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药品详细

Nitrofurazone(呋喃西林)

化学结构式图
中文名
呋喃西林
英文名
Nitrofurazone
分子式
C6H6N4O4
化学名
[(E)-[(5-nitrofuran-2-yl)methylidene]amino]urea
分子量
Average: 198.1362
Monoisotopic: 198.0389047
CAS号
59-87-0
ATC分类
B05C 未知;D08A 未知;P01C 未知;S02A 未知;S01A 抗感染药;D09A 未知
药物类型
small molecule
阶段
approved
商品名
同义名
基本介绍

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]

生产厂家
  • Ambix laboratories div organics corp america
  • Lannett co inc
  • Perrigo new york inc
  • Sherwood medical co
  • Shire development inc
  • Taro pharmaceuticals usa inc
  • Wendt laboratories inc
封装厂家
参考
Synthesis Reference Not Available
General Reference Not Available
剂型
规格
化合物类型
Type small molecule
Classes
  • Nitrofurans
Substructures
  • Semicarbazones
  • Oxoazaniums
  • Nitro compounds
  • Carbamates and Derivatives
  • Nitrofurans
  • Heterocyclic compounds
  • Aromatic compounds
  • Semicarbazides
  • Hydrazine Derivatives
  • Furans
  • Imines
适应症
药理
Indication For the treatement of bacterial skin infections including pyodermas, infected dermatoses and infections of cuts, wounds, burns and ulcers due to susceptible organisms.
Pharmacodynamics 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.
Mechanism of action The exact mechanism of action is unknown. Nitrofurazone inhibits several bacterial enzymes, especially those involved in the aerobic and anaerobic degradation of glucose and pyruvate. This activity is believed also to affect pyruvate dehydrogenase, citrate synthetase, malate dehydrogenase, glutathione reductase, and pyruvate decarboxylase.
Absorption Well absorbed.
Volume of distribution Not Available
Protein binding Not Available
Metabolism
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).
Route of elimination Not Available
Half life 5 hours
Clearance Not Available
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
Pathways Not Available
理化性质
Properties
State solid
Experimental Properties
Property Value Source
melting point 238 dec °C PhysProp
water solubility 210 mg/L (at 25 °C) BEILSTEIN
logP 0.23 HANSCH,C ET AL. (1995)
pKa 10 SANGSTER (1994)
Predicted Properties
Property Value Source
water solubility 2.68e-01 g/l ALOGPS
logP 0.23 ALOGPS
logP -0.14 ChemAxon
logS -2.9 ALOGPS
pKa (strongest acidic) 11.79 ChemAxon
pKa (strongest basic) -2 ChemAxon
physiological charge 0 ChemAxon
hydrogen acceptor count 4 ChemAxon
hydrogen donor count 2 ChemAxon
polar surface area 126.44 ChemAxon
rotatable bond count 3 ChemAxon
refractivity 45.21 ChemAxon
polarizability 16.92 ChemAxon
药物相互作用
食物相互作用
Not Available

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