U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ABSOLUTE
Molecular Formula C26H45NO6S.2H2O
Molecular Weight 535.734
Optical Activity UNSPECIFIED
Defined Stereocenters 10 / 10
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of TAURURSODIOL DIHYDRATE

SMILES

O.O.[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=BNXLUNVCHFIPFY-GUBAPICVSA-N
InChI=1S/C26H45NO6S.2H2O/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);2*1H2/t16-,17+,18-,19-,20+,21+,22+,24+,25+,26-;;/m1../s1

HIDE SMILES / InChI

Molecular Formula C26H45NO6S
Molecular Weight 499.704
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 9 / 10
E/Z Centers 0
Optical Activity UNSPECIFIED

Molecular Formula H2O
Molecular Weight 18.0153
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

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
Hydrophilic bile salts enhance differential distribution of sphingomyelin and phosphatidylcholine between micellar and vesicular phases: potential implications for their effects in vivo.
2001 Apr
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
[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
Protective role of tauroursodeoxycholate during harvesting and cold storage of human liver: a pilot study in transplant recipients.
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
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
Effects of hydrophobic and hydrophilic bile salt mixtures on cholesterol crystallization in model biles.
2002 Jul 11
Tauroursodeoxycholic acid mobilizes alpha-PKC after uptake in human HepG2 hepatoma cells.
2002 Jun
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
Effects of high taurocholate load on activities of hepatic alcohol metabolizing enzymes.
2002 May 31
Unique inhibition of bile salt-induced apoptosis by lecithins and cytoprotective bile salts in immortalized mouse cholangiocytes.
2003 Dec
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
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
[Effect of Tauroursodeoxycholic acid on cytochrome C-mediated apoptosis in HepG2 cells].
2003 May
Involvement of integrins and Src in tauroursodeoxycholate-induced and swelling-induced choleresis.
2003 May
Inhibition of ileal bile acid absorption by colestimide.
2003 May
Tauroursodeoxycholic acid reduces apoptosis and protects against neurological injury after acute hemorrhagic stroke in rats.
2003 May 13
What doesn't kill you makes you stronger: how hepatocytes survive prolonged cholestasis.
2004 Apr
Tauroursodeoxycholate inhibits human cholangiocarcinoma growth via Ca2+-, PKC-, and MAPK-dependent pathways.
2004 Jun
[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
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
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
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
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
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
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
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 Dec 16 13:44:43 GMT 2023
Edited
by admin
on Sat Dec 16 13:44:43 GMT 2023
Record UNII
U7XRV7RZ1I
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
TAURURSODIOL DIHYDRATE
Common Name English
URSODOXICOLTAURINE DIHYDRATE
Common Name English
ALBRIOZA component TAUROURSODEOXYCHOLIC ACID DIHYDRATE
Common Name English
AMX-0035 COMPONENT TAUROURSODEOXYCHOLIC ACID DIHYDRATE
Code English
TAUROURSODEOXYCHOLIC ACID DIHYDRATE
Common Name English
RELYVRIO COMPONENT TAURURSODIOL DIHYDRATE
Brand Name English
ETHANESULFONIC ACID, 2-(((3.ALPHA.,5.BETA.,7.BETA.)-3,7-DIHYDROXY-24-OXOCHOLAN-24-YL)AMINO)-, HYDRATE (1:2)
Systematic Name English
AMX0035 COMPONENT TAUROURSODEOXYCHOLIC ACID DIHYDRATE
Code English
TAURURSODIOL DIHYDRATE COMPONENT OF RELYVRIO
Brand Name English
Classification Tree Code System Code
FDA ORPHAN DRUG 588117
Created by admin on Sat Dec 16 13:44:44 GMT 2023 , Edited by admin on Sat Dec 16 13:44:44 GMT 2023
FDA ORPHAN DRUG 767720
Created by admin on Sat Dec 16 13:44:44 GMT 2023 , Edited by admin on Sat Dec 16 13:44:44 GMT 2023
Code System Code Type Description
SMS_ID
100000164529
Created by admin on Sat Dec 16 13:44:44 GMT 2023 , Edited by admin on Sat Dec 16 13:44:44 GMT 2023
PRIMARY
FDA UNII
U7XRV7RZ1I
Created by admin on Sat Dec 16 13:44:44 GMT 2023 , Edited by admin on Sat Dec 16 13:44:44 GMT 2023
PRIMARY
PUBCHEM
71306862
Created by admin on Sat Dec 16 13:44:44 GMT 2023 , Edited by admin on Sat Dec 16 13:44:44 GMT 2023
PRIMARY
CAS
117609-50-4
Created by admin on Sat Dec 16 13:44:44 GMT 2023 , Edited by admin on Sat Dec 16 13:44:44 GMT 2023
PRIMARY
Related Record Type Details
PARENT -> SALT/SOLVATE
ANHYDROUS->SOLVATE
Related Record Type Details
ACTIVE MOIETY