chenodeoxycholate

ケノデオキシコール酸

関

chenodeoxycholic acid

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出典(authority):フリー百科事典『ウィキペディア（Wikipedia）』「2013/01/23 22:34:10」(JST)

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Chenodeoxycholic acid
IUPAC name chenodiol OR 3α,7α-dihydroxy-5β-cholanic acid OR 5β-cholanic acid-3α,7α-diol OR (R)-((3R,5S,7R,8R,9S,10S,13R,14S,17R)-3,7-dihydroxy -10,13-dimethylhexadecahydro- 1H-cyclopenta[a]phenanthren-17-yl)pentanoic acid
Identifiers
CAS number	474-25-9 Y
ChemSpider	9728 Y
UNII	0GEI24LG0J Y
DrugBank	DB06777
KEGG	C02528 N
ChEBI	CHEBI:16755 N
ChEMBL	CHEMBL240597 N
ATC code	A05AA01
Jmol-3D images	Image 1
SMILES 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
InChI 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 Y Key: RUDATBOHQWOJDD-BSWAIDMHSA-N Y 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
Properties
Molecular formula	C24H40O4
Molar mass	392.57 g/mol
Melting point	165-167 °C
N (verify) (what is: Y/N?) Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references

Chenodeoxycholic acid (also known as chenodesoxycholic acid and chenocholic acid) is a bile acid. It occurs as a white crystalline substance insoluble in water but soluble in alcohol and acetic acid, with melting point at 165-167 °C. Salts of this carboxylic acid are called chenodeoxycholates. Chenodeoxycholic acid is one of the 4 main organic acids produced by the liver.

Chenodeoxycholic acid is synthesized in the liver from cholesterol. It was first isolated in the domestic goose, hence the 'cheno' portion of its name (Greek: χήνα = goose)

This compound, when altered by bacteria in the colon, will result in conversion to its secondary bile acid known as lithocholic acid. Both of these bile acids, in addition to the others, can be conjugated to taurine or glycine. Conjugation, a function carried out by the liver will result in a lowered pKa and therefore, the compounds will remain ionized. These ionized compounds will stay in the gastrointestinal tract until reaching the ileum where they will be reabsorbed. The purpose of this conjugation is to keep the bile acids in the tract until the end to facilitate lipid digestion all the way to the ileum.

In cases where bacteria overgrow in the small intestine, often due to a blind loop in the intestine retaining chyme in one place, the bacteria will de-conjugate the bile acids and therefore impede fat digestion and absorption. This can lead to steatorrhea.

Chenodeoxycholic acid and cholic acid are the most important human bile acids. Some other mammals synthesize predominantly deoxycholic acid.

Potential applications

The Australian biotechnology company Giaconda has developed a treatment for Hepatitis C infection that combines chenodeoxycholic acid with bezafibrate.

Chenodeoxycholic acid can be used in the treatment of cerebrotendinous xanthomatosis.

In supramolecular chemistry, molecular tweezers based on a chenodeoxycholic acid scaffold is a urea receptor that can contain anions in its binding pocket in order of affinity: H₂PO₄^- (dihydrogen phosphate) > Cl^- > Br^- > I^- reflecting their basicities (tetrabutylammonium counter ion).

References

UpToDate Contents

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• 1. 胆石の疫学および危険因子 epidemiology of and risk factors for gallstones
• 2. 妊婦における胆石症 gallstone disease in pregnant women

English Journal

• Retention data of bile acids and their oxo derivatives in characterization of pharmacokinetic properties and in silico ADME modeling.

• Trifunović J1, Borčić V2, Vukmirović S2, Kon SG3, Mikov M2.
• European journal of pharmaceutical sciences : official journal of the European Federation for Pharmaceutical Sciences.Eur J Pharm Sci.2016 Sep 20;92:194-202. doi: 10.1016/j.ejps.2016.07.011. Epub 2016 Jul 14.
• PURPOSE: Information on ADME properties of examined bile acids and their oxo derivatives are scarce, although the interest for bile acids and their use in nanochemistry and macromolecular chemistry is increasing. The purpose of this research was to evaluate the lipophilicity, a crucial physicochemic
• PMID 27423261

• Transporter-targeted cholic acid-cytarabine conjugates for improved oral absorption.

• Zhang D1, Li D2, Shang L3, He Z1, Sun J4.
• International journal of pharmaceutics.Int J Pharm.2016 Sep 10;511(1):161-9. doi: 10.1016/j.ijpharm.2016.06.139. Epub 2016 Jul 1.
• Cytarabine has a poor oral absorption due to its rapid deamination and poor membrane permeability. Bile acid transporters are highly expressed both in enterocytes and hepatocytes and to increase the oral bioavailability and investigate the potential application of cytarabine for liver cancers, a tra
• PMID 27377011

• The role of the bile acid chenodeoxycholic acid in the targeted oral delivery of the anti-diabetic drug gliclazide, and its applications in type 1 diabetes.

• Mathavan S1, Chen-Tan N2, Arfuso F3, Al-Salami H1.
• Artificial cells, nanomedicine, and biotechnology.Artif Cells Nanomed Biotechnol.2016 Sep;44(6):1508-19. doi: 10.3109/21691401.2015.1058807. Epub 2015 Jul 25.
• Gliclazide (G) is used to treat type 2 diabetes (T2D), and also has anti-platelet, anti-radical, and anti-inflammatory effects. G has poor water solubility and high inter-individual variations in absorption, limiting its application in type 1 diabetes (T1D). The bile acid, chenodeoxycholic acid (CDC
• PMID 26212118

Japanese Journal

• Alterations in the Detergent-Induced Membrane Permeability and Solubilization of Saturated Phosphatidylcholine/Cholesterol Liposomes: Effects of Poly(ethylene glycol)-Conjugated Lipid

• Chemical and Pharmaceutical Bulletin 60(9), 1105-1111, 2012
• NAID 130001852528

• Inhibition of Hepatocyte Growth Factor Production in Human Fibroblasts by Ursodeoxycholic Acid(Pharmacology)

• Biological & pharmaceutical bulletin 28(4), 619-624, 2005-04-01
• NAID 10016661983

• Binding of bile salts to soluble and insoluble dietary fibers of seaweeds

• Fisheries science : FS 67(6), 1169-1173, 2001-12-01
• NAID 10008271790

Related Links

• Sodium chenodeoxycholate ≥97% | Sigma-Aldrich

Sodium chenodeoxycholate ≥97%; CAS Number: 2646-38-0; Synonym: 3α,7α-Dihydroxy-5β-cholanic acid, 5β-Cholanic acid-3α,7α-diol, Chenodeoxycholic acid sodium salt, Chenodesoxycholic acid, Chenodiol; Linear Formula ...

• Sodium chenodeoxycholate | C24H40NaO4 - PubChem

Sodium chenodeoxycholate is a bile acid, usually conjugated with either glycine or taurine. It acts as a detergent to solubilize fats for intestinal absorption and is reabsorbed by the small intestine. It is used as cholagogue, a choleretic ...

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★リンクテーブル★

リンク元	「ケノデオキシコール酸」
拡張検索	「taurochenodeoxycholate」

「ケノデオキシコール酸」

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英

chenodeoxycholic acid CDCA、chenodeoxycholate

商

ケノコール、コラーザ、レガレン、チノ

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胆汁酸、胆石溶解剤

「taurochenodeoxycholate」

　　[★]

タウロケノデオキシコール酸

関

taurochenodeoxycholic acid