Ursodeoxycholic acid (CED0002306)

Record Information
Version1.0
Creation Date2016-05-25 18:13:22 UTC
Update Date2026-05-14 17:10:00 UTC
Accession NumberCHEM021821
Identification
Common NameUrsodeoxycholic acid
ClassSmall Molecule
Description
Ursodeoxycholic acid belongs to the bile acids, alcohols and derivatives, a subclass of steroids and steroid derivatives within the organic compounds. It has the chemical formula C24H40O4 and an average molecular weight of 392.57 g/mol. This compound is classified as a lipid and lipid-like molecule. In industrial applications, ursodeoxycholic acid is utilized as a humectant, as well as a softener and conditioner. It is found in 19 recorded sources, including building and construction materials such as tents or canopies, and household cleaning and consumer products including cigar cigarettes, non electric simulated smoking devices, and other smoking requisites. It is also associated with food, food processing and cookware, specifically the processing of meats and the preparation of vinegar, wine, sparkling wine, and fermentation processes for beer. Additionally, it is found in electrical and electronic equipment, including antennas, amplifiers, discharge lamps, electrically stimulated smoking devices, fixed capacitors and their manufacture, and five other sources. In the realm of healthcare, pharmaceuticals and veterinary products, it is used for bile therapy. Recorded exposure routes for the compound include oral and dental routes. Ursodeoxycholic acid interacts with four recorded protein targets. It acts as an activator, inhibitor, or partial agonist of Aldo-keto reductase family 1 member C2 (AKR1C2). Other protein targets include the bile acid receptor (NR1H4), biliverdin reductase A (BLVRA), and solute carrier family 23 member 2 (SLC23A2).
Contaminant TypeNot Available
Chemical Structure
Synonyms
ValueSource
(3alpha,5beta,7beta)-3,7-Dihydroxycholan-24-Oic acidChEBI
3alpha,7beta-Dihydroxy-5beta-cholan-24-Oic acidChEBI
ActigallChEBI
UrsodeoxycholateChEBI
UrsodiolChEBI
UrsoKegg
(3a,5b,7b)-3,7-Dihydroxycholan-24-OateGenerator
(3a,5b,7b)-3,7-Dihydroxycholan-24-Oic acidGenerator
(3alpha,5beta,7beta)-3,7-Dihydroxycholan-24-OateGenerator
(3Α,5β,7β)-3,7-dihydroxycholan-24-OateGenerator
(3Α,5β,7β)-3,7-dihydroxycholan-24-Oic acidGenerator
3a,7b-Dihydroxy-5b-cholan-24-OateGenerator
3a,7b-Dihydroxy-5b-cholan-24-Oic acidGenerator
3alpha,7beta-Dihydroxy-5beta-cholan-24-OateGenerator
3Α,7β-dihydroxy-5β-cholan-24-OateGenerator
3Α,7β-dihydroxy-5β-cholan-24-Oic acidGenerator
3 alpha,7 beta-Dihydroxy-5 beta-cholan-24-Oic acidHMDB
Acid, deoxyursocholicHMDB
Acid, ursacholicHMDB
Acid, ursodeoxycholicHMDB
Cholit-ursanHMDB
CholofalkHMDB
DelursanHMDB
Deoxyursocholic acidHMDB
UrsocholHMDB
UrsogalHMDB
UrsoliteHMDB
UrsolvanHMDB
Urso heumannHMDB
UrsobilaneHMDB
UrsofalkHMDB
DestolitHMDB
Sodium ursodeoxycholateHMDB
Ursacholic acidHMDB
Ursodeoxycholate, sodiumHMDB
3 alpha,7 beta Dihydroxy 5 beta cholan 24 Oic acidHMDB
UrdoxHMDB
(3a,5b,7b)-3,7-Dihydroxy-cholan-24-OateHMDB
(3a,5b,7b)-3,7-Dihydroxy-cholan-24-Oic acidHMDB
3,7-Dihydroxycholan-24-Oic acidHMDB
3-alpha,7-beta-Dihydroxy-5-beta-cholanoic acidHMDB
3-alpha,7-beta-Dihydroxycholanic acidHMDB
3-alpha,7-beta-Dioxycholanic acidHMDB
AntigallHMDB
UrosdesoxycholateHMDB
Urosdesoxycholic acidHMDB
UrsodeoxycholicacidHMDB
UrsodexycholateHMDB
Ursodexycholic acidHMDB
Aventis brand OF ursodeoxycholic acidHMDB
Axcan brand OF ursodeoxycholic acidHMDB
Falk brand OF ursodeoxycholic acidHMDB
Farmasa brand OF ursodeoxycholic acidHMDB
Galen brand OF ursodeoxycholic acidHMDB
Orphan brand OF ursodeoxycholic acidHMDB
Antigen brand OF ursodeoxycholic acidHMDB
CP Brand OF ursodeoxycholic acidHMDB
Heumann brand OF ursodeoxycholic acidHMDB
Niddapharm brand OF ursodeoxycholic acidHMDB
Norgine brand OF ursodeoxycholic acidHMDB
Sanofi synthelabo brand OF ursodeoxycholic acidHMDB
Estedi brand OF ursodeoxycholic acidHMDB
Provalis brand OF ursodeoxycholic acidHMDB
Tramedico brand OF ursodeoxycholic acidHMDB
Vita brand OF ursodeoxycholic acidHMDB
Zambon brand OF ursodeoxycholic acidHMDB
Chemical FormulaC24H40O4
Average Molecular Mass392.572 g/mol
Monoisotopic Mass392.293 g/mol
CAS Registry Number128-13-2
IUPAC Name(4R)-4-[(1S,2S,5R,7S,9S,10R,11S,14R,15R)-5,9-dihydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-yl]pentanoic acid
Traditional Name(4R)-4-[(1S,2S,5R,7S,9S,10R,11S,14R,15R)-5,9-dihydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]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
InChI IdentifierInChI=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
InChI KeyRUDATBOHQWOJDD-UZVSRGJWSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as dihydroxy bile acids, alcohols and derivatives. Dihydroxy bile acids, alcohols and derivatives are compounds containing or derived from a bile acid or alcohol, and which bears exactly two carboxylic acid groups.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassSteroids and steroid derivatives
Sub ClassBile acids, alcohols and derivatives
Direct ParentDihydroxy bile acids, alcohols and derivatives
Alternative Parents
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
  • Monocarboxylic acid or derivatives
  • Organic oxide
  • Alcohol
  • Organic oxygen compound
  • Carbonyl group
  • Hydrocarbon derivative
  • Organooxygen compound
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Organoleptic EffectsNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.02 g/LALOGPS
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 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity109.27 m³·mol⁻¹ChemAxon
Polarizability46.42 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyDeposition DateView
Predicted GC-MSPredicted GC-MS Spectrumsplash10-01rt-0419000000-6a92f910581240163a99Not AvailableView Spectrum
Predicted GC-MSPredicted GC-MS Spectrumsplash10-0006-1110390000-52bc66ab11fd14425d4fNot AvailableView Spectrum
Predicted GC-MSPredicted GC-MS SpectrumNot AvailableNot AvailableView Spectrum
Predicted GC-MSPredicted GC-MS SpectrumNot AvailableNot AvailableView Spectrum
Predicted GC-MSPredicted GC-MS SpectrumNot AvailableNot AvailableView Spectrum
Predicted GC-MSPredicted GC-MS SpectrumNot AvailableNot AvailableView Spectrum
Predicted GC-MSPredicted GC-MS SpectrumNot AvailableNot AvailableView Spectrum
Predicted GC-MSPredicted GC-MS SpectrumNot AvailableNot AvailableView Spectrum
Predicted GC-MSPredicted GC-MS SpectrumNot AvailableNot AvailableView Spectrum
Predicted GC-MSPredicted GC-MS SpectrumNot AvailableNot AvailableView Spectrum
Predicted GC-MSPredicted GC-MS SpectrumNot AvailableNot AvailableView Spectrum
Predicted GC-MSPredicted GC-MS SpectrumNot AvailableNot AvailableView Spectrum
Predicted GC-MSPredicted GC-MS SpectrumNot AvailableNot AvailableView Spectrum
Predicted GC-MSPredicted GC-MS SpectrumNot AvailableNot AvailableView Spectrum
Predicted GC-MSPredicted GC-MS SpectrumNot AvailableNot AvailableView Spectrum
Predicted GC-MSPredicted GC-MS SpectrumNot AvailableNot AvailableView Spectrum
Predicted GC-MSPredicted GC-MS SpectrumNot AvailableNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0a4l-3940000000-cf90a6f216d592e2ad4cNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-00di-0029000000-54929e08fef761ba2b28Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0002-2911000000-eec2b269eeb08a30ac6eNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-056r-0009000000-997e61e986e67265241cNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-056r-0009000000-81134947694f847d1c65Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-02t9-1219000000-6a0ddebebacac090c27eNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0006-0009000000-efdaad69eee0ae934dd5Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-006x-1009000000-15b4edab9d05e4c3693aNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0a4l-9006000000-9291e69db3a3c47ecd97Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0006-0009000000-7631731446db77938069Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-006x-0009000000-39e7e555dc6b36ada2afNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-000i-1009000000-351c21e3dab693818b22Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0006-0019000000-56dc67f71a8507c1433fNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0a4i-3039000000-510702cae19e3906b6e1Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0002-9550000000-7486a5f56afd302efa7eNot AvailableView Spectrum
1D NMR13C NMR Spectrum (1D, H2O, predicted)Not AvailableNot AvailableView Spectrum
1D NMR1H NMR Spectrum (1D, H2O, predicted)Not AvailableNot AvailableView Spectrum
Toxicity Profile
Mechanism of ToxicityNot Available
Carcinogenicity (IARC Classification)Not Available
Minimum Risk LevelNot Available
SymptomsNot Available
TreatmentNot Available
Toxicity Values
Toxicity ValueUnitValue RangeOrganismDose DescriptorRoute of ExposurePredicted or ExperimentalReference
2021.0Log mg/kg[1100:3600]RatLD50oralpredictedNot Available
Health Effects
Health EffectRelationshipDirectionReference
intrahepatic cholestasisis_treatment_forNot AvailablePMC5384842
Exposure Sources
Source IDSourceSectorReference
233BrushesPersonal care & cosmeticsNot Available
250Bile therapyHealthcare, pharmaceuticals & veterinary productsNot Available
503Tents Or CanopiesBuilding & ConstructionNot Available
505AmplifiersElectrical & Electronic EquipmentNot Available
506AntennasElectrical & Electronic EquipmentNot Available
514Discharge LampsElectrical & Electronic EquipmentNot Available
518Electrically Stimulated Smoking DevicesElectrical & Electronic EquipmentNot Available
521Fixed Capacitors And Their ManufactureElectrical & Electronic EquipmentNot Available
527MagnetsElectrical & Electronic EquipmentNot Available
530Radio Transmission SystemsElectrical & Electronic EquipmentNot Available
531RelaysElectrical & Electronic EquipmentNot Available
537Television SystemsElectrical & Electronic EquipmentNot Available
540X Ray TubesElectrical & Electronic EquipmentNot Available
544Fermentation Processes For BeerFood, food processing & cookwareNot Available
548Preparation Of VinegarFood, food processing & cookwareNot Available
549Preparation Of Wine Or Sparkling WineFood, food processing & cookwareNot Available
552Processing MeatsFood, food processing & cookwareNot Available
556Cigar CigarettesHousehold cleaning & consumer productsNot Available
559Non Electric Simulated Smoking DevicesHousehold cleaning & consumer productsNot Available
560Other Smoking RequisitesHousehold cleaning & consumer productsNot Available
579Manufacture Of Iron Or SteelIndustrial manufacturing & chemical processingNot Available
605Pest RepellantsAgriculture & land managementNot Available
609AftershavePersonal care & cosmeticsNot Available
613DepilatoriesPersonal care & cosmeticsNot Available
617Lip Care ProductsPersonal care & cosmeticsNot Available
630ToysRecreation & sports surfacesNot Available
643HeadwearTextiles, leather & furnishingsNot Available
663Sanitary EquipmentWastewater, sanitation & biosolidsNot Available
Pathways
1 pathway
Targets
StructureProteinUniProt IDOrganismRelationshipDetails
G-protein coupled bile acid receptor 1 structureClick to view 3D structureG-protein coupled bile acid receptor 1Q8TDU6HumansPredicted (SEA)0.0778492
Bile acid receptor structureClick to view 3D structureBile acid receptorQ96RI1HumansPredicted (SEA)0.700643
Click to view 3D structureCMP-N-acetylneuraminate-beta-galactosamide-alpha-2,3-sialyltransferase 2Q11205Rattus norvegicusPredicted (SEA)0.155698
Bile salt export pump structureClick to view 3D structureBile salt export pumpO95342HumansPredicted (SEA)2.41333
Click to view 3D structureHepatic sodium/bile acid cotransporterP26435Rattus norvegicusPredicted (SEA)0.856341
Hepatic sodium/bile acid cotransporter structureClick to view 3D structureHepatic sodium/bile acid cotransporterQ14973HumansPredicted (SEA)0.0778492
Vitamin D3 receptor structureClick to view 3D structureVitamin D3 receptorP11473HumansPredicted (SEA)5.91654
NPC1-like intracellular cholesterol transporter 1 structureClick to view 3D structureNPC1-like intracellular cholesterol transporter 1Q9UHC9HumansPredicted (SEA)2.02408
Autotaxin structureClick to view 3D structureAutotaxinQ13822HumansPredicted (SEA)5.44945
Click to view 3D structureIleal sodium/bile acid cotransporterQ12908HumansPredicted (SEA)0.155698
Nuclear receptor ROR-gamma structureClick to view 3D structureNuclear receptor ROR-gammaP51449HumansPredicted (SEA)29.8941
Click to view 3D structureG-protein coupled receptor 183D4A7K7Rattus norvegicusPredicted (SEA)1.55698
Oxysterol-binding protein 1 structureClick to view 3D structureOxysterol-binding protein 1P22059HumansPredicted (SEA)2.25763
Oxysterols receptor LXR-alpha structureClick to view 3D structureOxysterols receptor LXR-alphaQ13133HumansPredicted (SEA)25.8459
Click to view 3D structureOxysterol-binding protein 2Q969R2HumansPredicted (SEA)2.33548
Ephrin type-A receptor 2 structureClick to view 3D structureEphrin type-A receptor 2P29317HumansPredicted (SEA)194.39
Click to view 3D structureEphrin type-A receptor 2Q03145Mus musculusPredicted (SEA)1.86838
Click to view 3D structure3-hydroxy-3-methylglutaryl-coenzyme A reductaseP00347Cricetulus griseusPredicted (SEA)0.934191
G-protein coupled receptor 183 structureClick to view 3D structureG-protein coupled receptor 183P32249HumansPredicted (SEA)2.80257
Tyrosine-protein phosphatase non-receptor type 1 structureClick to view 3D structureTyrosine-protein phosphatase non-receptor type 1P18031HumansPredicted (SEA)28.1814
Click to view 3D structureEphrin type-A receptor 7Q61772Mus musculusPredicted (SEA)2.02408
Click to view 3D structureEphrin type-B receptor 3P54754Mus musculusPredicted (SEA)2.02408
Click to view 3D structureEphrin type-B receptor 1P09759Rattus norvegicusPredicted (SEA)2.02408
Click to view 3D structureEphrin type-A receptor 8O09127Mus musculusPredicted (SEA)2.02408
Click to view 3D structureOxysterols receptor LXR-betaQ62755Rattus norvegicusPredicted (SEA)1.71268
Concentrations
Not Available
External Links
DrugBank IDDB01586
HMDB IDHMDB0000946
FooDB IDFDB022332
Phenol Explorer IDNot Available
KNApSAcK IDC00032464
BiGG IDNot Available
BioCyc IDNot Available
METLIN ID5893
PDB IDNot Available
Wikipedia LinkUrsodiol
Chemspider ID29131
ChEBI ID9907
PubChem Compound ID31401
Kegg Compound IDC07880
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. Sawada, Haruji; Kulprecha, Songsri; Nilubol, Naline; Yoshida, Toshiomi; Kinoshita, Shinichi; Taguchi, Hisaharu. Microbial production of ursodeoxycholic acid from lithocholic acid by Fusarium equiseti M41. Applied and Environmental Microbiology (1982), 44(6):1249-52
2. Geetha A, Surendran R: Effect of ursodeoxycholic acid on copper induced oxidation of low density lipoprotein. Pharmazie. 2005 Aug;60(8):609-13.
3. Fiorucci S, Antonelli E, Morelli A: Nitric oxide and portal hypertension: a nitric oxide-releasing derivative of ursodeoxycholic acid that selectively releases nitric oxide in the liver. Dig Liver Dis. 2003 May;35 Suppl 2:S61-9.
4. Meyers RL, Book LS, O'Gorman MA, Jackson WD, Black RE, Johnson DG, Matlak ME: High-dose steroids, ursodeoxycholic acid, and chronic intravenous antibiotics improve bile flow after Kasai procedure in infants with biliary atresia. J Pediatr Surg. 2003 Mar;38(3):406-11.
5. Soderdahl G, Nowak G, Duraj F, Wang FH, Einarsson C, Ericzon BG: Ursodeoxycholic acid increased bile flow and affects bile composition in the early postoperative phase following liver transplantation. Transpl Int. 1998;11 Suppl 1:S231-8.
6. Brites D: Intrahepatic cholestasis of pregnancy: changes in maternal-fetal bile acid balance and improvement by ursodeoxycholic acid. Ann Hepatol. 2002 Jan-Mar;1(1):20-8.
7. Nobilis M, Pour M, Kunes J, Kopecky J, Kvetina J, Svoboda Z, Sladkova K, Vortel J: High-performance liquid chromatographic determination of ursodeoxycholic acid after solid phase extraction of blood serum and detection-oriented derivatization. J Pharm Biomed Anal. 2001 Mar;24(5-6):937-46.
8. Hillaire S, Ballet F, Franco D, Setchell KD, Poupon R: Effects of ursodeoxycholic acid and chenodeoxycholic acid on human hepatocytes in primary culture. Hepatology. 1995 Jul;22(1):82-7.
9. Serrano MA, Brites D, Larena MG, Monte MJ, Bravo MP, Oliveira N, Marin JJ: Beneficial effect of ursodeoxycholic acid on alterations induced by cholestasis of pregnancy in bile acid transport across the human placenta. J Hepatol. 1998 May;28(5):829-39.
10. Smith JL, Lewindon PJ, Hoskins AC, Pereira TN, Setchell KD, O'Connell NC, Shepherd RW, Ramm GA: Endogenous ursodeoxycholic acid and cholic acid in liver disease due to cystic fibrosis. Hepatology. 2004 Jun;39(6):1673-82.
11. Maton PN, Murphy GM, Dowling RH: Ursodeoxycholic acid treatment of gallstones. Dose-response study and possible mechanism of action. Lancet. 1977 Dec 24-31;2(8052-8053):1297-301.
12. Reyes H, Sjovall J: Bile acids and progesterone metabolites in intrahepatic cholestasis of pregnancy. Ann Med. 2000 Mar;32(2):94-106.
13. Ikegami T, Matsuzaki Y, Al Rashid M, Ceryak S, Zhang Y, Bouscarel B: Enhancement of DNA topoisomerase I inhibitor-induced apoptosis by ursodeoxycholic acid. Mol Cancer Ther. 2006 Jan;5(1):68-79.
14. Crosignani A, Setchell KD, Invernizzi P, Larghi A, Rodrigues CM, Podda M: Clinical pharmacokinetics of therapeutic bile acids. Clin Pharmacokinet. 1996 May;30(5):333-58.
15. Hofmann AF: The continuing importance of bile acids in liver and intestinal disease. Arch Intern Med. 1999 Dec 13-27;159(22):2647-58.
16. Lindblad A, Glaumann H, Strandvik B: A two-year prospective study of the effect of ursodeoxycholic acid on urinary bile acid excretion and liver morphology in cystic fibrosis-associated liver disease. Hepatology. 1998 Jan;27(1):166-74.
17. Eriksson LS, Olsson R, Glauman H, Prytz H, Befrits R, Ryden BO, Einarsson K, Lindgren S, Wallerstedt S, Weden M: Ursodeoxycholic acid treatment in patients with primary biliary cirrhosis. A Swedish multicentre, double-blind, randomized controlled study. Scand J Gastroenterol. 1997 Feb;32(2):179-86.
18. Kowdley KV: Ursodeoxycholic acid therapy in hepatobiliary disease. Am J Med. 2000 Apr 15;108(6):481-6.
19. Baruch Y, Assy N, Weisbruch F, Reisner SA, Rinkevich D, Enat R, Blendis LM, Bomzon A: A pilot study on the hemodynamic effect of short-term ursodeoxycholic acid therapy in patients with stable liver cirrhosis. Am J Gastroenterol. 1999 Oct;94(10):3000-4.
20. Marschall HU, Wagner M, Zollner G, Fickert P, Diczfalusy U, Gumhold J, Silbert D, Fuchsbichler A, Benthin L, Grundstrom R, Gustafsson U, Sahlin S, Einarsson C, Trauner M: Complementary stimulation of hepatobiliary transport and detoxification systems by rifampicin and ursodeoxycholic acid in humans. Gastroenterology. 2005 Aug;129(2):476-85.
21. Guarino MP, Carotti S, Sarzano M, Alloni R, Vanni M, Grosso M, Sironi G, Maffettone PL, Cicala M: Short-term ursodeoxycholic acid treatment improves gallbladder bile turnover in gallstone patients: a randomized trial. Neurogastroenterol Motil. 2005 Oct;17(5):680-6.
22. https://www.ncbi.nlm.nih.gov/pubmed/?term=14989050
23. https://www.ncbi.nlm.nih.gov/pubmed/?term=17489439
24. https://www.ncbi.nlm.nih.gov/pubmed/?term=24816727