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

• ChemBase编号: 104426
• 分子式: C8H6N4O5
• 平均质量: 238.15704
• 单一同位素质量: 238.03381931
• SMILES: [O-][N+](=O)c1ccc(o1)/C=N/N1CC(=O)NC1=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)
• InChIKey: NXFQHRVNIOXGAQ-UHFFFAOYSA-N

名称和登记号

名称

• IUPAC标准名: 1-{[(5-nitrofuran-2-yl)methylidene]amino}imidazolidine-2,4-dione; 1-[(E)-[(5-nitrofuran-2-yl)methylidene]amino]imidazolidine-2,4-dione
• IUPAC传统名: macrodantin; nitrofurantoin sodium; 1-[(E)-[(5-nitrofuran-2-yl)methylidene]amino]imidazolidine-2,4-dione
• 别名: N-(5-硝基-2-呋喃亚甲基)-1-氨基海因; 呋喃坦啶; 硝基呋喃妥因; 呋喃妥因; N-[5-Nitro-2-furfurylidene]-1-aminohydantoin; NITROFURANTOIN; Nitrofurantoin; N-(5-Nitro-2-furfurylidene)-1-aminohydantoin; Furadoxyl; Nitrofurantoine; 1-(((5-Nitrofuran-2-yl)methylene)amino)imidazolidine-2,4-dione; 1-((5-nitrofurfurylidene)amino)hydantoin; Furadantin; Macrodantin; Urantoin; 1-[[(5-Nitro-2-furanyl)methylene]amino]-2,4-imidazolidinedione; 1-(5-Nitro-2-furfurylideneamino)hydantoin; 5-Nitrofurantoin; Berkfurin; Chemiofuran; Cyantin; Cystit; Furadantoin; Furadoin; Furadoine; Nifurantin; Nitoin; Nitrofurantoin; Novofuran; Orafuran; Urodin; Zoofurin

登记号

• CAS号: 67-20-9
• EC号: 200-646-5
• MDL号: MFCD00003224
• Beilstein号: 893207
• PubChem SID: 162091898; 24897842; 24870238
• PubChem CID: 6604200

理论计算性质

• Acid pKa: 8.2330885
• 质子受体: 5
• 质子供体: 1
• LogD (pH = 5.5): -0.22224307
• LogD (pH = 7.4): -0.28023475
• 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

分子性质

理化性质

• 外观: yellow crystalline
• 熔点: 268°C

安全信息

• 保存条件: Room Temperature (15-30°C), Protect from light
• RTECS编号: MU2800000
• 欧盟危险性物质标志: 有害性(Harmful) (Xn)
• 德国WGK号: 3
• 危险公开号: 22-42/43; R:22-40-60
• 安全公开号: 22-36/37-45; S:38-46-36/37/39
• GHS危险品标识: GHS07; GHS08
• GHS警示词: Danger
• GHS危险声明: H302-H317-H334
• GHS警示性声明: P261-P280-P342 + P311
• 个人保护装置: dust mask type N95 (US), Eyeshields, Faceshields, Gloves

药理学性质

• 生物活性机理: Damaging bacterial DNA, ribosomal proteins, DNA, effecting respiration, pyruvate metabolism and other macromolecules within the cell

产品相关信息

• 纯度: 98%
• 级别: VETRANAL™, analytical standard
• 应用领域: activity against: Escherichia coli; Enterococcus; Antibacterial agent used to treat urinary-tract infections and Staphylococcus aureus; Antiseptic; bactericidal at high-dose; some strains of Klebsiella; some strains of Enterobacter.; Staphylococcus saprophyticus
• Empirical Formula (Hill Notation): C8H6N4O5

详细说明

MP Biomedicals - 02155881

(N-[5-Nitro-2-furfurylidene]-1-aminohydantoin) Yellow crystals.

Sigma Aldrich - N7878

Application
Nitrofurantoin is a nitrofuran antibiotic that is used as a substrate of bacterial nitrofuran reductase to study the interactions of active metabolites with DNA, ribosomal proteins and metabolic and pro-oxidant processes. It is used to study nitrofurantoin-induced toxicity 1 and antiobiotic resistance2.
Biochem/physiol Actions
Nitrofurantoin is activated by bacterial flavoproteins (nitrofuran reductase) to active reduced reactive intermediates that modulate and damage ribosomal proteins or other macromolecules, such as DNA. This inhibits DNA, RNA, protein, and cell wall synthesis which causes cell death3. Nitrofurantoin has a low resistance potential that is rapidly metabolized by mammals and is active against both Gram-positive and Gram-negative bacteria. It is also a pro-oxidant that is cytotoxic due to the generation of intracellular H 2O 2. It is an inhibitor of glutathione reductase. Nitrofurantoin produces hepatotoxicity caused by the redox cycling of the nitro group and its radical anion which leads to oxidative stress1.

Sigma Aldrich - 46502

法律信息
VETRANAL 商标 Sigma-Aldrich Co. LLC

Toronto Research Chemicals - N493850

A nitrofuran antibiotic with low resistance potential that is rapidly metabolized by mammals. Active against both Gram-positive and Gram-negative bacteria. Nitrofurantoin is also a prooxidant that is cytotoxic due to the generation of intracellular H2O2.

参考文献

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• Cadwallader, D.E. et al., Anal. Profiles Drug Subst., 1976, 5, 345, (rev)
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• Bryan, G.T., Carcinog. - Compr. Surv., (Ed. Bryan, G.T.), Vol 4. Nitrofurans, Raven Press, N.Y., 1978, (book)
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