# Cholic acid

> Mediated Wiki article. Canonical URL: https://mediated.wiki/source/Cholic_acid
> Markdown URL: https://mediated.wiki/source/Cholic_acid.md
> Source: https://en.wikipedia.org/wiki/Cholic_acid
> Source revision: 1329246664
> License: Creative Commons Attribution-ShareAlike 4.0 International (https://creativecommons.org/licenses/by-sa/4.0/)

{{Short description|Main bile acid}}
{{chembox
| Verifiedfields = changed
| Watchedfields = changed
| verifiedrevid = 401957444
| Name = Cholic acid
| ImageFile = Cholic acid.svg
| ImageSize = 
| ImageClass = skin-invert-image
| ImageName = Cholic acid
| ImageFile1 = Cholic-acid-from-xtal-view-1-3D-bs-17.png
| ImageClass1 = bg-transparent
| ImageSize1 = 
| IUPACName = 3α,7α,12α-Trihydroxy-5β-cholan-24-oic acid
| SystematicName = (6''R'')-6-[(1''R'',3a''S'',3b''R'',4''R'',5a''S'',7''R'',9a''S'',9b''S'',11''S'',11a''R'')-4,7,11-Trihydroxy-9a,11a-dimethylhexadecahydro-1''H''-cyclopenta[''a'']phenanthren-1-yl]heptanoic acid
| OtherNames = 
|Section1={{Chembox Identifiers
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = G1JO7801AE
| ChEMBL_Ref = {{ebicite|changed|EBI}}
| ChEMBL = 205596
| 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
| InChIKey = BHQCQFFYRZLCQQ-OELDTZBJBZ
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 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
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = BHQCQFFYRZLCQQ-OELDTZBJSA-N
| CASNo_Ref = {{cascite|correct|CAS}}
| CASNo = 81-25-4
| PubChem = 221493
| IUPHAR_ligand = 609
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 192176
| ChEBI_Ref = {{ebicite|changed|EBI}}
| ChEBI = 16359
| DrugBank_Ref = {{drugbankcite|changed|drugbank}}
| DrugBank = DB02659
| KEGG_Ref = {{keggcite|changed|kegg}}
| KEGG = D10699
| SMILES = 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
}}
|Section2={{Chembox Properties
| Formula = C<sub>24</sub>H<sub>40</sub>O<sub>5</sub>
| MolarMass = 408.57 g/mol
| Density = 
| MeltingPtC = 200 to 201
| MeltingPt_notes = 
| BoilingPt = 
| MagSus = −282.3·10<sup>−6</sup> cm<sup>3</sup>/mol
 }}
| Section6 = {{Chembox Pharmacology
| Pharmacology_ref = 
| ATCCode_prefix = A05
| ATCCode_suffix = AA03
| ATC_Supplemental = 
| ATCvet = 
| Licence_EU = yes
| INN = 
| INN_EMA = 
| Licence_US = Cholbam
| Legal_status = 
| Legal_AU = S4
| Legal_AU_comment = 
| Legal_CA = 
| Legal_CA_comment = 
| Legal_NZ = 
| Legal_NZ_comment = 
| Legal_UK = 
| Legal_UK_comment = 
| Legal_US = Rx-only
| Legal_US_comment = <ref name="Cholbam FDA label" />
| Legal_EU = Rx-only
| Legal_EU_comment = <ref name="Orphacol EPAR" />
| Legal_UN = 
| Legal_UN_comment = 
| Pregnancy_category = 
| Pregnancy_AU = B2
| Pregnancy_AU_comment = 
| Dependence_liability = 
| AdminRoutes = 
| Bioavail = 
| ProteinBound = 
| Metabolism = 
| Metabolites = 
| OnsetOfAction = 
| HalfLife = 
| DurationOfAction = 
| Excretion = 
  }}
}}
'''Cholic acid''', also known as '''3α,7α,12α-trihydroxy-5β-cholan-24-oic acid''' is a primary [bile acid](/source/bile_acid)<ref name="isbn0-7817-9340-8">{{cite book |author=Colleen Smith |author2=Lieberman, Michael |author3=Marks, Dawn B. |author4=Allan D. Marks |title=Marks' essential medical biochemistry |publisher=Lippincott Williams & Wilkins |location=Hagerstwon, MD |year=2007 |isbn=978-0-7817-9340-7 }}</ref> that is insoluble in water (soluble in [alcohol](/source/ethanol) and [acetic acid](/source/acetic_acid)),  it is a white crystalline substance.  Salts of cholic acid are called '''cholates'''.  Cholic acid, along with [chenodeoxycholic acid](/source/chenodeoxycholic_acid), is one of the two major [bile acid](/source/bile_acid)s produced by the [liver](/source/liver), where it is synthesized from [cholesterol](/source/cholesterol).  These two major bile acids are roughly equal in concentration in humans.<ref name="pmid1244533">{{cite journal |vauthors=Bennion LJ, Ginsberg RL, Gernick MB, Bennett PH |title=Effects of oral contraceptives on the gallbladder bile of normal women |journal=N. Engl. J. Med. |volume=294 |issue=4 |pages=189–92 | date=January 1976 |pmid=1244533 |doi=10.1056/NEJM197601222940403 }}</ref> Derivatives are made from cholyl-CoA, which exchanges its [CoA](/source/Coenzyme_A) with either [glycine](/source/glycine), or [taurine](/source/taurine), yielding [glycocholic](/source/glycocholic_acid) and [taurocholic acid](/source/taurocholic_acid), respectively.<ref name="pmid19346330">{{cite journal |author=Chiang JY |title=Bile acids: regulation of synthesis |journal=Journal of Lipid Research |volume=50 |issue=10 |pages=1955–66 |date=October 2009 |pmid=19346330 |pmc=2739756 |doi=10.1194/jlr.R900010-JLR200  |doi-access=free }}</ref>

Cholic acid downregulates [cholesterol-7-α-hydroxylase](/source/cholesterol-7-%CE%B1-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](/source/gallstone)s (because decreasing bile acid synthesis would supersaturate the stones even more).<ref name="pmid1152936">{{cite journal |vauthors=Iser JH, Dowling H, Mok HY, Bell GD |title=Chenodeoxycholic acid treatment of gallstones. A follow-up report and analysis of factors influencing response to therapy |journal=The New England Journal of Medicine |volume=293 |issue=8 |pages=378–83 |date=August 1975 |pmid=1152936 |doi=10.1056/NEJM197508212930804 }}</ref><ref>
{{cite journal |title=Chenotherapy for Gallstone Dissolution, II. Induced Changes in Bile Composition and Gallstone Response |author=Alan F. Hofmann |author2=Johnson L. Thistle |author3=Peter D. Klein|author4=Patricia A. Szczepanik |author5=Paulina Y. S. Yu |journal=JAMA |year=1978 |volume=239 |issue=12 |pages=1138–1144 |doi=10.1001/jama.1978.03280390034017 |pmid=628065 }}</ref>

Cholic acid and [chenodeoxycholic acid](/source/chenodeoxycholic_acid) are the most important human bile acids.  Other species may synthesize different bile acids as their predominant primary bile acids.<ref name="pmid19638645">{{cite journal |vauthors=Hofmann AF, Hagey LR, Krasowski MD |title=Bile salts of vertebrates: structural variation and possible evolutionary significance |journal=J. Lipid Res. |volume=51 |issue=2 |pages=226–46 |date=February 2010  |pmid=19638645 |pmc=2803226 |doi=10.1194/jlr.R000042  |doi-access=free }}</ref>

==Medical uses==
{{anchor|Medical}}

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](/source/Zellweger_syndrome).<ref>{{cite web | title=Cholbam (cholic acid) Capsules | website=U.S. [Food and Drug Administration](/source/Food_and_Drug_Administration) (FDA) | date=13 April 2015 | url=https://www.accessdata.fda.gov/drugsatfda_docs/nda/2015/205750Orig1s000TOC.cfm | archive-url=https://web.archive.org/web/20150601001001/http://www.accessdata.fda.gov/drugsatfda_docs/nda/2015/205750Orig1s000TOC.cfm | url-status=dead | archive-date=June 1, 2015 | access-date=3 May 2020}}</ref><ref name="Cholbam FDA label">{{cite web | title=Cholbam- cholic acid capsule | website=DailyMed | date=12 July 2019 | url=https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=e5b67402-8550-4604-97a0-c7b149fbf753 | access-date=2 May 2020}}</ref><ref>{{cite press release | title=FDA approves Cholbam to treat rare bile acid synthesis disorders | website=U.S. [Food and Drug Administration](/source/Food_and_Drug_Administration) (FDA) | date=17 March 2015 | url=https://www.fda.gov/NewsEvents/Newsroom/PressAnnouncements/ucm438572.htm | archive-url=https://web.archive.org/web/20180126023504/https://www.fda.gov/NewsEvents/Newsroom/PressAnnouncements/ucm438572.htm | archive-date=26 January 2018 | url-status=dead | access-date=19 May 2020}} {{PD-notice}}</ref>

It was approved for use in the European Union in September 2013, and is sold under the brand name '''Orphacol'''.<ref name="Orphacol EPAR">{{cite web | title=Orphacol EPAR | website=[European Medicines Agency](/source/European_Medicines_Agency) (EMA) | date=17 September 2018 | url=https://www.ema.europa.eu/en/medicines/human/EPAR/orphacol | access-date=2 May 2020}} Text was copied from this source which is under copyright of the European Medicines Agency. Reproduction is authorized provided the source is acknowledged.</ref> It is indicated for the treatment of inborn errors in primary bile-acid synthesis due to [3β-hydroxy-Δ<sup>5</sup>-C<sub>27</sub>-steroid oxidoreductase](/source/3%CE%B2-hydroxy-%CE%945-C27-steroid_oxidoreductase) deficiency or [Δ<sup>4</sup>-3-oxosteroid-5β-reductase](/source/%CE%944-3-oxosteroid-5%CE%B2-reductase) deficiency in infants, children and adolescents aged one month to 18 years and adults.<ref name="Orphacol EPAR" />

Cholic acid FGK (Kolbam) was approved for medical use in the European Union in November 2015.<ref name="Kolbam EPAR">{{cite web | title=Kolbam EPAR | website=[European Medicines Agency](/source/European_Medicines_Agency) (EMA) | date=17 September 2018 | url=https://www.ema.europa.eu/en/medicines/human/EPAR/kolbam | access-date=19 May 2020}} Text was copied from this source which is under copyright of the European Medicines Agency. Reproduction is authorized provided the source is acknowledged.</ref> 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:<ref name="Kolbam EPAR" />
* [sterol 27-hydroxylase](/source/sterol_27-hydroxylase) deficiency (presenting as [cerebrotendinous xanthomatosis](/source/cerebrotendinous_xanthomatosis), CTX);<ref name="Kolbam EPAR" />
* [2- (or alpha-) methylacyl-CoA racemase](/source/Alpha-methylacyl-CoA_racemase) (AMACR) deficiency;<ref name="Kolbam EPAR" />
* cholesterol 7 alpha-hydroxylase (CYP7A1) deficiency.<ref name="Kolbam EPAR" />

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).<ref name="Kolbam EPAR" />

thumb|right|Structure of cholic acid showing relationship to other bile acids

==Cancer==

A [meta-analysis](/source/meta-analysis) on the relationship of fecal [bile acid](/source/bile_acid) concentrations to the development and progression of [colorectal cancer](/source/colorectal_cancer) was reported in 2025.<ref name = Yang2025>{{cite journal |vauthors=Yang S, Wang Y, Sheng L, Cui W, Ma C |title=The effect of fecal bile acids on the incidence and risk-stratification of colorectal cancer: an updated systematic review and meta-analysis |journal=Sci Rep |volume=15 |issue=1 |article-number=740 |date=January 2025 |pmid=39753873 |doi=10.1038/s41598-024-84801-6 |url=|pmc=11698987 |bibcode=2025NatSR..15..740Y }}</ref>  It was found that higher fecal concentrations of cholic acid are associated with a higher risk/incidence of colorectal cancer.<ref name = Yang2025/>  Bile acids have been implicated as [carcinogen](/source/carcinogen)s in the [gastrointestinal tract](/source/gastrointestinal_tract).<ref>{{cite journal |vauthors=Bernstein H, Bernstein C |title=Bile acids as carcinogens in the colon and at other sites in the gastrointestinal system |journal=Exp Biol Med (Maywood) |volume=248 |issue=1 |pages=79–89 |date=January 2023 |pmid=36408538 |pmc=9989147 |doi=10.1177/15353702221131858 |url=}}</ref>

==Interactive pathway map==
{{StatinPathway_WP430|highlight=Cholic_acid}}
{{clear}}

==References==
{{reflist}}

{{Bile and liver therapy}}
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{{DEFAULTSORT:Cholic Acid}}
Category:Bile acids
Category:Triols
Category:Cholanes
Category:Orphan drugs

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Adapted from the Wikipedia article [Cholic acid](https://en.wikipedia.org/wiki/Cholic_acid) by Wikipedia contributors ([contributor history](https://en.wikipedia.org/wiki/Cholic_acid?action=history)). Available under [Creative Commons Attribution-ShareAlike 4.0 International](https://creativecommons.org/licenses/by-sa/4.0/). Changes may have been made.