U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ABSOLUTE
Molecular Formula C26H45NO6S
Molecular Weight 499.704
Optical Activity UNSPECIFIED
Defined Stereocenters 10 / 10
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of TAURURSODIOL

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

InChI

InChIKey=BHTRKEVKTKCXOH-LBSADWJPSA-N
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

HIDE SMILES / InChI
Tauroursodeoxycholic acid (TUDCA) is an endogenous hydrophilic bile acid used clinically to treat certain liver diseases. It is approved in Italy and Turkey for the treatment of cholesterol gallstones and is an investigational drug in China, Unites States, and Italy. Tauroursodeoxycholic acid is being investigated for use in several conditions such as Primary Biliary Cirrhosis (PBC), insulin resistance, amyloidosis, Cystic Fibrosis, Cholestasis, and Amyotrophic Lateral Sclerosis. Tauroursodeoxycholate (TUDC) promote choleresis by triggering the insertion of transport proteins for bile acids into the canalicular and basolateral membranes of hepatocytes. In addition, Tauroursodeoxycholate exerts hepatoprotective and anti-apoptotic effects, can counteract the action of toxic bile acids and reduce endoplasmic reticulum stress. Tauroursodeoxycholate can also initiate the differentiation of multipotent mesenchymal stem cells (MSC) including hepatic stellate cells and promote their development into hepatocyte-like cells. Although the hepatoprotective and choleretic action of TUDC is empirically used in clinical medicine since decades, the underlying molecular mechanisms remained largely unclear.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
30.0 µM [EC50]
10.0 µM [Kd]
PubMed

PubMed

TitleDatePubMed
Effects of bile salt supplementation on biliary secretion in estrogen-treated rats.
1990 Aug
Tauroursodeoxycholic acid (TUDCA) in the prevention of total parenteral nutrition-associated liver disease.
2002 Aug
Tauroursodeoxycholic acid reduces damaging effects of taurodeoxycholic acid on fundus gastric mucosa.
2002 Jul
Effects of bile acids on the muscle functions of guinea pig gallbladder.
2002 Jul
Effects of hydrophobic and hydrophilic bile salt mixtures on cholesterol crystallization in model biles.
2002 Jul 11
Tauroursodeoxycholic acid mobilizes alpha-PKC after uptake in human HepG2 hepatoma cells.
2002 Jun
Effect of tauroursodeoxycholic acid on endoplasmic reticulum stress-induced caspase-12 activation.
2002 Sep
Bile acids for viral hepatitis.
2003
3,4-dihydroxyphenylacetaldehyde: a potential target for neuroprotective therapy in Parkinson's disease.
2003 Apr
Taurohyodeoxycholate- and tauroursodeoxycholate-induced hypercholeresis is augmented in bile duct ligated rats.
2003 Feb
Peroxisome proliferator-activated receptor alpha (PPARalpha)-mediated regulation of multidrug resistance 2 (Mdr2) expression and function in mice.
2003 Feb 1
[Effect of Tauroursodeoxycholic acid on cytochrome C-mediated apoptosis in HepG2 cells].
2003 May
Involvement of integrins and Src in tauroursodeoxycholate-induced and swelling-induced choleresis.
2003 May
Inhibition of ileal bile acid absorption by colestimide.
2003 May
Tauroursodeoxycholic acid reduces apoptosis and protects against neurological injury after acute hemorrhagic stroke in rats.
2003 May 13
Bile salt-induced hepatocyte apoptosis involves epidermal growth factor receptor-dependent CD95 tyrosine phosphorylation.
2003 Sep
Tauroursodeoxycholic acid prevents amyloid-beta peptide-induced neuronal death via a phosphatidylinositol 3-kinase-dependent signaling pathway.
2003 Sep-Dec
What doesn't kill you makes you stronger: how hepatocytes survive prolonged cholestasis.
2004 Apr
Conjugation with taurine prevents side-chain desaturation of ursodeoxycholic and beta-muricholic acids in bile fistula rats.
2004 Aug
Trafficking of the bile salt export pump from the Golgi to the canalicular membrane is regulated by the p38 MAP kinase.
2004 Feb
Toxicity of ethanol and acetaldehyde in hepatocytes treated with ursodeoxycholic or tauroursodeoxycholic acid.
2004 Feb 2
Modulation of nuclear steroid receptors by ursodeoxycholic acid inhibits TGF-beta1-induced E2F-1/p53-mediated apoptosis of rat hepatocytes.
2004 Jul 6
Tauroursodeoxycholic acid protects rat hepatocytes from bile acid-induced apoptosis via activation of survival pathways.
2004 Jun
[Deoxycholic acid-induced signal transduction in HT-29 cells: role of NF-kappa B and interleukin-8].
2004 Mar
A mouse model of sitosterolemia: absence of Abcg8/sterolin-2 results in failure to secrete biliary cholesterol.
2004 Mar 24
The bile acid tauroursodeoxycholic acid modulates phosphorylation and translocation of bad via phosphatidylinositol 3-kinase in glutamate-induced apoptosis of rat cortical neurons.
2004 Nov
Ursodeoxycholic acid inhibits endothelin-1 production in human vascular endothelial cells.
2004 Nov 28
Biliary excretion of bile acids and organic anions in rats with dichloroethylene-induced bile canalicular injury.
2004 Oct
Hypothermic maintenance of hepatocyte spheroids.
2005
Gap junctional intercellular communication is not needed for the anticholestatic effect of tauroursodeoxycholic acid in mouse liver.
2005 Apr
Human hepatic mitochondria generate reactive oxygen species and undergo the permeability transition in response to hydrophobic bile acids.
2005 Aug
Conjugated bile acids promote ERK1/2 and AKT activation via a pertussis toxin-sensitive mechanism in murine and human hepatocytes.
2005 Dec
Preincubation of rat and human hepatocytes with cytoprotectants prior to cryopreservation can improve viability and function upon thawing.
2005 Dec
Similar patterns of mitochondrial vulnerability and rescue induced by genetic modification of alpha-synuclein, parkin, and DJ-1 in Caenorhabditis elegans.
2005 Dec 30
Mechanisms involved in spironolactone-induced choleresis in the rat. Role of multidrug resistance-associated protein 2.
2005 Feb 1
Vectorial transport of bile salts across MDCK cells expressing both rat Na+-taurocholate cotransporting polypeptide and rat bile salt export pump.
2005 Jan
Prevention of Mrp2 activity impairment in ethinylestradiol-induced cholestasis by ursodeoxycholate in the rat.
2005 Jul
Bile acids for liver-transplanted patients.
2005 Jul 20
Bile duct proliferation associated with bile salt-induced hypercholeresis in Mdr2 P-glycoprotein-deficient mice.
2005 Jun
A distinct microarray gene expression profile in primary rat hepatocytes incubated with ursodeoxycholic acid.
2005 Jun
Interferon-alpha-induced modulation of glucocorticoid and serotonin receptors as a mechanism of depression.
2005 Jun
Activation of CREB by tauroursodeoxycholic acid protects cholangiocytes from apoptosis induced by mTOR inhibition.
2005 Jun
A nuclear receptor ligand down-regulates cytosolic phospholipase A2 expression to reduce bile acid-induced cyclooxygenase 2 activity in cholangiocytes: implications of anticarcinogenic action of farnesoid X receptor agonists.
2005 Mar
Sustaining a bioartificial liver under hypothermic conditions.
2005 Mar-Apr
Biliary excretion of olmesartan, an anigotensin II receptor antagonist, in the rat.
2005 May
1H and 13C NMR characterization and stereochemical assignments of bile acids in aqueous media.
2005 Oct
Inhibition of MRP1-mediated efflux in human erythrocytes by mono-anionic bile salts.
2005 Sep-Oct
Tauroursodeoxycholic acid inserts the bile salt export pump into canalicular membranes of cholestatic rat liver.
2006 Feb
Preincubation of rat and human hepatocytes with cytoprotectants prior to cryopreservation can improve viability and function upon thawing.
2006 Jan
Bile acid transport and metabolism in rat liver slices.
2006 Mar
Patents
Name Type Language
TAURURSODIOL
USAN  
Official Name English
TAURURSODIOL [USAN]
Common Name English
TAUROURSODESOXYCHOLIC ACID
WHO-DD  
Common Name English
URSODOXICOLTAURINE
INN  
Official Name English
UR-906
Code English
ursodoxicoltaurine [INN]
Common Name English
TAUROURSODEOXYCHOLIC ACID
Common Name English
Ursodoxicoltaurine [WHO-DD]
Common Name English
3.ALPHA.,7.BETA.-DIHYDROXY-5.BETA.-CHOLANOYLTAURINE
Common Name English
URSODEOXYCHOLYLTAURINE
Common Name English
Classification Tree Code System Code
DSLD 3564 (Number of products:2)
Created by admin on Fri Dec 15 15:57:51 GMT 2023 , Edited by admin on Fri Dec 15 15:57:51 GMT 2023
EU-Orphan Drug EU/3/17/1844
Created by admin on Fri Dec 15 15:57:51 GMT 2023 , Edited by admin on Fri Dec 15 15:57:51 GMT 2023
Code System Code Type Description
EPA CompTox
DTXSID80932754
Created by admin on Fri Dec 15 15:57:51 GMT 2023 , Edited by admin on Fri Dec 15 15:57:51 GMT 2023
PRIMARY
FDA UNII
60EUX8MN5X
Created by admin on Fri Dec 15 15:57:51 GMT 2023 , Edited by admin on Fri Dec 15 15:57:51 GMT 2023
PRIMARY
RXCUI
2613950
Created by admin on Fri Dec 15 15:57:51 GMT 2023 , Edited by admin on Fri Dec 15 15:57:51 GMT 2023
PRIMARY
DAILYMED
60EUX8MN5X
Created by admin on Fri Dec 15 15:57:51 GMT 2023 , Edited by admin on Fri Dec 15 15:57:51 GMT 2023
PRIMARY
PUBCHEM
9848818
Created by admin on Fri Dec 15 15:57:51 GMT 2023 , Edited by admin on Fri Dec 15 15:57:51 GMT 2023
PRIMARY
CHEBI
80774
Created by admin on Fri Dec 15 15:57:51 GMT 2023 , Edited by admin on Fri Dec 15 15:57:51 GMT 2023
PRIMARY
CAS
14605-22-2
Created by admin on Fri Dec 15 15:57:51 GMT 2023 , Edited by admin on Fri Dec 15 15:57:51 GMT 2023
PRIMARY
NCI_THESAURUS
C175204
Created by admin on Fri Dec 15 15:57:51 GMT 2023 , Edited by admin on Fri Dec 15 15:57:51 GMT 2023
PRIMARY
MESH
C031655
Created by admin on Fri Dec 15 15:57:51 GMT 2023 , Edited by admin on Fri Dec 15 15:57:51 GMT 2023
PRIMARY
INN
11388
Created by admin on Fri Dec 15 15:57:51 GMT 2023 , Edited by admin on Fri Dec 15 15:57:51 GMT 2023
PRIMARY
DRUG BANK
DB08834
Created by admin on Fri Dec 15 15:57:51 GMT 2023 , Edited by admin on Fri Dec 15 15:57:51 GMT 2023
PRIMARY
SMS_ID
100000087027
Created by admin on Fri Dec 15 15:57:51 GMT 2023 , Edited by admin on Fri Dec 15 15:57:51 GMT 2023
PRIMARY
EVMPD
SUB20887
Created by admin on Fri Dec 15 15:57:51 GMT 2023 , Edited by admin on Fri Dec 15 15:57:51 GMT 2023
PRIMARY
WIKIPEDIA
TAUROURSODEOXYCHOLIC ACID
Created by admin on Fri Dec 15 15:57:51 GMT 2023 , Edited by admin on Fri Dec 15 15:57:51 GMT 2023
PRIMARY
USAN
GH-151
Created by admin on Fri Dec 15 15:57:51 GMT 2023 , Edited by admin on Fri Dec 15 15:57:51 GMT 2023
PRIMARY