Document Detail

Sulfonate analogues of chenodeoxycholic acid: metabolism of sodium 3 alpha, 7 alpha-dihydroxy-25-homo-5 beta-cholane-25-sulfonate and sodium 3 alpha, 7 alpha-dihydroxy-24-nor-5 beta-cholane-23-sulfonate in the hamster.
MedLine Citation:
PMID:  1464746     Owner:  NLM     Status:  MEDLINE    
This report describes the chemical synthesis of a new bile acid analogue, namely, sodium 3 alpha, 7 alpha-dihydroxy-25-homo-5 beta-cholane-25-sulfonate from homochenodeoxycholic acid. The structure of the new compound was assigned by proton magnetic resonance and infrared spectrometry. Its metabolism was studied in the hamster in comparison with sodium 3 alpha, 7 alpha-dihydroxy-24-nor-5 beta-cholane-23-sulfonate and sodium taurochenodeoxycholate. After intraduodenal administration of the 3H-labeled analogues into bile fistula hamsters, both sulfonates were absorbed from the intestine and nearly 80% of the radioactivity was secreted into bile within 8 h. Intra-ileal administration revealed that these compounds resembled taurochenodeoxycholate in that they were much more rapidly absorbed from the ileum than from the proximal small intestine: more than 85% of the radioactivity was recovered in bile within 1 h. After intravenous infusion the sulfonates were efficiently extracted by the liver at rates similar to that of sodium taurochenodeoxycholate. Chromatographic analysis of the bile showed that, regardless of the route of administration, most (> 95%) of the sulfonates were not biotransformed and they became major biliary bile acids. Sodium 3 alpha, 7 alpha-dihydroxy-25-homo-5 beta-cholane-25-sulfonate and, to a lesser extent, sodium 3 alpha, 7 alpha-dihydroxy-24-nor-5 beta-cholane-23-sulfonate induced cholestasis at infusion rates at which sodium taurochenodeoxycholate produced choleresis.
S Miki; E H Mosbach; B I Cohen; M Yoshii; N Ayyad; C K McSherry
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Publication Detail:
Type:  Comparative Study; Journal Article; Research Support, Non-U.S. Gov't; Research Support, U.S. Gov't, P.H.S.    
Journal Detail:
Title:  Journal of lipid research     Volume:  33     ISSN:  0022-2275     ISO Abbreviation:  J. Lipid Res.     Publication Date:  1992 Nov 
Date Detail:
Created Date:  1993-01-19     Completed Date:  1993-01-19     Revised Date:  2007-11-14    
Medline Journal Info:
Nlm Unique ID:  0376606     Medline TA:  J Lipid Res     Country:  UNITED STATES    
Other Details:
Languages:  eng     Pagination:  1629-37     Citation Subset:  IM    
Department of Surgery, Beth Israel Medical Center, New York, NY 10003.
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MeSH Terms
Bile / drug effects,  metabolism,  secretion
Chenodeoxycholic Acid / analogs & derivatives*,  chemical synthesis,  metabolism,  pharmacokinetics,  pharmacology
Intestinal Absorption
Sulfonic Acids / metabolism
Taurochenodeoxycholic Acid / metabolism
Grant Support
Reg. No./Substance:
0/Sulfonic Acids; 145523-79-1/3,7-dihydroxy-24-norcholane-23-sulfonate; 145523-80-4/3,7-dihydroxy-25-homocholane-25-sulfonate; 474-25-9/Chenodeoxycholic Acid; 516-35-8/Taurochenodeoxycholic Acid

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