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street name for lysergic acid diethylamide (同)back breaker, battery-acid, dose, dot, Elvis, loony toons, Lucy in the sky with diamonds, pane, superman, window pane, Zen
any of various water-soluble compounds having a sour taste and capable of turning litmus red and reacting with a base to form a salt
having the characteristics of an acid; "an acid reaction"

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酸性の / 酸味のある,すっぱい(sour) / (言葉・態度などが)厳しい,しんらつな / 酸 / すっぱいもの / 《俗》=LSD

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出典(authority):フリー百科事典『ウィキペディア（Wikipedia）』「2014/04/01 17:50:43」(JST)

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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) ^[1]

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[edit]

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 ^[1] that can contain anions in its binding pocket in order of affinity: H₂PO₄^- (dihydrogen phosphate) > Cl^- > Br^- > I^- reflecting their basicities (tetrabutylammonium counter ion).^[2]

References[edit]

^ Carey MC (December 1975). "Editorial: Cheno and urso: what the goose and the bear have in common". N. Engl. J. Med. 293 (24): 1255–7. doi:10.1056/NEJM197512112932412. PMID 1186807.
^ Molecular Tweezer Based on Chenodeoxycholic Acid:Synthesis, Anion Binding Properties Ki Soo Kim, Hong-Seok Kim Bulletin of the Korean Society 1411-1413 2004 Article

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1. 胆石の溶解療法 dissolution therapy for the treatment of gallstones
2. 脳腱黄色腫症 cerebrotendinous xanthomatosis
3. 妊娠性肝内胆汁うっ滞 intrahepatic cholestasis of pregnancy
4. 原発性胆汁性肝硬変の治療の概要 overview of the treatment of primary biliary cirrhosis
5. 肝線維症の新しい治療法 emerging therapies for hepatic fibrosis

English Journal

The wide spectrum of cerebrotendinous xanthomatosis: Case report of a rare but treatable disease.

Rosafio F1, Cavallieri F1, Guaraldi P2, Taroni F3, Nichelli PF1, Mandrioli J4.
Clinical neurology and neurosurgery.Clin Neurol Neurosurg.2016 Apr;143:1-3. doi: 10.1016/j.clineuro.2016.01.032. Epub 2016 Feb 4.
Cerebrotendinous xanthomatosis (CTX) is an autosomal-recessive disorder of lipid storage caused by mutations in the CYP27A1 gene, coding for a sterol 27-hydroxylase, leading to increased deposition of cholesterol in multiple tissues. CTX is characterized by the association of early non-neurological
PMID 26874936

A study of the impact of co-adsorbents on DSSC electron transfer processes: anti-π-stacking vs. shield effect.

Cisneros R1, Beley M2, Lapicque F3.
Physical chemistry chemical physics : PCCP.Phys Chem Chem Phys.2016 Mar 21. [Epub ahead of print]
In this study we report a detailed exploration of the use of two different co-adsorbents - namely bis-methoxyphenylphosphinic acid (BMPP) and chenodeoxycholic acid (CDCA) - known to increase photoconversion efficiency (PCE) of DSSCs sensitized with N719. We have explored the variation of their abili
PMID 26996609

Naphtho[2,3-c][1,2,5]thiadiazole and 2H-Naphtho[2,3-d][1,2,3]triazole-Containing D-A-π-A Conjugated Organic Dyes for Dye-Sensitized Solar Cells.

Yen YS1, Ni JS1, Hung WI1, Hsu CY1, Chou HH1, Lin JT1.
ACS applied materials & interfaces.ACS Appl Mater Interfaces.2016 Mar 9;8(9):6117-26. doi: 10.1021/acsami.6b00806. Epub 2016 Feb 25.
Dipolar dyes comprising an arylamine as the electron donor, a cyanoacrylic acid as electron acceptor, and an electron deficient naphtho[2,3-c][1,2,5]thiadiazole (NTD) or naphtho[2,3-d][1,2,3]triazole (NTz) entity in the conjugated spacer, were developed and used as the sensitizers in dye-sensitized
PMID 26891701

Japanese Journal

Clinical and Radiological Findings of a Cerebrotendinous Xanthomatosis Patient with a Novel p.A335V Mutation in the CYP27A1 Gene

Yoshinaga Tsuneaki,Sekijima Yoshiki,Koyama Shingo,Maruyama Keiko,Yoshida Toshikazu,Kato Takeo,Ikeda Shu-ichi
Internal Medicine 53(23), 2725-2729, 2014
… Making an early diagnosis of CTX is crucial, as the administration of chenodeoxycholic acid reverses metabolic derangement. …
NAID 130004713275

多発性巨大軟部腫瘤を認めた脳腱黄色腫症の1例

梅本勇基,上野弘貴,原直之 [他],中村毅,大槻俊輔,柳瀬哲至,山脇健盛,松本昌泰
日本内科学会雑誌 101(5), 1397-1400, 2012-05-10
… cerebrotendinous xanthomatosis：CTX）は知能低下，小脳失調，白内障，腱黄色腫を呈する遺伝性代謝疾患である．本例は53歳，女性．四肢に巨大な軟部腫瘤を認め生検により黄色腫と判明．小脳歯状核病変や血清コレスタノール高値からCTXと診断しケノデオキシコール酸（chenodeoxycholic acid：CDCA）とスタチンの投与を開始した．下腿の巨大黄色腫はMRIでT2WI高信号域を認め出血や粘液変性の存在が示唆された． …
NAID 10031130551

Aberrant activation of ubiquitin D at G2 phase and apoptosis by carcinogens that evoke cell proliferation after 28-day administration in rats

Taniai Eriko,Yafune Atsunori,Hayashi Hitomi,Itahashi Megu,Hara-Kudo Yukiko,Suzuki Kazuhiko,Mitsumori Kunitoshi,Shibutani Makoto
The Journal of Toxicological Sciences 37(6), 1093-1111, 2012
… All renal carcinogens tested (ferric nitrilotriacetic acid, ochratoxin A (OTA), monuron, tris(2-chloroethyl) phosphate, and potassium bromate) increased tubular cells immunoreactive for minichromosome maintenance 3 (Mcm3) or ubiquitin D (Ubd) or those showing apoptosis, compared with untreated controls or non-carcinogenic renal toxicants. …
NAID 130004447011

Related Pictures

★リンクテーブル★

リンク元	「ケノデオキシコール酸」「chenodeoxycholate」「CDCA」
拡張検索	「taurochenodeoxycholic acid」「glycochenodeoxycholic acid」

「ケノデオキシコール酸」

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
ChemSpider	9728
UNII	0GEI24LG0J
DrugBank	DB06777
KEGG	C02528
ChEBI	CHEBI:16755
ChEMBL	CHEMBL240597
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 ; Key: RUDATBOHQWOJDD-BSWAIDMHSA-N 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
	Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
	(verify) (what is: /?)
	Infobox references

　　[★]

英: chenodeoxycholic acid CDCA、chenodeoxycholate
商: ケノコール、コラーザ、レガレン、チノ
関: 胆汁酸、胆石溶解剤

「chenodeoxycholate」

　　[★]

ケノデオキシコール酸

関: chenodeoxycholic acid

「CDCA」

　　[★] ケノデオキシコール酸 chenodeoxycholic acid

「taurochenodeoxycholic acid」

　　[★]

タウロケノデオキシコール酸

関: taurochenodeoxycholate

「glycochenodeoxycholic acid」

　　[★]

グリコケノデオキシコール酸

[1] Carey MC (December 1975). "Editorial: Cheno and urso: what the goose and the bear have in common". N. Engl. J. Med. 293 (24): 1255–7. doi:10.1056/NEJM197512112932412. PMID 1186807.

[2] Molecular Tweezer Based on Chenodeoxycholic Acid:Synthesis, Anion Binding Properties Ki Soo Kim, Hong-Seok Kim Bulletin of the Korean Society 1411-1413 2004 Article

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案内

chenodeoxycholic acid