Identification

Name
Chenodeoxycholic acid
Accession Number
DB06777
Type
Small Molecule
Groups
Approved
Description

Chenodeoxycholic 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
  • Chenocholic acid
  • Chenodeoxycholic acid
  • Chenodesoxycholic acid
  • Chenodiol
  • Gallodesoxycholic acid
Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
ChenodalTablet, film coated250 mg/1OralManchester Pharmaceuticals2009-10-01Not applicableUs
ChenodalTablet, film coated250 mg/1OralRetrophin, Inc.2015-12-28Not applicableUs
ChenodiolTablet, film coated250 mg/1OralNexgen Pharma, Inc.2009-10-01Not applicableUs
International/Other Brands
Chenix (Sigma Tau)
Categories
UNII
0GEI24LG0J
CAS number
474-25-9
Weight
Average: 392.572
Monoisotopic: 392.292659768
Chemical Formula
C24H40O4
InChI Key
RUDATBOHQWOJDD-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

Pharmacology

Indication

Chenodiol 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
Pharmacodynamics

It 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 action

Chenodiol 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.

TargetActionsOrganism
UBile acid receptor
other
Human
UNuclear receptor subfamily 1 group I member 2Not AvailableHuman
UG-protein coupled bile acid receptor 1Not AvailableHuman
UAldo-keto reductase family 1 member C2
substrate
Human
Absorption

Chenodiol is well absorbed from the small intestine.

Volume of distribution
Not Available
Protein binding
Not 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 elimination

About 80% of its bacterial metabolite lithocholate is excreted in the feces.

Half life
Not Available
Clearance
Not Available
Toxicity

Hepatotoxic.

Affected organisms
Not Available
Pathways
PathwayCategory
Cerebrotendinous Xanthomatosis (CTX)Disease
27-Hydroxylase DeficiencyDisease
Bile Acid BiosynthesisMetabolic
Familial Hypercholanemia (FHCA)Disease
Congenital Bile Acid Synthesis Defect Type IIDisease
Zellweger SyndromeDisease
Congenital Bile Acid Synthesis Defect Type IIIDisease
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
DrugInteractionDrug group
Aluminium clofibrateThe therapeutic efficacy of Chenodeoxycholic acid can be decreased when used in combination with Aluminium clofibrate.Experimental
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
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, Withdrawn
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.Investigational, 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, Investigational
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, Investigational
ClofibrideThe therapeutic efficacy of Chenodeoxycholic acid can be decreased when used in combination with Clofibride.Experimental
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 estrogensThe therapeutic efficacy of Chenodeoxycholic acid can be decreased when used in combination with Conjugated 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
DaidzeinThe therapeutic efficacy of Chenodeoxycholic acid can be decreased when used in combination with Daidzein.Experimental
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
DienestrolThe therapeutic efficacy of Chenodeoxycholic acid can be decreased when used in combination with Dienestrol.Approved, Investigational
DiethylstilbestrolThe therapeutic efficacy of Chenodeoxycholic acid can be decreased when used in combination with Diethylstilbestrol.Approved, Investigational
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
EnzalutamideThe serum concentration of Chenodeoxycholic acid can be decreased when it is combined with Enzalutamide.Approved
EpimestrolThe therapeutic efficacy of Chenodeoxycholic acid can be decreased when used in combination with Epimestrol.Experimental
EquolThe therapeutic efficacy of Chenodeoxycholic acid can be decreased when used in combination with Equol.Investigational
ErythromycinThe metabolism of Chenodeoxycholic acid can be decreased when combined with Erythromycin.Approved, Vet 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, Investigational, 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
FenofibrateThe therapeutic efficacy of Chenodeoxycholic acid can be decreased when used in combination with Fenofibrate.Approved
Fenofibric acidThe therapeutic efficacy of Chenodeoxycholic acid can be decreased when used in combination with Fenofibric acid.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
MoxestrolThe therapeutic efficacy of Chenodeoxycholic acid can be decreased when used in combination with Moxestrol.Experimental
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
RonifibrateThe therapeutic efficacy of Chenodeoxycholic acid can be decreased when used in combination with Ronifibrate.Experimental
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
SimfibrateThe therapeutic efficacy of Chenodeoxycholic acid can be decreased when used in combination with Simfibrate.Experimental
St. John's WortThe serum concentration of Chenodeoxycholic acid can be decreased when it is combined with St. John's Wort.Investigational, 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, Withdrawn
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, Investigational
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 Interactions
Not 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 References
Not Available
External Links
Human Metabolome Database
HMDB00518
KEGG Drug
D00163
KEGG Compound
C02528
PubChem Compound
10133
PubChem Substance
99443291
ChemSpider
9728
BindingDB
21674
ChEBI
16755
ChEMBL
CHEMBL240597
PharmGKB
PA165958403
HET
JN3
Drugs.com
Drugs.com Drug Page
Wikipedia
Chenodeoxycholic_acid
ATC Codes
A05AA01 — Chenodeoxycholic acid
PDB Entries
2jn3 / 3o02 / 4qe6
FDA label
Download (190 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
0CompletedTreatmentFamilial hypertriglyceridaemia / Hyperlipidemia, Familial Combined / Metabolic Syndromes1
2Active Not RecruitingTreatmentSpastic Paraplegia, Hereditary1
2CompletedTreatmentConstipation-Predominant Irritable Bowel Syndrome1
2Unknown StatusTreatmentXanthomatosis, Cerebrotendinous1
4CompletedBasic ScienceObesity, Severe1
4Enrolling by InvitationDiagnosticBile Acid Malabsorption / Gallstone formation1
4RecruitingTreatmentObesity, Severe2
Not AvailableCompletedBasic ScienceBMI >30 kg/m2 / Type 2 Diabetes Mellitus1
Not AvailableTerminatedTreatmentAdrenoleukodystrophy / Bifunctional Enzyme Deficiency / Cerebrohepatorenal syndrome / Infantile Refsum's Disease1
Not AvailableWithdrawnNot AvailableXanthomatosis, Cerebrotendinous1

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage forms
FormRouteStrength
Tablet, film coatedOral250 mg/1
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)168-171Maeke, 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 RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.9766
Blood Brain Barrier+0.9288
Caco-2 permeable+0.73
P-glycoprotein substrateSubstrate0.6648
P-glycoprotein inhibitor INon-inhibitor0.8737
P-glycoprotein inhibitor IIInhibitor0.5368
Renal organic cation transporterNon-inhibitor0.8537
CYP450 2C9 substrateNon-substrate0.7818
CYP450 2D6 substrateNon-substrate0.9115
CYP450 3A4 substrateSubstrate0.7407
CYP450 1A2 substrateNon-inhibitor0.9045
CYP450 2C9 inhibitorNon-inhibitor0.9456
CYP450 2D6 inhibitorNon-inhibitor0.9781
CYP450 2C19 inhibitorNon-inhibitor0.9707
CYP450 3A4 inhibitorNon-inhibitor0.8405
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9563
Ames testNon AMES toxic0.8794
CarcinogenicityNon-carcinogens0.9329
BiodegradationNot ready biodegradable0.992
Rat acute toxicity2.5624 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9622
hERG inhibition (predictor II)Non-inhibitor0.7246
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
GC-MS Spectrum - GC-MS (3 TMS)GC-MSsplash10-0a6u-3920000000-ce93b24c6e2568b6087d
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
GC-MS Spectrum - GC-MSGC-MSsplash10-0a6u-3920000000-ce93b24c6e2568b6087d
MS/MS Spectrum - Quattro_QQQ 10V, N/ALC-MS/MSsplash10-0a4i-0009000000-82ed6dc62b49ac0340e6
MS/MS Spectrum - Quattro_QQQ 25V, N/ALC-MS/MSsplash10-01pa-2930000000-64edc819ad56b842cdba
MS/MS Spectrum - Quattro_QQQ 40V, N/ALC-MS/MSsplash10-053r-6900000000-c97325e1ca9bcff75af1
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available
LC-MS/MS Spectrum - LC-ESI-IT , negativeLC-MS/MSsplash10-0002-0009000000-ad2d2440db7f3f1c8a2e
1H NMR Spectrum1D NMRNot Applicable
[1H,13C] 2D NMR Spectrum2D NMRNot Applicable

Taxonomy

Description
This compound belongs to the class of organic compounds known as dihydroxy bile acids, alcohols and derivatives. These are compounds containing or derived from a bile acid or alcohol, and which bears exactly two carboxylic acid groups.
Kingdom
Organic compounds
Super Class
Lipids and lipid-like molecules
Class
Steroids and steroid derivatives
Sub Class
Bile acids, alcohols and derivatives
Direct Parent
Dihydroxy bile acids, alcohols and derivatives
Alternative Parents
7-hydroxysteroids / 3-alpha-hydroxysteroids / Secondary alcohols / Cyclic alcohols and derivatives / Monocarboxylic acids and derivatives / Carboxylic acids / Organic oxides / Hydrocarbon derivatives / Carbonyl compounds
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
Molecular Framework
Aliphatic homopolycyclic compounds
External Descriptors
bile acid, dihydroxy-5beta-cholanic acid (CHEBI:16755) / C24 bile acids, alcohols, and derivatives, Cholane and derivatives (C02528) / C24 bile acids, alcohols, and derivatives (LMST04010032)

Targets

Details
1. Bile acid receptor
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-hydroxyla...
Gene Name
NR1H4
Uniprot ID
Q96RI1
Uniprot Name
Bile acid receptor
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]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
Zinc ion binding
Specific Function
Nuclear receptor that binds and is activated by variety of endogenous and xenobiotic compounds. Transcription factor that activates the transcription of multiple genes involved in the metabolism an...
Gene Name
NR1I2
Uniprot ID
O75469
Uniprot Name
Nuclear receptor subfamily 1 group I member 2
Molecular Weight
49761.245 Da
References
  1. Katona BW, Cummins CL, Ferguson AD, Li T, Schmidt DR, Mangelsdorf DJ, Covey DF: Synthesis, characterization, and receptor interaction profiles of enantiomeric bile acids. J Med Chem. 2007 Nov 29;50(24):6048-58. Epub 2007 Oct 27. [PubMed:17963371]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
G-protein coupled bile acid receptor activity
Specific Function
Receptor for bile acid. Bile acid-binding induces its internalization, activation of extracellular signal-regulated kinase and intracellular cAMP production. May be involved in the suppression of m...
Gene Name
GPBAR1
Uniprot ID
Q8TDU6
Uniprot Name
G-protein coupled bile acid receptor 1
Molecular Weight
35247.795 Da
References
  1. Katona BW, Cummins CL, Ferguson AD, Li T, Schmidt DR, Mangelsdorf DJ, Covey DF: Synthesis, characterization, and receptor interaction profiles of enantiomeric bile acids. J Med Chem. 2007 Nov 29;50(24):6048-58. Epub 2007 Oct 27. [PubMed:17963371]
  2. Ishizawa M, Matsunawa M, Adachi R, Uno S, Ikeda K, Masuno H, Shimizu M, Iwasaki K, Yamada S, Makishima M: Lithocholic acid derivatives act as selective vitamin D receptor modulators without inducing hypercalcemia. J Lipid Res. 2008 Apr;49(4):763-72. doi: 10.1194/jlr.M700293-JLR200. Epub 2008 Jan 7. [PubMed:18180267]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Substrate
General Function
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase activity
Specific Function
Works in concert with the 5-alpha/5-beta-steroid reductases to convert steroid hormones into the 3-alpha/5-alpha and 3-alpha/5-beta-tetrahydrosteroids. Catalyzes the inactivation of the most potent...
Gene Name
AKR1C2
Uniprot ID
P52895
Uniprot Name
Aldo-keto reductase family 1 member C2
Molecular Weight
36734.97 Da
References
  1. Stolz A, Hammond L, Lou H, Takikawa H, Ronk M, Shively JE: cDNA cloning and expression of the human hepatic bile acid-binding protein. A member of the monomeric reductase gene family. J Biol Chem. 1993 May 15;268(14):10448-57. [PubMed:8486699]

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 a...
Gene Name
CYP27A1
Uniprot ID
Q02318
Uniprot Name
Sterol 26-hydroxylase, mitochondrial
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 react...
Gene Name
CYP3A4
Uniprot ID
P08684
Uniprot Name
Cytochrome P450 3A4
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 su...
Gene Name
UGT2B7
Uniprot ID
P16662
Uniprot Name
UDP-glucuronosyltransferase 2B7
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]

Drug created on September 14, 2010 10:21 / Updated on November 09, 2017 03:56