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"

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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）』「2013/10/02 00:35:23」(JST)

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Ursodiol, also known as ursodeoxycholic acid and the abbreviation UDCA, is one of the secondary bile acids, which are metabolic byproducts of intestinal bacteria.

Endogenous effects[edit]

Primary bile acids are produced by the liver and stored in the gall bladder. When secreted into the intestine, primary bile acids can be metabolized into secondary bile acids by intestinal bacteria. Primary and secondary bile acids help the body digest fats. Ursodeoxycholic acid helps regulate cholesterol by reducing the rate at which the intestine absorbs cholesterol molecules while breaking up micelles containing cholesterol. Because of this property, ursodeoxycholic acid is used to treat (cholesterol) gallstones non-surgically.

While some bile acids are known to be colon tumor promoters (e.g. deoxycholic acid), others such as ursodeoxycholic acid are thought to be chemopreventive, perhaps by inducing cellular differentiation and/or cellular senescence in colon epithelial cells.^[1]

It is believed to inhibit apoptosis.^[2]

Ursodeoxycholic acid has also been shown experimentally to suppress immune response such as immune cell phagocytosis. Prolonged exposure and/or increased quantities of systemic (throughout the body, not just in the digestive system) ursodeoxycholic acid can be toxic.^[3]

As a pharmaceutical[edit]

Ursodeoxycholic acid is marketed under the trade names Actigall, Ursosan, Ursofalk, BILIVER, Egyurso, Urso, Urso Forte, Deursil and Coric,Udiliv, Ursocol

Ursodeoxycholic acid can be chemically synthesized and was brought to market by the Montreal-based Axcan Pharma in 1998,^{[citation needed]} which continues to market the drug.

The drug reduces cholesterol absorption and is used to dissolve (cholesterol) gallstones in patients who want an alternative to surgery. The drug is very expensive, however, and if the patient stops taking it, the gallstones tend to recur if the condition that gave rise to their formation does not change. For these reasons, it has not supplanted surgical treatment by cholecystectomy.

It is the only FDA approved drug to treat primary biliary cirrhosis.^[4]

Ursodiol may be used for biliary stasis in pregnant women to relieve the symptoms of itching and decrease bile absorption.^[5]

A Cochrane review to evaluate if ursodeoxycholic acid has any beneficial effect in primary biliary cirrhosis patients included 16 randomized clinical trials with a total of 1447 patients. The primary outcome measures were mortality and mortality or liver transplantation. Although treatment with ursodeoxycholic acid showed a reduction in liver biochemistry, jaundice, and ascites, it did not decrease mortality or liver transplantation.^[6]

In absence of biochemical response to 13-15mg/kg/day ursodeoxycholic acid, its use is associated with an incidence of 20% hepatocellular carcinoma in patients with primary biliary cirrhosis in 15 years.^[7]

In children, its use is not licensed, as its safety and effectiveness are not established.^[8]^[9]^[10]

In double the recommended daily dose ursodeoxycholic acid reduces elevated liver enzyme levels in patients with primary sclerosing cholangitis, but its use was associated with an increased risk of serious adverse events (the development of cirrhosis, varices, death or liver transplantation) in patients who received ursodeoxycholic acid compared with those who received placebo). After adjustment for baseline stratification characteristics, the risk was 2.1 times greater for death,transplantation, or minimal listing criteria in patients on ursodeoxycholic acid than for those on placebo (P = 0.038). Serious adverse events, were more common in the ursodeoxycholic acid group than the placebo group (63% versus 37% [P < 0.01])).^[11]

Research by the Imperial College London has produced promising results in the treatment of arrhythmia, both in patients who have suffered a heart attack and in foetuses, by using ursodiol to change the electrical properties of myofibroblast cells. Myofibroblasts disrupt the transmission of electrical signals controlling heart rhythm. ^[12]

Production[edit]

The drug is generally not derived from animals.^{[citation needed]} However, it is believed up to 10,000^[13] bile bears are kept on farms in China, Vietnam and South Korea for the purpose of harvesting ursodeoxycholic acid.^[13] Ursodeoxycholic acid is found in large quantities in bear bile.^[14]

References[edit]

^ Akare S, Jean-Louis S, Chen W, Wood DJ, Powell AA, Martinez JD (December 2006). "Ursodeoxycholic acid modulates histone acetylation and induces differentiation and senescence". International Journal of Cancer. Journal International Du Cancer 119 (12): 2958–69. doi:10.1002/ijc.22231. PMID 17019713.
^ Amaral JD, Viana RJ, Ramalho RM, Steer CJ, Rodrigues CM (September 2009). "Bile acids: regulation of apoptosis by ursodeoxycholic acid". Journal of Lipid Research 50 (9): 1721–34. doi:10.1194/jlr.R900011-JLR200. PMC 2724780. PMID 19417220.
^ Material Safety Data Sheet on Ursodiol MSDS. https://fscimage.fishersci.com/msds/70916.htm
^ Jackson H, Solaymani-Dodaran M, Card TR, Aithal GP, Logan R, West J (October 2007). "Influence of ursodeoxycholic acid on the mortality and malignancy associated with primary biliary cirrhosis: a population-based cohort study". Hepatology 46 (4): 1131–7. doi:10.1002/hep.21795. PMID 17685473.
^ Mayo Clinic Staff. "Cholestasis of pregnancy: Treatment and Drugs". Mayo Clinic.
^ Gong Y, Huang ZB, Christensen E, Gluud C (2008). "Ursodeoxycholic acid for primary biliary cirrhosis". In Gong, Yan. Cochrane Database of Systematic Reviews (3): CD000551. doi:10.1002/14651858.CD000551.pub2. PMID 18677775.
^ Kuiper EM, Hansen BE, Adang RP, van Nieuwkerk CM, Timmer R, Drenth JP, Spoelstra P, Brouwer HT, Kuyvenhoven JP, van Buuren HR (December 2010). "Relatively high risk for hepatocellular carcinoma in patients with primary biliary cirrhosis not responding to ursodeoxycholic acid". European Journal of Gastroenterology & Hepatology 22 (12): 1495–502. doi:10.1097/MEG.0b013e32834059e7. PMID 21389798.
^ Kotb MA (July 2008). "Review of historical cohort: ursodeoxycholic acid in extrahepatic biliary atresia". Journal of Pediatric Surgery 43 (7): 1321–7. doi:10.1016/j.jpedsurg.2007.11.043. PMID 18639689.
^ Paediatric Formulary Committee (2008). British National Formulary for Children 2008. London: Pharmaceutical Press. p. 91. ISBN 0-85369-780-9.
^ Urso package insert. Birmingham, AL: Axcan Pharma U.S.; 2000 Jan.http://www.axcan.com/pdf/urso_patient_brochure.pdf
^ Lindor KD, Kowdley KV, Luketic VA et al. (September 2009). "High-dose ursodeoxycholic acid for the treatment of primary sclerosing cholangitis". Hepatology 50 (3): 808–14. doi:10.1002/hep.23082. PMC 2758780. PMID 19585548.
^ BBC News
^ ^a ^b Michael Bristow (29 February 2012). "China bear bile farms stir anger among campaigners". BBC News.
^ Hagey LR, Crombie DL, Espinosa E, Carey MC, Igimi H, Hofmann AF. Ursodeoxycholic acid in the Ursidae: biliary bile acids of bears, pandas, and related carnivores. J. Lipid Res. 1993 34:(11) 1911-1917. http://www.jlr.org/content/34/11/1911

External links[edit]

Ursodeoxycholic acid information at MedlinePlus

UpToDate Contents

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1. 原発性胆汁性肝硬変治療用ウルソデオキシコール酸の臨床試験 trials of ursodeoxycholic acid for the treatment of primary biliary cirrhosis
2. 原発性胆汁性肝硬変の治療の概要 overview of the treatment of primary biliary cirrhosis
3. 妊娠性肝内胆汁うっ滞 intrahepatic cholestasis of pregnancy
4. 造血細胞移植後の肝類洞閉塞症候群の治療および予防 treatment and prevention of hepatic sinusoidal obstruction syndrome following hematopoietic cell transplantation
5. 胆汁うっ滞関連そう痒症 pruritus associated with cholestasis

English Journal

Incretin secretion stimulated by ursodeoxycholic acid in healthy subjects.

Murakami M, Une N, Nishizawa M, Suzuki S, Ito H, Horiuchi T.SourceDivision on Endocrinology and Metabolism, Tokyo Metropolitan Health Medical Treatment Corporation Toshima Hospital, Itabashi, Japan.
SpringerPlus.Springerplus.2013 Dec;2(1):20. Epub 2013 Jan 22.
Bile acids play an important role in post-prandial glucose metabolism by stimulating release of glucagon-like peptide-1 (GLP-1) via the G-protein-coupled receptor TGR5, which is expressed in intestinal L cells. Thus, bile acid sequestrants are expected to stimulate secretion of endogenous GLP-1 thro
PMID 23450079

The effect of ursodeoxycholic acid on oxidative stress level and DNase activity in rat liver after bile duct ligation.

Sokolovic D, Nikolic J, Kocic G, Jevtovic-Stoimenov T, Veljkovic A, Stojanovic M, Stanojkovic Z, Sokolovic DM, Jelic M.SourceDepartment of Biochemistry, the University of Nis Medical School, Nis, Serbia. soko@medfak.ni.ac.rs
Drug and chemical toxicology.Drug Chem Toxicol.2013 Apr;36(2):141-8. doi: 10.3109/01480545.2012.658919. Epub 2012 Mar 2.
Accumulation of hydrophobic bile acids (BAs) during cholestasis plays an important role in apoptosis initiation as well as oxidative stress increase in liver cells. Ursodeoxycholic acid (UDCA) acts as a protector in BA-induced cell injury.The aim of the study was to evaluate the effect of UDCA on ox
PMID 22385135

Japanese Journal

Evaluation of a new histologic staging and grading system for primary biliary cirrhosis in comparison with classical systems

Kakuda Yuko,Harada Kenichi,Sawada-Kitamura Seiko,Ikeda Hiroko,Sato Yasunori,Sasaki Motoko,Okafuji Hirofumi,Mizukoshi Eishiro,Terasaki Shuichi,Ohta Hajime,Kasashima Satomi,Kawashima Atsuhiro,Kaizaki Yasuharu,Kaneko Shuichi,Nakanuma Yasuni
Human Pathology 44(6), 1107-1117, 2013-06-00
… A total of 152 liver biopsy specimens and clinical data (including outcomes in patients with PBC before treatment with ursodeoxycholic acid) were analyzed with respect to the new system. …
NAID 120005253269

症例報告肝組織像の経過を追えた中毒性表皮壊死症に合併した胆管消失症候群の1例

隅田幸佑,道免和文,相島慎一 [他],岩坂翔,久本仁美,原田由紀子,三宅典子,下野信行,下田慎治
肝臓 54(1), 67-73, 2013
… We observed on outpatient with administration of ursodeoxycholic acid, and the hepatic dysfunction and jaundice improved nine monthes after the first admission. …
NAID 130003368652

Related Pictures

★リンクテーブル★

リンク元	「ウルソデオキシコール酸」「ursodiol」「UDCA」
拡張検索	「tauroursodeoxycholic acid」

「ウルソデオキシコール酸」

Ursodeoxycholic acid
Systematic (IUPAC) name
	3α,7β-dihydroxy-5β-cholan-24-oic acid; OR; (R)-4-((3R,5S,7S,8R,9S,10S,13R,14S,17R)-3,7-dihydroxy-; 10,13-dimethylhexadecahydro-; 1H-cyclopenta[a]phenanthren-17-yl)pentanoic acid
Clinical data
Trade names	Actigall
AHFS/Drugs.com	monograph
MedlinePlus	a699047
Licence data	US Daily Med:link
Pregnancy cat.	B (US)
Legal status	℞-only (US)
Routes	oral
Identifiers
CAS number	128-13-2
ATC code	A05AA02
PubChem	CID 31401
DrugBank	DB01586
ChemSpider	29131
UNII	724L30Y2QR
KEGG	D00734
ChEBI	CHEBI:9907
ChEMBL	CHEMBL1551
Synonyms	ursodeoxycholic acid, Actigall, Ursosan, Urso, Urso Forte
Chemical data
Formula	C24H40O4
Mol. mass	392.56 g/mol
	SMILES O=C(O)CC[C@H]([C@H]1CC[C@@H]2[C@]1(C)CC[C@H]4[C@H]2[C@@H](O)C[C@@H]3C[C@H](O)CC[C@@]34C)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-UZVSRGJWSA-N ;
Physical data
Melt. point	203 °C (397 °F)
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　　[★]

英: ursodeoxycholic acid, UDCA
ラ: acidum ursodesoxycholicum
同: ウルソデスオキシコール酸 ursodesoxycholic acid
商: シキコール、TM配合、ウビロン、ウルサミック、ウルソ、ウルデストン、ウルデナシン、カルディオダイン、ゴクミシン、プレコート、レプター
関: ウルソジオール

特徴

利胆薬。肝機能の改善と胆石溶解を期待して使用する。

構造

C24H40O4

作用機序

ウルソ錠50mg／ウルソ錠100mg

ウルソデオキシコール酸は胆汁分泌を促進する作用（利胆作用）により胆汁うっ滞を改善する．また，投与されたウルソデオキシコール酸は肝臓において，細胞障害性の強い疎水性胆汁酸と置き換わり，その相対比率を上昇させ，疎水性胆汁酸の肝細胞障害作用を軽減する（置換効果）．さらに，ウルソデオキシコール酸はサイトカイン・ケモカイン産生抑制作用や肝臓への炎症細胞浸潤抑制作用により肝機能を改善する．そのほか，上記の胆石溶解作用，消化吸収改善作用が知られている．

薬理作用

動態

適応