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Nitrofurantoin

Catalog No. DB00698 Name DrugBank
CAS Number 67-20-9 Website http://www.ualberta.ca/
M. F. C8H6N4O5 Telephone (780) 492-3111
M. W. 238.15704 Fax (780) 492-1071
Purity Email david.wishart@ualberta.ca
Storage Chembase ID: 580

SYNONYMS

IUPAC name
1-[(Z)-[(5-nitrofuran-2-yl)methylidene]amino]imidazolidine-2,4-dione
IUPAC Traditional name
nitrofurantoin
Brand Name
Furan
Nitrofur-C
Trantoin
Fua Med
Macrodantin
Furatoin
Benkfuran
Furabid
Furanite
Furophen T-Caps
Nierofu
Nifurantin
Nitrofan
Novo-Furantoin
Novofuran
Orafuran
Siraliden
Upiol
Cistofuran
Cystit
Furadantin
Furadantin Retard
Furadantine Mc
Furadonin
Furalan
Furaloid
Furedan
Furina
Furobactina
Gerofuran
Ituran
Macpac
Macrodantina
Nitoin
Nitrex
Phenurin
Uro-Selz
Uro-Tablinen
Urofuran
Urofurin
Welfurin
Alfuran
Apo-Nitrofurantoin
Berkfurin
Ceduran
Chemiofuran
Cyantin
Dantafur
Fuamed
Fur-Ren
Furachel
Furadantina MC
Furadantine
Furadantine-Mc
Furadantoin
Furadoin
Furadoine
Furadonine
Furadontin
Furantoin
Furantoina
Furophen T
It-Uran
Ivadantin
Macrobid
Macrofuran
Macrofurin
N-Toin
Nitrofuradantin
Parfuran
Ro-Antoin
Uerineks
Urantoin
Urizept
Urodin
Urolisa
Urolong
USAF EA-2
Uvaleral
Zoofurin

DATABASE IDS

PubChem SID 46504447
CAS Number 67-20-9
PubChem CID 5353830

PROPERTIES

Hydrophobicity(logP) -0.1
Solubility 79.5 mg/L

DETAILS

Description (English)
Item Information
Drug Groups approved
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.
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.
Pharmacology Nitrofurantoin exhibits bacteriostatic or bactericidal effects by inhibiting the synthesis of DNA, RNA, protein and cell wall synthesis.
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
Biotransformation Partially metabolized in liver to aminofurantoin.
Absorption Readily absorbed in GI tract primarily in small intestine. Enhanced by food or delayed gastric emptying via enhanced dissolution rate of the drug.
Half Life 0.3-1 hour
Protein Binding 20-60% bound to plasma proteins
External Links
Wikipedia
RxList
Drugs.com

REFERENCES