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Chemical Compound Review

AC1LCUMK     (4S)-4-[ (3S,5R,7S,8S,9S,10S,12S,13R,14 S...

Synonyms: cholan-24-oic acid, 3,7,12-trihydroxy-
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Disease relevance of cholic acid


Psychiatry related information on cholic acid


High impact information on cholic acid


Chemical compound and disease context of cholic acid


Biological context of cholic acid

  • Scatchard analysis of the saturation kinetics as well as inhibition studies suggest that bile acids bind to a single and noninteracting class of anion that competes with bile acids for hepatic uptake, also inhibits cholic acid binding [17].
  • Description and simulation of a physiological pharmacokinetic model for the metabolism and enterohepatic circulation of bile acids in man. Cholic acid in healthy man [18].
  • These experiments demonstrate the existence of a pathway for side-chain degradation in cholic acid synthesis which does not involve hydroxylation at C-26 or the participation of mitochondria [19].
  • Taurine conjugates of the primary bile acids predominate throughout gestation and conjugates of cholic acid are synthesized in preference to those of chenodeoxycholic acid [20].
  • To find a possible explanation for the selective hepatic conjugation of bile acids with glycine or taurine, the N-acyl amidates of cholic acid and a number of amino acids and amino acid analogues were synthesized, and their susceptibility to hydrolysis by pancreatic juice, gastric juice, serum, or small intestinal mucosal enzymes was measured [21].

Anatomical context of cholic acid

  • Seven patients with radiolucent stones in the gallbladder and two patients with radiolucent stones in the biliary tree were treated with oral cholic acid and purified soya-bean lecithin for 6 months [22].
  • CONCLUSIONS: The expression of the ileal apical bile acid transporter is induced at a pretranslational level by free or taurine-conjugated cholic acid within the small intestine [23].
  • Induction of sodium-dependent bile acid transporter messenger RNA, protein, and activity in rat ileum by cholic acid [23].
  • Significant inhibition of lymphocyte transformation was observed with 250 mumol/liter of either chenodeoxycholic (CDCA) or cholic acid (CA); the former caused more pronounced inhibition at higher concentrations [24].
  • Similarly, proliferation of colon epithelial cells was stimulated in a dose-response manner by dietary cholic acid in rats [25].

Associations of cholic acid with other chemical compounds


Gene context of cholic acid


Analytical, diagnostic and therapeutic context of cholic acid

  • A bile acid tolerance test, which measures the plasma disappearance rate of injected cholyglycine by radioimmunoassay, was studied in 36 patients with biopsy-proved chronic liver disease and compared to fasting-state levels of conjugated cholic acid and other conventional liver tests [1].
  • After intravenous injection of this dose, conjugates of cholic acid increased 10-fold, but in all subjects the concentration of these bile acids had returned to 1 muM (the upper limit of normal, fasting state) by 10 minutes [34].
  • METHODS AND RESULTS: Cholic acid plus chenodeoxycholic acid levels measured by capillary gas-chromatography were 32 times higher than control in serum (34.7 vs. 1.1+/-0.4 microg/dL) but were not detected in liver and were reduced in gallbladder bile [35].
  • This hypothesis was tested and confirmed by hydrolyzing the purified metabolite by cholylglycine hydrolase after which: 2-fluoro-beta-alanine was demonstrated by using a sensitive HPLC technique capable of resolving all of the known putative FUra metabolites, and unconjugated cholic acid was identified by both GC and GC-MS [36].
  • Pool sizes, fractional turnover and synthesis rates of cholic acid and chenodeoxycholic acid were determined after oral administration of 50 mg [13C]cholic acid and 50 mg [13C]chenodeoxycholic acid [37].


  1. Validity and sensitivity of an intravenous bile acid tolerance test in patients with liver disease. LaRusso, N.F., Hoffman, N.E., Hofmann, A.F., Korman, M.G. N. Engl. J. Med. (1975) [Pubmed]
  2. Chenotherapy for gallstone dissolution. II. Induced changes in bile composition and gallstone response. Hofmann, A.F., Thistle, J.L., Klein, P.D., Szczepanik, P.A., Yu, P.Y. JAMA (1978) [Pubmed]
  3. The metabolism of 3alpha, 7alpha, 12alpha-trihydorxy-5beta-cholestan-26-oic acid in two siblings with cholestasis due to intrahepatic bile duct anomalies. An apparent inborn error of cholic acid synthesis. Hanson, R.F., Isenberg, J.N., Williams, G.C., Hachey, D., Szczepanik, P., Klein, P.D., Sharp, H.L. J. Clin. Invest. (1975) [Pubmed]
  4. Cholic acid biosynthesis: the enzymatic defect in cerebrotendinous xanthomatosis. Salen, G., Shefer, S., Cheng, F.W., Dayal, B., Batta, A.K., Tint, G.S. J. Clin. Invest. (1979) [Pubmed]
  5. Complex genetic control of HDL levels in mice in response to an atherogenic diet. Coordinate regulation of HDL levels and bile acid metabolism. Machleder, D., Ivandic, B., Welch, C., Castellani, L., Reue, K., Lusis, A.J. J. Clin. Invest. (1997) [Pubmed]
  6. Profile of urinary bile acids in infants and children: developmental pattern of excretion of unsaturated ketonic bile acids and 7beta-hydroxylated bile acids. Kimura, A., Mahara, R., Inoue, T., Nomura, Y., Murai, T., Kurosawa, T., Tohma, M., Noguchi, K., Hoshiyama, A., Fujisawa, T., Kato, H. Pediatr. Res. (1999) [Pubmed]
  7. Physical and chemical properties of DMP 504, a polyalkylammonium-based bile acid sequestrant. Raghavan, K.S., Chang, R.K., Pang, J., Figuly, G.D., Hussain, M.A. Pharmaceutical development and technology. (1997) [Pubmed]
  8. Defects of bile acid synthesis in Zellweger's syndrome. Hanson, R.F., Szczepanik-VanLeeuwen, P., Williams, G.C., Grabowski, G., Sharp, H.L. Science (1979) [Pubmed]
  9. 3 alpha-hydroxysteroid dehydrogenase activity of the Y' bile acid binders in rat liver cytosol. Identification, kinetics, and physiologic significance. Stolz, A., Takikawa, H., Sugiyama, Y., Kuhlenkamp, J., Kaplowitz, N. J. Clin. Invest. (1987) [Pubmed]
  10. Defective peroxisomal cleavage of the C27-steroid side chain in the cerebro-hepato-renal syndrome of Zellweger. Kase, B.F., Björkhem, I., Hågå, P., Pedersen, J.I. J. Clin. Invest. (1985) [Pubmed]
  11. Acute effects of dietary cholic acid and methylazoxymethanol acetate on colon epithelial cell proliferation; metabolism of bile salts and neutral sterols in conventional and germfree SD rats. Weidema, W.F., Deschner, E.E., Cohen, B.I., DeCosse, J.J. J. Natl. Cancer Inst. (1985) [Pubmed]
  12. Biosynthesis of bile acids in cerebrotendinous xanthomatosis. Relationship of bile acid pool sizes and synthesis rates to hydroxylations at C-12, C-25, and C-26. Salen, G., Shefer, S., Tint, G.S., Nicolau, G., Dayal, B., Batta, A.K. J. Clin. Invest. (1985) [Pubmed]
  13. Mechanism of cholic acid protection in lithocholate-induced intrahepatic cholestasis in rats. Kakis, G., Yousef, I.M. Gastroenterology (1980) [Pubmed]
  14. Endogenous ursodeoxycholic acid and cholic acid in liver disease due to cystic fibrosis. Smith, J.L., Lewindon, P.J., Hoskins, A.C., Pereira, T.N., Setchell, K.D., O'Connell, N.C., Shepherd, R.W., Ramm, G.A. Hepatology (2004) [Pubmed]
  15. Normal fasting-state levels of serum cholyl-conjugated bile acids in Gilbert's syndrome: an aid to the diagnosis. Vierling, J.M., Berk, P.D., Hofmann, A.F., Martin, J.F., Wolkoff, A.W., Scharschmidt, B.F. Hepatology (1982) [Pubmed]
  16. Cholic acid synthesis from 26-hydroxycholesterol and 3-hydroxy-5-cholestenoic acid in the rabbit. Ayaki, Y., Kok, E., Javitt, N.B. J. Biol. Chem. (1989) [Pubmed]
  17. Identification and characterization of a bile acid receptor in isolated liver surface membranes. Accatino, L., Simon, F.R. J. Clin. Invest. (1976) [Pubmed]
  18. Description and simulation of a physiological pharmacokinetic model for the metabolism and enterohepatic circulation of bile acids in man. Cholic acid in healthy man. Hofmann, A.F., Molino, G., Milanese, M., Belforte, G. J. Clin. Invest. (1983) [Pubmed]
  19. A 25-hydroxylation pathway of cholic acid biosynthesis in man and rat. Shefer, S., Cheng, F.W., Dayal, B., Hauser, S., Tint, G.S., Salen, G., Mosbach, E.H. J. Clin. Invest. (1976) [Pubmed]
  20. Bile acid conjugation in organ culture of human fetal liver. Haber, L.R., Vaupshas, V., Vitullo, B.B., Seemayer, T.A., de Belle, R.C. Gastroenterology (1978) [Pubmed]
  21. Pancreatic carboxypeptidase hydrolysis of bile acid-amino conjugates: selective resistance of glycine and taurine amidates. Huijghebaert, S.M., Hofmann, A.F. Gastroenterology (1986) [Pubmed]
  22. Gallstone dissolution in man using cholic acid and lecithin. Toouli, J., Jablonski, P., Watts, J.M. Lancet (1975) [Pubmed]
  23. Induction of sodium-dependent bile acid transporter messenger RNA, protein, and activity in rat ileum by cholic acid. Stravitz, R.T., Sanyal, A.J., Pandak, W.M., Vlahcevic, Z.R., Beets, J.W., Dawson, P.A. Gastroenterology (1997) [Pubmed]
  24. Bile acid-induced inhibition of the lymphoproliferative response to phytohemagglutinin and pokeweed mitogen: an in vitro study. Gianni, L., Di Padova, F., Zuin, M., Podda, M. Gastroenterology (1980) [Pubmed]
  25. Measurement in vivo of proliferation rates of slow turnover cells by 2H2O labeling of the deoxyribose moiety of DNA. Neese, R.A., Misell, L.M., Turner, S., Chu, A., Kim, J., Cesar, D., Hoh, R., Antelo, F., Strawford, A., McCune, J.M., Christiansen, M., Hellerstein, M.K. Proc. Natl. Acad. Sci. U.S.A. (2002) [Pubmed]
  26. Massive xanthomatosis and atherosclerosis in cholesterol-fed low density lipoprotein receptor-negative mice. Ishibashi, S., Goldstein, J.L., Brown, M.S., Herz, J., Burns, D.K. J. Clin. Invest. (1994) [Pubmed]
  27. Pathogenic factors in early recurrence of cholesterol gallstones. Berr, F., Mayer, M., Sackmann, M.F., Sauerbruch, T., Holl, J., Paumgartner, G. Gastroenterology (1994) [Pubmed]
  28. Benign recurrent intrahepatic cholestasis: altered bile acid metabolism. Bijleveld, C.M., Vonk, R.J., Kuipers, F., Havinga, R., Boverhof, R., Koopman, B.J., Wolthers, B.G., Fernandes, J. Gastroenterology (1989) [Pubmed]
  29. Pool size, synthesis, and turnover of sulfated and nonsulfated cholic acid and chenodeoxycholic acid in patients with cirrhosis of the liver. Stiehl, A., Ast, E., Czygan, P., Fröhling, W., Raedsch, R., Kommerell, B. Gastroenterology (1978) [Pubmed]
  30. Identification of bile acid precursors as endogenous ligands for the nuclear xenobiotic pregnane X receptor. Goodwin, B., Gauthier, K.C., Umetani, M., Watson, M.A., Lochansky, M.I., Collins, J.L., Leitersdorf, E., Mangelsdorf, D.J., Kliewer, S.A., Repa, J.J. Proc. Natl. Acad. Sci. U.S.A. (2003) [Pubmed]
  31. Regulation of rat organic anion transporters in bile salt-induced cholestatic hepatitis: effect of ursodeoxycholate. Rost, D., Herrmann, T., Sauer, P., Schmidts, H.L., Stieger, B., Meier, P.J., Stremmel, W., Stiehl, A. Hepatology (2003) [Pubmed]
  32. Severe cholestasis induced by cholic acid feeding in knockout mice of sister of P-glycoprotein. Wang, R., Lam, P., Liu, L., Forrest, D., Yousef, I.M., Mignault, D., Phillips, M.J., Ling, V. Hepatology (2003) [Pubmed]
  33. Hepatic overexpression of murine Abcb11 increases hepatobiliary lipid secretion and reduces hepatic steatosis. Figge, A., Lammert, F., Paigen, B., Henkel, A., Matern, S., Korstanje, R., Shneider, B.L., Chen, F., Stoltenberg, E., Spatz, K., Hoda, F., Cohen, D.E., Green, R.M. J. Biol. Chem. (2004) [Pubmed]
  34. Development of an intravenous bile acid tolerance test. Plasma disappearance of cholylglycine in health. Korman, M.G., LaRusso, N.F., Hoffman, N.E., Hofmann, A.F. N. Engl. J. Med. (1975) [Pubmed]
  35. 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]
  36. Metabolism of 5-fluorouracil to an N-cholyl-2-fluoro-beta-alanine conjugate: previously unrecognized role for bile acids in drug conjugation. Sweeny, D.J., Barnes, S., Heggie, G.D., Diasio, R.B. Proc. Natl. Acad. Sci. U.S.A. (1987) [Pubmed]
  37. Bile acid metabolism in human hyperthyroidism. Pauletzki, J., Stellaard, F., Paumgartner, G. Hepatology (1989) [Pubmed]
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