cholic acid

{{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

| ImageSize1 =

| IUPACName = 3α,7α,12α-Trihydroxy-5β-cholan-24-oic acid

| SystematicName = (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

| 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 = C₂₄H₄₀O₅

| MolarMass = 408.57 g/mol

| Density =

| MeltingPtC = 200 to 201

| MeltingPt_notes =

| BoilingPt =

| MagSus = −282.3·10⁻⁶ cm³/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 =

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| Legal_US = Rx-only

| Legal_US_comment =

| Legal_EU = Rx-only

| Legal_EU_comment =

| Legal_UN =

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| Pregnancy_category =

| Pregnancy_AU = B2

| Pregnancy_AU_comment =

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Cholic acid, also known as 3α,7α,12α-trihydroxy-5β-cholan-24-oic acid is a primary bile acid{{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 }} 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.{{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 }} Derivatives are made from cholyl-CoA, which exchanges its CoA with either glycine, or taurine, yielding glycocholic and taurocholic acid, respectively.{{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 }}

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).{{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 }}

{{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 }}

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.{{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 }}