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药品详细

Oxamniquine(Oxamniquine)

化学结构式图
中文名
Oxamniquine
英文名
Oxamniquine
分子式
C14H21N3O3
化学名
(7-nitro-2-{[(propan-2-yl)amino]methyl}-1,2,3,4-tetrahydroquinolin-6-yl)methanol
分子量
Average: 279.3348
Monoisotopic: 279.158291553
CAS号
21738-42-1
ATC分类
P02B 未知
药物类型
small molecule
阶段
approved
商品名
同义名
基本介绍

An anthelmintic with schistosomicidal activity against Schistosoma mansoni, but not against other Schistosoma spp. Oxamniquine causes worms to shift from the mesenteric veins to the liver where the male worms are retained; the female worms return to the mesentery, but can no longer release eggs. (From Martidale, The Extra Pharmacopoeia, 31st ed, p121)

生产厂家
  • Pfizer laboratories div pfizer inc
封装厂家
参考
Synthesis Reference

See General references, Filho et. al. for synthesis of oxamniquine methacylate.
General Reference
  1. Filho RP, de Souza Menezes CM, Pinto PL, Paula GA, Brandt CA, da Silveira MA: Design, synthesis, and in vivo evaluation of oxamniquine methacrylate and acrylamide prodrugs. Bioorg Med Chem. 2007 Feb 1;15(3):1229-36. Epub 2006 Nov 16. Pubmed
剂型
规格
化合物类型
Type small molecule
Classes
  • Nitrobenzenes
  • Phenylpropylamines
  • (Iso)quinolines and Derivatives
Substructures
  • Hydroxy Compounds
  • Nitrobenzenes
  • Benzyl Alcohols and Derivatives
  • Oxoazaniums
  • Aliphatic and Aryl Amines
  • Benzene and Derivatives
  • Nitro compounds
  • Alcohols and Polyols
  • Heterocyclic compounds
  • Aromatic compounds
  • Phenylpropylamines
  • (Iso)quinolines and Derivatives
  • Anilines
适应症
药理
Indication For treatment of Schistosomiasis caused by Schistosoma mansoni
Pharmacodynamics Oxamniquine is an anthelmintic with schistosomicidal activity against Schistosoma mansoni, but not against other Schistosoma spp. Oxamniquine causes worms to shift from the mesenteric veins to the liver where the male worms are retained; the female worms return to the mesentery, but can no longer release egg.
Mechanism of action Oxamniquine may associate with an irreversible inhibition of the nucleic acid metabolism of the parasites. A hypothesis has been put forth that the drug is activated by a single step, in which a schistosome sulfotransferase enzyme converts oxamniquine into an ester (probably acetate, phosphate, or sulfate). Subsequently, the ester spontaneously dissociates, the resulting electrophilic reactant is capable of alkylation of schistosome DNA.
Absorption Well absorbed orally
Volume of distribution Not Available
Protein binding Not Available
Metabolism
Probably hepatic
Route of elimination Not Available
Half life 1-2.5 hours
Clearance Not Available
Toxicity Not Available
Affected organisms
  • Schistosoma mansoni
Pathways Not Available
理化性质
Properties
State solid
Experimental Properties
Property Value Source
melting point 147-149 °C PhysProp
water solubility 820 mg/L Not Available
logP 2.24 SANGSTER (1993)
Predicted Properties
Property Value Source
water solubility 1.24e-01 g/l ALOGPS
logP 1.54 ALOGPS
logP 1.57 ChemAxon
logS -3.4 ALOGPS
pKa (strongest acidic) 14.55 ChemAxon
pKa (strongest basic) 9.9 ChemAxon
physiological charge 1 ChemAxon
hydrogen acceptor count 5 ChemAxon
hydrogen donor count 3 ChemAxon
polar surface area 90.11 ChemAxon
rotatable bond count 5 ChemAxon
refractivity 79.87 ChemAxon
polarizability 30.19 ChemAxon
药物相互作用
食物相互作用
Not Available

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