LIPID MAPS

Ursodeoxycholic acid (UDCA) is a secondary bile acid formed via epimerization of chenodeoxycholic acid (CDCA).^1,2 UDCA is also a metabolite of lithocholic acid (LCA) in human liver microsomes.³ It inhibits taurocholic acid uptake in HeLa cells expressing recombinant human sodium/taurocholate cotransporting polypeptide (NTCP) with an IC50 value of 3.6 μM.⁴ UDCA (50 μM) inhibits apoptosis induced by deoxycholic acid (DCA) or ethanol in primary rat hepatocytes.⁵ Dietary administration of UDCA blocks DCA-induced increases in the number of TUNEL-positive hepatocytes in rats. Formulations containing UDCA have been used in the treatment of primary biliary cirrhosis.

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References

1. Kim, R.B., Leake, B., Cvetkovic, M., et al. Modulation by drugs of human hepatic sodium-dependent bile acid transporter (sodium taurocholate cotransporting polypeptide) activity. J. Pharmacol. Exp. Ther. 291(3), 1204-1209 (1999).

2. Dawson, P.A., and Karpen, S.J. Intestinal transport and metabolism of bile acids. J. Lipid Res. 56(6), 1085-1099 (2015).

3. Chiang, J.Y.L. Bile acid metabolism and signaling in liver disease and therapy. Liver Res. 1(1), 3-9 (2017).

4. Deo, A.K., and Bandiera, S.M. 3-Ketocholanoic acid is the major in vitro human hepatic microsomal metabolite of lithocholic acid. Drug Metab. Dispos. 37(9), 1938-1947 (2009).

5. Rodrigues, C.M.P., Fan, G., Ma, X., et al. A novel role for ursodeoxycholic acid in inhibiting apoptosis by modulating mitochondrial membrane perturbation. J. Clin. Invest. 101(12), 2790-2799 (1998).

References

Taxonomy Information

Curated from

NCBI taxonomy class

Reference

Ursus americanus (#9643)

Mammalia (#40674)

Ursodeoxycholic acid in the Ursidae: biliary bile acids of bears, pandas, and related carnivores.,
J Lipid Res, 1993

Pubmed ID: 8263415

String Representations

InChiKey (Click to copy)

RUDATBOHQWOJDD-UZVSRGJWSA-N

InChi (Click to copy)

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

SMILES (Click to copy)

C1[C@]2(C)[C@@]3([H])CC[C@]4(C)[C@@]([H])([C@]([H])(C)CCC(O)=O)CC[C@@]4([H])[C@]3([H])[C@@H](O)C[C@]2([H])C[C@H](O)C1