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Details

Stereochemistry ABSOLUTE
Molecular Formula C26H45NO6S
Molecular Weight 499.704
Optical Activity UNSPECIFIED
Defined Stereocenters 10 / 10
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of TAURODEOXYCHOLIC ACID

SMILES

[H][C@@]1(CC[C@@]2([H])[C@]3([H])CC[C@]4([H])C[C@H](O)CC[C@]4(C)[C@@]3([H])C[C@H](O)[C@]12C)[C@H](C)CCC(=O)NCCS(O)(=O)=O

InChI

InChIKey=AWDRATDZQPNJFN-VAYUFCLWSA-N
InChI=1S/C26H45NO6S/c1-16(4-9-24(30)27-12-13-34(31,32)33)20-7-8-21-19-6-5-17-14-18(28)10-11-25(17,2)22(19)15-23(29)26(20,21)3/h16-23,28-29H,4-15H2,1-3H3,(H,27,30)(H,31,32,33)/t16-,17-,18-,19+,20-,21+,22+,23+,25+,26-/m1/s1

HIDE SMILES / InChI

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

Description
Curator's Comment: The description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/25664595 | https://www.ncbi.nlm.nih.gov/pubmed/23592128 | https://www.ncbi.nlm.nih.gov/pubmed/20522594

Sodium taurodeoxycholate is a bile salt-related, anionic detergent used for isolation of membrane proteins including inner mitochondrial membrane proteins. It is formed by the conjugation of ursodeoxycholic acid (UDCA) with taurine. Sodium taurodeoxycholate and ursodeoxycholic acid are major constituents of black bear bile, which has been used in traditional Chinese medicine for thousands of years. Bear bile was historically employed to treat a number of diseases including jaundice, summer diarrhea, abdominal pain due to hepatobiliary diseases and gastric malfunction, biliary ascariasis, infectious skin diseases, the common cold, intestinal worms, and inflammation of the throat. Sodium taurodeoxycholate has been shown to inhibit apoptosis by modulating mitochondrial membrane perturbation and pore formation, B cell lymphoma 2 (Bcl-2)-associated protein X (BAX) translocation, cytochrome c release, and caspase activation. Sodium taurodeoxycholate inhibits amyloid beta (Ab)-induced apoptosis and attenuates the endoplasmic reticulum (ER) stress, which are thought to be key components of the pathological process in certain diseases. In clinical studies, Sodium taurodeoxycholate is shown to be very safe with oral administration of 1500 mg/day for up to 6 months. In a more recent clinical study, a dose of 1750 mg/day for up to 4 weeks was well tolerated in healthy obese persons. One of the major adverse effects of Sodium taurodeoxycholate is diarrhea. Based on the related information from ursodeoxycholic acid, other gastrointestinal side effects are possible including abdominal pain, flatulence, nausea, dyspepsia, and anorexia.

Originator

Sources: Z. physiol. Chem. (1919), 106, 181-90.

Approval Year

Targets

Targets

Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown

Approved Use

Unknown
Primary
Unknown

Approved Use

Unknown
Primary
Unknown

Approved Use

Unknown
Overview

Overview

CYP3A4CYP2C9CYP2D6hERG

OverviewOther

Other InhibitorOther SubstrateOther Inducer



Drug as perpetrator​

Drug as perpetrator​

TargetModalityActivityMetaboliteClinical evidence
yes [Ki 17.2 uM]
Drug as victim
Sourcing

Sourcing

Vendor/AggregatorIDURL
PubMed

PubMed

TitleDatePubMed
Regulation of oxysterol 7alpha-hydroxylase (CYP7B1) in primary cultures of rat hepatocytes.
2002 Jun
[Effect of Tauroursodeoxycholic acid on cytochrome C-mediated apoptosis in HepG2 cells].
2003 May
Trafficking of the bile salt export pump from the Golgi to the canalicular membrane is regulated by the p38 MAP kinase.
2004 Feb
Hepatic overexpression of murine Abcb11 increases hepatobiliary lipid secretion and reduces hepatic steatosis.
2004 Jan 23
Deoxycholyltaurine-induced vasodilation of rodent aorta is nitric oxide- and muscarinic M(3) receptor-dependent.
2005 Jul 4
Inhibition of MRP1-mediated efflux in human erythrocytes by mono-anionic bile salts.
2005 Sep-Oct
The farnesoid X receptor FXRalpha/NR1H4 acquired ligand specificity for bile salts late in vertebrate evolution.
2007 Sep
Purification and characterization of the first reptile pancreatic lipase: the turtle.
2008 Apr
Store-operated Ca(2+) channels and Stromal Interaction Molecule 1 (STIM1) are targets for the actions of bile acids on liver cells.
2008 May
Trp-107 and trp-253 account for the increased steady state fluorescence that accompanies the conformational change in human pancreatic triglyceride lipase induced by tetrahydrolipstatin and bile salt.
2009 May 22
Contribution of high basolateral bile salt efflux to the lack of hepatotoxicity in rat in response to drugs inducing cholestasis in human.
2010 May
Loss of organic anion transporting polypeptide 1a1 increases deoxycholic acid absorption in mice by increasing intestinal permeability.
2011 Dec
The evolution of farnesoid X, vitamin D, and pregnane X receptors: insights from the green-spotted pufferfish (Tetraodon nigriviridis) and other non-mammalian species.
2011 Feb 3
Patents

Patents

Sample Use Guides

Tauroursodeoxycholic acid 1 g twice daily by mouth
Route of Administration: Oral
In Vitro Use Guide
Isolated rat hepatocytes were cultured in uncoated culture dishes (1x10^6 cells per plate) and treated with bile acids for 4 to 24 h. After treatment, the tissue-culture supernatant was harvested and assayed for enzymatic activity of lactate dehydrogenase (LDH) and aspartate aminotransferase (AST). Enzymatic activity was determined in accordance with standard techniques, using commercially available standard kits (Boehringer Mannheim, Germany).
Substance Class Chemical
Created
by admin
on Sat Dec 16 08:35:08 UTC 2023
Edited
by admin
on Sat Dec 16 08:35:08 UTC 2023
Record UNII
20668G0RPI
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
TAURODEOXYCHOLIC ACID
Common Name English
Taurodeoxycholic acid [WHO-DD]
Common Name English
J339.140J
Code English
TAURINE, N-(3.ALPHA.,12.ALPHA.-DIHYDROXY-5.BETA.-CHOLAN-24-OYL)-
Systematic Name English
3.ALPHA.,12.ALPHA.-DIHYDROXY-5.BETA.-CHOLANIC ACID-24-TAURINE
Systematic Name English
HY-209
Code English
TUDCABIL
Brand Name English
2-(((3.ALPHA.,5.BETA.,12.ALPHA.)-3,12-DIHYDROXY-24-OXOCHOLAN-24-YL)AMINO)ETHANESULFONIC ACID
Systematic Name English
TAURODESOXYCHOLIC ACID
Common Name English
HY209
Code English
DEOXYCHOLYLTAURINE
Common Name English
Code System Code Type Description
PUBCHEM
2733768
Created by admin on Sat Dec 16 08:35:08 UTC 2023 , Edited by admin on Sat Dec 16 08:35:08 UTC 2023
PRIMARY
WIKIPEDIA
Taurodeoxycholic acid
Created by admin on Sat Dec 16 08:35:08 UTC 2023 , Edited by admin on Sat Dec 16 08:35:08 UTC 2023
PRIMARY
EPA CompTox
DTXSID00873418
Created by admin on Sat Dec 16 08:35:08 UTC 2023 , Edited by admin on Sat Dec 16 08:35:08 UTC 2023
PRIMARY
FDA UNII
20668G0RPI
Created by admin on Sat Dec 16 08:35:08 UTC 2023 , Edited by admin on Sat Dec 16 08:35:08 UTC 2023
PRIMARY
CHEBI
9410
Created by admin on Sat Dec 16 08:35:08 UTC 2023 , Edited by admin on Sat Dec 16 08:35:08 UTC 2023
PRIMARY
SMS_ID
300000023937
Created by admin on Sat Dec 16 08:35:08 UTC 2023 , Edited by admin on Sat Dec 16 08:35:08 UTC 2023
PRIMARY
CAS
516-50-7
Created by admin on Sat Dec 16 08:35:08 UTC 2023 , Edited by admin on Sat Dec 16 08:35:08 UTC 2023
PRIMARY
Related Record Type Details
SALT/SOLVATE -> PARENT
Related Record Type Details
ACTIVE MOIETY