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Ursodeoxycholic acid
Identification
- Name
- Ursodeoxycholic acid
- Accession Number
- DB01586
- Description
Ursodeoxycholic acid is an epimer of chenodeoxycholic acid. 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.
- 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
The drug decreases the absorption of cholesterol and is used to dissolve (cholesterol) gallstones in patients as an alternative to a surgical procedure to remove the gallstones.
- Associated Conditions
- Contraindications & Blackbox Warnings
Learn about our commercial Contraindications & Blackbox Warnings data.
Learn More- Pharmacodynamics
Ursodiol (commonly known as ursodeoxycholic acid) is a product of metabolism of bacteria in the intestine. It is considered a secondary bile acid. The other type of bile acid, primary bile acids, are produced hepatically and subsequently stored in the gallbladder. When primary bile acids are secreted into the large intestine, they can be broken down into secondary bile acids by bacteria present in the intestine. Both types of bile acids assist in the metabolism of dietary fat. Ursodeoxycholic acid regulates cholesterol levels by slowing the rate at which the intestine is able to absorb cholesterol and also acts to break down micelles, which contain cholesterol. Because of this property, ursodeoxycholic acid is used to treat gall stones non-surgically.
- Mechanism of action
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.
Target Actions Organism AAldo-keto reductase family 1 member C2 inducerHumans UBile acid receptor Not Available Humans - Absorption
- Not Available
- Volume of distribution
- Not Available
- Protein binding
- Not Available
- Metabolism
- Not Available
- Route of elimination
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.
- Half-life
- Not Available
- Clearance
- Not Available
- Adverse Effects
Learn about our commercial Adverse Effects data.
Learn More- 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.
- Affected organisms
- Humans and other mammals
- 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 Unlock Additional DataAbciximab 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. Acetaminophen Ursodeoxycholic acid may increase the hepatotoxic activities of Acetaminophen. 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 The serum concentration of Ursodeoxycholic acid can be decreased when it is combined with Aluminium. Aluminium phosphate The serum concentration of Ursodeoxycholic acid can be decreased when it is combined with Aluminium phosphate. 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 hydroxide The serum concentration of Ursodeoxycholic acid can be decreased when it is combined with Aluminum hydroxide. Aluminum sulfate The serum concentration of Ursodeoxycholic acid can be decreased when it is combined with Aluminum sulfate. Additional Data Available- Extended DescriptionExtended Description
Extended description of the mechanism of action and particular properties of each drug interaction.
Learn more - Severity
- Evidence Level
- ActionAction
An effect category for each drug interaction. Know how this interaction affects the subject drug.
Learn more
- Food Interactions
- Take with food.
Products
- 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 Unlock Additional DataActigall Capsule 300 mg/1 Oral Actavis Pharma, Inc. 1987-12-31 2020-02-29 US 
Actigall Capsule 300 mg/1 Oral Allergan 1987-12-31 Not applicable US 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 Not applicable Canada 
Urso 250 Tablet, film coated 250 mg/1 Oral Allergan 1997-12-10 Not applicable US Urso DS Tablet Oral Aptalis Pharma Canada Ulc 2003-02-03 Not applicable Canada Urso Forte Tablet, film coated 500 mg/1 Oral Allergan 1997-12-10 Not applicable US Ursodiol Capsule 300 mg/1 Oral Cardinal Health 2009-11-05 2017-03-31 US Ursodiol Capsule 300 mg/1 Oral Stat Rx USA 1987-12-31 Not applicable US Ursodiol Capsule 300 mg/1 Oral Amerincan Health Packaging 2009-11-05 2017-03-31 US Additional Data Available- Application NumberApplication Number
A unique ID assigned by the FDA when a product is submitted for approval by the labeller.
Learn more - Product CodeProduct Code
A governmentally-recognized ID which uniquely identifies the product within its regulatory market.
Learn more
- Generic Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Unlock Additional DataDom-ursodiol C Tablet Oral Dominion Pharmacal 2006-08-17 Not applicable Canada Dom-ursodiol C Tablet Oral Dominion Pharmacal 2006-08-17 Not applicable Canada Jamp-ursodiol Tablet Oral Jamp Pharma Corporation 2018-09-28 Not applicable Canada Jamp-ursodiol Tablet Oral Jamp Pharma Corporation 2018-09-28 Not applicable Canada Mint-ursodiol Tablet Oral Mint Pharmaceuticals Inc Not applicable Not applicable Canada Mint-ursodiol Tablet Oral Mint Pharmaceuticals Inc Not applicable Not applicable Canada Novo-ursodiol Tablet Oral Novopharm Limited Not applicable Not applicable Canada Novo-ursodiol Tablet Oral Novopharm Limited Not applicable Not applicable Canada Pendo-ursodiol C Tablet Oral Pendopharm Division Of Pharmascience Inc Not applicable Not applicable Canada Pendo-ursodiol C Tablet Oral Pendopharm Division Of Pharmascience Inc Not applicable Not applicable Canada Additional Data Available- Application NumberApplication Number
A unique ID assigned by the FDA when a product is submitted for approval by the labeller.
Learn more - Product CodeProduct Code
A governmentally-recognized ID which uniquely identifies the product within its regulatory market.
Learn more
- Over the Counter Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Unlock Additional DataUrusa Capsule 250 mg/1 Oral OASIS TRADING 2018-11-15 Not applicable US Additional Data Available- Application NumberApplication Number
A unique ID assigned by the FDA when a product is submitted for approval by the labeller.
Learn more - Product CodeProduct Code
A governmentally-recognized ID which uniquely identifies the product within its regulatory market.
Learn more
- 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 CYP2E1 Inducers
- Cytochrome P-450 CYP2E1 Inducers (strength unknown)
- Cytochrome P-450 CYP2E1 Inhibitors
- Cytochrome P-450 CYP2E1 Inhibitors (strength unknown)
- Cytochrome P-450 Enzyme Inducers
- Cytochrome P-450 Enzyme Inhibitors
- 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)
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-[(1S,2S,5R,7S,9S,10R,11S,14R,15R)-5,9-dihydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-14-yl]pentanoic acid
- SMILES
- [H][[email protected]@]1(CC[[email protected]@]2([H])[[email protected]]3([H])[[email protected]@H](O)C[[email protected]]4([H])C[[email protected]](O)CC[[email protected]]4(C)[[email protected]@]3([H])CC[[email protected]]12C)[[email protected]](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
- 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: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: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 Oct;46(4):1131-7. [PubMed:17685473]
- 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
- Ursodiol
- AHFS Codes
- 56:14.00 — Cholelitholytic Agents
- FDA label
- Download (233 KB)
- MSDS
- Download (73.3 KB)
Clinical Trials
- Clinical Trials
Phase Status Purpose Conditions Count 4 Active Not Recruiting Treatment Diarrhea 1 4 Completed Basic Science Obesity, Severe 1 4 Completed Prevention Short bowel condition / Short Bowel Syndrome (SBS) 1 4 Completed Treatment Cholecystolithiasis 1 4 Completed Treatment Fatigue 2 4 Completed Treatment Primary Biliary Cholangitis 1 4 Not Yet Recruiting Treatment End-Stage Kidney Disease 1 4 Not Yet Recruiting Treatment Functional Dyspepsia 1 4 Not Yet Recruiting Treatment Gestational Diabetes Mellitus (GDM) 1 4 Terminated Prevention Gallstone formation / Hemolytic Disorders 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 Tablet Oral 150 MG Tablet Oral 300 MG Paste Dental Tablet Oral 225 MG Tablet, extended release 450 MG Capsule Oral 300 MG Capsule Oral 50 MG Capsule, extended release 225 MG Capsule, extended release 450 MG Tablet Oral Capsule, coated Oral 300 mg Tablet, film coated 250 mg Tablet, film coated 500 mg Capsule Oral 150 MG Capsule Oral 500 MG Tablet 500 MG Capsule Oral 250 MG Tablet, coated 250 mg Tablet Oral 450 MG Tablet Oral 50 MG Tablet Oral 600 mg Tablet, coated 500 mg Capsule 125 MG Capsule, extended release Oral 225 MG Capsule, extended release Oral 450 MG Granule, for suspension Oral 150 MG Granule, for suspension Oral 300 MG Tablet Oral 250 mg Tablet, film coated Oral 250 MG Tablet, film coated Oral 400 MG Tablet Oral Capsule Oral 100 MG Solution / drops Oral 254 MG/ML Syrup 31.7 MG/ML Tablet 150 mg Tablet 300 mg 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 Suspension 250 mg/5ml Tablet, film coated Oral 500 MG Capsule Oral Tablet, coated Oral 500 mg Capsule, coated Oral 250 mg Tablet, film coated 750 mg Capsule 150 mg Capsule 250 mg Capsule 300 mg Tablet, coated 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) 203 °C PhysProp water solubility 20 mg/L (at 20 °C) YALKOWSKY,SH & DANNENFELSER,RM (1992) logP 3.00 RODA,A ET AL. (1990) - 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 46.33 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
- 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. [PubMed:17139284]
- 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. [PubMed:17016423]
- Amaral JD, Sola S, Steer CJ, Rodrigues CM: Role of nuclear steroid receptors in apoptosis. Curr Med Chem. 2009;16(29):3886-902. [PubMed:19747134]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- 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. [PubMed:15935148]
Enzymes
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- InhibitorInducer
- General Function
- Steroid hydroxylase activity
- Specific Function
- Metabolizes several precarcinogens, drugs, and solvents to reactive metabolites. Inactivates a number of drugs and xenobiotics and also bioactivates many xenobiotic substrates to their hepatotoxic ...
- Gene Name
- CYP2E1
- Uniprot ID
- P05181
- Uniprot Name
- Cytochrome P450 2E1
- Molecular Weight
- 56848.42 Da
References
- Paolini M, Pozzetti L, Montagnani M, Potenza G, Sabatini L, Antelli A, Cantelli-Forti G, Roda A: Ursodeoxycholic acid (UDCA) prevents DCA effects on male mouse liver via up-regulation of CYP [correction of CXP] and preservation of BSEP activities. Hepatology. 2002 Aug;36(2):305-14. doi: 10.1053/jhep.2002.34939. [PubMed:12143038]
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. [PubMed:11509573]
- 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. [PubMed:10607905]
- 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. [PubMed:15297262]
- 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. [PubMed:11438506]
- 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. [PubMed:7557095]
- 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. [PubMed:8045503]
- 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. [PubMed:12842829]
- 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. [PubMed:11706036]
- 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. [PubMed:11438506]
- 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. [PubMed:12883481]
- 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. [PubMed:9458785]
- 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. [PubMed:10101301]
- 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. [PubMed:12092825]
- 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. [PubMed:8166278]
- 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. [PubMed:15297262]
Drug created on August 29, 2007 08:57 / Updated on September 17, 2020 23:29
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