N7878
呋喃妥因
98.0-102.0% (EP, UV)
别名:
N -（5-硝基-2-呋喃亚基）-1-氨基乙内酰脲, 呋喃坦啶, 硝基呋喃妥因
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关于此项目
经验公式（希尔记法）:
C8H6N4O5
化学文摘社编号:
分子量:
238.16
UNSPSC Code:
51102829
NACRES:
NA.85
PubChem Substance ID:
EC Number:
200-646-5
Beilstein/REAXYS Number:
893207
MDL number:
产品名称
呋喃妥因, 98.0-102.0% (EP, UV)
SMILES string
[O-][N+](=O)c1ccc(\C=N\N2CC(=O)NC2=O)o1
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+
InChI key
NXFQHRVNIOXGAQ-YCRREMRBSA-N
assay
98.0-102.0% (EP, UV)
form
(Crystalline Powder or crystals)
color
yellow
solubility
DMF: soluble 50 mg/mL
antibiotic activity spectrum
Gram-negative bacteria
Gram-positive bacteria
mode of action
DNA synthesis | interferes
cell wall synthesis | interferes
protein synthesis | interferes
Quality Level
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Application
呋喃妥因是一种硝基呋喃类抗生素，用作细菌硝基呋喃还原酶的底物，研究活性代谢物与 DNA、核糖体蛋白以及代谢和促氧化过程的相互作用。用于研究呋喃妥因引起的毒性 及抗生素耐药性 。呋喃妥因适合于体外杀灭单核细胞增生性李斯特菌。研究描述了使用抗氧化剂减轻呋喃妥因对培养人 WI-38 成纤维细胞的毒性作用。据报道，包括呋喃妥因在内的各种抗生素可引起离体牛乳腺多形核白细胞体外形态特征、活力和吞噬活性的改变。
Biochem/physiol Actions
呋喃妥因是一种抗菌化合物，历史上一直通过 1-氨基乙内酰硫酸酯与 5-硝基-2-呋喃甲醛二乙酸酯反应制备。对许多革兰阳性菌和革兰阴性菌有抗菌活性。呋喃妥因对肠球菌、葡萄球菌、链球菌、角质菌、许多大肠埃希氏菌 菌株和 变形杆菌属的大多数菌株有效 。且 假单胞菌绿脓杆菌 对该化合物的抗性更强。呋喃妥因被细菌黄素蛋白（硝基呋喃还原酶）激活，主动还原调节和损伤核糖体蛋白或其他大分子（如 DNA）的活性中间体。这抑制了导致细胞死亡的 DNA、RNA、蛋白质和细胞壁合成 。呋喃妥因具有较低的耐药潜力，可被哺乳动物迅速代谢，对革兰阳性菌和革兰阴性菌均有活性。它也是一种促氧化剂，由于产生细胞内 H2O2 而具有细胞毒性。为谷胱甘肽还原酶抑制剂。呋喃妥因通过硝基及其自由基阴离子的氧化还原循环产生肝毒性，导致氧化应激。
Other Notes
将容器密闭保存在干燥和通风良好的地方。对光敏感。
signalword
Danger
hcodes
Hazard Classifications
Acute Tox. 4 Oral - Resp. Sens. 1 - Skin Sens. 1
存储类别
11 - Combustible Solids
wgk
WGK 1
flash_point_f
Not applicable
flash_point_c
Not applicable
ppe
dust mask type N95 (US), Eyeshields, Faceshields, Gloves
J Pourahmad et al.
Advances in experimental medicine and biology, 500, 261-265 (2002-01-05)
1. The enzymes responsible for the reductive activation of NFT are not known. We have now shown that under aerobic conditions, inhibitors of cytochrome P450 or P450 reductase but not DT diaphorase prevented NFT induced cytotoxicity and reactive oxygen species
W Shen et al.
Human & experimental toxicology, 15(5), 428-434 (1996-05-01)
1. Nitrofurantoin is an antimicrobial agent which produces hepatotoxicity caused by the redox cycling of the nitro group and its radical anion. This futile cycling triggers a complex series of events known collectively as oxidative stress. 2. Our goal was
Mutations to Nitrofurantoin and Nitrofurazone Resistance in Escherichia coli K12
Anthony S. Breeze and EMMANUEL E. OBASEIKI-EBOR
Microbiology, 129, 99-103 (1983)
S C Nickerson et al.
American journal of veterinary research, 46(11), 2259-2265 (1985-11-01)
Effects of antibiotics and antibiotic vehicles on polymorphonuclear leukocytes (PMNL) isolated from bovine mammary glands were studied in vitro. Amikacin, dicloxacillin, erythromycin, gentamicin, lincomycin, nitrofurantoin, novobiocin-penicillin, polymyxin B, rifampin, tetracycline, or tiamulin was added to culture medium at 1 mg/ml
Martindale: The Extra Pharmacopoeia
Martindale: The Extra Pharmacopoeia, 1529-1531 (1996)
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