Identification

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Name
Taurochenodeoxycholic acid
Accession Number
DB08833
Type
Small Molecule
Groups
Experimental
Description

Taurochenodeoxycholic acid is an experimental drug that is normally produced in the liver. Its physiologic function is to emulsify lipids such as cholesterol in the bile. As a medication, taurochenodeoxycholic acid reduces cholesterol formation in the liver, and is likely used as a choleretic to increase the volume of bile secretion from the liver and as a cholagogue to increase bile discharge into the duodenum. It is also being investigated for its role in inflammation and cancer therapy.

Structure
Thumb
Synonyms
  • Chenodeoxycholoyltaurine
  • Taurine chenodeoxycholate
  • Taurochenodeoxycholate
  • Taurochenodeoxycholic acid
Categories
UNII
651KU15938
CAS number
516-35-8
Weight
Average: 499.704
Monoisotopic: 499.296758867
Chemical Formula
C26H45NO6S
InChI Key
BHTRKEVKTKCXOH-BJLOMENOSA-N
InChI
InChI=1S/C26H45NO6S/c1-16(4-7-23(30)27-12-13-34(31,32)33)19-5-6-20-24-21(9-11-26(19,20)3)25(2)10-8-18(28)14-17(25)15-22(24)29/h16-22,24,28-29H,4-15H2,1-3H3,(H,27,30)(H,31,32,33)/t16-,17+,18-,19-,20+,21+,22-,24+,25+,26-/m1/s1
IUPAC Name
2-[(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]pentanamido]ethane-1-sulfonic 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)NCCS(O)(=O)=O

Pharmacology

Indication

Taurochenodeoxycholic acid is likely indicated as a choleretic and cholagogue. It is also being investigated for its role in inflammation and cancer therapy.

Pharmacodynamics
Not Available
Mechanism of action

Chenodeoxycholic acid is a primary bile acid in the liver that combines with taurine to form the bile acid taurochenodeoxycholic acid. In the bile, taurochenodeoxycholic acid is either a sodium (most) or potassium salt. Taurochenodeoxycholic acid is normally produced in the liver, and its physiologic function as a bile salt is to emulsify lipids such as cholesterol in the bile. As a medication, taurochenodeoxycholic acid reduces cholesterol formation in the liver, and is likely used as a choleretic to increase the volume of bile secretion from the liver and as a cholagogue to increase bile discharge into the duodenum. The mechanism of action of taurochenodeoxycholic acid in inflammation and cancer has yet to be determined.

Absorption
Not Available
Volume of distribution
Not Available
Protein binding
Not Available
Metabolism
Not Available
Route of elimination
Not Available
Half life
Not Available
Clearance
Not Available
Toxicity
Not Available
Affected organisms
  • Humans and other mammals
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
(R)-warfarinThe risk or severity of bleeding and bruising can be increased when (R)-warfarin is combined with Taurochenodeoxycholic acid.
(S)-WarfarinThe risk or severity of bleeding and bruising can be increased when (S)-Warfarin is combined with Taurochenodeoxycholic acid.
4-hydroxycoumarinThe risk or severity of bleeding and bruising can be increased when 4-hydroxycoumarin is combined with Taurochenodeoxycholic acid.
AbciximabThe risk or severity of adverse effects can be increased when Abciximab is combined with Taurochenodeoxycholic acid.
AcenocoumarolThe risk or severity of bleeding and bruising can be increased when Acenocoumarol is combined with Taurochenodeoxycholic acid.
Acetylcysteine zincAcetylcysteine zinc can cause a decrease in the absorption of Taurochenodeoxycholic acid resulting in a reduced serum concentration and potentially a decrease in efficacy.
Acetylsalicylic acidThe risk or severity of adverse effects can be increased when Acetylsalicylic acid is combined with Taurochenodeoxycholic acid.
AloglutamolThe serum concentration of Taurochenodeoxycholic acid can be decreased when it is combined with Aloglutamol.
AlteplaseThe risk or severity of bleeding and bruising can be increased when Alteplase is combined with Taurochenodeoxycholic acid.
AluminiumThe serum concentration of Taurochenodeoxycholic acid can be decreased when it is combined with Aluminium.
Additional Data Available
  • Extended Description
    Extended Description

    Extended description of the mechanism of action and particular properties of each drug interaction.

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  • Severity
    Severity

    A severity rating for each drug interaction, from minor to major.

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  • Evidence Level
    Evidence Level

    A rating for the strength of the evidence supporting each drug interaction.

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  • Action
    Action

    An effect category for each drug interaction. Know how this interaction affects the subject drug.

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Food Interactions
Not Available

References

General References
  1. Schroeder A, Eckhardt U, Stieger B, Tynes R, Schteingart CD, Hofmann AF, Meier PJ, Hagenbuch B: Substrate specificity of the rat liver Na(+)-bile salt cotransporter in Xenopus laevis oocytes and in CHO cells. Am J Physiol. 1998 Feb;274(2 Pt 1):G370-5. [PubMed:9486191]
  2. Arndt H, Kullmann F, Scholmerich J, Palitzsch KD: Acute and chronic effects of different bile acids on indomethacin-induced intestinal inflammation. Inflammation. 1997 Dec;21(6):553-67. [PubMed:9429904]
  3. Fimognari C, Lenzi M, Cantelli-Forti G, Hrelia P: Apoptosis and modulation of cell cycle control by bile acids in human leukemia T cells. Ann N Y Acad Sci. 2009 Aug;1171:264-9. doi: 10.1111/j.1749-6632.2009.04710.x. [PubMed:19723064]
External Links
Human Metabolome Database
HMDB0000951
KEGG Compound
C05465
ChemSpider
343282
BindingDB
50375595
ChEBI
16525
ChEMBL
CHEMBL185878
HET
TUD
Wikipedia
Taurochenodeoxycholic_acid
PDB Entries
2b01 / 2b03 / 5epo / 6gw0 / 6gw2

Clinical Trials

Clinical Trials
Not Available

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage forms
Not Available
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.00748 mg/mLALOGPS
logP1.38ALOGPS
logP0.81ChemAxon
logS-4.8ALOGPS
pKa (Strongest Acidic)-0.99ChemAxon
pKa (Strongest Basic)0.18ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area123.93 Å2ChemAxon
Rotatable Bond Count7ChemAxon
Refractivity130.68 m3·mol-1ChemAxon
Polarizability56.64 Å3ChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.9774
Blood Brain Barrier+0.8416
Caco-2 permeable-0.8957
P-glycoprotein substrateNon-substrate0.5136
P-glycoprotein inhibitor INon-inhibitor0.6229
P-glycoprotein inhibitor IINon-inhibitor0.7598
Renal organic cation transporterNon-inhibitor0.8476
CYP450 2C9 substrateNon-substrate0.7519
CYP450 2D6 substrateNon-substrate0.7972
CYP450 3A4 substrateSubstrate0.654
CYP450 1A2 substrateNon-inhibitor0.7814
CYP450 2C9 inhibitorNon-inhibitor0.8625
CYP450 2D6 inhibitorNon-inhibitor0.8685
CYP450 2C19 inhibitorNon-inhibitor0.8426
CYP450 3A4 inhibitorNon-inhibitor0.8612
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.7175
Ames testNon AMES toxic0.6103
CarcinogenicityNon-carcinogens0.5359
BiodegradationNot ready biodegradable0.972
Rat acute toxicity2.0310 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.706
hERG inhibition (predictor II)Inhibitor0.5549
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
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
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/MSsplash10-02ar-0006900000-53366e607f8bd2e50783

Taxonomy

Description
This compound belongs to the class of organic compounds known as taurinated bile acids and derivatives. These are bile acid derivatives containing a taurine conjugated to the bile acid moiety.
Kingdom
Organic compounds
Super Class
Lipids and lipid-like molecules
Class
Steroids and steroid derivatives
Sub Class
Bile acids, alcohols and derivatives
Direct Parent
Taurinated bile acids and derivatives
Alternative Parents
Dihydroxy bile acids, alcohols and derivatives / 7-hydroxysteroids / 3-alpha-hydroxysteroids / N-acyl amines / Sulfonyls / Organosulfonic acids / Alkanesulfonic acids / Secondary carboxylic acid amides / Secondary alcohols / Cyclic alcohols and derivatives
show 5 more
Substituents
Taurinated bile acid / Dihydroxy bile acid, alcohol, or derivatives / Hydroxy bile acid, alcohol, or derivatives / 3-hydroxysteroid / Hydroxysteroid / 3-alpha-hydroxysteroid / 7-hydroxysteroid / Fatty acyl / Fatty amide / N-acyl-amine
show 21 more
Molecular Framework
Aliphatic homopolycyclic compounds
External Descriptors
bile acid taurine conjugate (CHEBI:16525) / C26 bile acids, alcohols, and derivatives, Taurine conjugates (C05465) / Taurine conjugates (LMST05040005)

Enzymes

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. Araya Z, Wikvall K: 6alpha-hydroxylation of taurochenodeoxycholic acid and lithocholic acid by CYP3A4 in human liver microsomes. Biochim Biophys Acta. 1999 Apr 19;1438(1):47-54. [PubMed:10216279]

Transporters

Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
Sodium-independent organic anion transmembrane transporter activity
Specific Function
Mediates the Na(+)-independent transport of organic anions such as sulfobromophthalein (BSP) and conjugated (taurocholate) and unconjugated (cholate) bile acids (By similarity). Selectively inhibit...
Gene Name
SLCO1A2
Uniprot ID
P46721
Uniprot Name
Solute carrier organic anion transporter family member 1A2
Molecular Weight
74144.105 Da
References
  1. Kullak-Ublick GA, Hagenbuch B, Stieger B, Schteingart CD, Hofmann AF, Wolkoff AW, Meier PJ: Molecular and functional characterization of an organic anion transporting polypeptide cloned from human liver. Gastroenterology. 1995 Oct;109(4):1274-82. [PubMed:7557095]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
Cystine:glutamate antiporter activity
Specific Function
Sodium-independent, high-affinity exchange of anionic amino acids with high specificity for anionic form of cystine and glutamate.
Gene Name
SLC7A11
Uniprot ID
Q9UPY5
Uniprot Name
Cystine/glutamate transporter
Molecular Weight
55422.44 Da
References
  1. Schroeder A, Eckhardt U, Stieger B, Tynes R, Schteingart CD, Hofmann AF, Meier PJ, Hagenbuch B: Substrate specificity of the rat liver Na(+)-bile salt cotransporter in Xenopus laevis oocytes and in CHO cells. Am J Physiol. 1998 Feb;274(2 Pt 1):G370-5. [PubMed:9486191]

Drug created on February 18, 2013 17:33 / Updated on December 02, 2019 08:29