Identification

Summary

Tauroursodeoxycholic acid is the taurine conjugate of ursodeoxycholic acid with antiapoptotic and ER stress response dampening effects used in some countries to treat gallstones. It is also being investigated for a wide variety of other conditions.

Generic Name
Tauroursodeoxycholic acid
DrugBank Accession Number
DB08834
Background

Tauroursodeoxycholic acid, also known as ursodoxicoltaurine, is a highly hydrophilic tertiary bile acid 3 that is produced in humans at a low concentration.3 It is a taurine conjugate of ursodeoxycholic acid 2 with comparable therapeutic efficacy and safety,3 but a much higher hydrophilicity.1 Normally, hydrophilic bile acids regulates hydrophobic bile acids and their cytotoxic effects. Tauroursodeoxycholic acid can reduce the absorption of cholesterol in the small intestine, thereby reducing the body's intake of dietary cholesterol and the body cholesterol content.4

Tauroursodeoxycholic acid is currently used in Europe to treat and prevent gallstones as a bile acid derivative.7 Due to a range of its molecular properties - namely its anti-apoptotic effects - tauroursodeoxycholic acid has been examined in inflammatory metabolic diseases and neurodegenerative diseases.2,3

Type
Small Molecule
Groups
Approved, Investigational
Structure
Weight
Average: 499.71
Monoisotopic: 499.296759347
Chemical Formula
C26H45NO6S
Synonyms
  • Tauroursodeoxycholate
  • Tauroursodesoxycholic acid
  • TUDCA
  • Ursodeoxycholyltaurine
  • Ursodoxicoltaurine
External IDs
  • UR-906

Pharmacology

Indication

Tauroursodeoxycholic acid is used to prevent and treat gallstone formation.7

Tauroursodeoxycholic acid is used in combination with phenylbutyric acid to treat amyotrophic lateral sclerosis (ALS) in adults.8

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Associated Conditions
Contraindications & Blackbox Warnings
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Pharmacodynamics

Tauroursodeoxycholic acid works to decrease bile acid 1 and cholesterol levels.4 It reduces the cholesterol content and increases the bile acid content in gallbladder bile to prevent the formation of cholesterol gallstones.4

Tauroursodeoxycholic acid possesses anti-apoptotic and anti-inflammatory properties. These findings provoked the investigations of tauroursodeoxycholic acid as a potential therapeutic agent for neurodegenerative diseases, such as amyotrophic lateral sclerosis, Alzheimer's disease, and Parkinson's disease.2 Other studies also suggest that tauroursodeoxycholic acid can promote angiogenesis and suppress adipogenesis of adipose-derived mesenchymal stem cells (MSCs). Anti-osteoporotic effects of tauroursodeoxycholic acid have also been documented, as it was shown to enhance osteogenic differentiation of bone marrow-derived MSCs.3

Mechanism of action

About 90% of gallstones are formed by cholesterol, which may be caused by altered gut microbiota from a high-fat diet and other factors. The gut microbiota regulates bile acid metabolism; thus, altered composition in gut microbiota may significantly change the bile acid pool and alter cholesterol secretion.4

While the exact mechanism of action of tauroursodeoxycholic acid in reducing and preventing gallstone formation is unclear, tauroursodeoxycholic acid may achieve this effect in a number of ways. A recent mouse study suggests that tauroursodeoxycholic acid inhibits intestinal cholesterol absorption and lowers liver cholesterol levels by upregulating the bile acid excretion from the liver to the gallbladder. Tauroursodeoxycholic acid lowers the bile cholesterol saturation in the gallbladder, thereby increasing the solubility of cholesterol in bile. It can also maintain a specific gut microbiota composition to promote the synthesis of bile acids and reduce liver inflammation caused by the lipopolysaccharide in the blood. Ultimately, tauroursodeoxycholic acid enhances the synthesis of bile acids in the liver and reduces cholesterol in the serum and liver.4

Tauroursodeoxycholic acid inhibits cell apoptosis by disrupting the mitochondrial pathway of cell death. It works by inhibiting oxygen-radical production, ameliorating endoplasmic reticulum (ER) stress, and stabilizing the unfolded protein response. Other anti-apoptotic processes mediated by tauroursodeoxycholic acid include cytochrome c release, caspase activation, DNA and nuclear fragmentation, and inhibition of p53 transactivation. It is believed that tauroursodeoxycholic acid works on multiple cellular targets to inhibit apoptosis and upregulate survival pathways.2

TargetActionsOrganism
UIntegrin alpha-5
activator
Humans
Absorption

Not Available

Volume of distribution

There is evidence that tauroursodeoxycholic acid crosses the blood brain barrier in humans.2

Protein binding

Not Available

Metabolism

There is little biotransformation of tauroursodeoxycholic acid. It is partially deconjugated by intestinal microflora to form unconjugated bile acids.5,6

Route of elimination

Not Available

Half-life

Not Available

Clearance

Not Available

Adverse Effects
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Toxicity

There is no information available regarding the LD50 and overdose of tauroursodeoxycholic acid.

Pathways
Not Available
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
AbciximabThe risk or severity of adverse effects can be increased when Abciximab is combined with Tauroursodeoxycholic acid.
AcenocoumarolThe risk or severity of bleeding and bruising can be increased when Acenocoumarol is combined with Tauroursodeoxycholic acid.
Acetylsalicylic acidThe risk or severity of adverse effects can be increased when Acetylsalicylic acid is combined with Tauroursodeoxycholic acid.
AlteplaseThe risk or severity of bleeding and bruising can be increased when Alteplase is combined with Tauroursodeoxycholic acid.
Aluminium phosphateAluminium phosphate can cause a decrease in the absorption of Tauroursodeoxycholic acid resulting in a reduced serum concentration and potentially a decrease in efficacy.
Aluminum chlorideAluminum chloride can cause a decrease in the absorption of Tauroursodeoxycholic acid resulting in a reduced serum concentration and potentially a decrease in efficacy.
Aluminum chlorohydrateAluminum chlorohydrate can cause a decrease in the absorption of Tauroursodeoxycholic acid resulting in a reduced serum concentration and potentially a decrease in efficacy.
Aluminum hydroxideAluminum hydroxide can cause a decrease in the absorption of Tauroursodeoxycholic acid resulting in a reduced serum concentration and potentially a decrease in efficacy.
Aluminum oxideAluminum oxide can cause a decrease in the absorption of Tauroursodeoxycholic acid resulting in a reduced serum concentration and potentially a decrease in efficacy.
Aluminum sulfateAluminum sulfate can cause a decrease in the absorption of Tauroursodeoxycholic acid resulting in a reduced serum concentration and potentially a decrease in efficacy.
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Food Interactions
No interactions found.

Products

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Product Ingredients
IngredientUNIICASInChI Key
Tauroursodeoxycholic acid dihydrateU7XRV7RZ1I117609-50-4BNXLUNVCHFIPFY-GUBAPICVSA-N
International/Other Brands
Tauro (Teofarma) / Taurolite (Bio-Gen)
Unapproved/Other Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing EndRegionImage
TAUROLITE 250 MG 100 KAPSULTauroursodeoxycholic acid (250 mg)CapsuleOralBİO-GEN İLAÇ SAN.TİC.LTD.ŞTİ.2020-08-14Not applicableTurkey flag

Categories

Drug Categories
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-alpha-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-alpha-hydroxysteroid / 7-hydroxysteroid / Alcohol / Aliphatic homopolycyclic compound / Alkanesulfonic acid / Carbonyl group / Carboxamide group / Carboxylic acid derivative
show 22 more
Molecular Framework
Aliphatic homopolycyclic compounds
External Descriptors
bile acid taurine conjugate (CHEBI:80774) / Taurine conjugates (LMST05040015)
Affected organisms
  • Humans and other mammals

Chemical Identifiers

UNII
60EUX8MN5X
CAS number
14605-22-2
InChI Key
BHTRKEVKTKCXOH-LBSADWJPSA-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,9S,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@@]12CC[C@H]([C@H](C)CCC(=O)NCCS(O)(=O)=O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])[C@@H](O)C[C@]2([H])C[C@H](O)CC[C@]12C

References

Synthesis Reference

Zhuo, Chao; Feng, Wei; Wu, Da-jun; Xiong, Zhi-gang. Synthesis of tauroursodeoxycholic acid. Hecheng Huaxue (2002), 10(5), 444-446.

General References
  1. Crosignani A, Battezzati PM, Setchell KD, Invernizzi P, Covini G, Zuin M, Podda M: Tauroursodeoxycholic acid for treatment of primary biliary cirrhosis. A dose-response study. Dig Dis Sci. 1996 Apr;41(4):809-15. doi: 10.1007/BF02213140. [Article]
  2. Vang S, Longley K, Steer CJ, Low WC: The Unexpected Uses of Urso- and Tauroursodeoxycholic Acid in the Treatment of Non-liver Diseases. Glob Adv Health Med. 2014 May;3(3):58-69. doi: 10.7453/gahmj.2014.017. [Article]
  3. Ahn TK, Kim KT, Joshi HP, Park KH, Kyung JW, Choi UY, Sohn S, Sheen SH, Shin DE, Lee SH, Han IB: Therapeutic Potential of Tauroursodeoxycholic Acid for the Treatment of Osteoporosis. Int J Mol Sci. 2020 Jun 16;21(12). pii: ijms21124274. doi: 10.3390/ijms21124274. [Article]
  4. Lu Q, Jiang Z, Wang Q, Hu H, Zhao G: The effect of Tauroursodeoxycholic acid (TUDCA) and gut microbiota on murine gallbladder stone formation. Ann Hepatol. 2021 Jul-Aug;23:100289. doi: 10.1016/j.aohep.2020.100289. Epub 2020 Nov 18. [Article]
  5. Setchell KD, Rodrigues CM, Podda M, Crosignani A: Metabolism of orally administered tauroursodeoxycholic acid in patients with primary biliary cirrhosis. Gut. 1996 Mar;38(3):439-46. doi: 10.1136/gut.38.3.439. [Article]
  6. Invernizzi P, Setchell KD, Crosignani A, Battezzati PM, Larghi A, O'Connell NC, Podda M: Differences in the metabolism and disposition of ursodeoxycholic acid and of its taurine-conjugated species in patients with primary biliary cirrhosis. Hepatology. 1999 Feb;29(2):320-7. doi: 10.1002/hep.510290220. [Article]
  7. AIFA: Tauro (Tauroursodeoxycholic Acid) Oral Capsules [Link]
  8. Health Canada Approved Drug Products: ALBRIOZA (sodium phenylbutyrate and ursodoxicoltaurine) Oral Powder for suspension [Link]
KEGG Compound
C16868
PubChem Compound
9848818
PubChem Substance
175427112
ChemSpider
8024531
BindingDB
50236230
ChEBI
80774
ChEMBL
CHEMBL272427
ZINC
ZINC000003914813
PDBe Ligand
5D5
Drugs.com
Drugs.com Drug Page
Wikipedia
Ursodoxicoltaurine
PDB Entries
5dlv / 5dlw

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
4Unknown StatusPreventionGallstone formation1
3Active Not RecruitingTreatmentTTR Cardiac Amyloidosis1
3CompletedTreatmentCholestatic Liver Disease1
3CompletedTreatmentPrimary Biliary Cholangitis1
3RecruitingTreatmentAmyotrophic Lateral Sclerosis (ALS)1
2Active Not RecruitingTreatmentType 1 Diabetes Mellitus1
2CompletedTreatmentAlzheimer's Disease (AD)1
2CompletedTreatmentAmyotrophic Lateral Sclerosis (ALS)1
2CompletedTreatmentTransthyretin Amyloidosis1
1RecruitingHealth Services ResearchUlcerative Colitis1

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage Forms
FormRouteStrength
CapsuleOral150 MG
CapsuleOral250 MG
Capsule, delayed releaseOral500 MG
Tablet, extended releaseOral500 MG
CapsuleOral
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.00748 mg/mLALOGPS
logP1.38ALOGPS
logP1.1ChemAxon
logS-4.8ALOGPS
pKa (Strongest Acidic)-0.8ChemAxon
pKa (Strongest Basic)-0.32ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area123.93 Å2ChemAxon
Rotatable Bond Count7ChemAxon
Refractivity130.68 m3·mol-1ChemAxon
Polarizability56.75 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 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

Targets

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Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Activator
General Function
Integrin alpha-5/beta-1 is a receptor for fibronectin and fibrinogen. It recognizes the sequence R-G-D in its ligands. ITGA5:ITGB1 binds to PLA2G2A via a site (site 2) which is distinct from the classical ligand-binding site (site 1) and this induces integrin conformational changes and enhanced ligand binding to site 1 (PubMed:18635536, PubMed:25398877). ITGA5:ITGB1 acts as a receptor for fibrillin-1 (FBN1) and mediates R-G-D-dependent cell adhesion to FBN1 (PubMed:12807887, PubMed:17158881).
Specific Function
Epidermal growth factor receptor binding
Gene Name
ITGA5
Uniprot ID
P08648
Uniprot Name
Integrin alpha-5
Molecular Weight
114535.52 Da
References
  1. Vang S, Longley K, Steer CJ, Low WC: The Unexpected Uses of Urso- and Tauroursodeoxycholic Acid in the Treatment of Non-liver Diseases. Glob Adv Health Med. 2014 May;3(3):58-69. doi: 10.7453/gahmj.2014.017. [Article]
  2. Beuers U: beta1 integrin is a long-sought sensor for tauroursodeoxycholic acid. Hepatology. 2013 Mar;57(3):867-9. doi: 10.1002/hep.26228. [Article]

Enzymes

Kind
Protein
Organism
Rat
Pharmacological action
Unknown
Actions
Inducer
General Function
Testosterone 6-beta-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 oxidizes a variety of structurally un...
Gene Name
Cyp3a1
Uniprot ID
P04800
Uniprot Name
Cytochrome P450 3A1
Molecular Weight
57917.375 Da
References
  1. Paolini M, Pozzetti L, Piazza F, Cantelli-Forti G, Roda A: Bile acid structure and selective modulation of murine hepatic cytochrome P450-linked enzymes. Hepatology. 1999 Sep;30(3):730-9. [Article]
Kind
Protein
Organism
Rat
Pharmacological action
Unknown
Actions
Inducer
General Function
Testosterone 6-beta-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 oxidizes a variety of structurally un...
Gene Name
Cyp3a2
Uniprot ID
P05183
Uniprot Name
Cytochrome P450 3A2
Molecular Weight
57731.215 Da
References
  1. Paolini M, Pozzetti L, Piazza F, Cantelli-Forti G, Roda A: Bile acid structure and selective modulation of murine hepatic cytochrome P450-linked enzymes. Hepatology. 1999 Sep;30(3):730-9. [Article]

Transporters

Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
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. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
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. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Downregulator
Curator comments
This drug-target relationship was established in mice. The significance of this target relationship in humans is unknown.
General Function
Protein heterodimerization activity
Specific Function
Transporter that appears to play an indispensable role in the selective transport of the dietary cholesterol in and out of the enterocytes and in the selective sterol excretion by the liver into bile.
Gene Name
ABCG5
Uniprot ID
Q9H222
Uniprot Name
ATP-binding cassette sub-family G member 5
Molecular Weight
72503.02 Da
References
  1. Lu Q, Jiang Z, Wang Q, Hu H, Zhao G: The effect of Tauroursodeoxycholic acid (TUDCA) and gut microbiota on murine gallbladder stone formation. Ann Hepatol. 2021 Jul-Aug;23:100289. doi: 10.1016/j.aohep.2020.100289. Epub 2020 Nov 18. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Downregulator
Curator comments
This drug-target relationship was established in mice. The significance of this target relationship in humans is unknown.
General Function
Sterol transporter activity
Specific Function
Transporter that appears to play an indispensable role in the selective transport of the dietary cholesterol in and out of the enterocytes and in the selective sterol excretion by the liver into bile.
Gene Name
ABCG8
Uniprot ID
Q9H221
Uniprot Name
ATP-binding cassette sub-family G member 8
Molecular Weight
75678.03 Da
References
  1. Lu Q, Jiang Z, Wang Q, Hu H, Zhao G: The effect of Tauroursodeoxycholic acid (TUDCA) and gut microbiota on murine gallbladder stone formation. Ann Hepatol. 2021 Jul-Aug;23:100289. doi: 10.1016/j.aohep.2020.100289. Epub 2020 Nov 18. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Regulator
Curator comments
This drug-target relationship was established in mice. The significance of this target relationship in humans is unknown.
General Function
Transporter activity
Specific Function
Involved in the ATP-dependent secretion of bile salts into the canaliculus of hepatocytes.
Gene Name
ABCB11
Uniprot ID
O95342
Uniprot Name
Bile salt export pump
Molecular Weight
146405.83 Da
References
  1. Lu Q, Jiang Z, Wang Q, Hu H, Zhao G: The effect of Tauroursodeoxycholic acid (TUDCA) and gut microbiota on murine gallbladder stone formation. Ann Hepatol. 2021 Jul-Aug;23:100289. doi: 10.1016/j.aohep.2020.100289. Epub 2020 Nov 18. [Article]

Drug created at February 19, 2013 00:42 / Updated at June 18, 2022 08:31