Cholic acid

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Cholic acid
Cholic acid
Cholic acid
File:Cholic-acid-from-xtal-view-1-3D-bs-17.png
Names
IUPAC name
3α,7α,12α-Trihydroxy-5β-cholan-24-oic acid
Systematic IUPAC name
(6R)-6-[(1R,3aS,3bR,4R,5aS,7R,9aS,9bS,11S,11aR)-4,7,11-Trihydroxy-9a,11a-dimethylhexadecahydro-1H-cyclopenta[a]phenanthren-1-yl]heptanoic acid
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
DrugBank
ECHA InfoCard Lua error in Module:Wikidata at line 880: attempt to index field 'wikibase' (a nil value). Lua error in Module:Wikidata at line 880: attempt to index field 'wikibase' (a nil value).Lua error in Module:EditAtWikidata at line 29: attempt to index field 'wikibase' (a nil value).
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KEGG
UNII
  • {{#property:P3117}}Lua error in Module:EditAtWikidata at line 29: attempt to index field 'wikibase' (a nil value).
  • InChI=1S/C24H40O5/c1-13(4-7-21(28)29)16-5-6-17-22-18(12-20(27)24(16,17)3)23(2)9-8-15(25)10-14(23)11-19(22)26/h13-20,22,25-27H,4-12H2,1-3H3,(H,28,29)/t13-,14+,15-,16-,17+,18+,19-,20+,22+,23+,24-/m1/s1 checkY
    Key: BHQCQFFYRZLCQQ-OELDTZBJSA-N checkY
  • InChI=1/C24H40O5/c1-13(4-7-21(28)29)16-5-6-17-22-18(12-20(27)24(16,17)3)23(2)9-8-15(25)10-14(23)11-19(22)26/h13-20,22,25-27H,4-12H2,1-3H3,(H,28,29)/t13-,14+,15-,16-,17+,18+,19-,20+,22+,23+,24-/m1/s1
    Key: BHQCQFFYRZLCQQ-OELDTZBJBZ
  • C[C@H](CCC(=O)O)[C@H]1CC[C@@H]2[C@@]1([C@H](C[C@H]3[C@H]2[C@@H](C[C@H]4[C@@]3(CC[C@H](C4)O)C)O)O)C
Properties
C24H40O5
Molar mass 408.57 g/mol
Melting point 200 to 201 °C (392 to 394 °F; 473 to 474 K)
−282.3·10−6 cm3/mol
Pharmacology
A05AA03 (WHO)
  • AU: B2
License data
Legal status
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Cholic acid, also known as 3α,7α,12α-trihydroxy-5β-cholan-24-oic acid is a primary bile acid[3] that is insoluble in water (soluble in alcohol and acetic acid), it is a white crystalline substance. Salts of cholic acid are called cholates. Cholic acid, along with chenodeoxycholic acid, is one of the two major bile acids produced by the liver, where it is synthesized from cholesterol. These two major bile acids are roughly equal in concentration in humans.[4] Derivatives are made from cholyl-CoA, which exchanges its CoA with either glycine, or taurine, yielding glycocholic and taurocholic acid, respectively.[5]

Cholic acid downregulates cholesterol-7-α-hydroxylase (rate-limiting step in bile acid synthesis), and cholesterol does the opposite. This is why chenodeoxycholic acid, and not cholic acid, can be used to treat gallstones (because decreasing bile acid synthesis would supersaturate the stones even more).[6][7]

Cholic acid and chenodeoxycholic acid are the most important human bile acids. Other species may synthesize different bile acids as their predominant primary bile acids.[8]

Medical uses

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Cholic acid, sold under the brand name Cholbam, is approved for use in the United States and is indicated as a treatment for children and adults with bile acid synthesis disorders due to single enzyme defects, and for peroxisomal disorders such as Zellweger syndrome.[9][1][10]

It was approved for use in the European Union in September 2013, and is sold under the brand name Orphacol.[2] It is indicated for the treatment of inborn errors in primary bile-acid synthesis due to 3β-hydroxy-Δ5-C27-steroid oxidoreductase deficiency or Δ4-3-oxosteroid-5β-reductase deficiency in infants, children and adolescents aged one month to 18 years and adults.[2]

Cholic acid FGK (Kolbam) was approved for medical use in the European Union in November 2015.[11] It is indicated for the treatment of inborn errors of primary bile acid synthesis, in infants from one month of age for continuous lifelong treatment through adulthood, encompassing the following single enzyme defects:[11]

The most common side effects include peripheral neuropathy (nerve damage in the hands and feet), diarrhea, nausea (feeling sick), acid reflux (stomach acid flowing up into the mouth), esophagitis (inflammation of the food pipe), jaundice (yellowing of the skin and eyes), skin problems (lesions) and malaise (feeling unwell).[11]

File:Cholic Acid vs Other Bile Acids.svg
Structure of cholic acid showing relationship to other bile acids

Cancer

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A meta-analysis on the relationship of fecal bile acid concentrations to the development and progression of colorectal cancer was reported in 2025.[12] It was found that higher fecal concentrations of cholic acid are associated with a higher risk/incidence of colorectal cancer.[12] Bile acids have been implicated as carcinogens in the gastrointestinal tract.[13]

Interactive pathway map

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Click on genes, proteins and metabolites below to link to respective articles.[§ 1]

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Statin pathway edit
  1. ^ The interactive pathway map can be edited at WikiPathways: Lua error in Module:Citation/CS1/Configuration at line 2172: attempt to index field '?' (a nil value).

References

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  1. ^ a b Lua error in Module:Citation/CS1/Configuration at line 2172: attempt to index field '?' (a nil value).
  2. ^ a b c Lua error in Module:Citation/CS1/Configuration at line 2172: attempt to index field '?' (a nil value). Text was copied from this source which is under copyright of the European Medicines Agency. Reproduction is authorized provided the source is acknowledged.
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  10. ^ Lua error in Module:Citation/CS1/Configuration at line 2172: attempt to index field '?' (a nil value). Public Domain This article incorporates text from this source, which is in the public domain.
  11. ^ a b c d e f Lua error in Module:Citation/CS1/Configuration at line 2172: attempt to index field '?' (a nil value). Text was copied from this source which is under copyright of the European Medicines Agency. Reproduction is authorized provided the source is acknowledged.
  12. ^ a b Lua error in Module:Citation/CS1/Configuration at line 2172: attempt to index field '?' (a nil value).
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