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Namespace Prefixes

PrefixIRI
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Statements

Subject Item
n2:DB01586
rdf:type
n3:Drug
n3:description
Ursodeoxycholic acid is an epimer of chenodeoxycholic acid (DB06777). It is a mammalian bile acid found first in the bear and is apparently either a precursor or a product of chenodeoxycholate. Its administration changes the composition of bile and may dissolve gallstones. It is used as a cholagogue and choleretic. [PubChem]
n3:dosage
n10:271B5876-363D-11E5-9242-09173F13E4C5 n10:271B5877-363D-11E5-9242-09173F13E4C5 n10:271B5878-363D-11E5-9242-09173F13E4C5 n10:271B5879-363D-11E5-9242-09173F13E4C5 n10:271B587A-363D-11E5-9242-09173F13E4C5
n3:generalReferences
# Akare S, Jean-Louis S, Chen W, Wood DJ, Powell AA, Martinez JD: Ursodeoxycholic acid modulates histone acetylation and induces differentiation and senescence. Int J Cancer. 2006 Dec 15;119(12):2958-69. "Pubmed":http://www.ncbi.nlm.nih.gov/pubmed/17019713 # Smith T, Befeler AS: High-dose ursodeoxycholic acid for the treatment of primary sclerosing cholangitis. Curr Gastroenterol Rep. 2007 Mar;9(1):54-9. "Pubmed":http://www.ncbi.nlm.nih.gov/pubmed/17335678 # Jackson H, Solaymani-Dodaran M, Card TR, Aithal GP, Logan R, West J: Influence of ursodeoxycholic acid on the mortality and malignancy associated with primary biliary cirrhosis: A population-based cohort study. Hepatology. 2007 Aug 8;46(4):1131-1137. "Pubmed":http://www.ncbi.nlm.nih.gov/pubmed/17685473
n3:group
investigational approved
n3:indication
The drug reduces cholesterol absorption and is used to dissolve (cholesterol) gallstones in patients who want an alternative to surgery.
owl:sameAs
n7:DB01586 n18:DB01586
dcterms:title
Ursodeoxycholic acid
adms:identifier
n12:PA451837 n13:Ursodiol n20:9907 n21:29131 n22:31401 n23:46508795 n24:0527-1326-01 n25:IU5 n26:C07880 n27:D00734 n28:DB01586
n3:mechanismOfAction
Ursodeoxycholic acid reduces elevated liver enzyme levels by facilitating bile flow through the liver and protecting liver cells. The main mechanism if anticholelithic. Although the exact process of ursodiol's anticholelithic action is not completely understood, it is thought that the drug is concentrated in bile and decreases biliary cholesterol by suppressing hepatic synthesis and secretion of cholesterol and by inhibiting its intestinal absorption. The reduced cholesterol saturation permits the gradual solubilization of cholesterol from gallstones, resulting in their eventual dissolution.
n3:packager
n8:271B5859-363D-11E5-9242-09173F13E4C5 n8:271B585A-363D-11E5-9242-09173F13E4C5 n8:271B5857-363D-11E5-9242-09173F13E4C5 n8:271B5858-363D-11E5-9242-09173F13E4C5 n8:271B585D-363D-11E5-9242-09173F13E4C5 n8:271B585E-363D-11E5-9242-09173F13E4C5 n8:271B585B-363D-11E5-9242-09173F13E4C5 n8:271B585C-363D-11E5-9242-09173F13E4C5 n8:271B5855-363D-11E5-9242-09173F13E4C5 n8:271B5856-363D-11E5-9242-09173F13E4C5 n8:271B5853-363D-11E5-9242-09173F13E4C5 n8:271B5854-363D-11E5-9242-09173F13E4C5 n8:271B5869-363D-11E5-9242-09173F13E4C5 n8:271B586A-363D-11E5-9242-09173F13E4C5 n8:271B5867-363D-11E5-9242-09173F13E4C5 n8:271B5868-363D-11E5-9242-09173F13E4C5 n8:271B586B-363D-11E5-9242-09173F13E4C5 n8:271B5861-363D-11E5-9242-09173F13E4C5 n8:271B5862-363D-11E5-9242-09173F13E4C5 n8:271B585F-363D-11E5-9242-09173F13E4C5 n8:271B5860-363D-11E5-9242-09173F13E4C5 n8:271B5865-363D-11E5-9242-09173F13E4C5 n8:271B5866-363D-11E5-9242-09173F13E4C5 n8:271B5863-363D-11E5-9242-09173F13E4C5 n8:271B5864-363D-11E5-9242-09173F13E4C5
n3:routeOfElimination
Only small quantities of ursodiol appear in the systemic circulation and very small amounts are excreted into urine. Eighty percent of lithocholic acid formed in the small bowel is excreted in the feces, but the 20% that is absorbed is sulfated at the 3-hydroxyl group in the liver to relatively insoluble lithocholyl conjugates which are excreted into bile and lost in feces.
n3:synonym
Acido ursodeoxicolico Acidum ursodeoxycholicum Acido ursodeossicolico UDCA 3alpha,7beta-Dihydroxy-5beta-cholan-24-oic acid Ursodeoxycholate Ursodiol Acide ursodesoxycholique Ursodeoxycholic acid (3α,5β,7β)-3,7-dihydroxycholan-24-oic acid (3alpha,5beta,7beta)-3,7-dihydroxycholan-24-oic acid Actigall
n3:toxicity
Neither accidental nor intentional overdosing with ursodeoxycholic acid has been reported. Doses of ursodeoxycholic acid in the range of 16-20 mg/kg/day have been tolerated for 6-37 months without symptoms by 7 patients. The LD50 for ursodeoxycholic acid in rats is over 5000 mg/kg given over 7-10 days and over 7500 mg/kg for mice. The most likely manifestation of severe overdose with ursodeoxycholic acid would probably be diarrhea, which should be treated symptomatically.
n14:hasAHFSCode
n15:56-14-00
n3:synthesisReference
Antonio Bonaldi, Egidio Molinari, "Process for preparing high purity ursodeoxycholic acid." U.S. Patent US4379093, issued July, 1980.
n16:hasConcept
n17:M0022413
n3:IUPAC-Name
n4:271B587F-363D-11E5-9242-09173F13E4C5
n3:InChI
n4:271B5885-363D-11E5-9242-09173F13E4C5
n3:Molecular-Formula
n4:271B5884-363D-11E5-9242-09173F13E4C5
n3:Molecular-Weight
n4:271B5881-363D-11E5-9242-09173F13E4C5
n3:Monoisotopic-Weight
n4:271B5882-363D-11E5-9242-09173F13E4C5
n3:SMILES
n4:271B5883-363D-11E5-9242-09173F13E4C5
n3:Water-Solubility
n4:271B5895-363D-11E5-9242-09173F13E4C5 n4:271B587D-363D-11E5-9242-09173F13E4C5
n3:logP
n4:271B5897-363D-11E5-9242-09173F13E4C5 n4:271B587E-363D-11E5-9242-09173F13E4C5 n4:271B587B-363D-11E5-9242-09173F13E4C5
n3:logS
n4:271B587C-363D-11E5-9242-09173F13E4C5
n14:hasATCCode
n19:A05AA02
n3:H-Bond-Acceptor-Count
n4:271B588B-363D-11E5-9242-09173F13E4C5
n3:H-Bond-Donor-Count
n4:271B588C-363D-11E5-9242-09173F13E4C5
n3:InChIKey
n4:271B5886-363D-11E5-9242-09173F13E4C5
n3:Polar-Surface-Area--PSA-
n4:271B5887-363D-11E5-9242-09173F13E4C5
n3:Polarizability
n4:271B5889-363D-11E5-9242-09173F13E4C5
n3:Refractivity
n4:271B5888-363D-11E5-9242-09173F13E4C5
n3:Rotatable-Bond-Count
n4:271B588A-363D-11E5-9242-09173F13E4C5
n3:affectedOrganism
Humans and other mammals
n3:casRegistryNumber
128-13-2
n3:category
n3:containedIn
n5:271B5874-363D-11E5-9242-09173F13E4C5 n5:271B5875-363D-11E5-9242-09173F13E4C5 n5:271B5872-363D-11E5-9242-09173F13E4C5 n5:271B5873-363D-11E5-9242-09173F13E4C5 n5:271B586C-363D-11E5-9242-09173F13E4C5 n5:271B586D-363D-11E5-9242-09173F13E4C5 n5:271B5870-363D-11E5-9242-09173F13E4C5 n5:271B5871-363D-11E5-9242-09173F13E4C5 n5:271B586E-363D-11E5-9242-09173F13E4C5 n5:271B586F-363D-11E5-9242-09173F13E4C5
n3:Bioavailability
n4:271B5891-363D-11E5-9242-09173F13E4C5
n3:Ghose-Filter
n4:271B5893-363D-11E5-9242-09173F13E4C5
n3:MDDR-Like-Rule
n4:271B5894-363D-11E5-9242-09173F13E4C5
n3:Melting-Point
n4:271B5896-363D-11E5-9242-09173F13E4C5
n3:Number-of-Rings
n4:271B5890-363D-11E5-9242-09173F13E4C5
n3:Physiological-Charge
n4:271B588F-363D-11E5-9242-09173F13E4C5
n3:Rule-of-Five
n4:271B5892-363D-11E5-9242-09173F13E4C5
n3:Traditional-IUPAC-Name
n4:271B5880-363D-11E5-9242-09173F13E4C5
n3:pKa--strongest-acidic-
n4:271B588D-363D-11E5-9242-09173F13E4C5
n3:pKa--strongest-basic-
n4:271B588E-363D-11E5-9242-09173F13E4C5