Ursodeoxycholic acid

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
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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Associated Conditions
Indication TypeIndicationCombined Product DetailsApproval LevelAge GroupPatient CharacteristicsDose Form
Treatment ofGallstones•••••••••••••••••••• ••••••••••••••••••••••
Treatment ofPrimary biliary cholangitis••••••••••••••••••
Prevention ofGallstone formation•••••••••••••••••••• •••••• •••••••••••
Contraindications & Blackbox Warnings
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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

TargetActionsOrganism
AAldo-keto reductase family 1 member C2
inhibitor
Humans
UBile acid receptor
partial agonist
Humans
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

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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

The estimated half-life ranges from 3.5 to 5.8 days.3,7

Clearance

Not Available

Adverse Effects
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Toxicity

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.
DrugInteraction
AbciximabThe risk or severity of adverse effects can be increased when Abciximab is combined with Ursodeoxycholic acid.
AcenocoumarolThe risk or severity of bleeding and bruising can be increased when Acenocoumarol is combined with Ursodeoxycholic acid.
Acetylsalicylic acidThe risk or severity of adverse effects can be increased when Acetylsalicylic acid is combined with Ursodeoxycholic acid.
AlteplaseThe risk or severity of bleeding and bruising can be increased when Alteplase is combined with Ursodeoxycholic acid.
Aluminium phosphateAluminium phosphate can cause a decrease in the absorption of Ursodeoxycholic acid resulting in a reduced serum concentration and potentially a decrease in efficacy.
Food Interactions
  • Take with food.

Products

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Product Images
International/Other Brands
Cholit-ursan / Delursan / Destolit / Deursil / Litursol / Solutrat / Ursacol / Ursochol / Ursolvan
Brand Name Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
ActigallCapsule300 mg/1OralActavis Pharma, Inc.1987-12-312020-02-29US flag
ActigallCapsule300 mg/1OralAllergan, Inc.1987-12-312021-09-30US flag
Gln-ursodiolTablet500 mgOralGlenmark Pharmaceuticals, Inc2016-04-04Not applicableCanada flag
Gln-ursodiolTablet250 mgOralGlenmark Pharmaceuticals, Inc2016-04-04Not applicableCanada flag
Nra-ursodiolTablet500 mgOralNora Pharma IncNot applicableNot applicableCanada flag
Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
Ag-ursodiolTablet250 mgOralAngita Pharma Inc.2021-04-30Not applicableCanada flag
Ag-ursodiolTablet500 mgOralAngita Pharma Inc.2021-04-30Not applicableCanada flag
Dom-ursodiol CTablet500 mgOralDominion Pharmacal2006-08-17Not applicableCanada flag
Dom-ursodiol CTablet250 mgOralDominion Pharmacal2006-08-17Not applicableCanada flag
Jamp-ursodiolTablet500 mgOralJamp Pharma Corporation2018-09-28Not applicableCanada flag
Over the Counter Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
UrusaCapsule250 mg/1OralOASIS TRADING2018-11-15Not applicableUS flag
Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing EndRegionImage
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 flag
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 flag
Festal PlusUrsodeoxycholic acid (10 mg/1) + Dimethicone (30 mg/1) + Pancrelipase (315 mg/1)TabletOralOASIS TRADING2018-11-21Not applicableUS flag
Unapproved/Other Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing EndRegionImage
Festal PlusUrsodeoxycholic acid (10 mg/1) + Dimethicone (30 mg/1) + Pancrelipase (315 mg/1)TabletOralOASIS TRADING2018-11-21Not applicableUS flag
UrusaUrsodeoxycholic acid (250 mg/1)CapsuleOralOASIS TRADING2018-11-15Not applicableUS flag

Categories

ATC Codes
A05AA02 — Ursodeoxycholic acid
Drug Categories
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
  1. Achufusi TGO, Safadi AO, Mahabadi N: Ursodeoxycholic Acid. . [Article]
  2. Authors unspecified: Ursodiol (Ursodeoxycholic Acid). . [Article]
  3. 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]
  4. 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]
  5. 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]
  6. 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]
  7. 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]
  8. Hofmann AF: Pharmacology of ursodeoxycholic acid, an enterohepatic drug. Scand J Gastroenterol Suppl. 1994;204:1-15. doi: 10.3109/00365529409103618. [Article]
  9. FDA Approved Drug Products: URSO 250 and URSO FORTE (ursodiol) tablets, for oral use [Link]
  10. Medisca: Ursodiol MSDS [Link]
  11. DailyMed Label: URSODIOL Oral Capsules [Link]
Human Metabolome Database
HMDB0000946
KEGG Drug
D00734
KEGG Compound
C07880
PubChem Compound
31401
PubChem Substance
46508795
ChemSpider
29131
BindingDB
53721
RxNav
11065
ChEBI
9907
ChEMBL
CHEMBL1551
ZINC
ZINC000003914809
Therapeutic Targets Database
DNC000420
PharmGKB
PA451837
PDBe Ligand
IU5
Wikipedia
Ursodeoxycholic_acid

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
4Active Not RecruitingPreventionCoronavirus Disease 2019 (COVID‑19) / Surgery, Cardiac1
4CompletedBasic ScienceObesity, Severe1
4CompletedPreventionShort Bowel Syndrome (SBS)1
4CompletedTreatment(NAFLD) / Type 2 Diabetes Mellitus1
4CompletedTreatmentCholecystolithiasis1

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
CapsuleOral225 MG
CapsuleOral450 MG
Capsule, extended releaseOral450 MG
Capsule, delayed release
PasteDental
Capsule, extended releaseOral
TabletOral225 MG
Tablet, extended releaseOral450 MG
CapsuleOral300 MG
CapsuleOral50 MG
Capsule, extended releaseOral225 MG
Tablet, film coatedOral
CapsuleOral
TabletOral
Capsule, coatedOral300 mg
CapsuleOral250.000 mg
CapsuleOral500 MG
CapsuleOral150 MG
TabletOral500 MG
TabletOral150 MG
TabletOral300 MG
Tablet, delayed releaseOral225 MG
Tablet, delayed releaseOral450 MG
TabletOral450 MG
TabletOral50 MG
TabletOral600 mg
CapsuleOral250 mg
CapsuleOral125 MG
Granule, for suspensionOral150 MG
Granule, for suspensionOral300 MG
TabletOral250 mg
Tablet, film coatedOral250 MG
Tablet, film coatedOral400 MG
CapsuleOral100 MG
Solution / dropsOral254 MG/ML
SyrupOral31.7 MG/ML
CapsuleOral300 mg/1
Powder1 g/1g
TabletOral250 mg/1
TabletOral500 mg/1
Tablet, film coatedOral250 mg/1
Tablet, film coatedOral500 mg/1
CapsuleOral200 mg/1
CapsuleOral400 mg/1
SuspensionOral250 mg/5ml
Tablet, film coatedOral500 MG
Tablet, film coatedOral500.00 mg
TabletOral500.000 mg
Tablet, coatedOral500 mg
Capsule, coatedOral250 mg
TabletOral
Tablet, film coatedOral750 mg
Solution / dropsOral25 G/100ML
SyrupOral3 G/100ML
CapsuleOral250 mg/1
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)200-205https://www.medisca.com/NDC_SPECS/MUS/1987/MSDS/1987.pdf
logP3https://www.medisca.com/NDC_SPECS/MUS/1987/MSDS/1987.pdf
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
Polarizability46.42 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-MSsplash10-01rt-0419000000-6a92f910581240163a99
LC-MS/MS Spectrum - LC-ESI-qTof , PositiveLC-MS/MSsplash10-0a4l-3940000000-cf90a6f216d592e2ad4c
LC-MS/MS Spectrum - LC-ESI-IT , negativeLC-MS/MSsplash10-00di-0029000000-54929e08fef761ba2b28
MS/MS Spectrum - , positiveLC-MS/MSsplash10-0002-2911000000-eec2b269eeb08a30ac6e
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-002f-0019000000-cc60cb157a6a09e463ec
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-0006-0009000000-d1f986325aed82b811c5
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-0006-0009000000-28f0706ed7c585f84229
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-0a4i-3139000000-4639b15eea0cf066cfcb
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-0096-1019000000-30e5463bbeadb794d43e
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-0f7k-4791000000-c2d40e5f723f22c3f4f1
Predicted 1H NMR Spectrum1D NMRNot Applicable
Predicted 13C NMR Spectrum1D NMRNot Applicable
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-197.0299715
predicted
DarkChem Lite v0.1.0
[M-H]-194.8766715
predicted
DarkChem Lite v0.1.0
[M-H]-195.2075715
predicted
DarkChem Lite v0.1.0
[M-H]-200.8897715
predicted
DarkChem Lite v0.1.0
[M-H]-202.25305
predicted
DeepCCS 1.0 (2019)
[M+H]+194.0692715
predicted
DarkChem Lite v0.1.0
[M+H]+193.8139715
predicted
DarkChem Lite v0.1.0
[M+H]+194.3308715
predicted
DarkChem Lite v0.1.0
[M+H]+200.9399715
predicted
DarkChem Lite v0.1.0
[M+H]+204.14848
predicted
DeepCCS 1.0 (2019)
[M+Na]+192.5462715
predicted
DarkChem Lite v0.1.0
[M+Na]+193.1903715
predicted
DarkChem Lite v0.1.0
[M+Na]+193.6992715
predicted
DarkChem Lite v0.1.0
[M+Na]+198.2678715
predicted
DarkChem Lite v0.1.0
[M+Na]+210.09752
predicted
DeepCCS 1.0 (2019)

Targets

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Kind
Protein
Organism
Humans
Pharmacological action
Yes
Actions
Inhibitor
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. [Article]
  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. [Article]
  3. Amaral JD, Sola S, Steer CJ, Rodrigues CM: Role of nuclear steroid receptors in apoptosis. Curr Med Chem. 2009;16(29):3886-902. [Article]
  4. Halim M, Yee DJ, Sames D: Imaging induction of cytoprotective enzymes in intact human cells: coumberone, a metabolic reporter for human AKR1C enzymes reveals activation by panaxytriol, an active component of red ginseng. J Am Chem Soc. 2008 Oct 29;130(43):14123-8. doi: 10.1021/ja801245y. Epub 2008 Oct 1. [Article]
  5. Burczynski ME, Lin HK, Penning TM: Isoform-specific induction of a human aldo-keto reductase by polycyclic aromatic hydrocarbons (PAHs), electrophiles, and oxidative stress: implications for the alternative pathway of PAH activation catalyzed by human dihydrodiol dehydrogenase. Cancer Res. 1999 Feb 1;59(3):607-14. [Article]
  6. Martin N, Salazar-Cardozo C, Vercamer C, Ott L, Marot G, Slijepcevic P, Abbadie C, Pluquet O: Identification of a gene signature of a pre-transformation process by senescence evasion in normal human epidermal keratinocytes. Mol Cancer. 2014 Jun 14;13:151. doi: 10.1186/1476-4598-13-151. [Article]
Details
2. Bile acid receptor
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
  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. [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:
References
  1. 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]
  2. 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
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. doi: 10.1074/jbc.M106340200. Epub 2001 Aug 16. [Article]
  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. [Article]
  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. [Article]
Kind
Protein
Organism
Humans
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. [Article]
  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. [Article]
  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. [Article]
  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. [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
  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. [Article]
  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. [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
  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. [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
  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. [Article]
  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. [Article]
  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. [Article]
Kind
Protein
Organism
Humans
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. [Article]
  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. [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
  1. Achufusi TGO, Safadi AO, Mahabadi N: Ursodeoxycholic Acid. . [Article]
  2. Medina JF, Martinez-Anso, Vazquez JJ, Prieto J: Decreased anion exchanger 2 immunoreactivity in the liver of patients with primary biliary cirrhosis. Hepatology. 1997 Jan;25(1):12-7. doi: 10.1002/hep.510250104. [Article]

Drug created at August 29, 2007 14:57 / Updated at February 27, 2024 23:09