Taurochenodeoxycholic Acid
From DrugPedia: A Wikipedia for Drug discovery
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==Description== | ==Description== | ||
A bile salt formed in the liver by conjugation of chenodeoxycholate with taurine, usually as the sodium salt. It acts as detergent to solubilize fats in the small intestine and is itself absorbed. It is used as a cholagogue and choleretic. | A bile salt formed in the liver by conjugation of chenodeoxycholate with taurine, usually as the sodium salt. It acts as detergent to solubilize fats in the small intestine and is itself absorbed. It is used as a cholagogue and choleretic. | ||
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| + | '''Chenodeoxycholic acid''' (also known as '''chenodesoxycholic acid''') is a [[bile acid]]. It occurs as a white crystalline substance insoluble in water but soluble in [[alcohol]] and [[acetic acid]], with melting point at 165-167 °C. Salts of this [[carboxylic acid]] are called '''chenodeoxycholates'''. Chenodeoxycholic acid is one of the 4 main [[organic acid]]s produced by the [[liver]]. | ||
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| + | Chenodeoxycholic acid is synthesized in the liver from [[cholesterol]]. It was first isolated in the domestic goose, hence the 'cheno' portion of its name (Greek: χήνα = goose) <ref>{{cite journal |author=Carey MC |title=Editorial: Cheno and urso: what the goose and the bear have in common |journal=N. Engl. J. Med. |volume=293 |issue=24 |pages=1255–7 |year=1975 |month=December |pmid=1186807 |doi= |url=}}</ref> | ||
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| + | This compound, when altered by [[bacteria]] in the [[Colon (anatomy)|colon]], will result in conversion to its secondary bile acid known as [[lithocholic acid]]. Both of these bile acids, in addition to the others, can be conjugated to [[taurine]] or [[glycine]]. Conjugation, a function carried out by the [[liver]] will result in a lowered pKa and therefore, the compounds will remain ionized. These ionized compounds will stay in the gastrointestinal tract until reaching the [[ileum]] where they will be reabsorbed. The purpose of this conjugation is to keep the bile acids in the tract until the end to facilitate lipid digestion all the way to the ileum. | ||
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| + | In cases where bacteria overgrow in the small intestine, often due to a blind loop in the intestine retaining chyme in one place, the bacteria will de-conjugate the bile acids and therefore impede fat digestion and absorption. This can lead to [[steatorrhea]]. | ||
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| + | Chenodeoxycholic acid and [[cholic acid]] are the most important human bile acids. Some other mammals synthesize predominantly [[deoxycholic acid]]. | ||
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| + | ==Potential applications== | ||
| + | The Australian biotechnology company [[Giaconda]] has developed a treatment for [[Hepatitis C]] infection that combines chenodeoxycholic acid with [[bezafibrate]]. | ||
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| + | In [[supramolecular chemistry]] [[molecular tweezers]] based on a [[chenodeoxycholic acid]] scaffold is a [[urea]] receptor {{Ref|1}} which can contain [[anion]]s in its binding pocket in order of affinity: H<sub>2</sub>PO<sub>4</sub><sup>-</sup> (dihydrogen [[phosphate]]) > [[chlorine|Cl]]<sup>-</sup> > [[bromine|Br]]<sup>-</sup> > [[iodine|I]]<sup>-</sup> reflecting their [[base (chemistry)|basicities]] (tetrabutylammonium counter ion).<ref>''Molecular Tweezer Based on Chenodeoxycholic Acid:Synthesis, Anion Binding Properties '' Ki Soo Kim, Hong-Seok Kim Bulletin of the Korean Society 1411-1413 '''2004''' [http://newjournal.kcsnet.or.kr/main/j_search/j_bkcs_archives_view2.htm?code=B040927&qpage=j_bkcs&spage=j_bkcs_01 Article]</ref> | ||
| + | :[[Image:MolecularTweezerEmpl1.gif|450px|Molecular tweezer based on chenodeoxycholic acid]] | ||
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==General Properties== | ==General Properties== | ||
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Revision as of 12:01, 16 February 2009
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Contents |
Description
A bile salt formed in the liver by conjugation of chenodeoxycholate with taurine, usually as the sodium salt. It acts as detergent to solubilize fats in the small intestine and is itself absorbed. It is used as a cholagogue and choleretic.
Chenodeoxycholic acid (also known as chenodesoxycholic acid) is a bile acid. It occurs as a white crystalline substance insoluble in water but soluble in alcohol and acetic acid, with melting point at 165-167 °C. Salts of this carboxylic acid are called chenodeoxycholates. Chenodeoxycholic acid is one of the 4 main organic acids produced by the liver.
Chenodeoxycholic acid is synthesized in the liver from cholesterol. It was first isolated in the domestic goose, hence the 'cheno' portion of its name (Greek: χήνα = goose) <ref>Carey MC (December 1975). "Editorial: Cheno and urso: what the goose and the bear have in common". N. Engl. J. Med. 293 (24): 1255–7. PMID 1186807.</ref>
This compound, when altered by bacteria in the colon, will result in conversion to its secondary bile acid known as lithocholic acid. Both of these bile acids, in addition to the others, can be conjugated to taurine or glycine. Conjugation, a function carried out by the liver will result in a lowered pKa and therefore, the compounds will remain ionized. These ionized compounds will stay in the gastrointestinal tract until reaching the ileum where they will be reabsorbed. The purpose of this conjugation is to keep the bile acids in the tract until the end to facilitate lipid digestion all the way to the ileum.
In cases where bacteria overgrow in the small intestine, often due to a blind loop in the intestine retaining chyme in one place, the bacteria will de-conjugate the bile acids and therefore impede fat digestion and absorption. This can lead to steatorrhea.
Chenodeoxycholic acid and cholic acid are the most important human bile acids. Some other mammals synthesize predominantly deoxycholic acid.
Potential applications
The Australian biotechnology company Giaconda has developed a treatment for Hepatitis C infection that combines chenodeoxycholic acid with bezafibrate.
In supramolecular chemistry molecular tweezers based on a chenodeoxycholic acid scaffold is a urea receptor Template:Ref which can contain anions in its binding pocket in order of affinity: H2PO4- (dihydrogen phosphate) > Cl- > Br- > I- reflecting their basicities (tetrabutylammonium counter ion).<ref>Molecular Tweezer Based on Chenodeoxycholic Acid:Synthesis, Anion Binding Properties Ki Soo Kim, Hong-Seok Kim Bulletin of the Korean Society 1411-1413 2004 Article</ref>
General Properties
*Molecular Weight
499.7
*Molecular Formula
C26H45NO6S
*IUPAC NAME
2-[4-[(3R,5S,7R,8R,9S,10S,13R,14S,17R)-3,7-dihydroxy-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl]pentanoylamino]ethanesulfonic acid
*Canonical Smiles
CC(CCC(=O)NCCS(=O)(=O)O)C1CCC2C1(CCC3C2C(CC4C3(CCC(C4)O)C)O)C
*Isomeric Smiles
CC(CCC(=O)NCCS(=O)(=O)O)[C@H]1CC[C@@H]2[C@@]1(CC[C@H]3[C@H]2[C@@H](C[C@H]4[C@@]3(CC[C@H](C4)O)C)O)C
PhysioChemical Properties
*Melting Point
*LogP
*Water Solubility
