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Chemical Compound Review

SureCN288251     (4R)-4- [(3R,5S,7S,10S,13R,17R)- 3,7...

Synonyms: BSPBio_001988, KBioGR_000865, KBioSS_001116, CCG-40274, NINDS_000416, ...
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Disease relevance of ursodiol


High impact information on ursodiol

  • Ursodiol for primary sclerosing cholangitis. Mayo Primary Sclerosing Cholangitis-Ursodeoxycholic Acid Study Group [3].
  • Abdominal pain after taking ursodiol [5].
  • On the basis of an intention-to-treat analysis of all 600 patients, 21 percent receiving ursodiol and 9 percent receiving placebo (P less than 0.0001) had gallbladders that were free of stones after six months [1].
  • On ursodiol therapy, hepatic bile acid synthesis was enhanced 2-fold compared with controls, and microscopy revealed chronic hepatitis without cholestasis [6].
  • Treatment with ursodiol, a more hydrophilic bile acid, improved pruritus, produced 37% weight gain, and after 2 years reduced serum primary bile acid concentrations about 85%, while accounting for 71% of serum and 24% of biliary bile acid conjugates [6].

Chemical compound and disease context of ursodiol


Biological context of ursodiol

  • Histology was favorably affected by ursodiol in patients in strata 1 and 2 but not in strata 3 and 4 [12].
  • There were no differences in peak concentration, time to peak, area under the serum concentration versus time curve, or bioavailability of oral cyclosporine when administered alone or with ursodiol [13].
  • RESULTS: There was no significant effect of ursodiol on CsA absorption: AUC was 5011 vs 5486, Cmax was 832 vs 871 and tmax was 2 vs 2 h, after ursodiol and placebo, respectively [14].
  • It was successfully applied to the pilot bioequivalence study of Ursodiol in male human subjects [15].

Anatomical context of ursodiol

  • Ursodiol prophylaxis against hepatic complications of allogeneic bone marrow transplantation. A randomized, double-blind, placebo-controlled trial [16].
  • Drug-induced vanishing bile duct syndrome: response to ursodiol [17].
  • RESULTS: Addition of Ursodiol to high-dose IBU and normal doses of PE showed a significant reduction in the percentage of rats with ulcers (P < 0.05), total number of serositis events (P < 0.01), total number of severe ulcers (P < 0.001), and an absence of ulcers in the large intestine [18].
  • The mechanisms by which ursodiol apparently directly stimulates the LDL receptor remain speculative but may involve alteration of cell membrane fluidity, change in the rate of LDL receptor cycling, and increase in the number of LDL receptors [19].

Associations of ursodiol with other chemical compounds

  • The hypothesis of diameter decrease proportional to treatment time was tested with data from 223 patients with radiolucent gallbladder stones up to 20 mm in diameter treated with 7-8 or 14-15 of either ursodiol or chenodiol for 1 year, followed up after 3, 6, and 12 months of treatment [20].
  • Liver biopsy was performed at the beginning and at the end of treatment and was evaluated blindly by our pathologist (F.C.). Alanine aminotransferase (ALT), aspartate aminotransferase (AST) and gammaglutamyltransferase (GGT) levels were significantly reduced by 25% from baseline values during treatment with ursodiol but not with placebo [21].
  • Oral administration of ursodeoxycholic acid (ursodiol) shifted the cholesterol composition of the bile from a supersaturated, potentially crystallized state to a liquid (micellar) state [22].
  • A suspension was prepared by opening commercially available 300-mg capsules of ursodiol, adding Glycerin, USP, to form a paste, and then adding Simple Syrup, NF [23].
  • S-Allylcysteine was only active for the growth inhibition endpoint, and DFMO, Iycopene, perillyl alcohol, ursodiol, and black tea polyphenols were only active for the involucrin endpoint [24].

Gene context of ursodiol


Analytical, diagnostic and therapeutic context of ursodiol


  1. The effect of ursodiol on the efficacy and safety of extracorporeal shock-wave lithotripsy of gallstones. The Dornier National Biliary Lithotripsy Study. Schoenfield, L.J., Berci, G., Carnovale, R.L., Casarella, W., Caslowitz, P., Chumley, D., Davis, R.C., Gillenwater, J.Y., Johnson, A.C., Jones, R.S. N. Engl. J. Med. (1990) [Pubmed]
  2. A multicenter, controlled trial of ursodiol for the treatment of primary biliary cirrhosis. UDCA-PBC Study Group. Poupon, R.E., Balkau, B., Eschwège, E., Poupon, R. N. Engl. J. Med. (1991) [Pubmed]
  3. Ursodiol for primary sclerosing cholangitis. Mayo Primary Sclerosing Cholangitis-Ursodeoxycholic Acid Study Group. Lindor, K.D. N. Engl. J. Med. (1997) [Pubmed]
  4. Ursodiol for the long-term treatment of primary biliary cirrhosis. The UDCA-PBC Study Group. Poupon, R.E., Poupon, R., Balkau, B. N. Engl. J. Med. (1994) [Pubmed]
  5. Abdominal pain after taking ursodiol. Pratt, D.S., Kaplan, M.M. N. Engl. J. Med. (1993) [Pubmed]
  6. Abnormal hepatic sinusoidal bile acid transport in an Amish kindred is not linked to FIC1 and is improved by ursodiol. Morton, D.H., Salen, G., Batta, A.K., Shefer, S., Tint, G.S., Belchis, D., Shneider, B., Puffenberger, E., Bull, L., Knisely, A.S. Gastroenterology (2000) [Pubmed]
  7. Lithotripsy plus ursodiol is superior to ursodiol alone for cholesterol gallstones. Tint, G.S., Dyrszka, H., Sanghavi, B., Patel, G., Patel, S., Shefer, S., Salen, G. Gastroenterology (1992) [Pubmed]
  8. Methotrexate improves biochemical tests in patients with primary biliary cirrhosis who respond incompletely to ursodiol. Bonis, P.A., Kaplan, M. Gastroenterology (1999) [Pubmed]
  9. Ursodiol use is associated with lower prevalence of colonic neoplasia in patients with ulcerative colitis and primary sclerosing cholangitis. Tung, B.Y., Emond, M.J., Haggitt, R.C., Bronner, M.P., Kimmey, M.B., Kowdley, K.V., Brentnall, T.A. Ann. Intern. Med. (2001) [Pubmed]
  10. Nonsurgical treatment of gallstone disease. Hofmann, A.F. Annu. Rev. Med. (1990) [Pubmed]
  11. Ursodeoxycholic acid in primary biliary cirrhosis. Combes, B. Semin. Liver Dis. (1997) [Pubmed]
  12. A randomized, double-blind, placebo-controlled trial of ursodeoxycholic acid in primary biliary cirrhosis. Combes, B., Carithers, R.L., Maddrey, W.C., Lin, D., McDonald, M.F., Wheeler, D.E., Eigenbrodt, E.H., Muñoz, S.J., Rubin, R., Garcia-Tsao, G. Hepatology (1995) [Pubmed]
  13. Influence of bile acid replacement on cyclosporine absorption in a patient with jejunoileal bypass. Kino, K.J., Wittkowsky, A.K. Pharmacotherapy (1995) [Pubmed]
  14. A single dose of ursodiol does not affect cyclosporine absorption in liver transplant patients. Maboundou, C.W., Paintaud, G., Vanlemmens, C., Magnette, J., Bresson-Hadni, S., Mantion, G., Miguet, J.P., Bechtel, P.R. Eur. J. Clin. Pharmacol. (1996) [Pubmed]
  15. Validation of LC/MS electrospray ionisation method for the estimation of ursodiol in human plasma and its application in bioequivalence study. Sundd Singh, S., Shah, H., Gupta, S., Jain, M., Sharma, K., Patel, H., Shah, B., Thakkar, P., Patel, N., Shah, R., Bhushan Lohary, B. Annali di chimica. (2004) [Pubmed]
  16. Ursodiol prophylaxis against hepatic complications of allogeneic bone marrow transplantation. A randomized, double-blind, placebo-controlled trial. Essell, J.H., Schroeder, M.T., Harman, G.S., Halvorson, R., Lew, V., Callander, N., Snyder, M., Lewis, S.K., Allerton, J.P., Thompson, J.M. Ann. Intern. Med. (1998) [Pubmed]
  17. Drug-induced vanishing bile duct syndrome: response to ursodiol. O'Brien, C.B., Shields, D.S., Saul, S.H., Reddy, K.R. Am. J. Gastroenterol. (1996) [Pubmed]
  18. Ursodeoxycholic acid ameliorates ibuprofen-induced enteropathy in the rat. Lloyd-Still, J.D., Beno, D.W., Uhing, M.R., Jiyamapa-Serna, V.A., Kimura, R.E. J. Pediatr. Gastroenterol. Nutr. (2001) [Pubmed]
  19. Bile acid-lipoprotein interactions: effects of ursodeoxycholic acid (ursodiol). Fromm, H. Dig. Dis. Sci. (1989) [Pubmed]
  20. In vivo kinetics of radiolucent gallstone dissolution by oral dihydroxy bile acids. Senior, J.R., Johnson, M.F., DeTurck, D.M., Bazzoli, F., Roda, E. Gastroenterology (1990) [Pubmed]
  21. Ursodiol in the long-term treatment of chronic hepatitis: a double-blind multicenter clinical trial. Bellentani, S., Podda, M., Tiribelli, C., Callea, F., Marazzi, M., Sodde, M., Merlini, R., Batezzati, P.M., Crosignani, A., Zuin, M. J. Hepatol. (1993) [Pubmed]
  22. Potential effect of cyclosporin A in formation of cholesterol gallstones in pediatric liver transplant recipients. Cao, S., Cox, K., So, S.S., Berquist, W., Lee, S.P., Haigh, W.G., Concepcion, W., Monge, H., Esquivel, C.O. Dig. Dis. Sci. (1997) [Pubmed]
  23. Stability of ursodiol in an extemporaneously compounded oral liquid. Johnson, C.E., Nesbitt, J. American journal of health-system pharmacy : AJHP : official journal of the American Society of Health-System Pharmacists. (1995) [Pubmed]
  24. Correlation of chemopreventive efficacy data from the human epidermal cell assay with in vivo data. Elmore, E., Luc, T.T., Li, H.R., Buckmeier, J.A., Steele, V.E., Kelloff, G.J., Redpath, J.L. Anticancer Res. (2000) [Pubmed]
  25. Ursodiol use is possibly associated with lower incidence of hepatocellular carcinoma in hepatitis C virus-associated liver cirrhosis. Tarao, K., Fujiyama, S., Ohkawa, S., Miyakawa, K., Tamai, S., Hirokawa, S., Masaki, T., Tanaka, K. Cancer Epidemiol. Biomarkers Prev. (2005) [Pubmed]
  26. Pilot trial of prophylactic ursodiol to decrease the incidence of veno-occlusive disease of the liver in allogeneic bone marrow transplant patients. Essell, J.H., Thompson, J.M., Harman, G.S., Halvorson, R.D., Snyder, M.J., Callander, N.S., Clement, D.J. Bone Marrow Transplant. (1992) [Pubmed]
  27. Use of external shock-wave lithotripsy and adjuvant ursodiol for treatment of radiolucent gallstones. A national multicenter study. Burnett, D., Ertan, A., Jones, R., O'Leary, J.P., Mackie, R., Robinson, J.E., Salen, G., Stahlgren, L., Van Thiel, D.H., Vassy, L. Dig. Dis. Sci. (1989) [Pubmed]
  28. Idiopathic biliary ductopenia in adults without symptoms of liver disease. Moreno, A., Carreño, V., Cano, A., González, C. N. Engl. J. Med. (1997) [Pubmed]
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