Tìm theo
Ursodeoxycholic acid
Các tên gọi khác (12 ) :
  • (3alpha,5beta,7beta)-3,7-dihydroxycholan-24-oic acid
  • (3α,5β,7β)-3,7-dihydroxycholan-24-oic acid
  • 3alpha,7beta-Dihydroxy-5beta-cholan-24-oic acid
  • Acide ursodesoxycholique
  • Acido ursodeossicolico
  • Acido ursodeoxicolico
  • Acidum ursodeoxycholicum
  • Actigall
  • UDCA
  • Ursodeoxycholate
  • Ursodeoxycholic acid
  • Ursodiol
cholagogues and choleretics
Thuốc Gốc
Small Molecule
CAS: 128-13-2
ATC: A05AA02
ĐG : Amerisource Health Services Corp. , http://www.amerisourcebergen.com
CTHH: C24H40O4
PTK: 392.572
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]
Nhận Dạng Quốc Tế & Đặc Tính Hóa Học
Công thức hóa học
C24H40O4
Phân tử khối
392.572
Monoisotopic mass
392.292659768
InChI
InChI=1S/C24H40O4/c1-14(4-7-21(27)28)17-5-6-18-22-19(9-11-24(17,18)3)23(2)10-8-16(25)12-15(23)13-20(22)26/h14-20,22,25-26H,4-13H2,1-3H3,(H,27,28)/t14-,15+,16-,17-,18+,19+,20+,22+,23+,24-/m1/s1
InChI Key
InChIKey=RUDATBOHQWOJDD-UZVSRGJWSA-N
IUPAC Name
(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
Traditional IUPAC Name
ursodeoxycholic acid
SMILES
[H][C@@]1(CC[C@@]2([H])[C@]3([H])[C@@H](O)C[C@]4([H])C[C@H](O)CC[C@]4(C)[C@@]3([H])CC[C@]12C)[C@H](C)CCC(O)=O
Độ tan chảy
203 °C
Độ hòa tan
20 mg/L (at 20 °C)
logP
3.00
logS
-4.3
pKa (strongest acidic)
4.6
pKa (Strongest Basic)
-0.54
PSA
77.76 Å2
Refractivity
109.27 m3·mol-1
Polarizability
46.33 Å3
Rotatable Bond Count
4
H Bond Acceptor Count
4
H Bond Donor Count
3
Physiological Charge
-1
Number of Rings
4
Bioavailability
1
Rule of Five
true
Ghose Filter
true
Dược Lực Học : 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.
Cơ Chế Tác Dụng : 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] 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.
Dược Động Học :

▧ 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.
Độc Tính : 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.
Chỉ Định : The drug reduces cholesterol absorption and is used to dissolve (cholesterol) gallstones in patients who want an alternative to surgery.
Tương Tác Thuốc :
  • 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
Liều Lượng & Cách Dùng : Tablet - Oral
Dữ Kiện Thương Mại
Giá thị trường
Nhà Sản Xuất
  • Công ty :
    Sản phẩm biệt dược : Actigall
  • Công ty :
    Sản phẩm biệt dược : Cholit-ursan
  • Công ty :
    Sản phẩm biệt dược : Delursan
  • Công ty :
    Sản phẩm biệt dược : Destolit
  • Công ty :
    Sản phẩm biệt dược : Deursil
  • Công ty :
    Sản phẩm biệt dược : Litursol
  • Công ty :
    Sản phẩm biệt dược : Solutrat
  • Công ty :
    Sản phẩm biệt dược : Ursacol
  • Công ty :
    Sản phẩm biệt dược : Urso
  • Công ty :
    Sản phẩm biệt dược : Urso forte
  • Công ty :
    Sản phẩm biệt dược : Ursochol
  • Công ty :
    Sản phẩm biệt dược : Ursofalk
  • Công ty :
    Sản phẩm biệt dược : Ursolvan
Đóng gói
Tài Liệu Tham Khảo Thêm
drugbank
http://www.drugbank.ca/drugs/DB01586
PubChem Compound
http://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?sid=31401
PubChem Substance
http://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?sid=46508795
KEGG Compound
http://www.genome.jp/dbget-bin/www_bget?cpd:C07880
KEGG Drug
http://www.genome.jp/dbget-bin/www_bget?drug:D00734
ChemSpider
http://www.chemspider.com/Chemical-Structure.29131.html
National Drug Code Directory
http://www.hipaaspace.com/Medical_Billing/Coding/National.Drug.Codes/PDF/0527-1326-01
PharmGKB
http://www.pharmgkb.org/drug/PA451837
Wikipedia
http://en.wikipedia.org/wiki/Ursodiol
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