Characterization of serum and urinary bile acids in patients with primary biliary cirrhosis by gas-liquid chromatography-mass spectrometry: effect of ursodeoxycholic acid treatment.

Batta, Ashok K.; Arora, Renu; Salen, Gerald; Tint, G. Stephen; Eskreis, David; Katz, Seymour

doi:10.1016/s0022-2275(20)38207-9

Cited by 102 publications

(13 citation statements)

References 30 publications

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“…In the patients studied, isoUDCA was only a minor compound during administration of UDCA. The relative amount of 1.3-2.5% of total bile acids is in the range reported by others for patients with PBC during treatment with UDCA (6)(7)(8). The relative amount of isoUDCA during administration of isoUDCA reached 6 -8% of total serum bile acids.…”

Section: Discussionsupporting

confidence: 76%

“…Total serum bile acids and, in particular, serum UDCA, did not differ significantly after administration of 0.75 g/d of isoUDCA or 0.75-1 g/d of UDCA. The bile acid profiles were in the range of those reported for patients with PBC during long-term treatment with UDCA (6,7,23,24). This indicates a good intestinal absorption and an efficient hepatic uptake of isoUDCA, which is then converted to UDCA, both in the PBC patients studied and in healthy humans (15).…”

Section: Discussionsupporting

confidence: 58%

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Isoursodeoxycholic acid: metabolism and therapeutic effects in primary biliary cirrhosis

Marschall

Broomé

Einarsson

et al. 2001

Journal of Lipid Research

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Significant amounts of ursodeoxycholic acid (UDCA) used for the treatment of patients with primary biliary cirrhosis (PBC) become epimerized at C-3 to isoUDCA. We investigated the metabolism of isoUDCA and a possible pharmacologic effect in five patients (51.4 ؎ 5.8 years old; 3 females, 2 males) with PBC and persistent elevations of ␥ -glutamyl transpeptidase ( ␥ -GT) and alkaline phosphatase despite treatment with UDCA for more than one year. Serum samples were analyzed for bile acid metabolites and surrogate markers of cholestasis in 4-week intervals after 1 g/d UDCA, wash-out, 0.5 g/d isoUDCA, 0.75 g/d isoUDCA, 0.75 g/d UDCA, and two further periods with 1 g/d UDCA. Bile acids in urine were analyzed after wash-out, 0.5 and 0.75 g/d isoUDCA, and 0.75 and 1 g/d UDCA. During wash-out, AST, AP, and ␥ -GT rose significantly ( P Ͻ 0.05) but reversed to previous levels during the first isoUDCA period, with 0.5 g/d only. No further improvements were observed after increasing the dose of isoUDCA or switching back to UDCA. In serum, the relative amounts of isoUDCA and UDCA were 8.1 ؎ 7.4% and 16.2 ؎ 6.4% during 0.5 g/d isoUDCA, 6.2 ؎ 2.5% and 45.0 ؎ 4.1% during 0.75 g/d isoUDCA, and 0.5 -3% and 56.4 -60.0%, respectively, during UDCA. In urine, UDCA was the predominant bile acid both during isoUDCA and UDCA medications. The similar serum enrichment and urinary excretion of UDCA during administration of either isoUDCA or UDCA together with low concentrations of the intermediate of isomerization, 3-dehydro-UDCA, indicate a first-pass epimerization of isoUDCA to UDCA in the liver. Approximately 25% of serum isoUDCA and 10% of serum UDCA were conjugated with either glucuronic acid or N -acetylglucosamine, indicating hepatic formation and systemic secretion of glycosidic conjugates.In PBC patients, isoUDCA becomes isomerized to UDCA and has similar effects on surrogate markers of cholestasis. Thus, isoUDCA has pro-drug characteristics. -Marschall, H-U., U. Broomé, C. Einarsson, G. Alvelius, H. G. Thomas, and S. Matern. I soursodeoxycholic acid: metabolism and therapeutic effects in primary biliary cirrhosis.

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Section: Discussionsupporting

confidence: 76%

Section: Discussionsupporting

confidence: 58%

Isoursodeoxycholic acid: metabolism and therapeutic effects in primary biliary cirrhosis

Marschall

Broomé

Einarsson

et al. 2001

Journal of Lipid Research

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“…(Chrompack, Inc., Raritan, NJ) and helium was used as the carrier gas at a flow rate of 1 ml/min. The GLC operating conditions were as described in earlier publication (15). The methyl ester of UDCA was formed with 3% anhydrous methanolic hydrochloric acid and was then reacted with Sil-Prep to obtain the trimethylsilyl (TMS) ether derivative (15).…”

Section: Gas-liquid Chromatography (Glc)mentioning

confidence: 99%

“…The GLC operating conditions were as described in earlier publication (15). The methyl ester of UDCA was formed with 3% anhydrous methanolic hydrochloric acid and was then reacted with Sil-Prep to obtain the trimethylsilyl (TMS) ether derivative (15). A 2 l aliquot of the derivative in hexane was injected into the GLC column.…”

Section: Gas-liquid Chromatography (Glc)mentioning

confidence: 99%

“…After evaporation of the solvent under N 2 at 55 Њ C, the product was subjected to TLC. The incubation product was then treated with 0.2 ml of 3% anhydrous methanolic hydrochloric acid for 2 h, solvent evaporated at 55 Њ C under reduced pressure, and an aliquot was silylated (15) and subjected to gas-liquid chromatography.…”

Section: Hydrolysis Of Udca-5-asa Conjugate With Cholylglycine Hydrolasementioning

confidence: 99%

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Synthesis and intestinal metabolism of ursodeoxycholic acid conjugate with an antiinflammatory agent, 5-aminosalicylic acid

Batta

Tint

et al. 1998

Journal of Lipid Research

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5-Aminosalicylic acid conjugate of ursodeoxycholic acid was synthesized in above 90% yield by adding a basic solution of 5-aminosalicylic acid into the mixed anhydride formed with ursodeoxycholic acid and ethyl chloroformate. The 5-aminosalicylic acid conjugate of ursodeoxycholic acid was poorly secreted into the bile and was deconjugated with cholylglycine hydrolase and Clostridium perfringens, that deconjugate naturally occurring glycine and taurine conjugates of bile acids. However, ursodeoxycholic acid 5-aminosalicylic acid conjugate was not absorbed from the duodenum but was concentrated in the colon wher e it was partially hydrolyzed by the intestinal bacteria to ursodeoxycholic acid and 5-aminosalicylic acid. We believe that this unique conjugation of ursodeoxycholic acid with 5-aminosalicylic acid may facilitate the transpor t of both 5aminosalicylic acid and ursodeoxycholic acid to the colon and may be useful for the treatment of colonic inflammatory bowel diseases, ulcerative colitis and Crohn's disease.-Batta, A. K., G. S. Tint, G. Xu, S. Shefer, and G. Salen. Synthesis and intestinal metabolism of ursodeoxycholic acid conjugate with an antiinflammatory agent, 5-aminosalicylic acid.

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Ursodeoxycholic acid for primary biliary cirrhosis

Gluud¹,

Christensen

2001

Cochrane Database of Systematic Reviews

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Characterization of serum and urinary bile acids in patients with primary biliary cirrhosis by gas-liquid chromatography-mass spectrometry: effect of ursodeoxycholic acid treatment.

Cited by 102 publications

References 30 publications

Isoursodeoxycholic acid: metabolism and therapeutic effects in primary biliary cirrhosis

Isoursodeoxycholic acid: metabolism and therapeutic effects in primary biliary cirrhosis

Synthesis and intestinal metabolism of ursodeoxycholic acid conjugate with an antiinflammatory agent, 5-aminosalicylic acid

Ursodeoxycholic acid for primary biliary cirrhosis

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