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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
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
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
Bile salt tauroursodeoxycholic acid modulation of Bax translocation to mitochondria protects the liver from warm ischemia-reperfusion injury in the rat.
2001 Dec 15
Amyloid beta-peptide disrupts mitochondrial membrane lipid and protein structure: protective role of tauroursodeoxycholate.
2001 Feb 23
[Modulation by tauroursodeoxycholic acid of proliferation of the rat ischemic liver hepatocytes].
2001 Jul-Aug
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 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
Neuroprotection by a bile acid in an acute stroke model in the rat.
2002 Apr
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
Tauroursodeoxycholic acid reduces damaging effects of taurodeoxycholic acid on fundus gastric mucosa.
2002 Jul
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
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
Taurohyodeoxycholate- and tauroursodeoxycholate-induced hypercholeresis is augmented in bile duct ligated rats.
2003 Feb
Bile salts potentiate adenylyl cyclase activity and cAMP-regulated secretion in human gallbladder epithelium.
2003 Feb
Peroxisome proliferator-activated receptor alpha (PPARalpha)-mediated regulation of multidrug resistance 2 (Mdr2) expression and function in mice.
2003 Feb 1
Effects of bile acids on biliary epithelial cells: proliferation, cytotoxicity, and cytokine secretion.
2003 Feb 7
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
Inhibition of ileal bile acid absorption by colestimide.
2003 May
Taurolithocholic acid exerts cholestatic effects via phosphatidylinositol 3-kinase-dependent mechanisms in perfused rat livers and rat hepatocyte couplets.
2003 May 16
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
Conjugation with taurine prevents side-chain desaturation of ursodeoxycholic and beta-muricholic acids in bile fistula rats.
2004 Aug
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
Role of mitochondrial dysfunction in combined bile acid-induced cytotoxicity: the switch between apoptosis and necrosis.
2004 May
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
Human hepatic mitochondria generate reactive oxygen species and undergo the permeability transition in response to hydrophobic bile acids.
2005 Aug
Preincubation of rat and human hepatocytes with cytoprotectants prior to cryopreservation can improve viability and function upon thawing.
2005 Dec
Vectorial transport of bile salts across MDCK cells expressing both rat Na+-taurocholate cotransporting polypeptide and rat bile salt export pump.
2005 Jan
Bile acids for liver-transplanted patients.
2005 Jul 20
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
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 GMT 2023
Edited
by admin
on Fri Dec 15 15:47:41 GMT 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 GMT 2023 , Edited by admin on Fri Dec 15 15:47:41 GMT 2023
PRIMARY
FDA UNII
6X4JLR867N
Created by admin on Fri Dec 15 15:47:41 GMT 2023 , Edited by admin on Fri Dec 15 15:47:41 GMT 2023
PRIMARY
PUBCHEM
46782978
Created by admin on Fri Dec 15 15:47:41 GMT 2023 , Edited by admin on Fri Dec 15 15:47:41 GMT 2023
PRIMARY
Related Record Type Details
PARENT -> SALT/SOLVATE
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ACTIVE MOIETY