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Details

Stereochemistry ABSOLUTE
Molecular Formula C26H44NO6S.Na
Molecular Weight 521.685
Optical Activity UNSPECIFIED
Defined Stereocenters 10 / 10
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of TAURURSODIOL SODIUM

SMILES

[Na+].[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=IYPNVUSIMGAJFC-JUWYWQLMSA-M
InChI=1S/C26H45NO6S.Na/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);/q;+1/p-1/t16-,17+,18-,19-,20+,21+,22+,24+,25+,26-;/m1./s1

HIDE SMILES / InChI

Molecular Formula Na
Molecular Weight 22.9898
Charge 1
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Molecular Formula C26H44NO6S
Molecular Weight 498.696
Charge -1
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
Stimulation of ATP secretion in the liver by therapeutic bile acids.
2001 Aug 15
Effect of tauroursodeoxycholate and S-adenosyl-L-methionine on 17beta-estradiol glucuronide-induced cholestasis.
2001 Feb
Tauroursodeoxycholic acid inserts the apical conjugate export pump, Mrp2, into canalicular membranes and stimulates organic anion secretion by protein kinase C-dependent mechanisms in cholestatic rat liver.
2001 May
Ursodeoxycholic acid diminishes Fas-ligand-induced apoptosis in mouse hepatocytes.
2002 Jul
Taurolithocholic acid-3 sulfate induces CD95 trafficking and apoptosis in a c-Jun N-terminal kinase-dependent manner.
2002 May
Functional expression of the canalicular bile salt export pump of human liver.
2002 Nov
Effect of tauroursodeoxycholic acid on endoplasmic reticulum stress-induced caspase-12 activation.
2002 Sep
Urinary excretion of bile acids in bile duct-ligated rats.
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
Taurohyodeoxycholate- and tauroursodeoxycholate-induced hypercholeresis is augmented in bile duct ligated rats.
2003 Feb
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
Tauroursodeoxycholic acid protects rat hepatocytes from bile acid-induced apoptosis via activation of survival pathways.
2004 Jun
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
Biliary excretion of bile acids and organic anions in rats with dichloroethylene-induced bile canalicular injury.
2004 Oct
Hypothermic maintenance of hepatocyte spheroids.
2005
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
Bile duct proliferation associated with bile salt-induced hypercholeresis in Mdr2 P-glycoprotein-deficient mice.
2005 Jun
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
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 15:47:41 UTC 2023
Edited
by admin
on Fri Dec 15 15:47:41 UTC 2023
Record UNII
6X4JLR867N
Record Status Validated (UNII)
Record Version
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Name Type Language
TAURURSODIOL SODIUM
Common Name English
TAUROURSODEOXYCHOLATE SODIUM SALT
Common Name English
URSODOXICOLTAURINE SODIUM
Common Name English
ETHANESULFONIC ACID, 2-(((3.ALPHA.,5.BETA.,7.BETA.)-3,7-DIHYDROXY-24-OXOCHOLAN-24-YL)AMINO)-, SODIUM SALT (1:1)
Common Name English
ETHANESULFONIC ACID, 2-(((3.ALPHA.,5.BETA.,7.BETA.)-3,7-DIHYDROXY-24-OXOCHOLAN-24-YL)AMINO)-, MONOSODIUM SALT
Systematic Name English
SODIUM TAUROURSODEOXYCHOLATE
Common Name English
URSODEOXYCHOLYLTAURINE SODIUM
Common Name English
SODIUM TAUROURSODESOXYCHOLATE
Common Name English
Ursodoxicoltaurine sodium [WHO-DD]
Common Name English
Code System Code Type Description
CAS
35807-85-3
Created by admin on Fri Dec 15 15:47:41 UTC 2023 , Edited by admin on Fri Dec 15 15:47:41 UTC 2023
PRIMARY
FDA UNII
6X4JLR867N
Created by admin on Fri Dec 15 15:47:41 UTC 2023 , Edited by admin on Fri Dec 15 15:47:41 UTC 2023
PRIMARY
PUBCHEM
46782978
Created by admin on Fri Dec 15 15:47:41 UTC 2023 , Edited by admin on Fri Dec 15 15:47:41 UTC 2023
PRIMARY
Related Record Type Details
PARENT -> SALT/SOLVATE
Related Record Type Details
ACTIVE MOIETY