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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
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
Micronuclei induction, cell cycle delay and apoptosis as markers of cellular stress caused by ursodeoxycholic acid in human lymphocytes.
2001 Aug 22
[Modulation by tauroursodeoxycholic acid of proliferation of the rat ischemic liver hepatocytes].
2001 Jul-Aug
Effect of bile acids on the proliferative activity and apoptosis of rat hepatocytes.
2001 Jun
Effect of sodium tauroursodeoxycholate on phalloidin-induced cholestasis in rats.
2001 Jun 1
[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
Tauroursodeoxycholic acid protects hepatocytes from ethanol-fed rats against tumor necrosis factor-induced cell death by replenishing mitochondrial glutathione.
2001 Nov
Bile-salt hydrophobicity is a key factor regulating rat liver plasma-membrane communication: relation to bilayer structure, fluidity and transporter expression and function.
2001 Nov 1
A bile acid protects against motor and cognitive deficits and reduces striatal degeneration in the 3-nitropropionic acid model of Huntington's disease.
2001 Oct
Tauroursodeoxycholic acid improves the survival and function of nigral transplants in a rat model of Parkinson's disease.
2002
Dapsone-induced cholestasis and impairment of bile salt output in the rat.
2002 Apr 15
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
Effects of bile acids on the muscle functions of guinea pig gallbladder.
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
3,4-dihydroxyphenylacetaldehyde: a potential target for neuroprotective therapy in Parkinson's disease.
2003 Apr
Resistance of rat hepatocytes against bile acid-induced apoptosis in cholestatic liver injury is due to nuclear factor-kappa B activation.
2003 Aug
Hepatoprotection by the farnesoid X receptor agonist GW4064 in rat models of intra- and extrahepatic cholestasis.
2003 Dec
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
Tauroursodeoxycholic acid prevents Bax-induced membrane perturbation and cytochrome C release in isolated mitochondria.
2003 Mar 18
Inhibitory effects of ursodeoxycholic acid on the induction of nitric oxide synthase in vascular smooth muscle cells.
2003 Mar 19
Involvement of integrins and Src in tauroursodeoxycholate-induced and swelling-induced choleresis.
2003 May
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
Tauroursodeoxycholate inhibits human cholangiocarcinoma growth via Ca2+-, PKC-, and MAPK-dependent pathways.
2004 Jun
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
Effects of colchicine on the maximum biliary excretion of cholephilic compounds in rats.
2004 Sep
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
Preincubation of rat and human hepatocytes with cytoprotectants prior to cryopreservation can improve viability and function upon thawing.
2005 Dec
Mechanisms involved in spironolactone-induced choleresis in the rat. Role of multidrug resistance-associated protein 2.
2005 Feb 1
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 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
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
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