Chenodeoxycholic acid

Identification

Summary

Chenodeoxycholic acid is a bile acid used for the treatment of primary biliary cirrhosis.

Brand Names
Chenodal
Generic Name
Chenodeoxycholic acid
DrugBank Accession Number
DB06777
Background

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.

Type
Small Molecule
Groups
Approved
Structure
Weight
Average: 392.572
Monoisotopic: 392.292659768
Chemical Formula
C24H40O4
Synonyms
  • 3alpha,7alpha-Dihydroxy-5beta-cholanic acid
  • 7α-hydroxylithocholic acid
  • Acide chenodeoxycholique
  • Acido chenodeoxicholico
  • Acidum chenodeoxycholicum
  • Anthropodeoxycholic acid
  • Anthropodesoxycholic acid
  • CDCA
  • Chenic acid
  • Chenocholic acid
  • Chenodeoxycholate
  • Chenodeoxycholic acid
  • Chenodesoxycholic acid
  • Chenodiol
  • Gallodesoxycholic acid

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.

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Associated Conditions
Indication TypeIndicationCombined Product DetailsApproval LevelAge GroupPatient CharacteristicsDose Form
Treatment ofRadiolucent cholesterol gallstones••••••••••••
Contraindications & Blackbox Warnings
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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
Humans
UNuclear receptor subfamily 1 group I member 2Not AvailableHumans
UG-protein coupled bile acid receptor 1Not AvailableHumans
UAldo-keto reductase family 1 member C2
substrate
Humans
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

Adverse Effects
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Toxicity

Hepatotoxic.

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

Interactions

Drug Interactions
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
DrugInteraction
AbametapirThe serum concentration of Chenodeoxycholic acid can be increased when it is combined with Abametapir.
AbciximabThe risk or severity of adverse effects can be increased when Abciximab is combined with Chenodeoxycholic acid.
AcemetacinThe metabolism of Acemetacin can be decreased when combined with Chenodeoxycholic acid.
AcenocoumarolThe risk or severity of bleeding and bruising can be increased when Acenocoumarol is combined with Chenodeoxycholic acid.
Acetylsalicylic acidThe risk or severity of adverse effects can be increased when Acetylsalicylic acid is combined with Chenodeoxycholic acid.
Food Interactions
No interactions found.

Products

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International/Other Brands
Chenix (Sigma Tau)
Brand Name Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
Chenodeoxycholic Acid LeadiantCapsule250 mgOralLeadiant Gmb H2020-12-16Not applicableEU flag
Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
ChenodalTablet, film coated250 mg/1OralManchester Pharmaceuticals2009-10-01Not applicableUS flag
ChenodalTablet, film coated250 mg/1OralTravere Therapeutics2015-12-28Not applicableUS flag
ChenodiolTablet, film coated250 mg/1OralNexgen Pharma, Inc.2009-10-22Not applicableUS flag
ChenodiolTablet, film coated250 mg/1OralLGM Pharma Solutions, LLC2009-10-22Not applicableUS flag

Categories

ATC Codes
A05AA01 — Chenodeoxycholic acid
Drug Categories
Chemical TaxonomyProvided by Classyfire
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
3-alpha-hydroxysteroid / 3-hydroxysteroid / 7-hydroxysteroid / Alcohol / Aliphatic homopolycyclic compound / Carbonyl group / Carboxylic acid / Carboxylic acid derivative / Cyclic alcohol / Dihydroxy bile acid, alcohol, or derivatives
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)
Affected organisms
Not Available

Chemical Identifiers

UNII
0GEI24LG0J
CAS number
474-25-9
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-[(1R,3aS,3bR,4R,5aS,7R,9aS,9bS,11aR)-4,7-dihydroxy-9a,11a-dimethyl-hexadecahydro-1H-cyclopenta[a]phenanthren-1-yl]pentanoic acid
SMILES
[H][C@@]1(CC[C@@]2([H])[C@]3([H])[C@H](O)C[C@]4([H])C[C@H](O)CC[C@]4(C)[C@@]3([H])CC[C@]12C)[C@H](C)CCC(O)=O

References

Synthesis Reference

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
Human Metabolome Database
HMDB0000518
KEGG Drug
D00163
KEGG Compound
C02528
PubChem Compound
10133
PubChem Substance
99443291
ChemSpider
9728
BindingDB
21674
RxNav
2323
ChEBI
16755
ChEMBL
CHEMBL240597
ZINC
ZINC000003914808
PharmGKB
PA165958403
PDBe Ligand
JN3
Drugs.com
Drugs.com Drug Page
Wikipedia
Chenodeoxycholic_acid
PDB Entries
2jn3 / 3o02 / 6hl1 / 6ie9 / 7svg / 8dml
FDA label
Download (190 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
4CompletedBasic ScienceObesity, Severe1
4CompletedDiagnosticBileacid Malabsorption1
4CompletedDiagnosticBileacid Malabsorption / Gallstones1
4CompletedTreatmentObesity, Severe2
3CompletedTreatmentCTX1

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage Forms
FormRouteStrength
CapsuleOral250 MG
Tablet, film coatedOral250 mg/1
CapsuleOral
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
Polarizability46.35 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-MSsplash10-01rt-0419000000-6a92f910581240163a99
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
LC-MS/MS Spectrum - LC-ESI-IT , negativeLC-MS/MSsplash10-0002-0009000000-ad2d2440db7f3f1c8a2e
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-0006-0009000000-d1f986325aed82b811c5
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-002f-0019000000-cc60cb157a6a09e463ec
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-0a4i-3139000000-4639b15eea0cf066cfcb
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-0006-0009000000-28f0706ed7c585f84229
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-0096-1019000000-30e5463bbeadb794d43e
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-0f7k-4791000000-c2d40e5f723f22c3f4f1
1H NMR Spectrum1D NMRNot Applicable
Predicted 1H NMR Spectrum1D NMRNot Applicable
Predicted 13C NMR Spectrum1D NMRNot Applicable
[1H,13C] 2D NMR Spectrum2D NMRNot Applicable
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-200.1895715
predicted
DarkChem Lite v0.1.0
[M-H]-197.2871715
predicted
DarkChem Lite v0.1.0
[M-H]-204.3790715
predicted
DarkChem Lite v0.1.0
[M-H]-202.13918
predicted
DeepCCS 1.0 (2019)
[M+H]+201.3469715
predicted
DarkChem Lite v0.1.0
[M+H]+197.1617715
predicted
DarkChem Lite v0.1.0
[M+H]+198.9391715
predicted
DarkChem Lite v0.1.0
[M+H]+204.03456
predicted
DeepCCS 1.0 (2019)
[M+Na]+200.2497715
predicted
DarkChem Lite v0.1.0
[M+Na]+194.1090715
predicted
DarkChem Lite v0.1.0
[M+Na]+197.7362715
predicted
DarkChem Lite v0.1.0
[M+Na]+209.90514
predicted
DeepCCS 1.0 (2019)

Targets

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Details
1. Bile acid receptor
Kind
Protein
Organism
Humans
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. [Article]
  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. [Article]
Kind
Protein
Organism
Humans
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. [Article]
Kind
Protein
Organism
Humans
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. [Article]
  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. [Article]
Kind
Protein
Organism
Humans
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. [Article]

Enzymes

Kind
Protein
Organism
Humans
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. [Article]
  2. Bjorkhem I: Inborn errors of metabolism with consequences for bile acid biosynthesis. A minireview. Scand J Gastroenterol Suppl. 1994;204:68-72. [Article]
  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. [Article]
  4. Keren Z, Falik-Zaccai TC: Cerebrotendinous xanthomatosis (CTX): a treatable lipid storage disease. Pediatr Endocrinol Rev. 2009 Sep;7(1):6-11. [Article]
  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. [Article]
  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. [Article]
  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. [Article]
Kind
Protein
Organism
Humans
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. [Article]
  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. [Article]
Kind
Protein
Organism
Humans
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. [Article]

Drug created at September 14, 2010 16:21 / Updated at February 21, 2021 18:52