Chenodeoxycholic acid

Source: Wikipedia, the free encyclopedia.

Chenodeoxycholic acid
Skeletal formula of chenodeoxycholic acid
Ball-and-stick model of the chenodeoxycholic acid molecule
Names
IUPAC name
3α,7α-Dihydroxy-5β-cholan-24-oic acid
Systematic IUPAC name
(4R)-4-[(1R,3aS,3bR,4R,5aS,7R,9aS,9bS,11aR)-4,7-Dihydroxy-9a,11a-dimethylhexadecahydro-1H-cyclopenta[a]phenanthren-1-yl]pentanoic acid
Other names
Chenodiol
Identifiers
3D model (
JSmol
)
ChEBI
ChEMBL
ChemSpider
DrugBank
ECHA InfoCard
 100.006.803 Edit this at Wikidata
EC Number
  • 207-481-8
IUPHAR/BPS
KEGG
UNII
  • InChI=1S/C24H40O4/c1-14(4-7-21(27)28)17-5-6-18-22-19(9-11-24(17,18)3)23(2)10-8-16(25)12-15(23)13-20(22)26/h14-20,22,25-26H,4-13H2,1-3H3,(H,27,28)/t14-,15+,16-,17-,18+,19+,20-,22+,23+,24-/m1/s1 checkY
    Key: RUDATBOHQWOJDD-BSWAIDMHSA-N checkY
  • InChI=1/C24H40O4/c1-14(4-7-21(27)28)17-5-6-18-22-19(9-11-24(17,18)3)23(2)10-8-16(25)12-15(23)13-20(22)26/h14-20,22,25-26H,4-13H2,1-3H3,(H,27,28)/t14-,15+,16-,17-,18+,19+,20-,22+,23+,24-/m1/s1
    Key: RUDATBOHQWOJDD-BSWAIDMHBF
  • C[C@H](CCC(=O)O)[C@H]1CC[C@@H]2[C@@]1(CC[C@H]3[C@H]2[C@@H](C[C@H]4[C@@]3(CC[C@H](C4)O)C)O)C
Properties
C24H40O4
Molar mass 392.57 g/mol
Melting point 165 to 167 °C (329 to 333 °F; 438 to 440 K)
Pharmacology
A05AA01 (WHO)
License data
Legal status
  • EU: Rx-only
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
☒N verify (what is checkY☒N ?)

Chenodeoxycholic acid (CDCA; also known as chenodesoxycholic acid, chenocholic acid and 3α,7α-dihydroxy-5β-cholan-24-oic acid) is a bile acid. Salts of this carboxylic acid are called chenodeoxycholates. Chenodeoxycholic acid is one of the main bile acids.[1][2][3] It was first isolated from the bile of the domestic goose, which gives it the "cheno" portion of its name (Greek: χήν = goose).[4]

Structure

Chenodeoxycholic acid and cholic acid are the two primary bile acids in humans. Chenodeoxycholic acid has two hydroxyl groups and is modified with the addition of another hydroxyl group to produce cholic acid. Some other mammals have muricholic acid or deoxycholic acid rather than chenodeoxycholic acid.[1] It occurs as a white crystalline substance insoluble in water but soluble in alcohol and acetic acid, with melting point at 165–167 °C.[citation needed]

Biosynthesis and function

Chenodeoxycholic acid is synthesized in the

taurochenodeoxycholate or glycochenodeoxycholate. Conjugation results in a lower pKa. This results in the conjugated bile acids being ionized at the usual pH in the intestine, and staying in the gastrointestinal tract until reaching the ileum to be reabsorbed.[3]

CDCA and other bile acids are

colon to form the secondary bile acid, lithocholic acid or the epimer, ursodeoxycholic acid.[3]

CDCA is the most potent natural bile acid at stimulating the nuclear bile acid receptor, farnesoid X receptor (FXR).[5] The transcription of many genes is activated by FXR, including those encoding FGF19 and small heterodimer partner.[6]

Therapeutic applications

Gallstones

CDCA has been used as medical therapy to dissolve gallstones.[7][8] Medical therapy with oral bile acids has been used in patients who have small cholesterol stones, and for patients with larger cholesterol gallstones who are unable or reluctant to have surgery. CDCA treatment can cause diarrhea, mild reversible hepatic injury, and a small increase in the plasma cholesterol level.[8]

Cerebrotendineous xanthomatosis

CDCA can be used in the treatment of cerebrotendineous xanthomatosis.[9]

Other

CDCA has been used in several other conditions.[10] As diarrhea is frequent when CDCA is used in gallstone dissolution, it has been studied as a possible treatment for constipation and has been shown to accelerate colonic transit and improve bowel function.[11]

The Australian biotechnology company Giaconda has tested a treatment for hepatitis C infection that combines chenodeoxycholic acid with bezafibrate.[12]

See also

References

  1. ^
    PMID 12543708
    .
  2. ISBN 9780124166875
    .
  3. ^
    PMID 25210150
    .
  4. PMID 1186807
    .
  5. PMID 10334993
    .
  6. S2CID 195327087
    .
  7. PMID 4580472
    .
  8. ^
    PMID 2672842
    .
  9. PMID 6504105
    .
  10. PMID 8291509.{{cite journal}}: CS1 maint: numeric names: authors list (link
    )
  11. PMID 20691689
    .
  12. ^ Giaconda. "Press release". Archived from the original on 7 April 2014. Retrieved 5 April 2014.

External links

Retrieved from "https://en.wikipedia.org/w/index.php?title=Chenodeoxycholic_acid&oldid=1214270150"