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

Molecular Formula C26H45NO6S
Molecular Weight 499.704
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 9 / 10
E/Z Centers 0
Optical Activity UNSPECIFIED

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 partially prevents apoptosis induced by 3-nitropropionic acid: evidence for a mitochondrial pathway independent of the permeability transition.
2000 Dec
Tauroursodesoxycholate-induced choleresis involves p38(MAPK) activation and translocation of the bile salt export pump in rats.
2001 Aug
Cholesterol crystallization in model biles: effects of bile salt and phospholipid species composition.
2001 Aug
Beneficial effects of silymarin on estrogen-induced cholestasis in the rat: a study in vivo and in isolated hepatocyte couplets.
2001 Aug
Stimulation of ATP secretion in the liver by therapeutic bile acids.
2001 Aug 15
Effect of bile acids on the proliferative activity and apoptosis of rat hepatocytes.
2001 Jun
Bile acid transport and regulating functions in the human biliary epithelium.
2001 Mar
Cellular distribution of thrombomodulin as an early marker for warm ischemic liver injury in porcine liver transplantation: protective effect of prostaglandin I2 analogue and tauroursodeoxycholic acid.
2001 Mar 27
[Effects of bile acid preparations on DNA biosynthesis, apoptosis, and necrosis in hepatocytes in vitro].
2001 Mar-Apr
Tauroursodeoxycholic acid for the cytoprotection of liver grafts during cold storage: a new aspect of its anti-apoptotic properties?
2001 May 15
Protective role of tauroursodeoxycholate during harvesting and cold storage of human liver: a pilot study in transplant recipients.
2001 May 15
Tauroursodeoxycholic acid improves the survival and function of nigral transplants in a rat model of Parkinson's disease.
2002
Tauroursodeoxycholic acid (TUDCA) in the prevention of total parenteral nutrition-associated liver disease.
2002 Aug
Comparative cytotoxic and cytoprotective effects of taurohyodeoxycholic acid (THDCA) and tauroursodeoxycholic acid (TUDCA) in HepG2 cell line.
2002 Jan 30
Ursodeoxycholic acid diminishes Fas-ligand-induced apoptosis in mouse hepatocytes.
2002 Jul
Hepatoprotection with tauroursodeoxycholate and beta muricholate against taurolithocholate induced cholestasis: involvement of signal transduction pathways.
2002 Jul
Tauroursodeoxycholic acid mobilizes alpha-PKC after uptake in human HepG2 hepatoma cells.
2002 Jun
Ursodeoxycholate and tauroursodeoxycholate inhibit cholangiocyte growth and secretion of BDL rats through activation of PKC alpha.
2002 May
Resistance of rat hepatocytes against bile acid-induced apoptosis in cholestatic liver injury is due to nuclear factor-kappa B activation.
2003 Aug
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
Hydrophilic bile salts have a cytoprotective effect against cyclosporine A-induced cholestasis through enhanced canalicular membrane fluidity and transporter activity.
2003 Jan
Ursodeoxycholate reduces ethinylestradiol glucuronidation in the rat: role in prevention of estrogen-induced cholestasis.
2003 Jul
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
Tauroursodeoxycholic acid prevents amyloid-beta peptide-induced neuronal death via a phosphatidylinositol 3-kinase-dependent signaling pathway.
2003 Sep-Dec
Conjugation with taurine prevents side-chain desaturation of ursodeoxycholic and beta-muricholic acids in bile fistula rats.
2004 Aug
Inhibition of the E2F-1/p53/Bax pathway by tauroursodeoxycholic acid in amyloid beta-peptide-induced apoptosis of PC12 cells.
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
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
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
Biliary excretion of bile acids and organic anions in rats with dichloroethylene-induced bile canalicular injury.
2004 Oct
Gap junctional intercellular communication is not needed for the anticholestatic effect of tauroursodeoxycholic acid in mouse liver.
2005 Apr
Conjugated bile acids promote ERK1/2 and AKT activation via a pertussis toxin-sensitive mechanism in murine and human hepatocytes.
2005 Dec
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
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
1H and 13C NMR characterization and stereochemical assignments of bile acids in aqueous media.
2005 Oct
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
Substance Class Chemical
Created
by admin
on Fri Dec 15 15:57:51 GMT 2023
Edited
by admin
on Fri Dec 15 15:57:51 GMT 2023
Record UNII
60EUX8MN5X
Record Status Validated (UNII)
Record Version
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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
Related Record Type Details
SALT/SOLVATE -> PARENT
SOLVATE->ANHYDROUS
SALT/SOLVATE -> PARENT
Related Record Type Details
PARENT -> METABOLITE
MAJOR
PLASMA
Related Record Type Details
ACTIVE MOIETY