Cholic acid, also known as 3α,7α,12α-trihydroxy-5β-cholan-24-oic acid is a primary bile acid that is insoluble in water (soluble in

alcohol Alcohol most commonly refers to: * Alcohol (chemistry), an organic compound in which a hydroxyl group is bound to a carbon atom * Alcohol (drug), an intoxicant found in alcoholic drinks Alcohol may also refer to: Chemicals * Ethanol, one of sev ...

and

acetic acid Acetic acid , systematically named ethanoic acid , is an acidic, colourless liquid and organic compound with the chemical formula (also written as , , or ). Vinegar is at least 4% acetic acid by volume, making acetic acid the main componen ...

), 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 The liver is a major organ only found in vertebrates which performs many essential biological functions such as detoxification of the organism, and the synthesis of proteins and biochemicals necessary for digestion and growth. In humans, it ...

, where it is synthesized from

cholesterol Cholesterol is any of a class of certain organic molecules called lipids. It is a sterol (or modified steroid), a type of lipid. Cholesterol is biosynthesized by all animal cells and is an essential structural component of animal cell membr ...

. These two major bile acids are roughly equal in concentration in humans. Derivatives are made from cholyl-CoA, which exchanges its

CoA Coa may refer to: Places * Coa, County Fermanagh, a rural community in County Fermanagh, Northern Ireland * Côa River, a tributary of the Douro, Portugal ** Battle of Coa, part of the Peninsular War period of the Napoleonic Wars ** Côa Vall ...

with either

glycine Glycine (symbol Gly or G; ) is an amino acid that has a single hydrogen atom as its side chain. It is the simplest stable amino acid ( carbamic acid is unstable), with the chemical formula NH2‐ CH2‐ COOH. Glycine is one of the proteinog ...

, or

taurine Taurine (), or 2-aminoethanesulfonic acid, is an organic compound that is widely distributed in animal tissues. It is a major constituent of bile and can be found in the large intestine, and accounts for up to 0.1% of total human body weight. It ...

, yielding glycocholic and taurocholic acid, respectively. 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

gallstone A gallstone is a stone formed within the gallbladder from precipitated bile components. The term cholelithiasis may refer to the presence of gallstones or to any disease caused by gallstones, and choledocholithiasis refers to the presence of ...

s (because decreasing bile acid synthesis would supersaturate the stones even more). 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.

Medical uses

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). It was approved for use in the European Union in September 2013, and is sold under the brand name Orphacol. Text was copied from this source which is under copyright of the European Medicines Agency. Reproduction is authorized provided the source is acknowledged. 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. Cholic acid FGK (Kolbam) was approved for medical use in the European Union in November 2015. Text was copied from this source which is under copyright of the European Medicines Agency. Reproduction is authorized provided the source is acknowledged. 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: * sterol 27-hydroxylase deficiency (presenting as cerebrotendinous xanthomatosis, CTX); * 2- (or alpha-) methylacyl-CoA racemase (AMACR) deficiency; * cholesterol 7 alpha-hydroxylase (CYP7A1) deficiency. 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). Cholic Acid vs Other Bile Acids

Interactive pathway map

References

External links

* {{DEFAULTSORT:Cholic Acid Bile acids Triols Cholanes Orphan drugs