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Identification
NameChenodeoxycholic acid
Accession NumberDB06777
TypeSmall Molecule
GroupsApproved
DescriptionChenodeoxycholic acid (or Chenodiol) is an epimer of ursodeoxycholic acid (DB01586). Chenodeoxycholic acid is a bile acid naturally found in the body. It works by dissolving the cholesterol that makes gallstones and inhibiting production of cholesterol in the liver and absorption in the intestines, which helps to decrease the formation of gallstones. It can also reduce the amount of other bile acids that can be harmful to liver cells when levels are elevated.
Structure
Thumb
Synonyms
3alpha,7alpha-Dihydroxy-5beta-cholanic acid
7alpha-Hydroxylithocholic acid
Anthropodeoxycholic acid
Anthropodesoxycholic acid
CDCA
Chenic acid
Chenix
Chenocholic acid
Chenodeoxycholic acid
Chenodesoxycholic acid
Chenodiol
Gallodesoxycholic acid
External Identifiers Not Available
Approved Prescription ProductsNot Available
Approved Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
ChenodalTablet, film coated250 mg/1OralManchester Pharmaceuticals Inc.2009-10-01Not applicableUs
ChenodalTablet, film coated250 mg/1OralRetrophin, Inc.2015-12-28Not applicableUs
ChenodiolTablet, film coated250 mg/1OralNexgen Pharma, Inc.2009-10-01Not applicableUs
Approved Over the Counter ProductsNot Available
Unapproved/Other Products Not Available
International Brands
NameCompany
ChenixSigma Tau
Brand mixturesNot Available
SaltsNot Available
Categories
UNII0GEI24LG0J
CAS number474-25-9
WeightAverage: 392.572
Monoisotopic: 392.292659768
Chemical FormulaC24H40O4
InChI KeyRUDATBOHQWOJDD-BSWAIDMHSA-N
InChI
InChI=1S/C24H40O4/c1-14(4-7-21(27)28)17-5-6-18-22-19(9-11-24(17,18)3)23(2)10-8-16(25)12-15(23)13-20(22)26/h14-20,22,25-26H,4-13H2,1-3H3,(H,27,28)/t14-,15+,16-,17-,18+,19+,20-,22+,23+,24-/m1/s1
IUPAC Name
(4R)-4-[(1S,2S,5R,7S,9R,10R,11S,14R,15R)-5,9-dihydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-14-yl]pentanoic acid
SMILES
[H][C@@]1(CC[C@@]2([H])[C@]3([H])[[email protected]](O)C[C@]4([H])C[[email protected]](O)CC[C@]4(C)[C@@]3([H])CC[C@]12C)[[email protected]](C)CCC(O)=O
Pharmacology
IndicationChenodiol is indicated for patients with radiolucent stones in well-opacifying gallbladders, in whom selective surgery would be undertaken except for the presence of increased surgical risk due to systemic disease or age. Chenodiol will not dissolve calcified (radiopaque) or radiolucent bile pigment stones.
Structured Indications
PharmacodynamicsIt acts by reducing levels of cholesterol in the bile, helping gallstones that are made predominantly of cholesterol to dissolve. Chenodeoxycholic acid is ineffective with stones of a high calcium or bile acid content.
Mechanism of actionChenodiol suppresses hepatic synthesis of both cholesterol and cholic acid, gradually replacing the latter and its metabolite, deoxycholic acid in an expanded bile acid pool. These actions contribute to biliary cholesterol desaturation and gradual dissolution of radiolucent cholesterol gallstones in the presence of a gall-bladder visualized by oral cholecystography. Bile acids may also bind the the bile acid receptor (FXR) which regulates the synthesis and transport of bile acids.
TargetKindPharmacological actionActionsOrganismUniProt ID
Bile acid receptorProteinunknown
other
HumanQ96RI1 details
Related Articles
AbsorptionChenodiol is well absorbed from the small intestine.
Volume of distributionNot Available
Protein bindingNot Available
Metabolism

Chenodiol is well absorbed from the small intestine and taken up by the liver where it is converted to its taurine and glycine conjugates and secreted in bile. At steady-state, an amount of chenodiol near the daily dose escapes to the colon and is converted by bacterial action to lithocholic acid. About 80% of the lithocholate is excreted in the feces; the remainder is absorbed and converted in the liver to its poorly absorbed sulfolithocholyl conjugates. During chenodiol therapy there is only a minor increase in biliary lithocholate, while fecal bile acids are increased three- to fourfold.

Route of eliminationAbout 80% of its bacterial metabolite lithocholate is excreted in the feces.
Half lifeNot Available
ClearanceNot Available
ToxicityHepatotoxic.
Affected organismsNot Available
Pathways
PathwayCategorySMPDB ID
Cerebrotendinous Xanthomatosis (CTX)DiseaseSMP00315
27-Hydroxylase DeficiencyDiseaseSMP00720
Bile Acid BiosynthesisMetabolicSMP00035
Familial Hypercholanemia (FHCA)DiseaseSMP00317
Congenital Bile Acid Synthesis Defect Type IIDiseaseSMP00314
Zellweger SyndromeDiseaseSMP00316
Congenital Bile Acid Synthesis Defect Type IIIDiseaseSMP00318
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
Interactions
Drug Interactions
DrugInteractionDrug group
Aluminum hydroxideThe serum concentration of Chenodeoxycholic acid can be decreased when it is combined with Aluminum hydroxide.Approved
AmiodaroneThe metabolism of Chenodeoxycholic acid can be decreased when combined with Amiodarone.Approved, Investigational
AprepitantThe serum concentration of Chenodeoxycholic acid can be increased when it is combined with Aprepitant.Approved, Investigational
AtazanavirThe metabolism of Chenodeoxycholic acid can be decreased when combined with Atazanavir.Approved, Investigational
AtomoxetineThe metabolism of Chenodeoxycholic acid can be decreased when combined with Atomoxetine.Approved
BazedoxifeneThe therapeutic efficacy of Chenodeoxycholic acid can be decreased when used in combination with Bazedoxifene.Approved, Investigational
BexaroteneThe serum concentration of Chenodeoxycholic acid can be decreased when it is combined with Bexarotene.Approved, Investigational
BezafibrateThe therapeutic efficacy of Chenodeoxycholic acid can be decreased when used in combination with Bezafibrate.Approved
BoceprevirThe metabolism of Chenodeoxycholic acid can be decreased when combined with Boceprevir.Approved
BortezomibThe metabolism of Chenodeoxycholic acid can be decreased when combined with Bortezomib.Approved, Investigational
BosentanThe serum concentration of Chenodeoxycholic acid can be decreased when it is combined with Bosentan.Approved, Investigational
CarbamazepineThe metabolism of Chenodeoxycholic acid can be increased when combined with Carbamazepine.Approved, Investigational
CeritinibThe serum concentration of Chenodeoxycholic acid can be increased when it is combined with Ceritinib.Approved
ChlorotrianiseneThe therapeutic efficacy of Chenodeoxycholic acid can be decreased when used in combination with Chlorotrianisene.Withdrawn
CholestyramineThe serum concentration of Chenodeoxycholic acid can be decreased when it is combined with Cholestyramine.Approved
CiprofibrateThe therapeutic efficacy of Chenodeoxycholic acid can be decreased when used in combination with Ciprofibrate.Approved
ClarithromycinThe metabolism of Chenodeoxycholic acid can be decreased when combined with Clarithromycin.Approved
ClemastineThe metabolism of Chenodeoxycholic acid can be decreased when combined with Clemastine.Approved
ClofibrateThe therapeutic efficacy of Chenodeoxycholic acid can be decreased when used in combination with Clofibrate.Approved
ClotrimazoleThe metabolism of Chenodeoxycholic acid can be decreased when combined with Clotrimazole.Approved, Vet Approved
CobicistatThe metabolism of Chenodeoxycholic acid can be decreased when combined with Cobicistat.Approved
ColesevelamThe serum concentration of Chenodeoxycholic acid can be decreased when it is combined with Colesevelam.Approved
ColestipolThe serum concentration of Chenodeoxycholic acid can be decreased when it is combined with Colestipol.Approved
ConivaptanThe serum concentration of Chenodeoxycholic acid can be increased when it is combined with Conivaptan.Approved, Investigational
Conjugated Equine EstrogensThe therapeutic efficacy of Chenodeoxycholic acid can be decreased when used in combination with Conjugated Equine Estrogens.Approved
CrizotinibThe metabolism of Chenodeoxycholic acid can be decreased when combined with Crizotinib.Approved
CyclosporineThe metabolism of Chenodeoxycholic acid can be decreased when combined with Cyclosporine.Approved, Investigational, Vet Approved
DabrafenibThe serum concentration of Chenodeoxycholic acid can be decreased when it is combined with Dabrafenib.Approved
DarunavirThe metabolism of Chenodeoxycholic acid can be decreased when combined with Darunavir.Approved
DasatinibThe serum concentration of Chenodeoxycholic acid can be increased when it is combined with Dasatinib.Approved, Investigational
DeferasiroxThe serum concentration of Chenodeoxycholic acid can be decreased when it is combined with Deferasirox.Approved, Investigational
DelavirdineThe metabolism of Chenodeoxycholic acid can be decreased when combined with Delavirdine.Approved
DexamethasoneThe serum concentration of Chenodeoxycholic acid can be decreased when it is combined with Dexamethasone.Approved, Investigational, Vet Approved
DienestrolThe therapeutic efficacy of Chenodeoxycholic acid can be decreased when used in combination with Dienestrol.Approved
DiethylstilbestrolThe therapeutic efficacy of Chenodeoxycholic acid can be decreased when used in combination with Diethylstilbestrol.Approved
DihydroergotamineThe metabolism of Chenodeoxycholic acid can be decreased when combined with Dihydroergotamine.Approved
DiltiazemThe metabolism of Chenodeoxycholic acid can be decreased when combined with Diltiazem.Approved
DoxycyclineThe metabolism of Chenodeoxycholic acid can be decreased when combined with Doxycycline.Approved, Investigational, Vet Approved
DronedaroneThe metabolism of Chenodeoxycholic acid can be decreased when combined with Dronedarone.Approved
EfavirenzThe serum concentration of Chenodeoxycholic acid can be decreased when it is combined with Efavirenz.Approved, Investigational
EnzalutamideThe serum concentration of Chenodeoxycholic acid can be decreased when it is combined with Enzalutamide.Approved
ErythromycinThe metabolism of Chenodeoxycholic acid can be decreased when combined with Erythromycin.Approved, Vet Approved
Eslicarbazepine acetateThe serum concentration of Chenodeoxycholic acid can be decreased when it is combined with Eslicarbazepine acetate.Approved
EstradiolThe therapeutic efficacy of Chenodeoxycholic acid can be decreased when used in combination with Estradiol.Approved, Investigational, Vet Approved
EstriolThe therapeutic efficacy of Chenodeoxycholic acid can be decreased when used in combination with Estriol.Approved, Vet Approved
EstroneThe therapeutic efficacy of Chenodeoxycholic acid can be decreased when used in combination with Estrone.Approved
Ethinyl EstradiolThe therapeutic efficacy of Chenodeoxycholic acid can be decreased when used in combination with Ethinyl Estradiol.Approved
EtofibrateThe therapeutic efficacy of Chenodeoxycholic acid can be decreased when used in combination with Etofibrate.Approved
EtravirineThe serum concentration of Chenodeoxycholic acid can be decreased when it is combined with Etravirine.Approved
FenofibrateThe therapeutic efficacy of Chenodeoxycholic acid can be decreased when used in combination with Fenofibrate.Approved
FluconazoleThe metabolism of Chenodeoxycholic acid can be decreased when combined with Fluconazole.Approved
FluvoxamineThe metabolism of Chenodeoxycholic acid can be decreased when combined with Fluvoxamine.Approved, Investigational
FosamprenavirThe metabolism of Chenodeoxycholic acid can be decreased when combined with Fosamprenavir.Approved
FosaprepitantThe serum concentration of Chenodeoxycholic acid can be increased when it is combined with Fosaprepitant.Approved
FosphenytoinThe metabolism of Chenodeoxycholic acid can be increased when combined with Fosphenytoin.Approved
Fusidic AcidThe serum concentration of Chenodeoxycholic acid can be increased when it is combined with Fusidic Acid.Approved
GemfibrozilThe therapeutic efficacy of Chenodeoxycholic acid can be decreased when used in combination with Gemfibrozil.Approved
GenisteinThe therapeutic efficacy of Chenodeoxycholic acid can be decreased when used in combination with Genistein.Investigational
HexestrolThe therapeutic efficacy of Chenodeoxycholic acid can be decreased when used in combination with Hexestrol.Withdrawn
IdelalisibThe serum concentration of Chenodeoxycholic acid can be increased when it is combined with Idelalisib.Approved
ImatinibThe metabolism of Chenodeoxycholic acid can be decreased when combined with Imatinib.Approved
IndinavirThe metabolism of Chenodeoxycholic acid can be decreased when combined with Indinavir.Approved
IsavuconazoniumThe metabolism of Chenodeoxycholic acid can be decreased when combined with Isavuconazonium.Approved, Investigational
IsradipineThe metabolism of Chenodeoxycholic acid can be decreased when combined with Isradipine.Approved
ItraconazoleThe metabolism of Chenodeoxycholic acid can be decreased when combined with Itraconazole.Approved, Investigational
IvacaftorThe serum concentration of Chenodeoxycholic acid can be increased when it is combined with Ivacaftor.Approved
KetoconazoleThe metabolism of Chenodeoxycholic acid can be decreased when combined with Ketoconazole.Approved, Investigational
LopinavirThe metabolism of Chenodeoxycholic acid can be decreased when combined with Lopinavir.Approved
LovastatinThe metabolism of Chenodeoxycholic acid can be decreased when combined with Lovastatin.Approved, Investigational
LuliconazoleThe serum concentration of Chenodeoxycholic acid can be increased when it is combined with Luliconazole.Approved
LumacaftorThe metabolism of Chenodeoxycholic acid can be increased when combined with Lumacaftor.Approved
MestranolThe therapeutic efficacy of Chenodeoxycholic acid can be decreased when used in combination with Mestranol.Approved
MethallenestrilThe therapeutic efficacy of Chenodeoxycholic acid can be decreased when used in combination with Methallenestril.Experimental
MifepristoneThe serum concentration of Chenodeoxycholic acid can be increased when it is combined with Mifepristone.Approved, Investigational
MitotaneThe serum concentration of Chenodeoxycholic acid can be decreased when it is combined with Mitotane.Approved
ModafinilThe serum concentration of Chenodeoxycholic acid can be decreased when it is combined with Modafinil.Approved, Investigational
NafcillinThe serum concentration of Chenodeoxycholic acid can be decreased when it is combined with Nafcillin.Approved
NefazodoneThe metabolism of Chenodeoxycholic acid can be decreased when combined with Nefazodone.Approved, Withdrawn
NelfinavirThe metabolism of Chenodeoxycholic acid can be decreased when combined with Nelfinavir.Approved
NetupitantThe serum concentration of Chenodeoxycholic acid can be increased when it is combined with Netupitant.Approved
NevirapineThe metabolism of Chenodeoxycholic acid can be increased when combined with Nevirapine.Approved
NilotinibThe metabolism of Chenodeoxycholic acid can be decreased when combined with Nilotinib.Approved, Investigational
OlaparibThe metabolism of Chenodeoxycholic acid can be decreased when combined with Olaparib.Approved
OsimertinibThe serum concentration of Chenodeoxycholic acid can be increased when it is combined with Osimertinib.Approved
PalbociclibThe serum concentration of Chenodeoxycholic acid can be increased when it is combined with Palbociclib.Approved
PentobarbitalThe metabolism of Chenodeoxycholic acid can be increased when combined with Pentobarbital.Approved, Vet Approved
PhenobarbitalThe metabolism of Chenodeoxycholic acid can be increased when combined with Phenobarbital.Approved
PhenytoinThe metabolism of Chenodeoxycholic acid can be increased when combined with Phenytoin.Approved, Vet Approved
Polyestradiol phosphateThe therapeutic efficacy of Chenodeoxycholic acid can be decreased when used in combination with Polyestradiol phosphate.Approved
PosaconazoleThe metabolism of Chenodeoxycholic acid can be decreased when combined with Posaconazole.Approved, Investigational, Vet Approved
PrimidoneThe metabolism of Chenodeoxycholic acid can be increased when combined with Primidone.Approved, Vet Approved
PromestrieneThe therapeutic efficacy of Chenodeoxycholic acid can be decreased when used in combination with Promestriene.Investigational
QuinestrolThe therapeutic efficacy of Chenodeoxycholic acid can be decreased when used in combination with Quinestrol.Approved
RanolazineThe metabolism of Chenodeoxycholic acid can be decreased when combined with Ranolazine.Approved, Investigational
RifabutinThe metabolism of Chenodeoxycholic acid can be increased when combined with Rifabutin.Approved
RifampicinThe metabolism of Chenodeoxycholic acid can be increased when combined with Rifampicin.Approved
RifapentineThe metabolism of Chenodeoxycholic acid can be increased when combined with Rifapentine.Approved
RitonavirThe metabolism of Chenodeoxycholic acid can be decreased when combined with Ritonavir.Approved, Investigational
S EquolThe therapeutic efficacy of Chenodeoxycholic acid can be decreased when used in combination with S Equol.Investigational
SaquinavirThe metabolism of Chenodeoxycholic acid can be decreased when combined with Saquinavir.Approved, Investigational
SecoisolariciresinolThe therapeutic efficacy of Chenodeoxycholic acid can be decreased when used in combination with Secoisolariciresinol.Investigational
SildenafilThe metabolism of Chenodeoxycholic acid can be decreased when combined with Sildenafil.Approved, Investigational
SiltuximabThe serum concentration of Chenodeoxycholic acid can be decreased when it is combined with Siltuximab.Approved
SimeprevirThe serum concentration of Chenodeoxycholic acid can be increased when it is combined with Simeprevir.Approved
St. John's WortThe serum concentration of Chenodeoxycholic acid can be decreased when it is combined with St. John's Wort.Nutraceutical
StiripentolThe serum concentration of Chenodeoxycholic acid can be increased when it is combined with Stiripentol.Approved
SulfisoxazoleThe metabolism of Chenodeoxycholic acid can be decreased when combined with Sulfisoxazole.Approved, Vet Approved
Synthetic Conjugated Estrogens, AThe therapeutic efficacy of Chenodeoxycholic acid can be decreased when used in combination with Synthetic Conjugated Estrogens, A.Approved
Synthetic Conjugated Estrogens, BThe therapeutic efficacy of Chenodeoxycholic acid can be decreased when used in combination with Synthetic Conjugated Estrogens, B.Approved
TelaprevirThe metabolism of Chenodeoxycholic acid can be decreased when combined with Telaprevir.Approved
TelithromycinThe metabolism of Chenodeoxycholic acid can be decreased when combined with Telithromycin.Approved
TiboloneThe therapeutic efficacy of Chenodeoxycholic acid can be decreased when used in combination with Tibolone.Approved
TiclopidineThe metabolism of Chenodeoxycholic acid can be decreased when combined with Ticlopidine.Approved
TocilizumabThe serum concentration of Chenodeoxycholic acid can be decreased when it is combined with Tocilizumab.Approved
VenlafaxineThe metabolism of Chenodeoxycholic acid can be decreased when combined with Venlafaxine.Approved
VerapamilThe metabolism of Chenodeoxycholic acid can be decreased when combined with Verapamil.Approved
VoriconazoleThe metabolism of Chenodeoxycholic acid can be decreased when combined with Voriconazole.Approved, Investigational
ZeranolThe therapeutic efficacy of Chenodeoxycholic acid can be decreased when used in combination with Zeranol.Vet Approved
ZiprasidoneThe metabolism of Chenodeoxycholic acid can be decreased when combined with Ziprasidone.Approved
Food InteractionsNot Available
References
Synthesis Reference

Henry Francis Frost, Fritz Fabian, Christopher James Sharpe, William Arthur Jones, “Process for preparing chenodeoxycholic acid.” U.S. Patent US4022806, issued October, 1974.

US4022806
General ReferencesNot Available
External Links
ATC CodesA05AA01
AHFS CodesNot Available
PDB EntriesNot Available
FDA labelDownload (190 KB)
MSDSNot Available
ADMET
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.9766
Blood Brain Barrier+0.9288
Caco-2 permeable+0.73
P-glycoprotein substrateSubstrate0.6648
P-glycoprotein inhibitor INon-inhibitor0.8737
P-glycoprotein inhibitor IIInhibitor0.5368
Renal organic cation transporterNon-inhibitor0.8537
CYP450 2C9 substrateNon-substrate0.7818
CYP450 2D6 substrateNon-substrate0.9115
CYP450 3A4 substrateSubstrate0.7407
CYP450 1A2 substrateNon-inhibitor0.9045
CYP450 2C9 inhibitorNon-inhibitor0.9456
CYP450 2D6 inhibitorNon-inhibitor0.9781
CYP450 2C19 inhibitorNon-inhibitor0.9707
CYP450 3A4 inhibitorNon-inhibitor0.8405
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9563
Ames testNon AMES toxic0.8794
CarcinogenicityNon-carcinogens0.9329
BiodegradationNot ready biodegradable0.992
Rat acute toxicity2.5624 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9622
hERG inhibition (predictor II)Non-inhibitor0.7246
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397 )
Pharmacoeconomics
ManufacturersNot Available
PackagersNot Available
Dosage forms
FormRouteStrength
Tablet, film coatedOral250 mg/1
PricesNot Available
PatentsNot Available
Properties
StateSolid
Experimental Properties
PropertyValueSource
melting point168-171Maeke, S. and Rambacher, P.; US. Patent 4,163,017; July 31,1979; assigned to Diamalt A.G. (Germany).
water solubility89.9 mg/L (at 20 °C)YALKOWSKY,SH & DANNENFELSER,RM (1992)
logP4.15SANGSTER (1993)
Predicted Properties
PropertyValueSource
Water Solubility0.0197 mg/mLALOGPS
logP3.01ALOGPS
logP3.71ChemAxon
logS-4.3ALOGPS
pKa (Strongest Acidic)4.6ChemAxon
pKa (Strongest Basic)-0.54ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area77.76 Å2ChemAxon
Rotatable Bond Count4ChemAxon
Refractivity109.27 m3·mol-1ChemAxon
Polarizability46.28 Å3ChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Mass Spec (NIST)Not Available
Spectra
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-MS (3 TMS)splash10-0a6u-3920000000-ce93b24c6e2568b6087dView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, N/A (Annotated)splash10-0a4i-0009000000-82ed6dc62b49ac0340e6View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, N/A (Annotated)splash10-01pa-2930000000-64edc819ad56b842cdbaView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, N/A (Annotated)splash10-053r-6900000000-c97325e1ca9bcff75af1View in MoNA
1D NMR1H NMR SpectrumNot Available
2D NMR[1H,13C] 2D NMR SpectrumNot Available
Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as dihydroxy bile acids, alcohols and derivatives. These are compounds containing or derived from a bile acid or alcohol, and which bears exactly two carboxylic acid groups.
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
  • 7-hydroxysteroid
  • 3-alpha-hydroxysteroid
  • Hydroxysteroid
  • 3-hydroxysteroid
  • Cyclic alcohol
  • Secondary alcohol
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Alcohol
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External Descriptors

Targets

Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
other
General Function:
Zinc ion binding
Specific Function:
Ligand-activated transcription factor. Receptor for bile acids such as chenodeoxycholic acid, lithocholic acid and deoxycholic acid. Represses the transcription of the cholesterol 7-alpha-hydroxylase gene (CYP7A1) through the induction of NR0B2 or FGF19 expression, via two distinct mechanisms. Activates the intestinal bile acid-binding protein (IBABP). Activates the transcription of bile salt e...
Gene Name:
NR1H4
Uniprot ID:
Q96RI1
Molecular Weight:
55913.915 Da
References
  1. Makishima M, Okamoto AY, Repa JJ, Tu H, Learned RM, Luk A, Hull MV, Lustig KD, Mangelsdorf DJ, Shan B: Identification of a nuclear receptor for bile acids. Science. 1999 May 21;284(5418):1362-5. [PubMed:10334992 ]
  2. Xu Y, Watanabe T, Tanigawa T, Machida H, Okazaki H, Yamagami H, Watanabe K, Tominaga K, Fujiwara Y, Oshitani N, Arakawa T: Bile acids induce cdx2 expression through the farnesoid x receptor in gastric epithelial cells. J Clin Biochem Nutr. 2010 Jan;46(1):81-6. doi: 10.3164/jcbn.09-71. Epub 2009 Dec 29. [PubMed:20104269 ]

Enzymes

Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
substrate
General Function:
Vitamin d3 25-hydroxylase activity
Specific Function:
Catalyzes the first step in the oxidation of the side chain of sterol intermediates; the 27-hydroxylation of 5-beta-cholestane-3-alpha,7-alpha,12-alpha-triol. Has also a vitamin D3-25-hydroxylase activity.
Gene Name:
CYP27A1
Uniprot ID:
Q02318
Molecular Weight:
60234.28 Da
References
  1. Matsuzaki Y, Bouscarel B, Ikegami T, Honda A, Doy M, Ceryak S, Fukushima S, Yoshida S, Shoda J, Tanaka N: Selective inhibition of CYP27A1 and of chenodeoxycholic acid synthesis in cholestatic hamster liver. Biochim Biophys Acta. 2002 Nov 20;1588(2):139-48. [PubMed:12385778 ]
  2. Bjorkhem I: Inborn errors of metabolism with consequences for bile acid biosynthesis. A minireview. Scand J Gastroenterol Suppl. 1994;204:68-72. [PubMed:7824882 ]
  3. Bjorkhem I, Araya Z, Rudling M, Angelin B, Einarsson C, Wikvall K: Differences in the regulation of the classical and the alternative pathway for bile acid synthesis in human liver. No coordinate regulation of CYP7A1 and CYP27A1. J Biol Chem. 2002 Jul 26;277(30):26804-7. Epub 2002 May 13. [PubMed:12011083 ]
  4. Keren Z, Falik-Zaccai TC: Cerebrotendinous xanthomatosis (CTX): a treatable lipid storage disease. Pediatr Endocrinol Rev. 2009 Sep;7(1):6-11. [PubMed:19696711 ]
  5. Honda A, Salen G, Matsuzaki Y, Batta AK, Xu G, Hirayama T, Tint GS, Doy M, Shefer S: Disrupted coordinate regulation of farnesoid X receptor target genes in a patient with cerebrotendinous xanthomatosis. J Lipid Res. 2005 Feb;46(2):287-96. Epub 2004 Dec 1. [PubMed:15576845 ]
  6. Goodwin B, Gauthier KC, Umetani M, Watson MA, Lochansky MI, Collins JL, Leitersdorf E, Mangelsdorf DJ, Kliewer SA, Repa JJ: Identification of bile acid precursors as endogenous ligands for the nuclear xenobiotic pregnane X receptor. Proc Natl Acad Sci U S A. 2003 Jan 7;100(1):223-8. Epub 2002 Dec 30. [PubMed:12509506 ]
  7. Honda A, Salen G, Matsuzaki Y, Batta AK, Xu G, Leitersdorf E, Tint GS, Erickson SK, Tanaka N, Shefer S: Differences in hepatic levels of intermediates in bile acid biosynthesis between Cyp27(-/-) mice and CTX. J Lipid Res. 2001 Feb;42(2):291-300. [PubMed:11181760 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
substrate
General Function:
Vitamin d3 25-hydroxylase activity
Specific Function:
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation reactions (e.g. caffeine 8-oxidation, omeprazole sulphoxidation, midazolam 1'-hydroxylation and midazolam 4-hydroxylation) of structurally unrelated compounds, including steroids, fatty acids, and xenobiot...
Gene Name:
CYP3A4
Uniprot ID:
P08684
Molecular Weight:
57342.67 Da
References
  1. Deo AK, Bandiera SM: Identification of human hepatic cytochrome p450 enzymes involved in the biotransformation of cholic and chenodeoxycholic acid. Drug Metab Dispos. 2008 Oct;36(10):1983-91. doi: 10.1124/dmd.108.022194. Epub 2008 Jun 26. [PubMed:18583509 ]
  2. Gnerre C, Blattler S, Kaufmann MR, Looser R, Meyer UA: Regulation of CYP3A4 by the bile acid receptor FXR: evidence for functional binding sites in the CYP3A4 gene. Pharmacogenetics. 2004 Oct;14(10):635-45. [PubMed:15454728 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
inhibitor
General Function:
Glucuronosyltransferase activity
Specific Function:
UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds.Its unique specificity for 3,4-catechol estrogens and estriol suggests it may play an important role in regulating the level and activity of these potent and active estrogen metabolites. Is also active with androsterone, hyodeoxycholic acid and tetrachlorocatechol...
Gene Name:
UGT2B7
Uniprot ID:
P16662
Molecular Weight:
60694.12 Da
References
  1. Lu Y, Heydel JM, Li X, Bratton S, Lindblom T, Radominska-Pandya A: Lithocholic acid decreases expression of UGT2B7 in Caco-2 cells: a potential role for a negative farnesoid X receptor response element. Drug Metab Dispos. 2005 Jul;33(7):937-46. Epub 2005 Apr 8. [PubMed:15821044 ]
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Drug created on September 14, 2010 10:21 / Updated on August 17, 2016 12:24