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
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
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
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: CHEMBL5409 Sources: https://www.ncbi.nlm.nih.gov/pubmed/18307294 |
30.0 µM [EC50] | ||
Target ID: CHEMBL4426 Sources: https://www.ncbi.nlm.nih.gov/pubmed/19102680 |
10.0 µM [Kd] |
PubMed
Title | Date | PubMed |
---|---|---|
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
Edited
Fri Dec 15 15:47:41 UTC 2023
by
admin
on
Fri Dec 15 15:47:41 UTC 2023
|
Record UNII |
6X4JLR867N
|
Record Status |
Validated (UNII)
|
Record Version |
|
-
Download
Name | Type | Language | ||
---|---|---|---|---|
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Systematic Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English |
Code System | Code | Type | Description | ||
---|---|---|---|---|---|
|
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 | |||
|
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 | |||
|
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 |
|