Ursodiol (Ursodeoxycholic Acid)

CAS No:
128-13-2 Category:
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Product Details:

  • CAS No: 128-13-2
  • AHFC code: 56:14.0
  • Synonyms: 17-beta-(1-Methyl-3-carboxypropyl)etiocholane-3-alpha,7-beta-diol, 3,7-Dihydroxycholan-24-oic acid, 3-alpha,7-beta-Dihydroxy-5-beta-cholanoic acid, 3-alpha,7-beta-Dihydroxycholanic acid, 3-alpha,7-beta-Dioxycholanic acid, 3alpha,7beta-Dihydroxy-5beta-cholan-24-oic acid, 4-10-00-01604 (Beilstein Handbook Reference), 7-beta-Hydroxylithocholic acid, Acide ursodesoxycholique, Acide ursodesoxycholique [INN-French], Acido ursodeossicolico, Acido ursodeossicolico [Italian], Acido ursodeoxicolico, Acido ursodeoxicolico [INN-Spanish], Acidum ursodeoxycholicum, Acidum ursodeoxycholicum [INN-Latin], Actigall, Arsacol, BRN 3219888, CCRIS 5502, Cholit-ursan, Delursan, Destolit, Deursil, EC 204-879-3, EINECS 204-879-3, Litursol, Lyeton, NSC 657950, NSC 683769, Peptarom, Solutrat, UNII-724L30Y2QR, Ursacol, UrSO, Urso 250, Urso DS, Urso Forte, Ursobilin, Ursochol, Ursocholic acid, deoxy-, Ursodamor, Ursodeoxycholate, Ursodeoxycholic acid, Ursodesoxycholic acid, Ursodiol, Ursofalk, Ursolvan
  • ATC Code: A05AA02
  • Chemical Formula: C24-H40-O4
  • Molecular Weight: 392.576
  • Assay/Purity: Typically NLT 98%
  • DrugBank: DB01586
  • 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
  • InChl: 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
  • PubChem:
  • IUPAC: (4R)-4-[(1S,2S,5R,7S,9S,10R,11S,14R,15R)-5,9-dihydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-14-yl]pentanoic acid

Additional Details

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.
Mode 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.
Metabolism:
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.
General Reference:
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. PubmedSmith T, Befeler AS: High-dose ursodeoxycholic acid for the treatment of primary sclerosing cholangitis. Curr Gastroenterol Rep. 2007 Mar;9(1):54-9. PubmedJackson 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
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