2721 T3D2679 Nitrofurantoin 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. 67-20-9 5353830 C8H6N4O5 238.033820 Solid (A308). 223-228°C 79.5 mg/L (at 24°C) Oral. Readily absorbed in GI tract primarily in small intestine. Enhanced by food or delayed gastric emptying via enhanced dissolution rate of the drug. 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. Nitrofurantoin inhibits bacterial acetyl-coenzyme A, interfering with the organism's carbohydrate metabolism. The drug also can disrupt bacterial cell wall formation. The overall effect is inhibition of bacterial growth or cell death. Hepatic (75%) (L1174). Partially metabolized in liver to aminofurantoin. Half Life: 0.3-1 hour 3, not classifiable as to its carcinogenicity to humans. (L135) 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. Sialadenitis, pancreatitis, peripheral neuropathy, Asthenia, vertigo, and nystagmus, benign intracranial hypertension (pseudotumor cerebri), confusion, depression, optic neuritis, and psychotic reactions (A308). 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. There is no specific antidote, but a high fluid intake should be maintained to promote urinary excretion of the drug. Nitrofurantoin is dialyzable. (L1712) 2009-07-15T20:48:38Z 2014-12-24T20:25:49Z Cytochrome P450 2E1 (CYP2E1) (P05181) (A308). Nitrofurantoin 1039679 Nitrofurantoin DB00698 true Cytochrome P450 2E1 (P05181) (A308) [H]\C(=N\N1CC(O)=NC1=O)C1=CC=C(O1)N(=O)=O C8H6N4O5 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-OQFOIZHKSA-N 238.157 238.033819322 Exogenous Solid -0.47 HMDB14836 CHEMBL572 4510228 <p>Tara Bielski, Kerry Benson, &#8220;Novel orally administrable formulation of nitrofurantoin and a method for preparing said formulation.&#8221; U.S. Patent US20050202079, issued September 15, 2005.</p>