Chenodeoxycholic acid

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Overview

Chenodeoxycholic acid
Chenodeoxycholic acid
Systematic name chenodiol
3α,7α-dihydroxy-5β-cholanic acid
5β-cholanic acid-3α,7α-diol
Chemical formula C24H40O4
Molecular mass xx.xx g/mol
Density x.xxx g/cm3
Melting point 165-167 °C
Boiling point xx.x °C
CAS number [474-25-9]
SMILES C[C@@]34[C@] (CC[C@@H]4[C@@H]
(CCC(O)=O)C) ([H])[C@]2([H]) [C@H](O)C[C@]1
([H])C[C@H](O) CC[C@@](C)1 [C@]([H])2CC3
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Chenodeoxycholic acid

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Chenodeoxycholic acid (also known as chenodesoxycholic acid) is a bile acid, a white crystalline substance insoluble in water, with melting point at 165-167 °C. Its salts is called chenodeoxycholates. Chenodeoxycholic acid is one of the 4 main organic acids produced by the liver. It is soluble in alcohol and acetic acid.

Chenodeoxycholic acid is synthesized in the liver from cholesterol.

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 an urea receptor [2] which can contain anions in its binding pocket in order of affinity: H2PO4- (dihydrogen phosphate) > Cl- > Br- > I- reflecting their basicities (tetrabutylammonium counter ion).[1]

Molecular tweezer based on chenodeoxycholic acid


External links

References

  1. 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
Cost Effectiveness of Chenodeoxycholic acid

| group5 = Clinical Trials Involving Chenodeoxycholic acid | list5 = Ongoing Trials on Chenodeoxycholic acid at Clinical Trials.govTrial results on Chenodeoxycholic acidClinical Trials on Chenodeoxycholic acid at Google


| group6 = Guidelines / Policies / Government Resources (FDA/CDC) Regarding Chenodeoxycholic acid | list6 = US National Guidelines Clearinghouse on Chenodeoxycholic acidNICE Guidance on Chenodeoxycholic acidNHS PRODIGY GuidanceFDA on Chenodeoxycholic acidCDC on Chenodeoxycholic acid


| group7 = Textbook Information on Chenodeoxycholic acid | list7 = Books and Textbook Information on Chenodeoxycholic acid


| group8 = Pharmacology Resources on Chenodeoxycholic acid | list8 = AND (Dose)}} Dosing of Chenodeoxycholic acidAND (drug interactions)}} Drug interactions with Chenodeoxycholic acidAND (side effects)}} Side effects of Chenodeoxycholic acidAND (Allergy)}} Allergic reactions to Chenodeoxycholic acidAND (overdose)}} Overdose information on Chenodeoxycholic acidAND (carcinogenicity)}} Carcinogenicity information on Chenodeoxycholic acidAND (pregnancy)}} Chenodeoxycholic acid in pregnancyAND (pharmacokinetics)}} Pharmacokinetics of Chenodeoxycholic acid


| group9 = Genetics, Pharmacogenomics, and Proteinomics of Chenodeoxycholic acid | list9 = AND (pharmacogenomics)}} Genetics of Chenodeoxycholic acidAND (pharmacogenomics)}} Pharmacogenomics of Chenodeoxycholic acidAND (proteomics)}} Proteomics of Chenodeoxycholic acid


| group10 = Newstories on Chenodeoxycholic acid | list10 = Chenodeoxycholic acid in the newsBe alerted to news on Chenodeoxycholic acidNews trends on Chenodeoxycholic acid</small>


| group11 = Commentary on Chenodeoxycholic acid | list11 = Blogs on Chenodeoxycholic acid

| group12 = Patient Resources on Chenodeoxycholic acid | list12 = Patient resources on Chenodeoxycholic acidDiscussion groups on Chenodeoxycholic acidPatient Handouts on Chenodeoxycholic acidDirections to Hospitals Treating Chenodeoxycholic acidRisk calculators and risk factors for Chenodeoxycholic acid


| group13 = Healthcare Provider Resources on Chenodeoxycholic acid | list13 = Symptoms of Chenodeoxycholic acidCauses & Risk Factors for Chenodeoxycholic acidDiagnostic studies for Chenodeoxycholic acidTreatment of Chenodeoxycholic acid

| group14 = Continuing Medical Education (CME) Programs on Chenodeoxycholic acid | list14 = CME Programs on Chenodeoxycholic acid

| group15 = International Resources on Chenodeoxycholic acid | list15 = Chenodeoxycholic acid en EspanolChenodeoxycholic acid en Francais

| group16 = Business Resources on Chenodeoxycholic acid | list16 = Chenodeoxycholic acid in the MarketplacePatents on Chenodeoxycholic acid

| group17 = Informatics Resources on Chenodeoxycholic acid | list17 = List of terms related to Chenodeoxycholic acid


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