Alfuran;Apo-Nitrofurantoin;Benkfuran;Berkfurin;Ceduran;Chemiofuran;Cistofuran;Cyantin;Cystit;Dantafur;Fua Med;Fuamed;Fur-Ren;Furabid;Furachel;Furadantin;Furadantin Retard;Furadantina MC;Furadantine;Furadantine Mc;Furadantine-Mc;Furadantoin;Furadoin;Furadoine;Furadonin;Furadonine;Furadontin;Furalan;Furaloid;Furan;Furanite;Furantoin;Furantoina;Furatoin;Furedan;Furina;Furobactina;Furophen T;Furophen T-Caps;Gerofuran;It-Uran;Ituran;Ivadantin;Macpac;Macrobid;Macrodantin;Macrodantina;Macrofuran;Macrofurin;N-Toin;Nierofu;Nifurantin;Nitoin;Nitrex;Nitrofan;Nitrofur-C;Nitrofuradantin;Novo-Furantoin;Novofuran;Orafuran;Parfuran;Phenurin;Ro-Antoin;Siraliden;Trantoin;Uerineks;Upiol;Urantoin;Urizept;Uro-Selz;Uro-Tablinen;Urodin;Urofuran;Urofurin;Urolisa;Urolong;USAF EA-2;Uvaleral;Welfurin;Zoofurin;

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.

• Alvogen inc
• Elkins sinn div ah robins co inc
• Ivax pharmaceuticals inc sub teva pharmaceuticals usa
• Lannett co inc
• Mylan pharmaceuticals inc
• Procter and gamble pharmaceuticals inc sub procter and gamble co
• Sandoz inc
• Shionogi pharma inc
• Watson laboratories inc
• Whiteworth towne paulsen inc

• Amerisource Health Services Corp.
• Apotheca Inc.
• A-S Medication Solutions LLC
• Bryant Ranch Prepack
• Buffalo Molasses LLC
• Caremark LLC
• Central Texas Community Health Centers
• Comprehensive Consultant Services Inc.
• Direct Dispensing Inc.
• Direct Pharmaceuticals Inc.
• Dispensing Solutions
• Diversified Healthcare Services Inc.
• Eon Labs
• Gallipot
• Goldline Laboratories Inc.
• H.J. Harkins Co. Inc.
• Heartland Repack Services LLC
• Ivax Pharmaceuticals
• Kaiser Foundation Hospital
• Liberty Pharmaceuticals
• Medvantx Inc.
• Murfreesboro Pharmaceutical Nursing Supply
• Mylan
• Norwich Pharmaceuticals Inc.
• Nucare Pharmaceuticals Inc.
• Palmetto Pharmaceuticals Inc.
• Patient First Corp.
• PCA LLC
• PD-Rx Pharmaceuticals Inc.
• Pharmaceutical Utilization Management Program VA Inc.
• Pharmacy Service Center
• Pharmedix
• Pharmpak Inc.
• Physicians Total Care Inc.
• Preferred Pharmaceuticals Inc.
• Prepackage Specialists
• Prepak Systems Inc.
• Promex Medical Inc.
• Ranbaxy Laboratories
• Rebel Distributors Corp.
• Redpharm Drug
• Remedy Repack
• Sandhills Packaging Inc.
• Sciele Pharma Inc.
• Scruggs Pharmacal Co. Inc.
• Shionogi Pharma Inc.
• Southwood Pharmaceuticals
• Teva Pharmaceutical Industries Ltd.
• Tya Pharmaceuticals
• UDL Laboratories
• United Research Laboratories Inc.
• Vangard Labs Inc.
• Warner Chilcott Co. Inc.
• Watson Pharmaceuticals
• WC Pharmaceuticals

Synthesis Reference	Not Available
General Reference	Not Available

Type	small molecule

Classes

Nitrofurans Imidazolidines

Substructures

Semicarbazones Carboxylic Acids and Derivatives Oxoazaniums Amino Ketones Nitro compounds Nitrofurans Imidazolidines Heterocyclic compounds Aromatic compounds Carboxamides and Derivatives Semicarbazides Hydrazine Derivatives Furans Imines

antibacterials 抗细菌;

Indication	May 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.
Pharmacodynamics	Nitrofurantoin exhibits bacteriostatic or bactericidal effects by inhibiting the synthesis of DNA, RNA, protein and cell wall synthesis.
Mechanism 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.
Absorption	Readily absorbed in GI tract primarily in small intestine. Enhanced by food or delayed gastric emptying via enhanced dissolution rate of the drug.
Volume of distribution	Not Available
Protein binding	20-60% bound to plasma proteins
Metabolism	Partially metabolized in liver to aminofurantoin. Important The metabolism module of DrugBank is currently in beta. Questions or suggestions? Please contact us. Substrate Enzymes Product Nitrofurantoin aminofurantoin Details
Route of elimination	Not Available
Half life	0.3-1 hour
Clearance	Not Available
Toxicity	Acute 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
Pathways	Not Available

Properties
State	solid
Experimental Properties	Property Value Source melting point 263 °C PhysProp water solubility 79.5 mg/L (at 24 °C) YALKOWSKY,SH & DANNENFELSER,RM (1992) logP -0.47 HANSCH,C ET AL. (1995) pKa 7.2 SANGSTER (1994)
Predicted Properties	Property Value Source water solubility 4.15e-01 g/l ALOGPS logP 0.03 ALOGPS logP -0.22 ChemAxon logS -2.8 ALOGPS pKa (strongest acidic) 9.23 ChemAxon pKa (strongest basic) -2.2 ChemAxon physiological charge 0 ChemAxon hydrogen acceptor count 5 ChemAxon hydrogen donor count 1 ChemAxon polar surface area 120.73 ChemAxon rotatable bond count 3 ChemAxon refractivity 53.11 ChemAxon polarizability 19.75 ChemAxon

• Do not take magnesium at the same time.
• Take with food since it increases bioavailability and reduces irritation.