Identification
- Summary
Ursodeoxycholic acid is a bile acid used for the treatment of primary biliary cirrhosis (PBC).
- Brand Names
- Reltone, Urso, Urso Forte
- Generic Name
- Ursodeoxycholic acid
- DrugBank Accession Number
- DB01586
- Background
Ursodeoxycholic acid (UDCA), also known as ursodiol, is a naturally-occurring bile acid that constitutes a minor fraction of the human bile acid pool.2,3 UDCA has been used to treat liver disease for decades: its first use in traditional medicine dates back more than a hundred years.1,6 UDCA was first characterized in the bile of the Chinese black bear and is formed by 7b-epimerization of chenodeoxycholic acid, which is a primary bile acid.2 Due to its hydrophilicity, UDCA is less toxic than cholic acid or chenodeoxycholic acid.2
UDCA was first approved by the FDA in 1987 for dissolution of gallstones and for primary biliary cirrhosis in 1996.2 UDCA works by replacing the hydrophobic or more toxic bile acids from the bile acid pool.2
- Type
- Small Molecule
- Groups
- Approved, Investigational
- Structure
Structure for Ursodeoxycholic acid (DB01586)
- Weight
- Average: 392.572
Monoisotopic: 392.292659768 - Chemical Formula
- C24H40O4
- Synonyms
- (3alpha,5beta,7beta)-3,7-dihydroxycholan-24-oic acid
- (3α,5β,7β)-3,7-dihydroxycholan-24-oic acid
- 3alpha,7beta-Dihydroxy-5beta-cholan-24-oic acid
- Acide ursodesoxycholique
- Acido ursodeossicolico
- Acido ursodeoxicolico
- Acidum ursodeoxycholicum
- UDCA
- Ursodeoxycholate
- Ursodeoxycholic acid
- Ursodiol
Pharmacology
- Indication
Ursodeoxycholic acid is indicated for the treatment of patients with primary biliary cholangitis.9
It is used for the short-term treatment of radiolucent, noncalcified gallbladder stones in patients selected for elective cholecystectomy. It is also used to prevent gallstone formation in obese patients experiencing rapid weight loss.11
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- Contraindications & Blackbox Warnings
Avoid life-threatening adverse drug eventsImprove clinical decision support with information on contraindications & blackbox warnings, population restrictions, harmful risks, & more.Avoid life-threatening adverse drug events & improve clinical decision support.- Pharmacodynamics
Ursodeoxycholic acid (UDCA) is a secondary bile acid with cytoprotectant, immunomodulating, and choleretic effects. It reduces the cholesterol fraction of biliary lipids.1
UDCA inhibits the absorption of cholesterol in the intestine and the secretion of cholesterol into bile, decreasing biliary cholesterol saturation.1 UDCA increases bile acid flow and promotes the secretion of bile acids.1,3,6
- Mechanism of action
Endogenous hydrophobic bile acids such as deoxycholic acid and chenodeoxycholic acid can exert hepatotoxic effects. Ursodeoxycholic acid is a hydrophilic bile acid that mediates its biological effects via several mechanisms. Ursodeoxycholic acid (UDCA) protects hepatocytes and cholangiocytes from bile acid-induced damage, such as reactive oxygen species (ROS)-induced inflammation and mitochondrial dysfunction.1 UDCA was shown to reserve hepatocyte cell structures and stimulate anti-apoptotic pathways.1,2,5,6 It was also shown to prevent the production of ROS by Kupffer cells and resident macrophages in the liver, thus attenuating oxidative stress in the liver.1
UDCA can also change the hydrophobicity index of the bile acid pool: following oral administration, UDCA forms a major fraction of the human bile acid pool and competitively displaces the hydrophobic or more toxic bile acids.2,1 It increases the absorption of hydrophilic bile acids.1 There are several proposed mechanisms of choleretic actions of UDCA: UDCA increases intracellular calcium levels, stimulating transport proteins and vesicular exocytosis in cholestatic hepatocytes.1 UDCA may also upregulate the expression of membrane transport proteins like the chloride-bicarbonate anion exchanger (AE2),1,5 which is involved in biliary secretion and is often observed to be defective in primary biliary cholangitis.4 In rats, UDCA reduced hepatic expression of major histocompatibility complex (MHC) class I antigens, suggesting immunomodulating effects.1 UDCA acts as a partial agonist at the bile acid receptor, also known as the farnesoid X receptor (FXR), and has negligible effects on cholesterol and lipid synthesis.2
Target Actions Organism AAldo-keto reductase family 1 member C2 inducerHumans UBile acid receptor partial agonistHumans - Absorption
Normally, endogenous ursodeoxycholic acid constitutes a minor fraction (about 5%) of the total human bile acid pool. Following oral administration, the majority of ursodiol is absorbed by passive diffusion, and its absorption is incomplete. Once absorbed, ursodiol undergoes hepatic extraction to about 50% in the absence of liver disease. As the severity of liver disease increases, the extent of extraction decreases. During chronic administration of ursodiol, it becomes a major biliary and plasma bile acid. At a chronic dose of 13 to 15 mg/kg/day, ursodiol constitutes 30-50% of biliary and plasma bile acids.9
- Volume of distribution
The volume of distribution of ursodeoxycholic acid (UDCA) has not been determined; however, it is expected to be small since UDCA is mostly distributed in the bile in the gallbladder and small intestines.3,9
- Protein binding
Unconjugated ursodeoxycholic acid is at least 70% bound to plasma proteins in health individuals. There is no information regarding the protein binding of conjugated ursodeoxycholic acid.9
- Metabolism
Upon administration, ursodeoxycholic acid (UDCA) enters the portal vein and into the liver, where it undergoes conjugation with glycine or taurine.3 UDCA is also decreased into bile. Glycine or taurine conjugates are absorbed in the small intestine via passive and active mechanisms. The conjugates can also be deconjugated in the ileum by intestinal enzymes, leading to the formation of free UDCA that can be reabsorbed and re-conjugated in the liver.9
Nonabsorbed UDCA passes into the colon, where it undergoes 7-dehydroxylation by intestinal bacteria to lithocholic acid.8 Some UDCA is epimerized to chenodeoxycholic acid via a 7-oxo intermediate. Chenodeoxycholic acid also undergoes 7-dehydroxylation to form lithocholic acid. These metabolites are poorly soluble and excreted in the feces. A small portion of lithocholic acid is reabsorbed, conjugated in the liver with glycine or taurine, and sulfated at the 3 position. The resulting sulfated lithocholic acid conjugates are excreted in bile and then lost in feces.9
Hover over products below to view reaction partners
- Route of elimination
Ursodeoxycholic acid is excreted primarily in the feces. Renal elimination is a minor elimination pathway. With treatment, urinary excretion increases but remains less than 1% except in severe cholestatic liver disease.7,9
- Half-life
- Clearance
Not Available
- Adverse Effects
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The oral LD50 in rats is >4600-5000 mg/kg.10,11 It is over 7500 mg/kg for mice.11
Ursodeoxycholic acid (UDCA) is associated with rare hepatotoxicities, such as jaundice, worsening pre-existing liver diseases, and hepatitis.2,3 There have been no reports of accidental or intentional overdosage with UDCA. A single oral dose of UDCA at 1.5 g/kg was lethal in hamsters. Single oral doses of UDCA at 10 g/kg in mice and dogs and 5 g/kg in rats were not lethal. Symptoms of acute toxicity were salivation and vomiting in dogs, while ataxia, dyspnea, ptosis, agonal convulsions and coma were observed in hamsters.9
- Pathways
- Not Available
- Pharmacogenomic Effects/ADRs
- Not Available
Interactions
- Drug Interactions
- This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
Drug Interaction Integrate drug-drug
interactions in your softwareAbciximab The risk or severity of adverse effects can be increased when Abciximab is combined with Ursodeoxycholic acid. Acenocoumarol The risk or severity of bleeding and bruising can be increased when Acenocoumarol is combined with Ursodeoxycholic acid. Acetylsalicylic acid The risk or severity of adverse effects can be increased when Acetylsalicylic acid is combined with Ursodeoxycholic acid. Alteplase The risk or severity of bleeding and bruising can be increased when Alteplase is combined with Ursodeoxycholic acid. Aluminium phosphate Aluminium phosphate can cause a decrease in the absorption of Ursodeoxycholic acid resulting in a reduced serum concentration and potentially a decrease in efficacy. Aluminum chloride Aluminum chloride can cause a decrease in the absorption of Ursodeoxycholic acid resulting in a reduced serum concentration and potentially a decrease in efficacy. Aluminum chlorohydrate Aluminum chlorohydrate can cause a decrease in the absorption of Ursodeoxycholic acid resulting in a reduced serum concentration and potentially a decrease in efficacy. Aluminum hydroxide Aluminum hydroxide can cause a decrease in the absorption of Ursodeoxycholic acid resulting in a reduced serum concentration and potentially a decrease in efficacy. Aluminum oxide Aluminum oxide can cause a decrease in the absorption of Ursodeoxycholic acid resulting in a reduced serum concentration and potentially a decrease in efficacy. Aluminum sulfate Aluminum sulfate can cause a decrease in the absorption of Ursodeoxycholic acid resulting in a reduced serum concentration and potentially a decrease in efficacy. 
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- Take with food.
Products
Drug product information from 10+ global regionsOur datasets provide approved product information including:dosage, form, labeller, route of administration, and marketing period.Access drug product information from over 10 global regions.- Product Images
- International/Other Brands
- Cholit-ursan / Delursan / Destolit / Deursil / Litursol / Solutrat / Ursacol / Ursochol / Ursolvan
- Brand Name Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Actigall Capsule 300 mg/1 Oral Actavis Pharma, Inc. 1987-12-31 2020-02-29 US 
Actigall Capsule 300 mg/1 Oral Allergan, Inc. 1987-12-31 2021-09-30 US Gln-ursodiol Tablet 500 mg Oral Glenmark Pharmaceuticals, Inc 2016-04-04 Not applicable Canada 
Gln-ursodiol Tablet 250 mg Oral Glenmark Pharmaceuticals, Inc 2016-04-04 Not applicable Canada Urso Tablet, film coated 250 mg/1 Oral Cardinal Health 1997-12-10 2013-12-31 US Urso Tablet 250 mg Oral Aptalis Pharma Canada Ulc 1998-11-08 2022-12-16 Canada Urso 250 Tablet, film coated 250 mg/1 Oral Allergan, Inc. 1997-12-10 Not applicable US Urso DS Tablet 500 mg Oral Aptalis Pharma Canada Ulc 2003-02-03 Not applicable Canada Urso Forte Tablet, film coated 500 mg/1 Oral Allergan, Inc. 1997-12-10 Not applicable US Ursodiol Capsule 300 mg/1 Oral Cardinal Health 2009-11-05 2017-03-31 US - Generic Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Ag-ursodiol Tablet 500 mg Oral Angita Pharma Inc. 2021-04-30 Not applicable Canada Ag-ursodiol Tablet 250 mg Oral Angita Pharma Inc. 2021-04-30 Not applicable Canada Dom-ursodiol C Tablet 250 mg Oral Dominion Pharmacal 2006-08-17 Not applicable Canada Dom-ursodiol C Tablet 500 mg Oral Dominion Pharmacal 2006-08-17 Not applicable Canada Jamp-ursodiol Tablet 500 mg Oral Jamp Pharma Corporation 2018-09-28 Not applicable Canada Jamp-ursodiol Tablet 250 mg Oral Jamp Pharma Corporation 2018-09-28 Not applicable Canada Mint-ursodiol Tablet 500 mg Oral Mint Pharmaceuticals Inc Not applicable Not applicable Canada Mint-ursodiol Tablet 250 mg Oral Mint Pharmaceuticals Inc Not applicable Not applicable Canada Novo-ursodiol Tablet 500 mg Oral Novopharm Limited Not applicable Not applicable Canada Novo-ursodiol Tablet 250 mg Oral Novopharm Limited Not applicable Not applicable Canada - Over the Counter Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Urusa Capsule 250 mg/1 Oral OASIS TRADING 2018-11-15 Not applicable US - Mixture Products
Name Ingredients Dosage Route Labeller Marketing Start Marketing End Region Image BAMBOO SALT Eunganggo Jook Yeom Ursodeoxycholic acid (0.02 g/100g) + Aminocaproic acid (0.05 g/100g) + Curcuma xanthorrhiza oil (0.025 g/100g) + Glycyrrhizinate dipotassium (0.04 g/100g) + Sea salt (3 g/100g) + Silicon dioxide (20 g/100g) + Sodium fluoride (0.22 g/100g) Paste Dental Lg Household & Health Care Ltd. 2011-03-15 Not applicable US BAMBOO SALT Eunganggo Jook Yeom Toothpaste Ursodeoxycholic acid (0.02 g/100g) + Aminocaproic acid (0.05 g/100g) + Curcuma xanthorrhiza oil (0.025 g/100g) + Glycyrrhizinate dipotassium (0.04 g/100g) + Sea salt (3 g/100g) + Silicon dioxide (20 g/100g) + Sodium fluoride (0.22 g/100g) Paste Dental Lg Household & Health Care Ltd. 2010-05-25 Not applicable US Festal Plus Ursodeoxycholic acid (10 mg/1) + Dimethicone (30 mg/1) + Pancrelipase (315 mg/1) Tablet Oral OASIS TRADING 2018-11-21 Not applicable US - Unapproved/Other Products
Name Ingredients Dosage Route Labeller Marketing Start Marketing End Region Image Festal Plus Ursodeoxycholic acid (10 mg/1) + Dimethicone (30 mg/1) + Pancrelipase (315 mg/1) Tablet Oral OASIS TRADING 2018-11-21 Not applicable US Urusa Ursodeoxycholic acid (250 mg/1) Capsule Oral OASIS TRADING 2018-11-15 Not applicable US
Categories
- ATC Codes
- A05AA02 — Ursodeoxycholic acid
- Drug Categories
- Alimentary Tract and Metabolism
- Bile Acid Preparations
- Bile acids and derivatives
- Bile Acids and Salts
- Bile and Liver Therapy
- Bile Therapy
- BSEP/ABCB11 inducers
- BSEP/ABCB11 Inhibitors
- BSEP/ABCB11 Substrates
- Cholagogues and Choleretics
- Cholanes
- Cholelitholytic Agents
- Cholic Acids
- Cytochrome P-450 CYP3A Inducers
- Cytochrome P-450 Enzyme Inducers
- Fused-Ring Compounds
- Gastrointestinal Agents
- Steroids
- Chemical TaxonomyProvided by Classyfire
- Description
- This compound belongs to the class of organic compounds known as dihydroxy bile acids, alcohols and derivatives. These are compounds containing or derived from a bile acid or alcohol, and which bears exactly two carboxylic acid groups.
- Kingdom
- Organic compounds
- Super Class
- Lipids and lipid-like molecules
- Class
- Steroids and steroid derivatives
- Sub Class
- Bile acids, alcohols and derivatives
- Direct Parent
- Dihydroxy bile acids, alcohols and derivatives
- Alternative Parents
- 7-alpha-hydroxysteroids / 3-alpha-hydroxysteroids / Secondary alcohols / Cyclic alcohols and derivatives / Monocarboxylic acids and derivatives / Carboxylic acids / Organic oxides / Hydrocarbon derivatives / Carbonyl compounds
- Substituents
- 3-alpha-hydroxysteroid / 3-hydroxysteroid / 7-alpha-hydroxysteroid / 7-hydroxysteroid / Alcohol / Aliphatic homopolycyclic compound / Carbonyl group / Carboxylic acid / Carboxylic acid derivative / Cyclic alcohol
- Molecular Framework
- Aliphatic homopolycyclic compounds
- External Descriptors
- bile acid, dihydroxy-5beta-cholanic acid (CHEBI:9907) / C24 bile acids, alcohols, and derivatives, Cholane and derivatives (C07880) / C24 bile acids, alcohols, and derivatives (LMST04010033)
- Affected organisms
- Humans and other mammals
Chemical Identifiers
- UNII
- 724L30Y2QR
- CAS number
- 128-13-2
- InChI Key
- RUDATBOHQWOJDD-UZVSRGJWSA-N
- 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
- IUPAC Name
- (4R)-4-[(1R,3aS,3bR,4S,5aS,7R,9aS,9bS,11aR)-4,7-dihydroxy-9a,11a-dimethyl-hexadecahydro-1H-cyclopenta[a]phenanthren-1-yl]pentanoic acid
- SMILES
- [H][C@@]1(CC[C@@]2([H])[C@]3([H])[C@@H](O)C[C@]4([H])C[C@H](O)CC[C@]4(C)[C@@]3([H])CC[C@]12C)[C@H](C)CCC(O)=O
References
- Synthesis Reference
Antonio Bonaldi, Egidio Molinari, "Process for preparing high purity ursodeoxycholic acid." U.S. Patent US4379093, issued July, 1980.
US4379093- General References
- Achufusi TGO, Safadi AO, Mahabadi N: Ursodeoxycholic Acid. . [Article]
- Authors unspecified: Ursodiol (Ursodeoxycholic Acid). . [Article]
- Kotb MA: Molecular mechanisms of ursodeoxycholic acid toxicity & side effects: ursodeoxycholic acid freezes regeneration & induces hibernation mode. Int J Mol Sci. 2012;13(7):8882-8914. doi: 10.3390/ijms13078882. Epub 2012 Jul 17. [Article]
- Trampert DC, van de Graaf SFJ, Jongejan A, Oude Elferink RPJ, Beuers U: Hepatobiliary acid-base homeostasis: Insights from analogous secretory epithelia. J Hepatol. 2021 Feb;74(2):428-441. doi: 10.1016/j.jhep.2020.10.010. Epub 2020 Oct 24. [Article]
- Festi D, Montagnani M, Azzaroli F, Lodato F, Mazzella G, Roda A, Di Biase AR, Roda E, Simoni P, Colecchia A: Clinical efficacy and effectiveness of ursodeoxycholic acid in cholestatic liver diseases. Curr Clin Pharmacol. 2007 May;2(2):155-77. doi: 10.2174/157488407780598171. [Article]
- Paumgartner G, Beuers U: Ursodeoxycholic acid in cholestatic liver disease: mechanisms of action and therapeutic use revisited. Hepatology. 2002 Sep;36(3):525-31. doi: 10.1053/jhep.2002.36088. [Article]
- Angulo P: Use of ursodeoxycholic acid in patients with liver disease. Curr Gastroenterol Rep. 2002 Feb;4(1):37-44. doi: 10.1007/s11894-002-0036-9. [Article]
- Hofmann AF: Pharmacology of ursodeoxycholic acid, an enterohepatic drug. Scand J Gastroenterol Suppl. 1994;204:1-15. doi: 10.3109/00365529409103618. [Article]
- FDA Approved Drug Products: URSO 250 and URSO FORTE (ursodiol) tablets, for oral use [Link]
- Medisca: Ursodiol MSDS [Link]
- DailyMed Label: URSODIOL Oral Capsules [Link]
- External Links
- Human Metabolome Database
- HMDB0000946
- KEGG Drug
- D00734
- KEGG Compound
- C07880
- PubChem Compound
- 31401
- PubChem Substance
- 46508795
- ChemSpider
- 29131
- BindingDB
- 53721
- 11065
- ChEBI
- 9907
- ChEMBL
- CHEMBL1551
- ZINC
- ZINC000003914809
- Therapeutic Targets Database
- DNC000420
- PharmGKB
- PA451837
- PDBe Ligand
- IU5
- Wikipedia
- Ursodeoxycholic_acid
Clinical Trials
- Clinical Trials
Phase Status Purpose Conditions Count 4 Completed Basic Science Obesity, Severe 1 4 Completed Prevention Short Bowel Syndrome (SBS) 1 4 Completed Treatment (NAFLD) / Type 2 Diabetes Mellitus 1 4 Completed Treatment Cholecystolithiasis 1 4 Completed Treatment Diarrhea 1 4 Completed Treatment Fatigue 2 4 Completed Treatment Non Alcoholic Steatohepatitis (NASH) 1 4 Completed Treatment Primary Biliary Cholangitis 1 4 Not Yet Recruiting Treatment Patients With Dyspeptic Symptoms After Cholecystectomy 1 4 Recruiting Other Gastric Cancer 1
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Amerisource Health Services Corp.
- Axcan Pharma Inc.
- Cardinal Health
- Corepharma LLC
- DispenseXpress Inc.
- Giuliani SPA
- Heartland Repack Services LLC
- Lannett Co. Inc.
- Mckesson Corp.
- Murfreesboro Pharmaceutical Nursing Supply
- Mylan
- Novartis AG
- Patheon Inc.
- Pharmaceutical Utilization Management Program VA Inc.
- Physicians Total Care Inc.
- Prasco Labs
- Qualitest
- Resource Optimization and Innovation LLC
- Rising Pharmaceuticals
- Schering Corp.
- Southwood Pharmaceuticals
- Summit Pharmaceuticals
- Teva Pharmaceutical Industries Ltd.
- UDL Laboratories
- Watson Pharmaceuticals
- Dosage Forms
Form Route Strength Capsule Oral 225 MG Capsule Oral 450 MG Capsule, extended release Oral 450 MG Tablet Oral 50 MG Capsule, delayed release Paste Dental Capsule, extended release Oral Tablet Oral 225 MG Tablet, extended release Oral 450 MG Capsule, extended release Oral 225 MG Tablet, film coated Oral 250 MG Tablet, film coated Oral 500 MG Tablet, film coated Oral Tablet Oral Capsule, coated Oral 300 mg Capsule Oral 150 MG Capsule Oral 500 MG Tablet Oral 500 MG Tablet Oral 150 MG Tablet Oral 300 MG Tablet, delayed release Oral 225 MG Tablet, delayed release Oral 450 MG Tablet Oral 450 MG Tablet Oral 600 mg Capsule Oral 250 mg Capsule Oral 125 MG Granule, for suspension Oral 150 MG Granule, for suspension Oral 300 MG Tablet Oral 250 mg Tablet, film coated Oral 400 MG Capsule Oral 100 MG Solution / drops Oral 254 MG/ML Syrup Oral 31.7 MG/ML Capsule Oral 300 mg/1 Powder 1 g/1g Tablet Oral 250 mg/1 Tablet Oral 500 mg/1 Tablet, film coated Oral 250 mg/1 Tablet, film coated Oral 500 mg/1 Capsule Oral 200 mg/1 Capsule Oral 400 mg/1 Capsule Oral Suspension Oral Suspension Oral 250 mg/5ml Tablet, film coated Oral 500.00 mg Tablet, coated Oral 500 mg Capsule, coated Oral 250 mg Capsule Oral 300 MG Capsule Oral 50 MG Tablet Oral Tablet, film coated Oral 750 mg Solution / drops Oral 25 G/100ML Syrup Oral 3 G/100ML Capsule Oral 250 mg/1 - Prices
Unit description Cost Unit Urso forte 500 mg tablet 6.3USD tablet Actigall 300 mg capsule 5.52USD capsule Ursodiol 500 mg tablet 4.75USD tablet Urso 250 mg tablet 4.41USD tablet Urso 250 250 mg tablet 3.55USD tablet Urso Ds 500 mg Tablet 2.69USD tablet Ursodiol 250 mg tablet 2.68USD tablet Pms-Ursodiol C 500 mg Tablet 1.75USD tablet Urso 250 mg Tablet 1.42USD tablet Pms-Ursodiol C 250 mg Tablet 0.92USD tablet DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.- Patents
- Not Available
Properties
- State
- Solid
- Experimental Properties
Property Value Source melting point (°C) 200-205 https://www.medisca.com/NDC_SPECS/MUS/1987/MSDS/1987.pdf logP 3 https://www.medisca.com/NDC_SPECS/MUS/1987/MSDS/1987.pdf - Predicted Properties
Property Value Source Water Solubility 0.0197 mg/mL ALOGPS logP 3.01 ALOGPS logP 3.71 Chemaxon logS -4.3 ALOGPS pKa (Strongest Acidic) 4.6 Chemaxon pKa (Strongest Basic) -0.54 Chemaxon Physiological Charge -1 Chemaxon Hydrogen Acceptor Count 4 Chemaxon Hydrogen Donor Count 3 Chemaxon Polar Surface Area 77.76 Å2 Chemaxon Rotatable Bond Count 4 Chemaxon Refractivity 109.27 m3·mol-1 Chemaxon Polarizability 46.42 Å3 Chemaxon Number of Rings 4 Chemaxon Bioavailability 1 Chemaxon Rule of Five Yes Chemaxon Ghose Filter Yes Chemaxon Veber's Rule No Chemaxon MDDR-like Rule No Chemaxon - Predicted ADMET Features
Property Value Probability Human Intestinal Absorption + 0.9766 Blood Brain Barrier + 0.9288 Caco-2 permeable + 0.73 P-glycoprotein substrate Substrate 0.6648 P-glycoprotein inhibitor I Non-inhibitor 0.8737 P-glycoprotein inhibitor II Inhibitor 0.5368 Renal organic cation transporter Non-inhibitor 0.8537 CYP450 2C9 substrate Non-substrate 0.7818 CYP450 2D6 substrate Non-substrate 0.9115 CYP450 3A4 substrate Substrate 0.7407 CYP450 1A2 substrate Non-inhibitor 0.9045 CYP450 2C9 inhibitor Non-inhibitor 0.9456 CYP450 2D6 inhibitor Non-inhibitor 0.9781 CYP450 2C19 inhibitor Non-inhibitor 0.9707 CYP450 3A4 inhibitor Non-inhibitor 0.8405 CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.9563 Ames test Non AMES toxic 0.8794 Carcinogenicity Non-carcinogens 0.9329 Biodegradation Not ready biodegradable 0.992 Rat acute toxicity 2.5624 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.9622 hERG inhibition (predictor II) Non-inhibitor 0.7246
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Spectrum Spectrum Type Splash Key Predicted GC-MS Spectrum - GC-MS Predicted GC-MS Not Available Predicted MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS Not Available LC-MS/MS Spectrum - LC-ESI-qTof , Positive LC-MS/MS Not Available LC-MS/MS Spectrum - LC-ESI-IT , negative LC-MS/MS splash10-00di-0029000000-54929e08fef761ba2b28 MS/MS Spectrum - , positive LC-MS/MS splash10-0002-2911000000-eec2b269eeb08a30ac6e
Targets
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- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- Inducer
- General Function
- Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase activity
- Specific Function
- Works in concert with the 5-alpha/5-beta-steroid reductases to convert steroid hormones into the 3-alpha/5-alpha and 3-alpha/5-beta-tetrahydrosteroids. Catalyzes the inactivation of the most potent...
- Gene Name
- AKR1C2
- Uniprot ID
- P52895
- Uniprot Name
- Aldo-keto reductase family 1 member C2
- Molecular Weight
- 36734.97 Da
References
- Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [Article]
- Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [Article]
- Amaral JD, Sola S, Steer CJ, Rodrigues CM: Role of nuclear steroid receptors in apoptosis. Curr Med Chem. 2009;16(29):3886-902. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Partial agonist
- General Function
- Zinc ion binding
- Specific Function
- Ligand-activated transcription factor. Receptor for bile acids such as chenodeoxycholic acid, lithocholic acid and deoxycholic acid. Represses the transcription of the cholesterol 7-alpha-hydroxyla...
- Gene Name
- NR1H4
- Uniprot ID
- Q96RI1
- Uniprot Name
- Bile acid receptor
- Molecular Weight
- 55913.915 Da
References
- Campana G, Pasini P, Roda A, Spampinato S: Regulation of ileal bile acid-binding protein expression in Caco-2 cells by ursodeoxycholic acid: role of the farnesoid X receptor. Biochem Pharmacol. 2005 Jun 15;69(12):1755-63. [Article]
Enzymes
- Kind
- Protein group
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Inducer
- Curator comments
- Induction of CYP3A has been suggested as a mechanism of action of ursodeoxycholic acid. However, this enzyme interaction requires further investigation.
- General Function
- Vitamin d3 25-hydroxylase activity
- Specific Function
- Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation react...
Components:
| Name | UniProt ID |
|---|---|
| Cytochrome P450 3A4 | P08684 |
| Cytochrome P450 3A43 | Q9HB55 |
| Cytochrome P450 3A5 | P20815 |
| Cytochrome P450 3A7 | P24462 |
References
- Dilger K, Denk A, Heeg MH, Beuers U: No relevant effect of ursodeoxycholic acid on cytochrome P450 3A metabolism in primary biliary cirrhosis. Hepatology. 2005 Mar;41(3):595-602. doi: 10.1002/hep.20568. [Article]
- Paumgartner G, Beuers U: Ursodeoxycholic acid in cholestatic liver disease: mechanisms of action and therapeutic use revisited. Hepatology. 2002 Sep;36(3):525-31. doi: 10.1053/jhep.2002.36088. [Article]
Transporters
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- SubstrateInhibitorInducer
- General Function
- Transporter activity
- Specific Function
- Involved in the ATP-dependent secretion of bile salts into the canaliculus of hepatocytes.
- Gene Name
- ABCB11
- Uniprot ID
- O95342
- Uniprot Name
- Bile salt export pump
- Molecular Weight
- 146405.83 Da
References
- Schuetz EG, Strom S, Yasuda K, Lecureur V, Assem M, Brimer C, Lamba J, Kim RB, Ramachandran V, Komoroski BJ, Venkataramanan R, Cai H, Sinal CJ, Gonzalez FJ, Schuetz JD: Disrupted bile acid homeostasis reveals an unexpected interaction among nuclear hormone receptors, transporters, and cytochrome P450. J Biol Chem. 2001 Oct 19;276(42):39411-8. doi: 10.1074/jbc.M106340200. Epub 2001 Aug 16. [Article]
- Green RM, Hoda F, Ward KL: Molecular cloning and characterization of the murine bile salt export pump. Gene. 2000 Jan 4;241(1):117-23. [Article]
- Mita S, Suzuki H, Akita H, Stieger B, Meier PJ, Hofmann AF, Sugiyama Y: Vectorial transport of bile salts across MDCK cells expressing both rat Na+-taurocholate cotransporting polypeptide and rat bile salt export pump. Am J Physiol Gastrointest Liver Physiol. 2005 Jan;288(1):G159-67. Epub 2004 Aug 5. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- SubstrateInhibitorInducer
- General Function
- Sodium-independent organic anion transmembrane transporter activity
- Specific Function
- Mediates the Na(+)-independent transport of organic anions such as sulfobromophthalein (BSP) and conjugated (taurocholate) and unconjugated (cholate) bile acids (By similarity). Selectively inhibit...
- Gene Name
- SLCO1A2
- Uniprot ID
- P46721
- Uniprot Name
- Solute carrier organic anion transporter family member 1A2
- Molecular Weight
- 74144.105 Da
References
- Fickert P, Zollner G, Fuchsbichler A, Stumptner C, Pojer C, Zenz R, Lammert F, Stieger B, Meier PJ, Zatloukal K, Denk H, Trauner M: Effects of ursodeoxycholic and cholic acid feeding on hepatocellular transporter expression in mouse liver. Gastroenterology. 2001 Jul;121(1):170-83. [Article]
- Kullak-Ublick GA, Hagenbuch B, Stieger B, Schteingart CD, Hofmann AF, Wolkoff AW, Meier PJ: Molecular and functional characterization of an organic anion transporting polypeptide cloned from human liver. Gastroenterology. 1995 Oct;109(4):1274-82. [Article]
- Kullak-Ublick GA, Hagenbuch B, Stieger B, Wolkoff AW, Meier PJ: Functional characterization of the basolateral rat liver organic anion transporting polypeptide. Hepatology. 1994 Aug;20(2):411-6. [Article]
- Hata S, Wang P, Eftychiou N, Ananthanarayanan M, Batta A, Salen G, Pang KS, Wolkoff AW: Substrate specificities of rat oatp1 and ntcp: implications for hepatic organic anion uptake. Am J Physiol Gastrointest Liver Physiol. 2003 Nov;285(5):G829-39. Epub 2003 Jul 3. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Inducer
- General Function
- Organic anion transmembrane transporter activity
- Specific Function
- Mediates hepatobiliary excretion of numerous organic anions. May function as a cellular cisplatin transporter.
- Gene Name
- ABCC2
- Uniprot ID
- Q92887
- Uniprot Name
- Canalicular multispecific organic anion transporter 1
- Molecular Weight
- 174205.64 Da
References
- Kast HR, Goodwin B, Tarr PT, Jones SA, Anisfeld AM, Stoltz CM, Tontonoz P, Kliewer S, Willson TM, Edwards PA: Regulation of multidrug resistance-associated protein 2 (ABCC2) by the nuclear receptors pregnane X receptor, farnesoid X-activated receptor, and constitutive androstane receptor. J Biol Chem. 2002 Jan 25;277(4):2908-15. Epub 2001 Nov 12. [Article]
- Fickert P, Zollner G, Fuchsbichler A, Stumptner C, Pojer C, Zenz R, Lammert F, Stieger B, Meier PJ, Zatloukal K, Denk H, Trauner M: Effects of ursodeoxycholic and cholic acid feeding on hepatocellular transporter expression in mouse liver. Gastroenterology. 2001 Jul;121(1):170-83. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Inhibitor
- General Function
- Atpase activity, coupled to transmembrane movement of substances
- Specific Function
- May be an organic anion pump relevant to cellular detoxification.
- Gene Name
- ABCC4
- Uniprot ID
- O15439
- Uniprot Name
- Multidrug resistance-associated protein 4
- Molecular Weight
- 149525.33 Da
References
- Rius M, Nies AT, Hummel-Eisenbeiss J, Jedlitschky G, Keppler D: Cotransport of reduced glutathione with bile salts by MRP4 (ABCC4) localized to the basolateral hepatocyte membrane. Hepatology. 2003 Aug;38(2):374-84. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Inhibitor
- General Function
- Bile acid:sodium symporter activity
- Specific Function
- Plays a critical role in the sodium-dependent reabsorption of bile acids from the lumen of the small intestine. Plays a key role in cholesterol metabolism.
- Gene Name
- SLC10A2
- Uniprot ID
- Q12908
- Uniprot Name
- Ileal sodium/bile acid cotransporter
- Molecular Weight
- 37713.405 Da
References
- Craddock AL, Love MW, Daniel RW, Kirby LC, Walters HC, Wong MH, Dawson PA: Expression and transport properties of the human ileal and renal sodium-dependent bile acid transporter. Am J Physiol. 1998 Jan;274(1 Pt 1):G157-69. [Article]
- Saeki T, Matoba K, Furukawa H, Kirifuji K, Kanamoto R, Iwami K: Characterization, cDNA cloning, and functional expression of mouse ileal sodium-dependent bile acid transporter. J Biochem. 1999 Apr;125(4):846-51. [Article]
- Saeki T, Takahashi N, Kanamoto R, Iwami K: Characterization of cloned mouse Na+/taurocholate cotransporting polypeptide by transient expression in COS-7 cells. Biosci Biotechnol Biochem. 2002 May;66(5):1116-8. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- SubstrateInhibitor
- General Function
- Virus receptor activity
- Specific Function
- The hepatic sodium/bile acid uptake system exhibits broad substrate specificity and transports various non-bile acid organic compounds as well. It is strictly dependent on the extracellular presenc...
- Gene Name
- SLC10A1
- Uniprot ID
- Q14973
- Uniprot Name
- Sodium/bile acid cotransporter
- Molecular Weight
- 38118.64 Da
References
- Boyer JL, Ng OC, Ananthanarayanan M, Hofmann AF, Schteingart CD, Hagenbuch B, Stieger B, Meier PJ: Expression and characterization of a functional rat liver Na+ bile acid cotransport system in COS-7 cells. Am J Physiol. 1994 Mar;266(3 Pt 1):G382-7. [Article]
- Mita S, Suzuki H, Akita H, Stieger B, Meier PJ, Hofmann AF, Sugiyama Y: Vectorial transport of bile salts across MDCK cells expressing both rat Na+-taurocholate cotransporting polypeptide and rat bile salt export pump. Am J Physiol Gastrointest Liver Physiol. 2005 Jan;288(1):G159-67. Epub 2004 Aug 5. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Upregulator
- General Function
- Chloride/bicarbonate exchanger. Mediates the efficient absorption of chloride ions in the colon, participating in fluid homeostasis. Plays a role in the chloride and bicarbonate homeostasis during sperm epididymal maturation and capacitation.
- Specific Function
- Bicarbonate transmembrane transporter activity
- Gene Name
- SLC26A3
- Uniprot ID
- P40879
- Uniprot Name
- Chloride anion exchanger
- Molecular Weight
- 84504.035 Da
References
Drug created at August 29, 2007 14:57 / Updated at March 21, 2023 17:58