{[(5-nitrofuran-2-yl)methylidene]amino}urea

• ChemBase编号: 220
• 分子式: C6H6N4O4
• 平均质量: 198.13624
• 单一同位素质量: 198.03890469
• SMILES: o1c(ccc1[N+](=O)[O-])/C=N/NC(=O)N
• Canonical SMILES: NC(=O)N/N=C/c1ccc(o1)[N+](=O)[O-]
• InChI: InChI=1S/C6H6N4O4/c7-6(11)9-8-3-4-1-2-5(14-4)10(12)13/h1-3H,(H3,7,9,11)/b8-3+
• InChIKey: IAIWVQXQOWNYOU-FPYGCLRLSA-N

名称和登记号

名称

• IUPAC标准名: {[(5-nitrofuran-2-yl)methylidene]amino}urea; [(E)-[(5-nitrofuran-2-yl)methylidene]amino]urea
• IUPAC传统名: 5-nitrofurfural semicarbazone; nitrofurazone
• 商标名: Actin-N; Aldomycin; Alfucin; Amifur; Babrocid; Becafurazone; Biofuracina; Biofurea; Chemofuran; Chixin; Cocafurin; Coxistat; Dermofural; Dymazone; Dynazone; Eldezol; Eldezol F-6; Fedacin; Flavazone; Fracine; Furacilin; Furacillin; Furacin; Furacin Soluble Dressing; Furacin Topical Cream; Furacin Topical Solution; Furacin-E; Furacin-HC; Furacine; Furacinetten; Furacoccid; Furacort; Furacycline; Furaderm; Furagent; Furalcyn; Furaldon; Furalone; Furametral; Furan-Ofteno; Furaplast; Furaseptyl; Furaskin; Furatsilin; Furaziline; Furazin; Furazina; Furazol W; Furazone; Furazyme; Furesol; Furfurin; Furosem; Fuvacillin; Hemofuran; Ibiofural; Mammex; Mastofuran; Monafuracin; Monafuracis; Monofuracin; NF-7; NFS; Nefco; Nifucin; Nifurid; Nifuzon; Nitrofural; Nitrofuran; Nitrofurane; Nitrofurol; Nitrozone; Otofural; Otofuran; Sanfuran; Spray-Dermis; Spray-Foral; Vabrocid; Vadrocid; Yatrocin
• 别名: 5-硝基-2-亚糠基半卡巴腙; 呋喃西林 溶液; 5-硝基-2-呋喃甲醛半卡腙; 呋喃西林; 硝呋醛; 5-硝基-2-糠醛半卡巴腙; Nitrofurazone solution; 5-Nitro-2-furaldehyde semicarbazone; 5-Nitro-2-furfural semicarbazone; Furacin; 2-[(5-Nitro-2-furanyl)methylene]hydrazinecarboxamide; (5-Nitro-2-furfurylidenamino)urea; 1-(5-Nitro-2-furfurylidene)semicarbazide; Aldomycin; Alfucin; Amifur; Babrocid; Chemofuran; Coxistat; Furesol; Mammex; Mastofuran; Nitrozone; Otofural; Vabrocid; Nitrofural; Nitrofurazone; 5-NITRO-2-FURALDEHYDE SEMICARBAZONE; 5-NITROFURFURALSEMICARBAZONE; NF; NFZ; Nitrofurazan; Nitrofurazone; Nitrofural; Furacilin; ACTIN-N; Otofuran

登记号

• CAS号: 59-87-0
• EC号: 200-835-2; 200-443-1
• MDL号: MFCD00003225
• Beilstein号: 1347298; 86403
• 默克索引号: 146600
• PubChem SID: 160963683; 24886543; 46506509; 24869937
• PubChem CID: 5447130
• ATC码: QP51AC02; D09AA03; S01AX04; S02AA02; P01CC02; D08AF01; QG01AX90; B05CA03
• CHEMBL: 869
• Chemspider ID: 4566720
• DrugBank ID: DB00336
• KEGG ID: C08042
• 美国药典/FDA物质标识码: X8XI70B5Z6
• 维基百科标题: Nitrofural

理论计算性质

JChem

• LogD (pH = 5.5): -0.13506359
• LogD (pH = 7.4): -0.13507833
• Log P: -0.13506338
• 摩尔折射率: 44.2064 cm^3
• 极化性: 16.137276 Å^3
• 极化表面积: 123.76 Å^2
• 可自由旋转的化学键: 3
• 里宾斯基五规则: true
• Acid pKa: 11.794831
• 质子受体: 4
• 质子供体: 2

ALOGPS 2.1

• Log P: 0.23
• LOG S: -2.87
• 溶解度: 2.68e-01 g/l

分子性质

理化性质

• 溶解度: 210 mg/L (Approximately 50%); DMSO
• 外观: Yellow Solid
• 熔点: 235-237°C; 242-244 °C(lit.); 242-244°C; ca 240°C dec.
• 闪点: 2 °C; 35.6 °F
• 疏水性(logP): 0.2

安全信息

• 保存条件: -20°C; 2-8°C, Protect from light; Refrigerator
• 保存注意事项: Light Sensitive
• RTECS编号: LT7700000
• 欧盟危险性物质标志: 易燃性(Flammable) (F); X; 有害性(Harmful) (Xn)
• 联合国危险货物编号: 1648
• 德国WGK号: 2; 3
• 联合国危险货物等级: 3
• 联合国危险货物包装类别(PG): 2
• 危险公开号: 11-20/21/22-36; 22; 22-40-62-68; R:22
• 安全公开号: 16-36/37; 36; 36/37; S:36/37/39
• TSCA收录: 是
• GHS危险品标识: GHS02; GHS06; GHS07; GHS08
• GHS警示词: Danger; Warning
• GHS危险声明: H225-H302-H312-H319-H332; H301-H341-H351-H361; H302-H317
• GHS警示性声明: P210-P280-P305 + P351 + P338; P280; P281-P301+P310-P321-P308+P313-P405-P501A
• 个人保护装置: dust mask type N95 (US), Eyeshields, Faceshields, Gloves; Eyeshields, Faceshields, full-face respirator (US), Gloves, multi-purpose combination respirator cartridge (US), type ABEK (EN14387) respirator filter
• RID/ADR: UN 1648 3/PG 2
• 保存温度: 2-8°C

药理学性质

• 妊娠期药物分类: C (US)

产品相关信息

• 纯度: ≥97.0% (HPLC); 97%; 98+%
• 浓度: 100 ng/μL in acetonitrile
• 级别: VETRANAL™, analytical standard
• 成盐信息: Free Base
• Empirical Formula (Hill Notation): C6H6N4O4

详细说明

MP Biomedicals - 02155880

(Nitrofurazone)

MP Biomedicals - 05216984

MP Biomedicals Rare Chemical collection

DrugBank - DB00336

• Drug Groups: approved
• Description: A topical anti-infective agent effective against gram-negative and gram-positive bacteria. It is used for superficial wounds, burns, ulcers, and skin infections. Nitrofurazone has also been administered orally in the treatment of trypanosomiasis. [PubChem]
• Indication: For the treatement of bacterial skin infections including pyodermas, infected dermatoses and infections of cuts, wounds, burns and ulcers due to susceptible organisms.
• Pharmacology: Nitrofurazone is a topical antibacterial agent indicated as an adjunctive therapy for second and third degree burns when resistance to other agents is a real or potential problem. Nitrofurazone is also indicated in skin grafting when bacterial contamination may cause graft rejection or donor site infection, especially in hospitals with a history of resistant bacteria.
• Toxicity: Rat LD₅₀ = 590 mg/kg; Allergic contact dermatitis is the most frequently reported adverse effect, occurring in approximately 1 % of patients treated.
• Affected Organisms: Gram negative and gram positive bacteria
• Biotransformation: Nitrofurans, including nitrofural, undergo metabolic reduction at the nitro group to generate reactive species which can covalently bind to cellular macromolecules (Polnaszek et al., 1984; Kutcher & McCalla, 1984; McCalla 1979; McCalla et al., 1975).
• Absorption: Well absorbed.
• Half Life: 5 hours
• External Links: Wikipedia; Drugs.com

Selleck Chemicals - S1644

Research Area: Infection
Biological Activity:
Nitrofurazone is a topical anti-infective agent with an IC50 of 22.83 ± 1.2 µM, and effective against gram-negative and gram-positive bacteria. (Rat LD50 = 590 mg/kg)[1] Nitrofurazone (NF) and its derivative, hydroxymethylnitrofurazone (NFOH), have presented antichagasic activity. In vitro cruzain inhibition tests were performed for both compounds, and the 50% inhibitory concentration (IC50) for NF and NFOH presented values of 22.83 ± 1.2 µM and 10.55 ± 0.81 µM, respectively. AM1 semi-empirical molecular modeling studies were performed to understand the activity of the compounds, corroborating the observed cruzain inhibitory activity. [2]

Sigma Aldrich - 73340

包装
100, 500 g in poly bottle

Sigma Aldrich - 31706

法律信息
VETRANAL 商标 Sigma-Aldrich Co. LLC

Toronto Research Chemicals - N493880

Anti-infective (topical). Antimicrobial.

参考文献

• http://en.wikipedia.org/wiki/Nitrofurazone
• Morris, et al.: Cancer Res., 29, 2145 (1969)
• Sanderson, H., et al.: Toxicol. Lett., 144, 383 (1969)