Chenodeoxycholic acid (CED0002895)

Record Information
Version1.0
Creation Date2016-05-22 03:24:40 UTC
Update Date2026-05-14 18:24:18 UTC
Accession NumberCHEM016254
Identification
Common NameChenodeoxycholic acid
ClassSmall Molecule
Description
Chenodeoxycholic acid (C24H40O4) is a compound with an average molecular weight of 392.57 g/mol. Chenodeoxycholic acid belongs to the bile acids, alcohols and derivatives, a subclass of steroids and steroid derivatives within the organic compounds. It serves as a biological ligand (PMC3676171). The compound is found in or released from 25 recorded sources, including drinking water and water supply. Within healthcare, pharmaceuticals and veterinary products, it is used in bile therapy. Other recorded sources include food, food processing and cookware—specifically the processing of meats, food preservation, and fermentation processes for beer and the preparation of wine or sparkling wine—as well as household cleaning and consumer products such as soap detergents, perfumes within detergents and soaps, tobacco smoke filters, tobacco product cases, and cigar cigarettes. Additionally, it is associated with electrical and electronic equipment, including antennas, amplifiers, electric switches, auxiliary devices, and conductors or conductive bodies characterised by the conductive materials. The recorded exposure route for this compound is oral. Chenodeoxycholic acid interacts with four recorded protein targets, acting as an agonist, antagonist, or substrate of the bile acid receptor (NR1H4), the G-protein coupled bile acid receptor 1 (GPBAR1), the nuclear receptor subfamily 1 group I member 2 (NR1I2), and the aldo-keto reductase family 1 member C2 (AKR1C2). Regarding health effects, the compound is associated with cholestasis (PMC9488005) and has been observed to decrease in the blood in cases of pancreatic cancer (PMC7399932).
Contaminant TypeNot Available
Chemical Structure
Synonyms
ValueSource
3alpha,7alpha-Dihydroxy-5beta-cholanic acidChEBI
7alpha-Hydroxylithocholic acidChEBI
Anthropodeoxycholic acidChEBI
Anthropodesoxycholic acidChEBI
CDCAChEBI
Chenic acidChEBI
ChenixChEBI
ChenodiolChEBI
Gallodesoxycholic acidChEBI
3a,7a-Dihydroxy-5b-cholanateGenerator
3a,7a-Dihydroxy-5b-cholanic acidGenerator
3alpha,7alpha-Dihydroxy-5beta-cholanateGenerator
3Α,7α-dihydroxy-5β-cholanateGenerator
3Α,7α-dihydroxy-5β-cholanic acidGenerator
7a-HydroxylithocholateGenerator
7a-Hydroxylithocholic acidGenerator
7alpha-HydroxylithocholateGenerator
7Α-hydroxylithocholateGenerator
7Α-hydroxylithocholic acidGenerator
AnthropodeoxycholateGenerator
AnthropodesoxycholateGenerator
ChenateGenerator
GallodesoxycholateGenerator
ChenodeoxycholateGenerator
(+)-ChenodeoxycholateHMDB
(+)-Chenodeoxycholic acidHMDB
(3a,5b,7a)-3,7-Dihydroxy-cholan-24-OateHMDB
(3a,5b,7a)-3,7-Dihydroxy-cholan-24-Oic acidHMDB
3a,7a-Dihydroxy-5b,14a,17b-cholanateHMDB
3a,7a-Dihydroxy-5b,14a,17b-cholanic acidHMDB
3a,7a-Dihydroxy-5b-cholan-24-OateHMDB
3a,7a-Dihydroxy-5b-cholan-24-Oic acidHMDB
7a-Hydroxy-desoxycholsaeureHMDB
ChenodesoxycholsaeureHMDB
Acid, cheniqueHMDB
ChenofalkHMDB
ChenophalkHMDB
Acid, chenodeoxycholicHMDB
Chenodeoxycholate, sodiumHMDB
QuenocolHMDB
Solvay brand OF chenodeoxycholic acidHMDB
Antigen brand OF chenodeoxycholic acidHMDB
Falk brand OF chenodeoxycholic acidHMDB
QuenobilanHMDB
Sodium chenodeoxycholateHMDB
Tramedico brand OF chenodeoxycholic acidHMDB
Zambon brand OF chenodeoxycholic acidHMDB
Acid, chenicHMDB
Acid, gallodesoxycholicHMDB
Chenique acidHMDB
Estedi brand OF chenodeoxycholic acidHMDB
HenoholHMDB
Chemical FormulaC24H40O4
Average Molecular Mass392.572 g/mol
Monoisotopic Mass392.293 g/mol
CAS Registry Number474-25-9
IUPAC Name(4R)-4-[(1S,2S,5R,7S,9R,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,9R,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-BSWAIDMHSA-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
  • Hydroxysteroid
  • 3-alpha-hydroxysteroid
  • 7-hydroxysteroid
  • Cyclic alcohol
  • Secondary alcohol
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Organooxygen compound
  • Alcohol
  • Organic oxygen compound
  • Carbonyl group
  • Hydrocarbon derivative
  • Organic oxide
  • 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 Roles
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
Polarizability46.35 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyDeposition DateView
GC-MSGC-MS Spectrumsplash10-0a6u-3920000000-ce93b24c6e2568b6087dNot AvailableView Spectrum
GC-MSGC-MS Spectrumsplash10-0a6u-3920000000-ce93b24c6e2568b6087dNot AvailableView Spectrum
Predicted GC-MSPredicted GC-MS Spectrumsplash10-01rt-0419000000-6a92f910581240163a99Not AvailableView Spectrum
Predicted GC-MSPredicted GC-MS Spectrumsplash10-0006-1110390000-7a6c62344d1371b74081Not 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 Spectrumsplash10-0a4i-0009000000-82ed6dc62b49ac0340e6Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-01pa-2930000000-64edc819ad56b842cdbaNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-053r-6900000000-c97325e1ca9bcff75af1Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0002-0009000000-ad2d2440db7f3f1c8a2eNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0006-0009000000-2df562379077bf0f4b2aNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0006-0009000000-ff13f6ad8405e3969b6cNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0006-0009000000-1af3ba6ee17285da06a2Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0006-0009000000-5409557fb9a76a8a8e74Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0006-0009000000-c77d97d0dfe48497b263Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0006-0009000000-d38671ccaaa16ac6d1f1Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0596-0529000000-1ed436cc96fa78f90b88Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0006-0009000000-25ba2afe78d7d8070765Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0006-0019000000-c31d129de7de9df05167Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0006-0009000000-fc161813afdb6d319d8dNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0006-0009000000-ee319e0cbd9987920debNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0006-0009000000-858f2baceacfba406468Not 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
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
pancreatic cancerdecreased_in_blood_indecreasePMC7399932
cholestasisassociated_withNot AvailablePMC9488005
cerebrotendinous xanthomatosisis_treatment_forNot AvailablePMC13318692
cholangiocarcinomadecreased_in_blood_indecreasePMC7399932
Exposure Sources
Source IDSourceSectorReference
10InsecticidesAgriculture & land managementNot Available
115Drinking waterDrinking water & water supplyNot Available
233BrushesPersonal care & cosmeticsNot Available
250Bile therapyHealthcare, pharmaceuticals & veterinary productsNot Available
505AmplifiersElectrical & Electronic EquipmentNot Available
506AntennasElectrical & Electronic EquipmentNot Available
507Auxiliary DevicesElectrical & Electronic EquipmentNot Available
511Conductors Or Conductive Bodies Characterised By The Conductive MaterialsElectrical & Electronic EquipmentNot Available
517Electric SwitchesElectrical & Electronic EquipmentNot Available
518Electrically Stimulated Smoking DevicesElectrical & Electronic EquipmentNot Available
519ElectrodesElectrical & Electronic EquipmentNot Available
521Fixed Capacitors And Their ManufactureElectrical & Electronic EquipmentNot Available
524Hybrid CapacitorsElectrical & Electronic EquipmentNot Available
525Line Transmission SystemsElectrical & 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
545Food PreservationFood, 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
561Perfumes Within Detergents And SoapsHousehold cleaning & consumer productsNot Available
563Soap DetergentsHousehold cleaning & consumer productsNot Available
567Tobacco Product CasesHousehold cleaning & consumer productsNot Available
569Tobacco Smoke FiltersHousehold cleaning & consumer productsNot Available
578Making CigarsIndustrial manufacturing & chemical processingNot Available
580Manufacture Preparation Of Tobacco ProductsIndustrial manufacturing & chemical processingNot Available
609AftershavePersonal care & cosmeticsNot Available
610Aftersun ProductsPersonal care & cosmeticsNot Available
611Anti Perspirants Or Body DeoderantsPersonal care & cosmeticsNot Available
615Eye Makeup ProductsPersonal care & cosmeticsNot Available
617Lip Care ProductsPersonal care & cosmeticsNot Available
618Lip Makeup ProductsPersonal care & cosmeticsNot Available
619Manicure PedicurePersonal care & cosmeticsNot Available
632ApparelTextiles, leather & furnishingsNot Available
642FootwearTextiles, leather & furnishingsNot Available
650Purses Luggage Hand BagsTextiles, leather & furnishingsNot Available
Pathways
12 pathways
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 IDDB06777
HMDB IDHMDB0000518
FooDB IDFDB022087
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN ID207
PDB IDNot Available
Wikipedia LinkChenodiol
Chemspider ID9728
ChEBI ID16755
PubChem Compound ID10133
Kegg Compound IDC02528
YMDB IDNot Available
ECMDB IDM2MDB005111
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. Sato, Yoshio; Ikekawa, Nobuo. Preparation of chenodeoxycholic acid. Journal of Organic Chemistry (1959), 24 1367-8.
2. Sato, Yoshio; Ikekawa, Nobuo. Preparation of chenodeoxycholic acid. Journal of Organic Chemistry (1959), 24 1367-8.
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. 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.
7. Dohmen K, Mizuta T, Nakamuta M, Shimohashi N, Ishibashi H, Yamamoto K: Fenofibrate for patients with asymptomatic primary biliary cirrhosis. World J Gastroenterol. 2004 Mar 15;10(6):894-8.
8. Lupton JR, Steinbach G, Chang WC, O'Brien BC, Wiese S, Stoltzfus CL, Glober GA, Wargovich MJ, McPherson RS, Winn RJ: Calcium supplementation modifies the relative amounts of bile acids in bile and affects key aspects of human colon physiology. J Nutr. 1996 May;126(5):1421-8.
9. 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.
10. Kitani K, Kanai S, Ivy GO, Carrillo MC: Pharmacological modifications of endogenous antioxidant enzymes with special reference to the effects of deprenyl: a possible antioxidant strategy. Mech Ageing Dev. 1999 Nov;111(2-3):211-21.
11. 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.
12. Reyes H, Sjovall J: Bile acids and progesterone metabolites in intrahepatic cholestasis of pregnancy. Ann Med. 2000 Mar;32(2):94-106.
13. Stark M, Jornvall H, Johansson J: Isolation and characterization of hydrophobic polypeptides in human bile. Eur J Biochem. 1999 Nov;266(1):209-14.
14. Hofmann AF: The continuing importance of bile acids in liver and intestinal disease. Arch Intern Med. 1999 Dec 13-27;159(22):2647-58.
15. Morton DH, Salen G, Batta AK, Shefer S, Tint GS, Belchis D, Shneider B, Puffenberger E, Bull L, Knisely AS: Abnormal hepatic sinusoidal bile acid transport in an Amish kindred is not linked to FIC1 and is improved by ursodiol. Gastroenterology. 2000 Jul;119(1):188-95.
16. Virovic L, Supanc V, Duvnjak M: [Primary sclerosing cholangitis--diagnosis and therapy]. Acta Med Croatica. 2003;57(3):207-19.
17. Gatzen M, Pausch J: [Treatment of cholestatic liver diseases]. Med Klin (Munich). 2002 Mar 15;97(3):152-9.
18. 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.
19. 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.
20. Kowdley KV: Ursodeoxycholic acid therapy in hepatobiliary disease. Am J Med. 2000 Apr 15;108(6):481-6.
21. Azer SA, Coverdale SA, Byth K, Farrell GC, Stacey NH: Sequential changes in serum levels of individual bile acids in patients with chronic cholestatic liver disease. J Gastroenterol Hepatol. 1996 Mar;11(3):208-15.
22. Tadano T, Kanoh M, Matsumoto M, Sakamoto K, Kamano T: Studies of serum and feces bile acids determination by gas chromatography-mass spectrometry. Rinsho Byori. 2006 Feb;54(2):103-10.
23. St-Pierre MV, Kullak-Ublick GA, Hagenbuch B, Meier PJ: Transport of bile acids in hepatic and non-hepatic tissues. J Exp Biol. 2001 May;204(Pt 10):1673-86.
24. Claudel T, Staels B, Kuipers F: The Farnesoid X receptor: a molecular link between bile acid and lipid and glucose metabolism. Arterioscler Thromb Vasc Biol. 2005 Oct;25(10):2020-30. Epub 2005 Jul 21.
25. Chiang JY: Bile acid regulation of hepatic physiology: III. Bile acids and nuclear receptors. Am J Physiol Gastrointest Liver Physiol. 2003 Mar;284(3):G349-56.
26. Davis RA, Miyake JH, Hui TY, Spann NJ: Regulation of cholesterol-7alpha-hydroxylase: BAREly missing a SHP. J Lipid Res. 2002 Apr;43(4):533-43.
27. https://www.ncbi.nlm.nih.gov/pubmed/?term=11530998
28. https://www.ncbi.nlm.nih.gov/pubmed/?term=16037564
29. https://www.ncbi.nlm.nih.gov/pubmed/?term=24448653
30. https://www.ncbi.nlm.nih.gov/pubmed/?term=24464484