USD capsule
Nitrofurantoin mcr 100 mg capsule1.86USD capsule
Macrodantin 50 mg capsule1.67USD capsule
Macrodantin 25 mg capsule1.3USD capsule
Nitrofurantoin Macrocrystal 50 mg capsule1.14USD capsule
Nitrofurantoin mcr 50 mg capsule1.09USD capsule
Macrobid 100 mg Capsule (Macrocrystals/Monohydrate)0.78USD capsule
Novo-Furantoin 100 mg Capsule (Macrocrystals)0.66USD capsule
Novo-Furantoin 50 mg Capsule (Macrocrystals)0.35USD capsule
Apo-Nitrofurantoin 100 mg Tablet0.23USD tablet
Apo-Nitrofurantoin 50 mg Tablet0.17USD tablet
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
PatentsNot Available
Properties
StateSolid
Experimental Properties
PropertyValueSource
melting point223-228Gever, G.; U.S. Patent 2,802,002; August 6, 1957; assigned to The Norwich Pharmacal Co.
water solubility79.5 mg/L (at 24 °C)YALKOWSKY,SH & DANNENFELSER,RM (1992)
logP-0.47HANSCH,C ET AL. (1995)
pKa7.2SANGSTER (1994)
Predicted Properties
PropertyValueSource
Water Solubility0.415 mg/mLALOGPS
logP0.03ALOGPS
logP-0.22ChemAxon
logS-2.8ALOGPS
pKa (Strongest Acidic)9.23ChemAxon
pKa (Strongest Basic)-2.2ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area120.73 Å2ChemAxon
Rotatable Bond Count3ChemAxon
Refractivity53.11 m3·mol-1ChemAxon
Polarizability19.75 Å3ChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Mass Spec (NIST)Not Available
SpectraNot Available
References
Synthesis Reference

Tara Bielski, Kerry Benson, “Novel orally administrable formulation of nitrofurantoin and a method for preparing said formulation.” U.S. Patent US20050202079, issued September 15, 2005.

US20050202079
General ReferencesNot Available
External Links
ATC CodesJ01XE01
AHFS Codes
  • 08:36.00
PDB Entries
FDA labelDownload (923 KB)
MSDSDownload (73.6 KB)
Interactions
Drug Interactions
Drug
DapsoneThe risk or severity of adverse effects can be increased when Dapsone is combined with Nitrofurantoin.
EplerenoneNitrofurantoin may increase the hyperkalemic activities of Eplerenone.
Magnesium TrisilicateThe serum concentration of Nitrofurantoin can be decreased when it is combined with Magnesium Trisilicate.
Nitric OxideThe risk or severity of adverse effects can be increased when Nitric Oxide is combined with Nitrofurantoin.
NorfloxacinThe therapeutic efficacy of Norfloxacin can be decreased when used in combination with Nitrofurantoin.
PrilocaineThe risk or severity of adverse effects can be increased when Nitrofurantoin is combined with Prilocaine.
ProbenecidThe serum concentration of Nitrofurantoin can be increased when it is combined with Probenecid.
Sodium NitriteThe risk or severity of adverse effects can be increased when Nitrofurantoin is combined with Sodium Nitrite.
Sodium picosulfateThe therapeutic efficacy of Sodium picosulfate can be decreased when used in combination with Nitrofurantoin.
SpironolactoneNitrofurantoin may increase the hyperkalemic activities of Spironolactone.
Food Interactions
  • Do not take magnesium at the same time.
  • Take with food since it increases bioavailability and reduces irritation.

Targets

1. Probable pyruvate-flavodoxin oxidoreductase

Kind: Protein

Organism: Escherichia coli (strain K12)

Pharmacological action: yes

Actions: potentiator

Components

Name UniProt ID Details
Probable pyruvate-flavodoxin oxidoreductase P52647 Details

References:

  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. Pubmed
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. Pubmed
  3. Breeze AS, Obaseiki-Ebor EE: Nitrofuran reductase activity in nitrofurantoin-resistant strains of Escherichia coli K12: some with chromosomally determined resistance and others carrying R-plasmids. J Antimicrob Chemother. 1983 Dec;12(6):543-7. Pubmed
  4. Sisson G, Goodwin A, Raudonikiene A, Hughes NJ, Mukhopadhyay AK, Berg DE, Hoffman PS: Enzymes associated with reductive activation and action of nitazoxanide, nitrofurans, and metronidazole in Helicobacter pylori. Antimicrob Agents Chemother. 2002 Jul;46(7):2116-23. Pubmed

2. Oxygen-insensitive NADPH nitroreductase

Kind: Protein

Organism: Escherichia coli (strain K12)

Pharmacological action: yes

Actions: potentiator

Components

Name UniProt ID Details
Oxygen-insensitive NADPH nitroreductase P17117 Details

References:

  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. Pubmed
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. Pubmed
  3. Kutty R, Bennett GN: Biochemical characterization of trinitrotoluene transforming oxygen-insensitive nitroreductases from Clostridium acetobutylicum ATCC 824. Arch Microbiol. 2005 Nov;184(3):158-67. Epub 2005 Nov 10. Pubmed
  4. Lightfoot RT, Shuman D, Ischiropoulos H: Oxygen-insensitive nitroreductases of Escherichia coli do not reduce 3-nitrotyrosine. Free Radic Biol Med. 2000 Apr 1;28(7):1132-6. Pubmed

3. 30S ribosomal protein S10

Kind: Protein

Organism: Escherichia coli (strain K12)

Pharmacological action: unknown

Components

Name UniProt ID Details
30S ribosomal protein S10 P0A7R5 Details

References:

  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. Pubmed
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. Pubmed

Enzymes

1. NADPH--cytochrome P450 reductase

Kind: Protein

Organism: Human

Pharmacological action: unknown

Actions: substrate

Components

Name UniProt ID Details
NADPH--cytochrome P450 reductase P16435 Details

References:

  1. Wang Y, Gray JP, Mishin V, Heck DE, Laskin DL, Laskin JD: Role of cytochrome P450 reductase in nitrofurantoin-induced redox cycling and cytotoxicity. Free Radic Biol Med. 2008 Mar 15;44(6):1169-79. Epub 2007 Dec 23. Pubmed

Transporters

1. ATP-binding cassette sub-family G member 2

Kind: Protein

Organism: Human

Pharmacological action: unknown

Actions: substrate

Components

Name UniProt ID Details
ATP-binding cassette sub-family G member 2 Q9UNQ0 Details

References:

  1. Perez M, Real R, Mendoza G, Merino G, Prieto JG, Alvarez AI: Milk secretion of nitrofurantoin, as a specific BCRP/ABCG2 substrate, in assaf sheep: modulation by isoflavones. J Vet Pharmacol Ther. 2009 Oct;32(5):498-502. Pubmed

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Drug created on June 13, 2005 07:24 / Updated on November 30, 2015 12:10