1-[(Z)-[(5-nitrofuran-2-yl)methylidene]amino]imidazolidine-2,4-dione

• ChemBase ID: 580
• Molecular Formular: C8H6N4O5
• Molecular Mass: 238.15704
• Monoisotopic Mass: 238.03381931
• SMILES: o1c(/C=N\N2CC(=O)NC2=O)ccc1[N+](=O)[O-]
• Canonical SMILES: O=C1NC(=O)N(C1)/N=C\c1ccc(o1)[N+](=O)[O-]
• 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-
• InChIKey: NXFQHRVNIOXGAQ-OQFOIZHKSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 1-[(Z)-[(5-nitrofuran-2-yl)methylidene]amino]imidazolidine-2,4-dione
• IUPAC Traditional name: nitrofurantoin
• Brand Name: 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
• Synonyms: Nitrofurantoin; N-(5-Nitro-2-furfurylidene)-1-aminohydantoin; Nitrofurantoin; 呋喃妥英

Database IDs

• CAS Number: 67-20-9
• EC Number: 200-646-5
• MDL Number: MFCD00003224
• PubChem SID: 46504447; 160964043
• PubChem CID: 5353830

CALCULATED PROPERTIES

JChem

• Acid pKa: 9.233153
• H Acceptors: 5
• H Donor: 1
• LogD (pH = 5.5): -0.22152936
• LogD (pH = 7.4): -0.22770812
• Log P: -0.22144999
• Molar Refractivity: 52.1099 cm^3
• Polarizability: 19.238554 Å^3
• Polar Surface Area: 118.05 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 0.03
• LOG S: -2.76
• Solubility (Water): 4.15e-01 g/l

PROPERTIES

Physical Property

• Solubility: 79.5 mg/L
• Melting Point: ca 265°C dec.
• Hydrophobicity(logP): -0.1

Safety Information

• Storage Warning: Light Sensitive & Hygroscopic
• European Hazard Symbols: X
• Risk Statements: 22-40-42/43-62-68
• Safety Statements: 22-36/37-45
• TSCA Listed: 是
• GHS Pictograms: GHS06; GHS08
• GHS Hazard statements: H301-H317-H334-H341-H351-H361
• GHS Precautionary statements: P285-P301+P310-P302+P352-P321-P405-P501A

Product Information

• Purity: 98%

DETAILS

DrugBank - DB00698

• 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