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Details

Stereochemistry ABSOLUTE
Molecular Formula C26H45NO6S
Molecular Weight 499.7057
Optical Activity UNSPECIFIED
Defined Stereocenters 10 / 10
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of URSODOXICOLTAURINE

SMILES

C[C@]([H])(CCC(=NCCS(=O)(=O)O)O)[C@@]1([H])CC[C@@]2([H])[C@@]3([H])[C@]([H])(CC[C@]12C)[C@@]4(C)CC[C@]([H])(C[C@@]4([H])C[C@]3([H])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 499.7057
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 10 / 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
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
Micronuclei induction, cell cycle delay and apoptosis as markers of cellular stress caused by ursodeoxycholic acid in human lymphocytes.
2001 Aug 22
Effect of tauroursodeoxycholate and S-adenosyl-L-methionine on 17beta-estradiol glucuronide-induced cholestasis.
2001 Feb
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
High metabolic function of primary human and porcine hepatocytes in a polyurethane foam/spheroid culture system in plasma from patients with fulminant hepatic failure.
2002
Comparative cytotoxic and cytoprotective effects of taurohyodeoxycholic acid (THDCA) and tauroursodeoxycholic acid (TUDCA) in HepG2 cell line.
2002 Jan 30
Effects of hydrophobic and hydrophilic bile salt mixtures on cholesterol crystallization in model biles.
2002 Jul 11
Taurolithocholic acid-3 sulfate induces CD95 trafficking and apoptosis in a c-Jun N-terminal kinase-dependent manner.
2002 May
Ursodeoxycholate and tauroursodeoxycholate inhibit cholangiocyte growth and secretion of BDL rats through activation of PKC alpha.
2002 May
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
Unique inhibition of bile salt-induced apoptosis by lecithins and cytoprotective bile salts in immortalized mouse cholangiocytes.
2003 Dec
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
Regulation of synthesis and trafficking of canalicular transporters and its alteration in acquired hepatocellular cholestasis. Experimental therapeutic strategies for its prevention.
2004 Feb
Trafficking of the bile salt export pump from the Golgi to the canalicular membrane is regulated by the p38 MAP kinase.
2004 Feb
[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
Role of mitochondrial dysfunction in combined bile acid-induced cytotoxicity: the switch between apoptosis and necrosis.
2004 May
Gap junctional intercellular communication is not needed for the anticholestatic effect of tauroursodeoxycholic acid in mouse liver.
2005 Apr
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
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
1H and 13C NMR characterization and stereochemical assignments of bile acids in aqueous media.
2005 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
Substance Class Chemical
Created
by admin
on Sat Jun 26 15:43:12 UTC 2021
Edited
by admin
on Sat Jun 26 15:43:12 UTC 2021
Record UNII
60EUX8MN5X
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
URSODOXICOLTAURINE
INN  
Official Name English
TAUROURSODESOXYCHOLIC ACID [WHO-DD]
Common Name English
TAURURSODIOL
USAN  
Official Name English
TAURURSODIOL [USAN]
Common Name English
TAUROURSODESOXYCHOLIC ACID
WHO-DD  
Common Name English
UR-906
Common Name English
URSODOXICOLTAURINE [INN]
Common Name English
TAUROURSODEOXYCHOLIC ACID
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 Sat Jun 26 15:43:13 UTC 2021 , Edited by admin on Sat Jun 26 15:43:13 UTC 2021
EU-Orphan Drug EU/3/17/1844
Created by admin on Sat Jun 26 15:43:13 UTC 2021 , Edited by admin on Sat Jun 26 15:43:13 UTC 2021
Code System Code Type Description
FDA UNII
60EUX8MN5X
Created by admin on Sat Jun 26 15:43:13 UTC 2021 , Edited by admin on Sat Jun 26 15:43:13 UTC 2021
PRIMARY
PUBCHEM
9848818
Created by admin on Sat Jun 26 15:43:13 UTC 2021 , Edited by admin on Sat Jun 26 15:43:13 UTC 2021
PRIMARY
CAS
14605-22-2
Created by admin on Sat Jun 26 15:43:13 UTC 2021 , Edited by admin on Sat Jun 26 15:43:13 UTC 2021
PRIMARY
NCI_THESAURUS
C175204
Created by admin on Sat Jun 26 15:43:13 UTC 2021 , Edited by admin on Sat Jun 26 15:43:13 UTC 2021
PRIMARY
MESH
C031655
Created by admin on Sat Jun 26 15:43:13 UTC 2021 , Edited by admin on Sat Jun 26 15:43:13 UTC 2021
PRIMARY
INN
11388
Created by admin on Sat Jun 26 15:43:13 UTC 2021 , Edited by admin on Sat Jun 26 15:43:13 UTC 2021
PRIMARY
DRUG BANK
DB08834
Created by admin on Sat Jun 26 15:43:13 UTC 2021 , Edited by admin on Sat Jun 26 15:43:13 UTC 2021
PRIMARY
EVMPD
SUB20887
Created by admin on Sat Jun 26 15:43:13 UTC 2021 , Edited by admin on Sat Jun 26 15:43:13 UTC 2021
PRIMARY
WIKIPEDIA
TAUROURSODEOXYCHOLIC ACID
Created by admin on Sat Jun 26 15:43:13 UTC 2021 , Edited by admin on Sat Jun 26 15:43:13 UTC 2021
PRIMARY
Related Record Type Details
SALT/SOLVATE -> PARENT
SALT/SOLVATE -> PARENT
Related Record Type Details
PARENT -> METABOLITE
MAJOR
PLASMA
Related Record Type Details
ACTIVE MOIETY