Identification

Name
Ursodeoxycholic acid
Accession Number
DB01586
Type
Small Molecule
Groups
Approved, Investigational
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]

Structure
Thumb
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
Product Images
Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
ActigallCapsule300 mg/1OralAllergan1987-12-31Not applicableUs
ActigallCapsule300 mg/1OralActavis Pharma Company1987-12-31Not applicableUs
UrsoTablet250 mgOralAptalis Pharma Inc.1998-11-08Not applicableCanada
UrsoTablet, film coated250 mg/1OralCardinal Health1997-12-102013-12-31Us
Urso 250Tablet, film coated250 mg/1OralAllergan1997-12-10Not applicableUs
Urso DSTablet500 mgOralAptalis Pharma Inc.2003-02-03Not applicableCanada
Urso ForteTablet, film coated500 mg/1OralAllergan1997-12-10Not applicableUs
UrsodiolCapsule300 mg/1OralStat Rx USA1987-12-31Not applicableUs
UrsodiolCapsule300 mg/1OralAmerincan Health Packaging2009-11-052017-03-31Us
UrsodiolCapsule300 mg/1OralCardinal Health2009-11-052017-03-31Us
Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Dom-ursodiol CTablet250 mgOralDominion Pharmacal2006-08-17Not applicableCanada
Dom-ursodiol CTablet500 mgOralDominion Pharmacal2006-08-17Not applicableCanada
Jamp-ursodiolTablet250 mgOralJamp Pharma CorporationNot applicableNot applicableCanada
Jamp-ursodiolTablet500 mgOralJamp Pharma CorporationNot applicableNot applicableCanada
Mint-ursodiolTablet500 mgOralMint Pharmaceuticals IncNot applicableNot applicableCanada
Mint-ursodiolTablet250 mgOralMint Pharmaceuticals IncNot applicableNot applicableCanada
Novo-ursodiolTablet250 mgOralNovopharm LimitedNot applicableNot applicableCanada
Novo-ursodiolTablet500 mgOralNovopharm LimitedNot applicableNot applicableCanada
Pendo-ursodiol CTablet250 mgOralPendopharm Division Of De Pharmascience IncNot applicableNot applicableCanada
Pendo-ursodiol CTablet500 mgOralPendopharm Division Of De Pharmascience IncNot applicableNot applicableCanada
Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing End
BAMBOO SALT Eunganggo Jook YeomUrsodeoxycholic 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)PasteDentalLg Household & Health Care Ltd.2011-03-15Not applicableUs
BAMBOO SALT Eunganggo Jook Yeom ToothpasteUrsodeoxycholic 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)PasteDentalLg Household & Health Care Ltd.2010-05-25Not applicableUs
International/Other Brands
Actigall / Cholit-ursan / Delursan / Destolit / Deursil / Litursol / Solutrat / Ursacol / Ursochol / Ursolvan
Categories
UNII
724L30Y2QR
CAS number
128-13-2
Weight
Average: 392.572
Monoisotopic: 392.292659768
Chemical Formula
C24H40O4
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][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

Pharmacology

Indication

The drug reduces cholesterol absorption and is used to dissolve (cholesterol) gallstones in patients who want an alternative to surgery.

Associated Conditions
Pharmacodynamics

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

TargetActionsOrganism
AAldo-keto reductase family 1 member C2
inducer
Human
UBile acid receptorNot AvailableHuman
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
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
DrugInteraction
Aluminium clofibrateThe therapeutic efficacy of Ursodeoxycholic acid can be decreased when used in combination with Aluminium clofibrate.
Aluminum hydroxideThe serum concentration of Ursodeoxycholic acid can be decreased when it is combined with Aluminum hydroxide.
AtenololUrsodeoxycholic acid may decrease the excretion rate of Atenolol which could result in a higher serum level.
BazedoxifeneThe therapeutic efficacy of Ursodeoxycholic acid can be decreased when used in combination with Bazedoxifene.
BezafibrateThe therapeutic efficacy of Ursodeoxycholic acid can be decreased when used in combination with Bezafibrate.
BosentanThe risk or severity of liver damage can be increased when Ursodeoxycholic acid is combined with Bosentan.
BudesonideUrsodeoxycholic acid may decrease the excretion rate of Budesonide which could result in a higher serum level.
CelecoxibUrsodeoxycholic acid may decrease the excretion rate of Celecoxib which could result in a higher serum level.
ChlorotrianiseneThe therapeutic efficacy of Ursodeoxycholic acid can be decreased when used in combination with Chlorotrianisene.
ChlorpromazineThe risk or severity of liver damage can be increased when Ursodeoxycholic acid is combined with Chlorpromazine.
Food Interactions
Not Available

References

Synthesis Reference

Antonio Bonaldi, Egidio Molinari, "Process for preparing high purity ursodeoxycholic acid." U.S. Patent US4379093, issued July, 1980.

US4379093
General References
  1. 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]
  2. 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]
  3. 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
ChEBI
9907
ChEMBL
CHEMBL1551
Therapeutic Targets Database
DNC000420
PharmGKB
PA451837
HET
IU5
Wikipedia
Ursodiol
ATC Codes
A05AA02 — Ursodeoxycholic acid
AHFS Codes
  • 56:14.00 — Cholelitholytic Agents
FDA label
Download (233 KB)
MSDS
Download (73.3 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
1Active Not RecruitingTreatmentColorectal Cancers1
1CompletedNot AvailableHealthy Volunteers4
1CompletedBasic ScienceHealthy Volunteers1
1CompletedTreatmentHealthy Volunteers2
1CompletedTreatmentPrimary Sclerosing Cholangitis (PSC)1
1RecruitingBasic ScienceGastric Bypass Surgery / Glucose tolerance impaired1
1RecruitingTreatmentAbnormal Liver Function Tests / BMI >27 kg/m21
1RecruitingTreatmentAgeing1
1RecruitingTreatmentParkinson's Disease (PD)1
1RecruitingTreatmentRhegmatogenous Retinal Detachments1
1Unknown StatusTreatmentHuntington's Disease (HD)1
1Unknown StatusTreatmentPrimary Biliary Cirrhosis (PBC)1
1, 2Active Not RecruitingTreatmentPrimary Sclerosing Cholangitis (PSC)1
1, 2RecruitingTreatmentPrimary Biliary Cirrhosis (PBC)1
1, 2Unknown StatusTreatmentDigestive System Diseases / Fibrosis / Liver Cirrhosis / Liver Diseases1
2Active Not RecruitingTreatmentChronic Lymphocytic Leukaemia (CLL) / Lymphoma, Hodgkins / Lymphoma, Large B-Cell, Diffuse (DLBCL) / Lymphoma, Low-Grade / Mantle Cell Lymphoma (MCL) / Small Lymphocytic Lymphoma (SLL) / T-Cell Lymphomas1
2CompletedPreventionColorectal Cancers / Hepatic Metastases / Irradiation Damage / Radiation Induced Liver Disease1
2CompletedPreventionEsophagus, Barrett / Oesophageal Carcinoma1
2CompletedTreatmentAmyotrophic Lateral Sclerosis (ALS)1
2CompletedTreatmentAutosomal Dominant Polycystic Kidney Disease (ADPKD) / Polycystic Liver Disease (PLD)1
2CompletedTreatmentIntrahepatic Cholestasis1
2CompletedTreatmentLiver Cirrhosis, Biliary1
2CompletedTreatmentPrimary Biliary Cirrhosis (PBC)1
2CompletedTreatmentProphylaxis of cardiomyopathy / Transthyretin Amyloidosis1
2CompletedTreatmentType 2 Diabetes Mellitus1
2Not Yet RecruitingTreatmentAdolescents / Bile Duct Diseases / Cholangitis / Digestive System Diseases / Functional disorders of the biliary tract / Primary Sclerosing Cholangitis (PSC) / Sclerosing Cholangitis1
2RecruitingTreatmentHepatic Sarcoidosis, Elevated Alkaline Phosphatase1
2RecruitingTreatmentLiver Diseases1
2TerminatedPreventionColorectal Cancers1
2TerminatedTreatmentNonalcoholic Fatty Liver Disease (NAFLD)1
2Unknown StatusSupportive CareJaundice, Obstructive1
2Unknown StatusTreatmentCholestasis / Cystic Fibrosis (CF) / Gastrointestinal Diseases1
2Unknown StatusTreatmentCongestive Heart Failure (CHF)1
2WithdrawnTreatmentCholestasis / Liver Diseases1
2, 3CompletedPreventionDuodenal Neoplasms / Duodenal Polyps / Familial Adenomatous Polyposis (FAP)1
2, 3CompletedTreatmentCholestasis1
2, 3CompletedTreatmentSclerosing Cholangitis1
2, 3Not Yet RecruitingTreatmentComplications, Pregnancy / Intrahepatic Cholestases1
2, 3Unknown StatusTreatmentAdenomatous Polyposis Coli, Familial1
3CompletedTreatmentCholestatic Liver Disease1
3CompletedTreatmentChronic Hepatitis C Virus (HCV) Infection1
3CompletedTreatmentIntrahepatic Cholestasis / Pregnancy1
3CompletedTreatmentLiver Cirrhosis, Biliary2
3CompletedTreatmentPrimary Biliary Cirrhosis (PBC)1
3RecruitingPreventionGallstone formation1
3RecruitingTreatmentPrimary Biliary Cirrhosis (PBC)5
3WithdrawnTreatmentIntrahepatic Cholestasis of Pregnancy1
4CompletedBasic ScienceObesity, Severe1
4CompletedPreventionShort Bowel Syndrome (SBS)1
4CompletedTreatmentCholecystolithiasis1
4CompletedTreatmentPrimary Biliary Cirrhosis (PBC)1
4Not Yet RecruitingTreatmentEnd-Stage Kidney Disease1
4Not Yet RecruitingTreatmentFunctional Dyspepsia1
4RecruitingTreatmentDiarrhea1
4TerminatedPreventionGallstone formation / Hemolytic Disorders1
4TerminatedTreatmentGallstone formation1
4Unknown StatusTreatmentChronic Liver Diseases (CLD) / Type 2 Diabetes Mellitus1
4Unknown StatusTreatmentHepatitis, Toxic1
Not AvailableCompletedBasic ScienceGastroesophageal Reflux Disease1
Not AvailableCompletedBasic ScienceNon-Alcoholic Fatty Liver Disease (NAFLD) / Obesity, Morbid1
Not AvailableCompletedTreatmentCholestasis / Ischemia-Reperfusion Injury / Transplantation, Liver1
Not AvailableCompletedTreatmentCystic Fibrosis (CF)1
Not AvailableCompletedTreatmentFibrosis, Liver1
Not AvailableRecruitingNot AvailablePrimary Biliary Cholangitis (PBC)1
Not AvailableRecruitingPreventionObesity, Morbid1
Not AvailableRecruitingTreatmentAtypical Teratoid/Rhabdoid Tumor (AT/RT) / CNS Tumors / Ewing's Family Tumors / Germ Cell Tumors / Hepatoblastomas / Medulloblastomas / Primary Malignant Brain Neoplasms / Renal Tumors / Retinoblastoma / Rhabdomyosarcomas / Soft Tissue Sarcoma (STS) / Supra-tentorial Primative Neuro-Ectodermal Tumor (PNET)1
Not AvailableRecruitingTreatmentCholangitis / Cholestasis / Hepatitis, Autoimmune / Liver Cirrhosis, Biliary1
Not AvailableRecruitingTreatmentNon-Alcoholic Steatohepatitis1
Not AvailableRecruitingTreatmentPrimary Biliary Cirrhosis (PBC)1
Not AvailableRecruitingTreatmentPrimary Biliary Cirrhosis (PBC) / Ursodeoxycholic Acid1
Not AvailableTerminatedTreatmentAdrenoleukodystrophy / Bifunctional Enzyme Deficiency / Cerebrohepatorenal syndrome / Infantile Refsum's Disease1

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
FormRouteStrength
PasteDental
TabletOral250 mg
TabletOral500 mg
CapsuleOral300 mg/1
TabletOral250 mg/1
TabletOral500 mg/1
Tablet, film coatedOral250 mg/1
Tablet, film coatedOral500 mg/1
CapsuleOral250 mg
Prices
Unit descriptionCostUnit
Urso forte 500 mg tablet6.3USD tablet
Actigall 300 mg capsule5.52USD capsule
Ursodiol 500 mg tablet4.75USD tablet
Urso 250 mg tablet4.41USD tablet
Urso 250 250 mg tablet3.55USD tablet
Urso Ds 500 mg Tablet2.69USD tablet
Ursodiol 250 mg tablet2.68USD tablet
Pms-Ursodiol C 500 mg Tablet1.75USD tablet
Urso 250 mg Tablet1.42USD tablet
Pms-Ursodiol C 250 mg Tablet0.92USD tablet
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents
Not Available

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)203 °CPhysProp
water solubility20 mg/L (at 20 °C)YALKOWSKY,SH & DANNENFELSER,RM (1992)
logP3.00RODA,A ET AL. (1990)
Predicted Properties
PropertyValueSource
Water Solubility0.0197 mg/mLALOGPS
logP3.01ALOGPS
logP3.71ChemAxon
logS-4.3ALOGPS
pKa (Strongest Acidic)4.6ChemAxon
pKa (Strongest Basic)-0.54ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area77.76 Å2ChemAxon
Rotatable Bond Count4ChemAxon
Refractivity109.27 m3·mol-1ChemAxon
Polarizability46.33 Å3ChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.9766
Blood Brain Barrier+0.9288
Caco-2 permeable+0.73
P-glycoprotein substrateSubstrate0.6648
P-glycoprotein inhibitor INon-inhibitor0.8737
P-glycoprotein inhibitor IIInhibitor0.5368
Renal organic cation transporterNon-inhibitor0.8537
CYP450 2C9 substrateNon-substrate0.7818
CYP450 2D6 substrateNon-substrate0.9115
CYP450 3A4 substrateSubstrate0.7407
CYP450 1A2 substrateNon-inhibitor0.9045
CYP450 2C9 inhibitorNon-inhibitor0.9456
CYP450 2D6 inhibitorNon-inhibitor0.9781
CYP450 2C19 inhibitorNon-inhibitor0.9707
CYP450 3A4 inhibitorNon-inhibitor0.8405
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9563
Ames testNon AMES toxic0.8794
CarcinogenicityNon-carcinogens0.9329
BiodegradationNot ready biodegradable0.992
Rat acute toxicity2.5624 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9622
hERG inhibition (predictor II)Non-inhibitor0.7246
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available
LC-MS/MS Spectrum - LC-ESI-qTof , PositiveLC-MS/MSNot Available
LC-MS/MS Spectrum - LC-ESI-IT , negativeLC-MS/MSsplash10-00di-0029000000-54929e08fef761ba2b28
MS/MS Spectrum - , positiveLC-MS/MSsplash10-0002-2911000000-eec2b269eeb08a30ac6e

Taxonomy

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
Dihydroxy bile acid, alcohol, or derivatives / 3-hydroxysteroid / 7-hydroxysteroid / 7-alpha-hydroxysteroid / 3-alpha-hydroxysteroid / Hydroxysteroid / Cyclic alcohol / Secondary alcohol / Carboxylic acid derivative / Carboxylic acid
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)

Targets

Kind
Protein
Organism
Human
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
  1. 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]
  2. 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]
  3. 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]
Details
2. Bile acid receptor
Kind
Protein
Organism
Human
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
  1. 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
Human
Pharmacological action
Unknown
Actions
Inhibitor
Inducer
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
  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256]
  2. 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
Human
Pharmacological action
Unknown
Actions
Substrate
Inhibitor
Inducer
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
  1. 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. Epub 2001 Aug 16. [PubMed:11509573]
  2. 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]
  3. 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
Human
Pharmacological action
Unknown
Actions
Substrate
Inhibitor
Inducer
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
  1. 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]
  2. 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]
  3. 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]
  4. 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
Human
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
  1. 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]
  2. 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
Human
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
  1. 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
Human
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
  1. 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]
  2. 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]
  3. 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
Human
Pharmacological action
Unknown
Actions
Substrate
Inhibitor
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
  1. 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]
  2. 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 25, 2018 03:14