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

• ChemBase编号: 580
• 分子式: C8H6N4O5
• 平均质量: 238.15704
• 单一同位素质量: 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

名称和登记号

名称

• IUPAC标准名: 1-[(Z)-[(5-nitrofuran-2-yl)methylidene]amino]imidazolidine-2,4-dione
• IUPAC传统名: nitrofurantoin
• 商标名: 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
• 别名: 呋喃妥英; Nitrofurantoin; N-(5-Nitro-2-furfurylidene)-1-aminohydantoin; Nitrofurantoin

登记号

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

理论计算性质

JChem

• Acid pKa: 9.233153
• 质子受体: 5
• 质子供体: 1
• LogD (pH = 5.5): -0.22152936
• LogD (pH = 7.4): -0.22770812
• Log P: -0.22144999
• 摩尔折射率: 52.1099 cm^3
• 极化性: 19.238554 Å^3
• 极化表面积: 118.05 Å^2
• 可自由旋转的化学键: 3
• 里宾斯基五规则: true

ALOGPS 2.1

• Log P: 0.03
• LOG S: -2.76
• 溶解度: 4.15e-01 g/l

分子性质

理化性质

• 溶解度: 79.5 mg/L
• 熔点: ca 265°C dec.
• 疏水性(logP): -0.1

安全信息

• 保存注意事项: Light Sensitive & Hygroscopic
• 欧盟危险性物质标志: X
• 危险公开号: 22-40-42/43-62-68
• 安全公开号: 22-36/37-45
• TSCA收录: 是
• GHS危险品标识: GHS06; GHS08
• GHS危险声明: H301-H317-H334-H341-H351-H361
• GHS警示性声明: P285-P301+P310-P302+P352-P321-P405-P501A

产品相关信息

• 纯度: 98%

详细说明

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