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药品详细

Albendazole(阿苯达唑)

化学结构式图
中文名
阿苯达唑
英文名
Albendazole
分子式
C12H15N3O2S
化学名
methyl N-[6-(propylsulfanyl)-1H-1,3-benzodiazol-2-yl]carbamate
分子量
Average: 265.331
Monoisotopic: 265.088497429
CAS号
54965-21-8
ATC分类
P02C 未知
药物类型
small molecule
阶段
approved
商品名
同义名
基本介绍

A benzimidazole broad-spectrum anthelmintic structurally related to mebendazole that is effective against many diseases. (From Martindale, The Extra Pharmacopoeia, 30th ed, p38)

生产厂家
  • Glaxosmithkline llc
封装厂家
参考
Synthesis Reference Not Available
General Reference
  1. Molina AJ, Merino G, Prieto JG, Real R, Mendoza G, Alvarez AI: Absorption and metabolism of albendazole after intestinal ischemia/reperfusion. Eur J Pharm Sci. 2007 May;31(1):16-24. Epub 2007 Feb 6. Pubmed
  2. Oxberry ME, Reynoldson JA, Thompson RC: The binding and distribution of albendazole and its principal metabolites in Giardia duodenalis. J Vet Pharmacol Ther. 2000 Jun;23(3):113-20. Pubmed
  3. Ramirez T, Benitez-Bribiesca L, Ostrosky-Wegman P, Herrera LA: In vitro effects of albendazole and its metabolites on the cell proliferation kinetics and micronuclei frequency of stimulated human lymphocytes. Arch Med Res. 2001 Mar-Apr;32(2):119-22. Pubmed
  4. Haque A, Hollister WS, Willcox A, Canning EU: The antimicrosporidial activity of albendazole. J Invertebr Pathol. 1993 Sep;62(2):171-7. Pubmed
剂型
规格
化合物类型
Type small molecule
Classes
  • Benzimidazoles
Substructures
  • Ethers
  • Carbamates and Derivatives
  • Benzimidazoles
  • Benzene and Derivatives
  • Imidazoles
  • Heterocyclic compounds
  • Aromatic compounds
  • Cyanamides
适应症
药理
Indication For the treatment of parenchymal neurocysticercosis due to active lesions caused by larval forms of the pork tapeworm, Taenia solium and for the treatment of cystic hydatid disease of the liver, lung, and peritoneum, caused by the larval form of the dog tapeworm, Echinococcus granulosus.
Pharmacodynamics Albendazole is a broad-spectrum anthelmintic. The principal mode of action for albendazole is by its inhibitory effect on tubulin polymerization which results in the loss of cytoplasmic microtubules.
Mechanism of action Albendazole causes degenerative alterations in the tegument and intestinal cells of the worm by binding to the colchicine-sensitive site of tubulin, thus inhibiting its polymerization or assembly into microtubules. The loss of the cytoplasmic microtubules leads to impaired uptake of glucose by the larval and adult stages of the susceptible parasites, and depletes their glycogen stores. Degenerative changes in the endoplasmic reticulum, the mitochondria of the germinal layer, and the subsequent release of lysosomes result in decreased production of adenosine triphosphate (ATP), which is the energy required for the survival of the helminth. Due to diminished energy production, the parasite is immobilized and eventually dies.
Absorption Poorly absorbed from the gastrointestinal tract due to its low aqueous solubility. Oral bioavailability appears to be enhanced when coadministered with a fatty meal (estimated fat content 40 g)
Volume of distribution Not Available
Protein binding 70% bound to plasma protein
Metabolism
Hepatic. Rapidly converted in the liver to the primary metabolite, albendazole sulfoxide, which is further metabolized to albendazole sulfone and other primary oxidative metabolites that have been identified in human urine.

Important The metabolism module of DrugBank is currently in beta. Questions or suggestions? Please contact us.

Substrate Enzymes Product
Albendazole
    		albendazole sulfone Details
    Albendazole
      		albendazole sulfoxide Details
      Route of elimination Albendazole is rapidly converted in the liver to the primary metabolite, albendazole sulfoxide, which is further metabolized to albendazole sulfone and other primary oxidative metabolites that have been identified in human urine. Urinary excretion of albendazole sulfoxide is a minor elimination pathway with less than 1% of the dose recovered in the urine. Biliary elimination presumably accounts for a portion of the elimination as evidenced by biliary concentrations of albendazole sulfoxide similar to those achieved in plasma.
      Half life Terminal elimination half-life ranges from 8 to 12 hours (single dose, 400mg).
      Clearance Not Available
      Toxicity Symptoms of overdose include elevated liver enzymes, headaches, hair loss, low levels of white blood cells (neutropenia), fever, and itching.
      Affected organisms
      • Helminthic Microorganisms
      Pathways Not Available
      理化性质
      Properties
      State solid
      Experimental Properties
      Property Value Source
      melting point 209 °C PhysProp
      water solubility Practically insoluble Not Available
      logP 2.7 Not Available
      Predicted Properties
      Property Value Source
      water solubility 2.28e-02 g/l ALOGPS
      logP 3.22 ALOGPS
      logP 3.2 ChemAxon
      logS -4.1 ALOGPS
      pKa (strongest acidic) 9.51 ChemAxon
      pKa (strongest basic) 4.27 ChemAxon
      physiological charge 0 ChemAxon
      hydrogen acceptor count 3 ChemAxon
      hydrogen donor count 2 ChemAxon
      polar surface area 67.01 ChemAxon
      rotatable bond count 5 ChemAxon
      refractivity 73.01 ChemAxon
      polarizability 29.3 ChemAxon
      药物相互作用
      食物相互作用
      Not Available

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