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药品详细

Ursodeoxycholic acid(熊去氧胆酸)

化学结构式图
中文名
熊去氧胆酸
英文名
Ursodeoxycholic acid
分子式
C24H40O4
化学名
(4R)-4-[(1S,2S,5R,7S,9S,10R,11S,14R,15R)-5,9-dihydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-yl]pentanoic acid
分子量
Average: 392.572
Monoisotopic: 392.292659768
CAS号
128-13-2
ATC分类
A05A 未知
药物类型
small molecule
阶段
approved
商品名
同义名
基本介绍

Ursodeoxycholic acid is an epimer of chenodeoxycholic acid (DB06777). It is a mammalian bile acid found first in the bear and is apparently either a precursor or a product of chenodeoxycholate. Its administration changes the composition of bile and may dissolve gallstones. It is used as a cholagogue and choleretic. [PubChem]

生产厂家
  • Axcan pharma us inc
  • Corepharma llc
  • Epic pharma llc
  • Lannett holdings inc
  • Mylan pharmaceuticals inc
  • Teva pharmaceuticals usa
  • Watson pharmaceuticals inc
封装厂家
参考
Synthesis Reference Not Available
General Reference
  1. Akare S, Jean-Louis S, Chen W, Wood DJ, Powell AA, Martinez JD: Ursodeoxycholic acid modulates histone acetylation and induces differentiation and senescence. Int J Cancer. 2006 Dec 15;119(12):2958-69. Pubmed
  2. Smith T, Befeler AS: High-dose ursodeoxycholic acid for the treatment of primary sclerosing cholangitis. Curr Gastroenterol Rep. 2007 Mar;9(1):54-9. Pubmed
  3. Jackson H, Solaymani-Dodaran M, Card TR, Aithal GP, Logan R, West J: Influence of ursodeoxycholic acid on the mortality and malignancy associated with primary biliary cirrhosis: A population-based cohort study. Hepatology. 2007 Aug 8;46(4):1131-1137. Pubmed
剂型
规格
化合物类型
Type small molecule
Classes
  • Bile Acids
Substructures
  • Bile Acids
  • Steroids and Steroid Derivatives
  • Hydroxy Compounds
  • Acetates
  • Sterols
  • Carboxylic Acids and Derivatives
  • Bicyclohexanes
  • Alcohols and Polyols
适应症
药理
Indication The drug reduces cholesterol absorption and is used to dissolve (cholesterol) gallstones in patients who want an alternative to surgery.
Pharmacodynamics Ursodiol (also known as ursodeoxycholic acid) is one of the secondary bile acids, which are metabolic byproducts of intestinal bacteria. Primary bile acids are produced by the liver and stored in the gall bladder. When secreted into the colon, primary bile acids can be metabolized into secondary bile acids by intestinal bacteria. Primary and secondary bile acids help the body digest fats. Ursodeoxycholic acid helps regulate cholesterol by reducing the rate at which the intestine absorbs cholesterol molecules while breaking up micelles containing cholesterol. Because of this property, ursodeoxycholic acid is used to treat gall stones non-surgically.
Mechanism of action Ursodeoxycholic acid reduces elevated liver enzyme levels by facilitating bile flow through the liver and protecting liver cells. The main mechanism if anticholelithic. Although the exact process of ursodiol's anticholelithic action is not completely understood, it is thought that the drug is concentrated in bile and decreases biliary cholesterol by suppressing hepatic synthesis and secretion of cholesterol and by inhibiting its intestinal absorption. The reduced cholesterol saturation permits the gradual solubilization of cholesterol from gallstones, resulting in their eventual dissolution.
Absorption Not Available
Volume of distribution Not Available
Protein binding Not Available
Metabolism
Not Available
Route of elimination Only small quantities of ursodiol appear in the systemic circulation and very small amounts are excreted into urine. Eighty percent of lithocholic acid formed in the small bowel is excreted in the feces, but the 20% that is absorbed is sulfated at the 3-hydroxyl group in the liver to relatively insoluble lithocholyl conjugates which are excreted into bile and lost in feces.
Half life Not Available
Clearance Not Available
Toxicity Neither accidental nor intentional overdosing with ursodeoxycholic acid has been reported. Doses of ursodeoxycholic acid in the range of 16-20 mg/kg/day have been tolerated for 6-37 months without symptoms by 7 patients. The LD50 for ursodeoxycholic acid in rats is over 5000 mg/kg given over 7-10 days and over 7500 mg/kg for mice. The most likely manifestation of severe overdose with ursodeoxycholic acid would probably be diarrhea, which should be treated symptomatically.
Affected organisms
  • Humans and other mammals
Pathways Not Available
理化性质
Properties
State solid
Experimental Properties
Property Value Source
melting point 203 °C PhysProp
water solubility 20 mg/L (at 20 °C) YALKOWSKY,SH & DANNENFELSER,RM (1992)
logP 3.00 RODA,A ET AL. (1990)
Predicted Properties
Property Value Source
water solubility 1.97e-02 g/l ALOGPS
logP 3.01 ALOGPS
logP 3.71 ChemAxon
logS -4.3 ALOGPS
pKa (strongest acidic) 4.6 ChemAxon
pKa (strongest basic) -0.54 ChemAxon
physiological charge -1 ChemAxon
hydrogen acceptor count 4 ChemAxon
hydrogen donor count 3 ChemAxon
polar surface area 77.76 ChemAxon
rotatable bond count 4 ChemAxon
refractivity 109.27 ChemAxon
polarizability 46.33 ChemAxon
药物相互作用
Drug Interaction
Cholestyramine The resin decreases the effect of ursodiol
Clofibrate The fibric acid derivative decreases the effect of ursodiol
Clomifene Estrogens decreases the effect of ursodiol
Colesevelam Bile Acid Sequestrants may decrease the serum concentration of Ursodiol. Consider administration of ursodiol 5 hours or more after bile acid sequestrants to minimize ursodiol adsorption in the gastrointestinal tract. Monitor for decreased therapeutic effects of ursodiol in patients receiving bile acid sequestrants.
Colestipol The resin decreases the effect of ursodiol
Conjugated Estrogens Estrogens decreases the effect of ursodiol
Cyclosporine Ursodiol increases the levels of cyclosporine
Diethylstilbestrol Estrogens decreases the effect of ursodiol
Estradiol Estrogens decreases the effect of ursodiol
Ethinyl Estradiol Estrogens decreases the effect of ursodiol
Fenofibrate The fibric acid derivative decreases the effect of ursodiol
Gemfibrozil The fibric acid derivative decreases the effect of ursodiol
食物相互作用
Not Available

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