Ursodiol
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Ursodiol
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| Systematic (IUPAC) name | |
| 3α,7β-dihydroxy-5β-cholan-24-oic acid (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 |
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| Identifiers | |
| CAS number | |
| ATC code | A05 |
| PubChem | ? |
| Chemical data | |
| Formula | C24H40O4 |
| Mol. mass | 392.56 g/mol |
| SMILES | & |
| Synonyms | ursodeoxycholic acid, Actigall, Ursosan, Urso, Urso Forte |
| Physical data | |
| Melt. point | 203 °C (397 °F) |
| Pharmacokinetic data | |
| Bioavailability | ? |
| Metabolism | ? |
| Half life | ? |
| Excretion | ? |
| Therapeutic considerations | |
| Pregnancy cat. |
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| Legal status | |
| Routes | ? |
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This article needs additional citations for verification. Please help improve this article by adding reliable references. Unsourced material may be challenged and removed. (January 2009) |
Ursodiol, also known as ursodeoxycholic acid and the abbreviation UDCA, is one of the secondary bile acids, which are metabolic byproducts of intestinal bacteria.
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[edit] Endogenous use
Primary bile acids are produced by the liver and stored in the gall bladder. When secreted into the colon, 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 (eg. deoxycholic acid), others such as ursodeoxycholic acid are 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. Increased quantities of systemic (throughout the body, not just in the digestive system) ursodeoxycholic acid can be toxic.[citation needed]
Bile acids are important signaling molecules that help regulate the regrowth of liver tissue, recent research has shown. Ursodeoxycholic acid has been used as an experimental tool in liver regrowth studies. There is a possible link between the immune-repression and liver-regeneration properties of this substance, but clinical studies have yet to confirm these suspicions.[citation needed]
[edit] As a pharmaceutical
Ursodeoxycholic acid goes by the trade names Actigall, Ursosan, Urso, and Urso Forte. In Italy, it is marketed under the name Deursil.
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 used to treat primary biliary cirrhosis.[3][4] In children, its use is not licensed, as its safety and effectiveness are not established. [5][6][7]
Ursodeoxycholic acid reduces elevated liver enzyme levels by facilitating bile flow through the liver and protecting liver cells.
[edit] Production
The drug is generally not derived from animals. However, it is believed more than 12,000 bile bears are kept on farms in China, Vietnam and South Korea for the purpose of harvesting ursodeoxycholic acid.[8] Ursodeoxycholic acid is found in large quantities in bear bile.
[edit] References
- ^ Akare S, Jean-Louis S, Chen W, Wood DJ, Powell AA, Martinez JD (2006). "Ursodeoxycholic acid modulates histone acetylation and induces differentiation and senescence". Int. J. Cancer 119 (12): 2958–69. doi:. PMID 17019713.
- ^ Amaral JD, Viana RJ, Ramalho RM, Steer CJ, Rodrigues CM (May 2009). "Bile acids: regulation of apoptosis by ursodeoxycholic ccid". J. Lipid Res.. doi:. PMID 19417220. http://www.jlr.org/cgi/pmidlookup?view=long&pmid=19417220.
- ^ Smith T, Befeler AS (2007). "High-dose ursodeoxycholic acid for the treatment of primary sclerosing cholangitis". Current gastroenterology reports 9 (1): 54–9. doi:. PMID 17335678.
- ^ Jackson H, Solaymani-Dodaran M, Card TR, Aithal GP, Logan R, West J (2007). "Influence of ursodeoxycholic acid on the mortality and malignancy associated with primary biliary cirrhosis: A population-based cohort study". Hepatology 46 (4): 1131–1137. doi:. PMID 17685473.
- ^ Kotb MA. Review of historical cohort: ursodeoxycholic acid in extrahepatic biliary atresia. J Ped Surg 43:(7), 1321–1327,2008 [1]
- ^ British National Formulary for Children 2008, BMJ Publishing Group Ltd p91,2008
- ^ Urso package insert. Birmingham, AL: Axcan Pharma U.S.; 2000 Jan.http://www.axcan.com/pdf/urso_patient_brochure.pdf
- ^ Richard Black (11 June 2007). "BBC Test kit targets cruel bear trade". BBC News. http://news.bbc.co.uk/2/hi/science/nature/6742671.stm.
[edit] External links
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