Identification
- Generic Name
- Taurochenodeoxycholic acid
- DrugBank Accession Number
- DB08833
- Background
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.
- Type
- Small Molecule
- Groups
- Experimental
- Structure
Structure for Taurochenodeoxycholic acid (DB08833)
- Weight
- Average: 499.704
Monoisotopic: 499.296758867 - Chemical Formula
- C26H45NO6S
- Synonyms
- Chenodeoxycholoyltaurine
- Taurine chenodeoxycholate
- Taurochenodeoxycholate
- Taurochenodeoxycholic acid
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.
Reduce drug development failure ratesBuild, train, & validate machine-learning modelswith evidence-based and structured datasets.Build, train, & validate predictive machine-learning models with structured datasets.- Contraindications & Blackbox Warnings
Prevent Adverse Drug Events TodayTap into our Clinical API for life-saving information on contraindications & blackbox warnings, population restrictions, harmful risks, & more.Avoid life-threatening adverse drug events with our Clinical API- 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
- Adverse Effects
Improve decision support & research outcomesWith structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates. View sample adverse effects data in our new Data Library!Improve decision support & research outcomes with our structured adverse effects data.- Toxicity
Not Available
- Pathways
Pathway Category Zellweger Syndrome Disease Congenital Bile Acid Synthesis Defect Type II Disease 27-Hydroxylase Deficiency Disease Bile Acid Biosynthesis Metabolic Cerebrotendinous Xanthomatosis (CTX) Disease Familial Hypercholanemia (FHCA) Disease Congenital Bile Acid Synthesis Defect Type III Disease - 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.
Drug Interaction Integrate drug-drug
interactions in your softwareAbametapir The serum concentration of Taurochenodeoxycholic acid can be increased when it is combined with Abametapir. Abciximab The risk or severity of adverse effects can be increased when Abciximab is combined with Taurochenodeoxycholic acid. Acenocoumarol The risk or severity of bleeding and bruising can be increased when Acenocoumarol is combined with Taurochenodeoxycholic acid. Acetylsalicylic acid The risk or severity of adverse effects can be increased when Acetylsalicylic acid is combined with Taurochenodeoxycholic acid. Alteplase The risk or severity of bleeding and bruising can be increased when Alteplase is combined with Taurochenodeoxycholic acid. - Food Interactions
- Not Available
Categories
- Drug Categories
- Alkanes
- Alkanesulfonic Acids
- Bile Acids and Salts
- Cholagogues and Choleretics
- Cholanes
- Cholic Acids
- Compounds used in a research, industrial, or household setting
- Cytochrome P-450 CYP3A Substrates
- Cytochrome P-450 CYP3A4 Substrates
- Cytochrome P-450 Substrates
- Detergents
- Fused-Ring Compounds
- Gastrointestinal Agents
- Household Products
- Hydrocarbons, Acyclic
- Steroids
- Sulfonic Acids
- Sulfur Acids
- Sulfur Compounds
- Surface-Active Agents
- Taurodeoxycholic Acid
- Chemical TaxonomyProvided by Classyfire
- 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
- 3-alpha-hydroxysteroid / 3-hydroxysteroid / 7-hydroxysteroid / Alcohol / Aliphatic homopolycyclic compound / Alkanesulfonic acid / Carbonyl group / Carboxamide group / Carboxylic acid derivative / Cyclic alcohol 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)
- Affected organisms
- Humans and other mammals
Chemical Identifiers
- UNII
- 651KU15938
- CAS number
- 516-35-8
- 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-[(1R,3aS,3bR,4R,5aS,7R,9aS,9bS,11aR)-4,7-dihydroxy-9a,11a-dimethyl-hexadecahydro-1H-cyclopenta[a]phenanthren-1-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
References
- General References
- 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. [Article]
- 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. [Article]
- 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. [Article]
- External Links
- Human Metabolome Database
- HMDB0000951
- KEGG Compound
- C05465
- ChemSpider
- 343282
- BindingDB
- 50375595
- ChEBI
- 16525
- ChEMBL
- CHEMBL185878
- ZINC
- ZINC000005822376
- PDBe Ligand
- TUD
- Wikipedia
- Taurochenodeoxycholic_acid
- PDB Entries
- 2b01 / 2b03 / 5epo / 6gw0 / 6gw2
Clinical Trials
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
Property Value Source Water Solubility 0.00748 mg/mL ALOGPS logP 1.38 ALOGPS logP 1.1 Chemaxon logS -4.8 ALOGPS pKa (Strongest Acidic) -0.8 Chemaxon pKa (Strongest Basic) -0.32 Chemaxon Physiological Charge -1 Chemaxon Hydrogen Acceptor Count 6 Chemaxon Hydrogen Donor Count 4 Chemaxon Polar Surface Area 123.93 Å2 Chemaxon Rotatable Bond Count 7 Chemaxon Refractivity 130.68 m3·mol-1 Chemaxon Polarizability 56.66 Å3 Chemaxon Number of Rings 4 Chemaxon Bioavailability 1 Chemaxon Rule of Five Yes Chemaxon Ghose Filter No Chemaxon Veber's Rule No Chemaxon MDDR-like Rule Yes Chemaxon - Predicted ADMET Features
Property Value Probability Human Intestinal Absorption + 0.9774 Blood Brain Barrier + 0.8416 Caco-2 permeable - 0.8957 P-glycoprotein substrate Non-substrate 0.5136 P-glycoprotein inhibitor I Non-inhibitor 0.6229 P-glycoprotein inhibitor II Non-inhibitor 0.7598 Renal organic cation transporter Non-inhibitor 0.8476 CYP450 2C9 substrate Non-substrate 0.7519 CYP450 2D6 substrate Non-substrate 0.7972 CYP450 3A4 substrate Substrate 0.654 CYP450 1A2 substrate Non-inhibitor 0.7814 CYP450 2C9 inhibitor Non-inhibitor 0.8625 CYP450 2D6 inhibitor Non-inhibitor 0.8685 CYP450 2C19 inhibitor Non-inhibitor 0.8426 CYP450 3A4 inhibitor Non-inhibitor 0.8612 CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.7175 Ames test Non AMES toxic 0.6103 Carcinogenicity Non-carcinogens 0.5359 Biodegradation Not ready biodegradable 0.972 Rat acute toxicity 2.0310 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.706 hERG inhibition (predictor II) Inhibitor 0.5549
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
- Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 223.342197 predictedDarkChem Lite v0.1.0 [M-H]- 206.4027547 predictedDarkChem Standard v0.1.0 [M-H]- 225.236697 predictedDarkChem Lite v0.1.0 [M-H]- 219.39052 predictedDeepCCS 1.0 (2019) [M+H]+ 222.322197 predictedDarkChem Lite v0.1.0 [M+H]+ 226.229597 predictedDarkChem Lite v0.1.0 [M+H]+ 225.880697 predictedDarkChem Lite v0.1.0 [M+H]+ 221.11423 predictedDeepCCS 1.0 (2019) [M+Na]+ 223.191797 predictedDarkChem Lite v0.1.0 [M+Na]+ 224.911497 predictedDarkChem Lite v0.1.0 [M+Na]+ 224.882697 predictedDarkChem Lite v0.1.0 [M+Na]+ 227.44342 predictedDeepCCS 1.0 (2019)
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
- 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. [Article]
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
- 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. [Article]
- 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
- 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. [Article]
Drug created at February 19, 2013 00:33 / Updated at June 12, 2020 16:52