WordNet
- 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"
PrepTutorEJDIC
- 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
Wikipedia preview
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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This article needs additional citations for verification. Please help improve this article by adding citations to reliable sources. Unsourced material may be challenged and removed. (January 2009) |
Chenodeoxycholic acid |
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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
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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 |
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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
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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
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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) |
N (verify) (what is: Y/N?) |
Infobox references |
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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
Bile and liver therapy (A05)
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Bile therapy |
- bile acid (Chenodeoxycholic acid
- Cholic acid
- Ursodeoxycholic acid)
- Obeticholic acid
- Nicotinyl methylamide
- Piprozolin
- Hymecromone
- Cyclobutyrol
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Liver therapy |
- Arginine glutamate
- Silymarin
- Citiolone
- Epomediol
- Ornithine oxoglutarate
- Tidiacic arginine
- Glycyrrhizin
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anat (t, g, p)/phys/devp/enzy
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noco/cong/tumr, sysi/epon
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proc, drug (A2A/2B/3/4/5/6/7/14/16), blte
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UpToDate Contents
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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
- 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 Links
- Sigma-Aldrich offers Sigma-C9377, Chenodeoxycholic acid for your research needs. Find product specific information including CAS, MSDS, protocols and references. ... Application Do you have application information on this ...
- chenodeoxycholic acid | C24H40O4 | CID 10133 - structure, chemical names, physical and chemical properties, classification, patents, literature, biological activities, safety/hazards/toxicity information, supplier lists, and more. ... A ...
Related Pictures
★リンクテーブル★
[★]
- 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
[★]
ケノデオキシコール酸
- 関
- chenodeoxycholic acid
[★]
ケノデオキシコール酸 chenodeoxycholic acid
[★]
タウロケノデオキシコール酸
- 関
- taurochenodeoxycholate
[★]
グリコケノデオキシコール酸