Ursodeoxycholic acid

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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

Similar Structures

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

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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 Type	Indication	Approval Level	Patient Characteristics	Dose Form
Treatment of	Gallstones	••••••••••••	•••••••• •••••••••••••••	•••••••
Treatment of	Primary biliary cholangitis	••••••••••••		••••••
Prevention of	Gallstone 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

Target	Actions	Organism
AAldo-keto reductase family 1 member C2	inhibitor	Humans
ABiliverdin reductase A	activator	Humans
ASolute carrier family 23 member 2	activator	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

Hover over products below to view reaction partners

Ursodeoxycholic acid
- Lithocholic acid
- 7-oxo-lithocholic acid
  - Chenodeoxycholic acid

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.

Drug	Interaction
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Abciximab	The risk or severity of adverse effects can be increased when Abciximab is combined with Ursodeoxycholic acid.
Acenocoumarol	The risk or severity of bleeding and bruising can be increased when Acenocoumarol is combined with Ursodeoxycholic acid.
Acetylsalicylic acid	The risk or severity of adverse effects can be increased when Acetylsalicylic acid is combined with Ursodeoxycholic acid.
Alteplase	The risk or severity of bleeding and bruising can be increased when Alteplase is combined with Ursodeoxycholic acid.
Aluminium phosphate	Aluminium phosphate can cause a decrease in the absorption of Ursodeoxycholic acid resulting in a reduced serum concentration and potentially a decrease in efficacy.

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

Name	Dosage	Strength	Route	Labeller	Marketing Start	Marketing End
Actigall	Capsule	300 mg/1	Oral	Actavis Pharma, Inc.	1987-12-31	2020-02-29
Actigall	Capsule	300 mg/1	Oral	Allergan, Inc.	1987-12-31	2021-09-30
Gln-ursodiol	Tablet	500 mg	Oral	Glenmark Pharmaceuticals, Inc	2016-04-04	Not applicable
Gln-ursodiol	Tablet	250 mg	Oral	Glenmark Pharmaceuticals, Inc	2016-04-04	Not applicable
Nra-ursodiol	Tablet	500 mg	Oral	Nora Pharma Inc	2024-07-17	Not applicable

Generic Prescription Products

Name	Dosage	Strength	Route	Labeller	Marketing Start	Marketing End
Ag-ursodiol	Tablet	250 mg	Oral	Angita Pharma Inc.	2021-04-30	Not applicable
Ag-ursodiol	Tablet	500 mg	Oral	Angita Pharma Inc.	2021-04-30	Not applicable
Dom-ursodiol C	Tablet	500 mg	Oral	Dominion Pharmacal	2006-08-17	Not applicable
Dom-ursodiol C	Tablet	250 mg	Oral	Dominion Pharmacal	2006-08-17	Not applicable
Jamp-ursodiol	Tablet	500 mg	Oral	Jamp Pharma Corporation	2018-09-28	Not applicable

Over the Counter Products

Name	Dosage	Strength	Route	Labeller	Marketing Start	Marketing End	Region	Image
Urusa	Capsule	250 mg/1	Oral	OASIS TRADING	2018-11-15	Not applicable

Mixture Products

Name	Ingredients	Dosage	Route	Labeller	Marketing Start	Marketing End
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
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
Festal Plus	Ursodeoxycholic acid (10 mg/1) + Dimethicone (30 mg/1) + Pancrelipase (315 mg/1)	Tablet	Oral	OASIS TRADING	2018-11-21	Not applicable

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
Urusa	Ursodeoxycholic acid (250 mg/1)	Capsule	Oral	OASIS TRADING	2018-11-15	Not applicable

Chemical Identifiers

UNII: 724L30Y2QR
CAS number: 128-13-2
InChI Key: RUDATBOHQWOJDD-UZVSRGJWSA-N
InChI: InChI=1S/C24H40O4/c1-14(4-7-21(27)28)17-5-6-18-22-19(9-11-24(17,18)3)23(2)10-8-16(25)12-15(23)13-20(22)26/h14-20,22,25-26H,4-13H2,1-3H3,(H,27,28)/t14-,15+,16-,17-,18+,19+,20+,22+,23+,24-/m1/s1
IUPAC Name: (4R)-4-[(1R,3aS,3bR,4S,5aS,7R,9aS,9bS,11aR)-4,7-dihydroxy-9a,11a-dimethyl-hexadecahydro-1H-cyclopenta[a]phenanthren-1-yl]pentanoic acid
SMILES: [H][C@@]1(CC[C@@]2([H])[C@]3([H])[C@@H](O)C[C@]4([H])C[C@H](O)CC[C@]4(C)[C@@]3([H])CC[C@]12C)[C@H](C)CCC(O)=O

References

Synthesis Reference

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

US4379093

General References

Achufusi TGO, Safadi AO, Mahabadi N: Ursodeoxycholic Acid. . [Article]
Authors unspecified: Ursodiol (Ursodeoxycholic Acid). . [Article]
Kotb MA: Molecular mechanisms of ursodeoxycholic acid toxicity & side effects: ursodeoxycholic acid freezes regeneration & induces hibernation mode. Int J Mol Sci. 2012;13(7):8882-8914. doi: 10.3390/ijms13078882. Epub 2012 Jul 17. [Article]
Trampert DC, van de Graaf SFJ, Jongejan A, Oude Elferink RPJ, Beuers U: Hepatobiliary acid-base homeostasis: Insights from analogous secretory epithelia. J Hepatol. 2021 Feb;74(2):428-441. doi: 10.1016/j.jhep.2020.10.010. Epub 2020 Oct 24. [Article]
Festi D, Montagnani M, Azzaroli F, Lodato F, Mazzella G, Roda A, Di Biase AR, Roda E, Simoni P, Colecchia A: Clinical efficacy and effectiveness of ursodeoxycholic acid in cholestatic liver diseases. Curr Clin Pharmacol. 2007 May;2(2):155-77. doi: 10.2174/157488407780598171. [Article]
Paumgartner G, Beuers U: Ursodeoxycholic acid in cholestatic liver disease: mechanisms of action and therapeutic use revisited. Hepatology. 2002 Sep;36(3):525-31. doi: 10.1053/jhep.2002.36088. [Article]
Angulo P: Use of ursodeoxycholic acid in patients with liver disease. Curr Gastroenterol Rep. 2002 Feb;4(1):37-44. doi: 10.1007/s11894-002-0036-9. [Article]
Hofmann AF: Pharmacology of ursodeoxycholic acid, an enterohepatic drug. Scand J Gastroenterol Suppl. 1994;204:1-15. doi: 10.3109/00365529409103618. [Article]
FDA Approved Drug Products: URSO 250 and URSO FORTE (ursodiol) tablets, for oral use [Link]
Medisca: Ursodiol MSDS [Link]
DailyMed Label: URSODIOL Oral Capsules [Link]

External Links

Human Metabolome Database: HMDB0000946
KEGG Drug: D00734
KEGG Compound: C07880
PubChem Compound: 31401
PubChem Substance: 46508795
ChemSpider: 29131
BindingDB: 53721
RxNav: 11065
ChEBI: 9907
ChEMBL: CHEMBL1551
ZINC: ZINC000003914809
Therapeutic Targets Database: DNC000420
PharmGKB: PA451837
PDBe Ligand: IU5
Wikipedia: Ursodeoxycholic_acid

Clinical Trials

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Phase	Status	Purpose	Conditions	Count	Start Date	Why Stopped	100+ additional columns
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Not Available	Completed	Not Available	Primary Biliary Cholangitis	1	somestatus	stop reason	just information to hide
Not Available	Completed	Basic Science	Endoplasmic Reticulum Stress / HIV Related Insulin Resistance / Protease Inhibitor Related Insulin Resistance	1	somestatus	stop reason	just information to hide
Not Available	Completed	Basic Science	Fatty Liver, Non-alcoholic Fatty Liver Disease, NAFLD / Obesity, Morbid	1	somestatus	stop reason	just information to hide
Not Available	Completed	Basic Science	Gastro-esophageal Reflux Disease (GERD)	1	somestatus	stop reason	just information to hide
Not Available	Completed	Other	Atypical teratoid/rhabdoid tumour of CNS / Central Nervous System Neoplasm / Ewing's Sarcoma / Germ Cell Neoplasms / Hepatoblastomas / Medulloblastomas / Primary Malignant Brain Neoplasms / Renal Neoplasms / Retinoblastoma / Rhabdomyosarcomas / Soft Tissue Sarcoma / Supra-tentorial Primative Neuro-Ectodermal Tumor (PNET)	1	somestatus	stop reason	just information to hide

Pharmacoeconomics

Manufacturers

Not Available

Packagers

Amerisource Health Services Corp.
Axcan Pharma Inc.
Cardinal Health
Corepharma LLC
DispenseXpress Inc.
Giuliani SPA
Heartland Repack Services LLC
Lannett Co. Inc.
Mckesson Corp.
Murfreesboro Pharmaceutical Nursing Supply
Mylan
Novartis AG
Patheon Inc.
Pharmaceutical Utilization Management Program VA Inc.
Physicians Total Care Inc.
Prasco Labs
Qualitest
Resource Optimization and Innovation LLC
Rising Pharmaceuticals
Schering Corp.
Southwood Pharmaceuticals
Summit Pharmaceuticals
Teva Pharmaceutical Industries Ltd.
UDL Laboratories
Watson Pharmaceuticals

Dosage Forms

Form	Route	Strength
Capsule	Oral	225 MG
Capsule	Oral	450 MG
Capsule, extended release	Oral	450 MG
Capsule, delayed release
Paste	Dental
Capsule, extended release	Oral
Capsule	Oral
Tablet	Oral	225 MG
Tablet, extended release	Oral	450 MG
Capsule	Oral	300 MG
Capsule	Oral	50 MG
Capsule, extended release	Oral	225 MG
Tablet, film coated	Oral
Tablet	Oral
Capsule, coated	Oral	300 mg
Capsule	Oral	250.000 mg
Capsule	Oral	500 MG
Capsule	Oral	150 MG
Tablet	Oral	500 MG
Tablet, delayed release	Oral	225 MG
Tablet, delayed release	Oral	450 MG
Tablet	Oral	450 MG
Tablet	Oral	50 MG
Tablet	Oral	600 mg
Capsule	Oral	250 mg
Capsule	Oral	125 MG
Granule, for suspension	Oral	150 MG
Granule, for suspension	Oral	300 MG
Tablet	Oral	250 mg
Tablet, film coated	Oral	250 MG
Tablet, film coated	Oral	400 MG
Capsule	Oral	100 MG
Solution / drops	Oral	254 MG/ML
Syrup	Oral	31.7 MG/ML
Tablet	Oral	150 mg
Tablet	Oral	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	Oral	250 mg/5ml
Tablet, film coated	Oral	500 MG
Tablet, film coated	Oral	500.00 mg
Tablet	Oral	500.000 mg
Tablet, coated	Oral	500 mg
Capsule, coated	Oral	250 mg
Tablet	Oral
Tablet, film coated	Oral	750 mg
Solution / drops	Oral	25 G/100ML
Syrup	Oral	3 G/100ML
Capsule	Oral	250 mg/1

Prices

Unit description	Cost	Unit
Urso forte 500 mg tablet	6.3USD	tablet
Actigall 300 mg capsule	5.52USD	capsule
Ursodiol 500 mg tablet	4.75USD	tablet
Urso 250 mg tablet	4.41USD	tablet
Urso 250 250 mg tablet	3.55USD	tablet
Urso Ds 500 mg Tablet	2.69USD	tablet
Ursodiol 250 mg tablet	2.68USD	tablet
Pms-Ursodiol C 500 mg Tablet	1.75USD	tablet
Urso 250 mg Tablet	1.42USD	tablet
Pms-Ursodiol C 250 mg Tablet	0.92USD	tablet

DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.

Patents

Not Available

Properties

State

Solid

Experimental Properties

Property	Value	Source
melting point (°C)	200-205	https://www.medisca.com/NDC_SPECS/MUS/1987/MSDS/1987.pdf
logP	3	https://www.medisca.com/NDC_SPECS/MUS/1987/MSDS/1987.pdf

Predicted Properties

Property	Value	Source
Water Solubility	0.0197 mg/mL	ALOGPS
logP	3.01	ALOGPS
logP	3.71	Chemaxon
logS	-4.3	ALOGPS
pKa (Strongest Acidic)	4.6	Chemaxon
pKa (Strongest Basic)	-0.54	Chemaxon
Physiological Charge	-1	Chemaxon
Hydrogen Acceptor Count	4	Chemaxon
Hydrogen Donor Count	3	Chemaxon
Polar Surface Area	77.76 Å²	Chemaxon
Rotatable Bond Count	4	Chemaxon
Refractivity	109.27 m³·mol^-1	Chemaxon
Polarizability	46.42 Å³	Chemaxon
Number of Rings	4	Chemaxon
Bioavailability	1	Chemaxon
Rule of Five	Yes	Chemaxon
Ghose Filter	Yes	Chemaxon
Veber's Rule	No	Chemaxon
MDDR-like Rule	No	Chemaxon

Predicted ADMET Features

Property	Value	Probability
Human Intestinal Absorption	+	0.9766
Blood Brain Barrier	+	0.9288
Caco-2 permeable	+	0.73
P-glycoprotein substrate	Substrate	0.6648
P-glycoprotein inhibitor I	Non-inhibitor	0.8737
P-glycoprotein inhibitor II	Inhibitor	0.5368
Renal organic cation transporter	Non-inhibitor	0.8537
CYP450 2C9 substrate	Non-substrate	0.7818
CYP450 2D6 substrate	Non-substrate	0.9115
CYP450 3A4 substrate	Substrate	0.7407
CYP450 1A2 substrate	Non-inhibitor	0.9045
CYP450 2C9 inhibitor	Non-inhibitor	0.9456
CYP450 2D6 inhibitor	Non-inhibitor	0.9781
CYP450 2C19 inhibitor	Non-inhibitor	0.9707
CYP450 3A4 inhibitor	Non-inhibitor	0.8405
CYP450 inhibitory promiscuity	Low CYP Inhibitory Promiscuity	0.9563
Ames test	Non AMES toxic	0.8794
Carcinogenicity	Non-carcinogens	0.9329
Biodegradation	Not ready biodegradable	0.992
Rat acute toxicity	2.5624 LD50, mol/kg	Not applicable
hERG inhibition (predictor I)	Weak inhibitor	0.9622
hERG inhibition (predictor II)	Non-inhibitor	0.7246

ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)

Not Available

Spectra

Spectrum	Spectrum Type	Splash Key
Predicted GC-MS Spectrum - GC-MS	Predicted GC-MS	splash10-01rt-0419000000-6a92f910581240163a99
LC-MS/MS Spectrum - LC-ESI-qTof , Positive	LC-MS/MS	splash10-0a4l-3940000000-cf90a6f216d592e2ad4c
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
Predicted MS/MS Spectrum - 10V, Positive (Annotated)	Predicted LC-MS/MS	splash10-002f-0019000000-cc60cb157a6a09e463ec
Predicted MS/MS Spectrum - 10V, Negative (Annotated)	Predicted LC-MS/MS	splash10-0006-0009000000-d1f986325aed82b811c5
Predicted MS/MS Spectrum - 20V, Negative (Annotated)	Predicted LC-MS/MS	splash10-0006-0009000000-28f0706ed7c585f84229
Predicted MS/MS Spectrum - 20V, Positive (Annotated)	Predicted LC-MS/MS	splash10-0a4i-3139000000-4639b15eea0cf066cfcb
Predicted MS/MS Spectrum - 40V, Negative (Annotated)	Predicted LC-MS/MS	splash10-0096-1019000000-30e5463bbeadb794d43e
Predicted MS/MS Spectrum - 40V, Positive (Annotated)	Predicted LC-MS/MS	splash10-0f7k-4791000000-c2d40e5f723f22c3f4f1
Predicted 1H NMR Spectrum	1D NMR	Not Applicable
Predicted 13C NMR Spectrum	1D NMR	Not Applicable

Chromatographic Properties

Collision Cross Sections (CCS)

Adduct	CCS Value (Å²)	Source type	Source
[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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Details1. Aldo-keto reductase family 1 member C2

Kind: Protein
Organism: Humans
Pharmacological action: Yes
Actions: Inhibitor

General Function: Cytosolic aldo-keto reductase that catalyzes the NADH and NADPH-dependent reduction of ketosteroids to hydroxysteroids (PubMed:19218247). Most probably acts as a reductase in vivo since the oxidase activity measured in vitro is inhibited by physiological concentrations of NADPH (PubMed:14672942). Displays a broad positional specificity acting on positions 3, 17 and 20 of steroids and regulates the metabolism of hormones like estrogens and androgens (PubMed:10998348). 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 androgen 5-alpha-dihydrotestosterone (5-alpha-DHT) to 5-alpha-androstane-3-alpha,17-beta-diol (3-alpha-diol) (PubMed:15929998, PubMed:17034817, PubMed:17442338, PubMed:8573067). Also specifically able to produce 17beta-hydroxy-5alpha-androstan-3-one/5alphaDHT (PubMed:10998348). May also reduce conjugated steroids such as 5alpha-dihydrotestosterone sulfate (PubMed:19218247). Displays affinity for bile acids (PubMed:8486699)
Specific Function: Aldose reductase (nadph) activity
Gene Name: AKR1C2
Uniprot ID: P52895
Uniprot Name: Aldo-keto reductase family 1 member C2
Molecular Weight: 36734.97 Da

References

Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [Article]
Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [Article]
Amaral JD, Sola S, Steer CJ, Rodrigues CM: Role of nuclear steroid receptors in apoptosis. Curr Med Chem. 2009;16(29):3886-902. [Article]
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]
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]
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]

Details2. Biliverdin reductase A

Kind: Protein
Organism: Humans
Pharmacological action: Yes
Actions: Activator

General Function: Reduces the gamma-methene bridge of the open tetrapyrrole, biliverdin IXalpha, to bilirubin with the concomitant oxidation of a NADH or NADPH cofactor (PubMed:10858451, PubMed:7929092, PubMed:8424666, PubMed:8631357). Does not reduce bilirubin IXbeta (PubMed:10858451). Uses the reactants NADH or NADPH depending on the pH; NADH is used at the acidic pH range (6-6.9) and NADPH at the alkaline range (8.5-8.7) (PubMed:7929092, PubMed:8424666, PubMed:8631357). NADPH, however, is the probable reactant in biological systems (PubMed:7929092)
Specific Function: Biliberdin reductase nad+ activity
Gene Name: BLVRA
Uniprot ID: P53004
Uniprot Name: Biliverdin reductase A
Molecular Weight: 33428.225 Da

References

Zhou Y, Zhang Y, Zhao D, Yu X, Shen X, Zhou Y, Wang S, Qiu Y, Chen Y, Zhu F: TTD: Therapeutic Target Database describing target druggability information. Nucleic Acids Res. 2024 Jan 5;52(D1):D1465-D1477. doi: 10.1093/nar/gkad751. [Article]

Details3. Solute carrier family 23 member 2

Kind: Protein
Organism: Humans
Pharmacological action: Yes
Actions: Activator

General Function: Sodium/ascorbate cotransporter (PubMed:10471399, PubMed:10556521). Mediates electrogenic uptake of vitamin C, with a stoichiometry of 2 Na(+) for each ascorbate (PubMed:10471399)
Specific Function: L-ascorbate
Gene Name: SLC23A2
Uniprot ID: Q9UGH3
Uniprot Name: Solute carrier family 23 member 2
Molecular Weight: 70336.235 Da

References

Zhou Y, Zhang Y, Zhao D, Yu X, Shen X, Zhou Y, Wang S, Qiu Y, Chen Y, Zhu F: TTD: Therapeutic Target Database describing target druggability information. Nucleic Acids Res. 2024 Jan 5;52(D1):D1465-D1477. doi: 10.1093/nar/gkad751. [Article]

Property	Measurement	pH	Temperature (°C)	References
EC 50 (nM)	>50000	N/A	N/A	A29696

Details4. Bile acid receptor

Kind: Protein
Organism: Humans
Pharmacological action: Unknown
Actions: Partial agonist

General Function: Ligand-activated transcription factor. Receptor for bile acids (BAs) such as chenodeoxycholic acid (CDCA), lithocholic acid, deoxycholic acid (DCA) and allocholic acid (ACA). Plays a essential role in BA homeostasis through the regulation of genes involved in BA synthesis, conjugation and enterohepatic circulation. Also regulates lipid and glucose homeostasis and is involved innate immune response (PubMed:10334992, PubMed:10334993, PubMed:21383957, PubMed:22820415). The FXR-RXR heterodimer binds predominantly to farnesoid X receptor response elements (FXREs) containing two inverted repeats of the consensus sequence 5'-AGGTCA-3' in which the monomers are spaced by 1 nucleotide (IR-1) but also to tandem repeat DR1 sites with lower affinity, and can be activated by either FXR or RXR-specific ligands. It is proposed that monomeric nuclear receptors such as NR5A2/LRH-1 bound to coregulatory nuclear responsive element (NRE) halfsites located in close proximity to FXREs modulate transcriptional activity (By similarity). In the liver activates transcription of the corepressor NR0B2 thereby indirectly inhibiting CYP7A1 and CYP8B1 (involved in BA synthesis) implicating at least in part histone demethylase KDM1A resulting in epigenomic repression, and SLC10A1/NTCP (involved in hepatic uptake of conjugated BAs). Activates transcription of the repressor MAFG (involved in regulation of BA synthesis) (By similarity). Activates transcription of SLC27A5/BACS and BAAT (involved in BA conjugation), ABCB11/BSEP (involved in bile salt export) by directly recruiting histone methyltransferase CARM1, and ABCC2/MRP2 (involved in secretion of conjugated BAs) and ABCB4 (involved in secretion of phosphatidylcholine in the small intestine) (PubMed:12754200, PubMed:15471871, PubMed:17895379). Activates transcription of SLC27A5/BACS and BAAT (involved in BA conjugation), ABCB11/BSEP (involved in bile salt export) by directly recruiting histone methyltransferase CARM1, and ABCC2/MRP2 (involved in secretion of conjugated BAs) and ABCB4 (involved in secretion of phosphatidylcholine in the small intestine) (PubMed:10514450, PubMed:15239098, PubMed:16269519). In the intestine activates FGF19 expression and secretion leading to hepatic CYP7A1 repression (PubMed:12815072, PubMed:19085950). The function also involves the coordinated induction of hepatic KLB/beta-klotho expression (By similarity). Regulates transcription of liver UGT2B4 and SULT2A1 involved in BA detoxification; binding to the UGT2B4 promoter seems to imply a monomeric transactivation independent of RXRA (PubMed:12806625, PubMed:16946559). Modulates lipid homeostasis by activating liver NR0B2/SHP-mediated repression of SREBF1 (involved in de novo lipogenesis), expression of PLTP (involved in HDL formation), SCARB1 (involved in HDL hepatic uptake), APOE, APOC1, APOC4, PPARA (involved in beta-oxidation of fatty acids), VLDLR and SDC1 (involved in the hepatic uptake of LDL and IDL remnants), and inhibiting expression of MTTP (involved in VLDL assembly (PubMed:12554753, PubMed:12660231, PubMed:15337761). Increases expression of APOC2 (promoting lipoprotein lipase activity implicated in triglyceride clearance) (PubMed:11579204). Transrepresses APOA1 involving a monomeric competition with NR2A1 for binding to a DR1 element (PubMed:11927623, PubMed:21804189). Also reduces triglyceride clearance by inhibiting expression of ANGPTL3 and APOC3 (both involved in inhibition of lipoprotein lipase) (PubMed:12891557). Involved in glucose homeostasis by modulating hepatic gluconeogenesis through activation of NR0B2/SHP-mediated repression of respective genes. Modulates glycogen synthesis (inducing phosphorylation of glycogen synthase kinase-3) (By similarity). Modulates glucose-stimulated insulin secretion and is involved in insulin resistance (PubMed:20447400). Involved in intestinal innate immunity. Plays a role in protecting the distal small intestine against bacterial overgrowth and preservation of the epithelial barrier (By similarity). Down-regulates inflammatory cytokine expression in several types of immune cells including macrophages and mononuclear cells (PubMed:21242261). Mediates trans-repression of TLR4-induced cytokine expression; the function seems to require its sumoylation and prevents N-CoR nuclear receptor corepressor clearance from target genes such as IL1B and NOS2 (PubMed:19864602). Involved in the TLR9-mediated protective mechanism in intestinal inflammation. Plays an anti-inflammatory role in liver inflammation; proposed to inhibit pro-inflammatory (but not antiapoptotic) NF-kappa-B signaling) (By similarity)
Specific Function: Bile acid binding
Gene Name: NR1H4
Uniprot ID: Q96RI1
Uniprot Name: Bile acid receptor
Molecular Weight: 55913.915 Da

References

Campana G, Pasini P, Roda A, Spampinato S: Regulation of ileal bile acid-binding protein expression in Caco-2 cells by ursodeoxycholic acid: role of the farnesoid X receptor. Biochem Pharmacol. 2005 Jun 15;69(12):1755-63. [Article]

Enzymes

Details1. Cytochrome P450 3A Subfamily (Protein Group)

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: A cytochrome P450 monooxygenase involved in the metabolism of sterols, steroid hormones, retinoids and fatty acids (PubMed:10681376, PubMed:11093772, PubMed:11555828, PubMed:12865317, PubMed:14559847, PubMed:15373842, PubMed:15764715, PubMed:19965576, PubMed:20702771, PubMed:21490593, PubMed:21576599). Mechanistically, uses molecular oxygen inserting one oxygen atom into a substrate, and reducing the second into a water molecule, with two electrons provided by NADPH via cytochrome P450 reductase (NADPH--hemoprotein reductase). Catalyzes the hydroxylation of carbon-hydrogen bonds (PubMed:12865317, PubMed:14559847, PubMed:15373842, PubMed:15764715, PubMed:21490593, PubMed:21576599, PubMed:2732228). Exhibits high catalytic activity for the formation of hydroxyestrogens from estrone (E1) and 17beta-estradiol (E2), namely 2-hydroxy E1 and E2, as well as D-ring hydroxylated E1 and E2 at the C-16 position (PubMed:11555828, PubMed:12865317, PubMed:14559847). Plays a role in the metabolism of androgens, particularly in oxidative deactivation of testosterone (PubMed:15373842, PubMed:15764715, PubMed:22773874, PubMed:2732228). Metabolizes testosterone to less biologically active 2beta- and 6beta-hydroxytestosterones (PubMed:15373842, PubMed:15764715, PubMed:2732228). Contributes to the formation of hydroxycholesterols (oxysterols), particularly A-ring hydroxylated cholesterol at the C-4beta position, and side chain hydroxylated cholesterol at the C-25 position, likely contributing to cholesterol degradation and bile acid biosynthesis (PubMed:21576599). Catalyzes bisallylic hydroxylation of polyunsaturated fatty acids (PUFA) (PubMed:9435160). Catalyzes the epoxidation of double bonds of PUFA with a preference for the last double bond (PubMed:19965576). Metabolizes endocannabinoid arachidonoylethanolamide (anandamide) to 8,9-, 11,12-, and 14,15-epoxyeicosatrienoic acid ethanolamides (EpETrE-EAs), potentially modulating endocannabinoid system signaling (PubMed:20702771). Plays a role in the metabolism of retinoids. Displays high catalytic activity for oxidation of all-trans-retinol to all-trans-retinal, a rate-limiting step for the biosynthesis of all-trans-retinoic acid (atRA) (PubMed:10681376). Further metabolizes atRA toward 4-hydroxyretinoate and may play a role in hepatic atRA clearance (PubMed:11093772). Responsible for oxidative metabolism of xenobiotics. Acts as a 2-exo-monooxygenase for plant lipid 1,8-cineole (eucalyptol) (PubMed:11159812). Metabolizes the majority of the administered drugs. Catalyzes sulfoxidation of the anthelmintics albendazole and fenbendazole (PubMed:10759686). Hydroxylates antimalarial drug quinine (PubMed:8968357). Acts as a 1,4-cineole 2-exo-monooxygenase (PubMed:11695850). Also involved in vitamin D catabolism and calcium homeostasis. Catalyzes the inactivation of the active hormone calcitriol (1-alpha,25-dihydroxyvitamin D(3)) (PubMed:29461981)
Specific Function: 1,8-cineole 2-exo-monooxygenase activity

Components:

Name	UniProt ID
Cytochrome P450 3A4	P08684
Cytochrome P450 3A43	Q9HB55
Cytochrome P450 3A5	P20815
Cytochrome P450 3A7	P24462

References

Dilger K, Denk A, Heeg MH, Beuers U: No relevant effect of ursodeoxycholic acid on cytochrome P450 3A metabolism in primary biliary cirrhosis. Hepatology. 2005 Mar;41(3):595-602. doi: 10.1002/hep.20568. [Article]
Paumgartner G, Beuers U: Ursodeoxycholic acid in cholestatic liver disease: mechanisms of action and therapeutic use revisited. Hepatology. 2002 Sep;36(3):525-31. doi: 10.1053/jhep.2002.36088. [Article]

Transporters

Details1. Bile salt export pump

Kind: Protein
Organism: Humans
Pharmacological action: Unknown
Actions: Substrate
Inhibitor
Inducer

General Function: Catalyzes the transport of the major hydrophobic bile salts, such as taurine and glycine-conjugated cholic acid across the canalicular membrane of hepatocytes in an ATP-dependent manner, therefore participates in hepatic bile acid homeostasis and consequently to lipid homeostasis through regulation of biliary lipid secretion in a bile salts dependent manner (PubMed:15791618, PubMed:16332456, PubMed:18985798, PubMed:19228692, PubMed:20010382, PubMed:20398791, PubMed:22262466, PubMed:24711118, PubMed:29507376, PubMed:32203132). Transports taurine-conjugated bile salts more rapidly than glycine-conjugated bile salts (PubMed:16332456). Also transports non-bile acid compounds, such as pravastatin and fexofenadine in an ATP-dependent manner and may be involved in their biliary excretion (PubMed:15901796, PubMed:18245269)
Specific Function: Abc-type bile acid transporter activity
Gene Name: ABCB11
Uniprot ID: O95342
Uniprot Name: Bile salt export pump
Molecular Weight: 146405.83 Da

References

Schuetz EG, Strom S, Yasuda K, Lecureur V, Assem M, Brimer C, Lamba J, Kim RB, Ramachandran V, Komoroski BJ, Venkataramanan R, Cai H, Sinal CJ, Gonzalez FJ, Schuetz JD: Disrupted bile acid homeostasis reveals an unexpected interaction among nuclear hormone receptors, transporters, and cytochrome P450. J Biol Chem. 2001 Oct 19;276(42):39411-8. doi: 10.1074/jbc.M106340200. Epub 2001 Aug 16. [Article]
Green RM, Hoda F, Ward KL: Molecular cloning and characterization of the murine bile salt export pump. Gene. 2000 Jan 4;241(1):117-23. [Article]
Mita S, Suzuki H, Akita H, Stieger B, Meier PJ, Hofmann AF, Sugiyama Y: Vectorial transport of bile salts across MDCK cells expressing both rat Na+-taurocholate cotransporting polypeptide and rat bile salt export pump. Am J Physiol Gastrointest Liver Physiol. 2005 Jan;288(1):G159-67. Epub 2004 Aug 5. [Article]

Details2. Solute carrier organic anion transporter family member 1A2

Kind: Protein
Organism: Humans
Pharmacological action: Unknown
Actions: Substrate
Inhibitor
Inducer

General Function: Na(+)-independent transporter that mediates the cellular uptake of a broad range of organic anions such as the endogenous bile salts cholate and deoxycholate, either in their unconjugated or conjugated forms (taurocholate and glycocholate), at the plasmam membrane (PubMed:19129463, PubMed:7557095). Responsible for intestinal absorption of bile acids (By similarity). Transports dehydroepiandrosterone 3-sulfate (DHEAS), a major circulating steroid secreted by the adrenal cortex, as well as estrone 3-sulfate and 17beta-estradiol 17-O-(beta-D-glucuronate) (PubMed:11159893, PubMed:12568656, PubMed:19129463, PubMed:23918469, PubMed:25560245, PubMed:9539145). Mediates apical uptake of all-trans-retinol (atROL) across human retinal pigment epithelium, which is essential to maintaining the integrity of the visual cycle and thus vision (PubMed:25560245). Involved in the uptake of clinically used drugs (PubMed:17301733, PubMed:20686826, PubMed:27777271). Capable of thyroid hormone transport (both T3 or 3,3',5'-triiodo-L-thyronine, and T4 or L-tyroxine) (PubMed:19129463, PubMed:20358049). Also transports prostaglandin E2 (PubMed:19129463). Plays roles in blood-brain and -cerebrospinal fluid barrier transport of organic anions and signal mediators, and in hormone uptake by neural cells (By similarity). May also play a role in the reuptake of neuropeptides such as substance P/TAC1 and vasoactive intestinal peptide/VIP released from retinal neurons (PubMed:25132355). May play an important role in plasma and tissue distribution of the structurally diverse chemotherapeutic drugs methotrexate and paclitaxel (PubMed:23243220). Shows a pH-sensitive substrate specificity which may be ascribed to the protonation state of the binding site and leads to a stimulation of substrate transport in an acidic microenvironment (PubMed:19129463). Hydrogencarbonate/HCO3(-) acts as the probable counteranion that exchanges for organic anions (PubMed:19129463). May contribute to regulate the transport of organic compounds in testis across the blood-testis-barrier (Probable)
Specific Function: Bile acid transmembrane transporter activity
Gene Name: SLCO1A2
Uniprot ID: P46721
Uniprot Name: Solute carrier organic anion transporter family member 1A2
Molecular Weight: 74144.105 Da

References

Fickert P, Zollner G, Fuchsbichler A, Stumptner C, Pojer C, Zenz R, Lammert F, Stieger B, Meier PJ, Zatloukal K, Denk H, Trauner M: Effects of ursodeoxycholic and cholic acid feeding on hepatocellular transporter expression in mouse liver. Gastroenterology. 2001 Jul;121(1):170-83. [Article]
Kullak-Ublick GA, Hagenbuch B, Stieger B, Schteingart CD, Hofmann AF, Wolkoff AW, Meier PJ: Molecular and functional characterization of an organic anion transporting polypeptide cloned from human liver. Gastroenterology. 1995 Oct;109(4):1274-82. [Article]
Kullak-Ublick GA, Hagenbuch B, Stieger B, Wolkoff AW, Meier PJ: Functional characterization of the basolateral rat liver organic anion transporting polypeptide. Hepatology. 1994 Aug;20(2):411-6. [Article]
Hata S, Wang P, Eftychiou N, Ananthanarayanan M, Batta A, Salen G, Pang KS, Wolkoff AW: Substrate specificities of rat oatp1 and ntcp: implications for hepatic organic anion uptake. Am J Physiol Gastrointest Liver Physiol. 2003 Nov;285(5):G829-39. Epub 2003 Jul 3. [Article]

Details3. ATP-binding cassette sub-family C member 2

Kind: Protein
Organism: Humans
Pharmacological action: Unknown
Actions: Inducer

General Function: ATP-dependent transporter of the ATP-binding cassette (ABC) family that binds and hydrolyzes ATP to enable active transport of various substrates including many drugs, toxicants and endogenous compound across cell membranes. Transports a wide variety of conjugated organic anions such as sulfate-, glucuronide- and glutathione (GSH)-conjugates of endo- and xenobiotics substrates (PubMed:10220572, PubMed:10421658, PubMed:11500505, PubMed:16332456). Mediates hepatobiliary excretion of mono- and bis-glucuronidated bilirubin molecules and therefore play an important role in bilirubin detoxification (PubMed:10421658). Mediates also hepatobiliary excretion of others glucuronide conjugates such as 17beta-estradiol 17-glucosiduronic acid and leukotriene C4 (PubMed:11500505). Transports sulfated bile salt such as taurolithocholate sulfate (PubMed:16332456). Transports various anticancer drugs, such as anthracycline, vinca alkaloid and methotrexate and HIV-drugs such as protease inhibitors (PubMed:10220572, PubMed:11500505, PubMed:12441801). Confers resistance to several anti-cancer drugs including cisplatin, doxorubicin, epirubicin, methotrexate, etoposide and vincristine (PubMed:10220572, PubMed:11500505)
Specific Function: Abc-type glutathione s-conjugate transporter activity
Gene Name: ABCC2
Uniprot ID: Q92887
Uniprot Name: ATP-binding cassette sub-family C member 2
Molecular Weight: 174205.64 Da

References

Kast HR, Goodwin B, Tarr PT, Jones SA, Anisfeld AM, Stoltz CM, Tontonoz P, Kliewer S, Willson TM, Edwards PA: Regulation of multidrug resistance-associated protein 2 (ABCC2) by the nuclear receptors pregnane X receptor, farnesoid X-activated receptor, and constitutive androstane receptor. J Biol Chem. 2002 Jan 25;277(4):2908-15. Epub 2001 Nov 12. [Article]
Fickert P, Zollner G, Fuchsbichler A, Stumptner C, Pojer C, Zenz R, Lammert F, Stieger B, Meier PJ, Zatloukal K, Denk H, Trauner M: Effects of ursodeoxycholic and cholic acid feeding on hepatocellular transporter expression in mouse liver. Gastroenterology. 2001 Jul;121(1):170-83. [Article]

Details4. ATP-binding cassette sub-family C member 4

Kind: Protein
Organism: Humans
Pharmacological action: Unknown
Actions: Inhibitor

General Function: ATP-dependent transporter of the ATP-binding cassette (ABC) family that actively extrudes physiological compounds and xenobiotics from cells. Transports a range of endogenous molecules that have a key role in cellular communication and signaling, including cyclic nucleotides such as cyclic AMP (cAMP) and cyclic GMP (cGMP), bile acids, steroid conjugates, urate, and prostaglandins (PubMed:11856762, PubMed:12523936, PubMed:12835412, PubMed:12883481, PubMed:15364914, PubMed:15454390, PubMed:16282361, PubMed:17959747, PubMed:18300232, PubMed:26721430). Mediates the ATP-dependent efflux of glutathione conjugates such as leukotriene C4 (LTC4) and leukotriene B4 (LTB4) too. The presence of GSH is necessary for the ATP-dependent transport of LTB4, whereas GSH is not required for the transport of LTC4 (PubMed:17959747). Mediates the cotransport of bile acids with reduced glutathione (GSH) (PubMed:12523936, PubMed:12883481, PubMed:16282361). Transports a wide range of drugs and their metabolites, including anticancer, antiviral and antibiotics molecules (PubMed:11856762, PubMed:12105214, PubMed:15454390, PubMed:17344354, PubMed:18300232). Confers resistance to anticancer agents such as methotrexate (PubMed:11106685)
Specific Function: 15-hydroxyprostaglandin dehydrogenase (nad+) activity
Gene Name: ABCC4
Uniprot ID: O15439
Uniprot Name: ATP-binding cassette sub-family C member 4
Molecular Weight: 149525.33 Da

References

Rius M, Nies AT, Hummel-Eisenbeiss J, Jedlitschky G, Keppler D: Cotransport of reduced glutathione with bile salts by MRP4 (ABCC4) localized to the basolateral hepatocyte membrane. Hepatology. 2003 Aug;38(2):374-84. [Article]

Property	Measurement	pH	Temperature (°C)	References
Ki (nM)	75000	N/A	N/A	A15990

Details5. Ileal sodium/bile acid cotransporter

Kind: Protein
Organism: Humans
Pharmacological action: Unknown
Actions: Inhibitor

General Function: Plays a critical role in the sodium-dependent reabsorption of bile acids from the lumen of the small intestine (PubMed:7592981, PubMed:9458785, PubMed:9856990). Transports various bile acids, unconjugated or conjugated, such as cholate and taurocholate (PubMed:7592981, PubMed:9458785, PubMed:9856990). Also responsible for bile acid transport in the renal proximal tubules, a salvage mechanism that helps conserve bile acids (Probable). Works collaboratively with the Na(+)-taurocholate cotransporting polypeptide (NTCP), the organic solute transporter (OST), and the bile salt export pump (BSEP), to ensure efficacious biological recycling of bile acids during enterohepatic circulation (PubMed:33222321)
Specific Function: Bile acid
Gene Name: SLC10A2
Uniprot ID: Q12908
Uniprot Name: Ileal sodium/bile acid cotransporter
Molecular Weight: 37713.405 Da

References

Craddock AL, Love MW, Daniel RW, Kirby LC, Walters HC, Wong MH, Dawson PA: Expression and transport properties of the human ileal and renal sodium-dependent bile acid transporter. Am J Physiol. 1998 Jan;274(1 Pt 1):G157-69. [Article]
Saeki T, Matoba K, Furukawa H, Kirifuji K, Kanamoto R, Iwami K: Characterization, cDNA cloning, and functional expression of mouse ileal sodium-dependent bile acid transporter. J Biochem. 1999 Apr;125(4):846-51. [Article]
Saeki T, Takahashi N, Kanamoto R, Iwami K: Characterization of cloned mouse Na+/taurocholate cotransporting polypeptide by transient expression in COS-7 cells. Biosci Biotechnol Biochem. 2002 May;66(5):1116-8. [Article]

Property	Measurement	pH	Temperature (°C)	References
IC 50 (nM)	3600	N/A	N/A	A27311

Details6. Hepatic sodium/bile acid cotransporter

Kind: Protein
Organism: Humans
Pharmacological action: Unknown
Actions: Substrate
Inhibitor

General Function: As a major transporter of conjugated bile salts from plasma into the hepatocyte, it plays a key role in the enterohepatic circulation of bile salts necessary for the solubilization and absorption of dietary fat and fat-soluble vitamins (PubMed:14660639, PubMed:24867799, PubMed:34060352, PubMed:8132774). It is strictly dependent on the extracellular presence of sodium (PubMed:14660639, PubMed:24867799, PubMed:34060352, PubMed:8132774). It exhibits broad substrate specificity and transports various bile acids, such as taurocholate, cholate, as well as non-bile acid organic compounds, such as estrone sulfate (PubMed:14660639, PubMed:34060352). Works collaboratively with the ileal transporter (NTCP2), the organic solute transporter (OST), and the bile salt export pump (BSEP), to ensure efficacious biological recycling of bile acids during enterohepatic circulation (PubMed:33222321)
Specific Function: Bile acid
Gene Name: SLC10A1
Uniprot ID: Q14973
Uniprot Name: Hepatic sodium/bile acid cotransporter
Molecular Weight: 38118.64 Da

References

Boyer JL, Ng OC, Ananthanarayanan M, Hofmann AF, Schteingart CD, Hagenbuch B, Stieger B, Meier PJ: Expression and characterization of a functional rat liver Na+ bile acid cotransport system in COS-7 cells. Am J Physiol. 1994 Mar;266(3 Pt 1):G382-7. [Article]
Mita S, Suzuki H, Akita H, Stieger B, Meier PJ, Hofmann AF, Sugiyama Y: Vectorial transport of bile salts across MDCK cells expressing both rat Na+-taurocholate cotransporting polypeptide and rat bile salt export pump. Am J Physiol Gastrointest Liver Physiol. 2005 Jan;288(1):G159-67. Epub 2004 Aug 5. [Article]

Details7. Chloride anion exchanger

Kind: Protein
Organism: Humans
Pharmacological action: Unknown
Actions: Upregulator

General Function: Mediates chloride-bicarbonate exchange with a chloride bicarbonate stoichiometry of 2:1 in the intestinal epithelia (PubMed:16606687, PubMed:19321737, PubMed:22159084, PubMed:22627094). Plays a role in the chloride and bicarbonate homeostasis during sperm epididymal maturation and capacitation (By similarity)
Specific Function: Bicarbonate transmembrane transporter activity
Gene Name: SLC26A3
Uniprot ID: P40879
Uniprot Name: Chloride anion exchanger
Molecular Weight: 84504.035 Da

References

Achufusi TGO, Safadi AO, Mahabadi N: Ursodeoxycholic Acid. . [Article]
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 September 15, 2024 21:55

Ursodeoxycholic acid

Identification

Structure for Ursodeoxycholic acid (DB01586)

Pharmacology

Interactions

Products

Categories

Chemical Identifiers

References

Clinical Trials

Clinical Trial & Rare Diseases Add-on Data Package

Pharmacoeconomics

Properties

Spectra

Collision Cross Sections (CCS)

Targets

References

References

References

References

Enzymes

Components:

References

Transporters

References

References

References

References

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References

References