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Details

Stereochemistry ABSOLUTE
Molecular Formula C26H45NO7S
Molecular Weight 515.7051
Optical Activity UNSPECIFIED
Defined Stereocenters 11 / 11
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of TAUROCHOLIC ACID

SMILES

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

InChI

InChIKey=WBWWGRHZICKQGZ-HZAMXZRMSA-N
InChI=1S/C26H45NO7S/c1-15(4-7-23(31)27-10-11-35(32,33)34)18-5-6-19-24-20(14-22(30)26(18,19)3)25(2)9-8-17(28)12-16(25)13-21(24)29/h15-22,24,28-30H,4-14H2,1-3H3,(H,27,31)(H,32,33,34)/t15-,16+,17-,18-,19+,20+,21-,22+,24+,25+,26-/m1/s1

HIDE SMILES / InChI

Molecular Formula C26H45NO7S
Molecular Weight 515.7051
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 11 / 11
E/Z Centers 0
Optical Activity UNSPECIFIED

Taurocholic acid is a bile acid and is the product of conjugation of cholic acid with taurine. Its sodium salt is the chief ingredient of the bile of carnivorous animals. Taurocholic acid, as with all bile acids, acts as a detergent to solubilize fats for absorption and is itself absorbed. It is used as a cholagogue and cholerectic (a bile purging agent). Hydrolysis of taurocholic acid yields taurine, a nonessential amino acid. Taurocholic acid is one of the main components of urinary nonsulfated bile acids in biliary atresia. Raised levels of the bile acid taurocholate in the fetal serum in obstetric cholestasis may result in the development of a fetal dysrhythmia and in sudden intra-uterine death. In medical use, it is administered as a cholagogue and choleretic. Taurocholic acid is a potent TGR5 ligand, and in dogs, colonic perfusion with TCA induces PYY secretion. TCA enemas could stimulate GLP-1 and PYY secretion in obese patients with type 2 diabetes receiving the dipeptidyl peptidase-4 (DPP-4) inhibitor, sitagliptin. Satiogen Pharmaceuticals is developing rectally administered taurocholic acid, a bile acid, for the treatment of obesity and type 2 diabetes mellitus.

Approval Year

PubMed

PubMed

TitleDatePubMed
Inhibitory effect of short-term bile duct ligation on hepatic cytochrome P450 of bile acid-depleted rats.
2001
The absorption of retinoic acids from the gastrointestinal tract is dependent upon chemical structure.
2001
Temporary pancreatic duct occlusion by ethibloc: cause of microcirculatory shutdown, acute inflammation, and pancreas necrosis.
2001 Apr
Sinusoidal efflux of taurocholate is enhanced in Mrp2-deficient rat liver.
2001 Aug
Tauroursodesoxycholate-induced choleresis involves p38(MAPK) activation and translocation of the bile salt export pump in rats.
2001 Aug
Interrelationship between colonic muscularis mucosae activity and changes in transmucosal potential difference.
2001 Aug
Bile salt export pump is highly conserved during vertebrate evolution and its expression is inhibited by PFIC type II mutations.
2001 Aug
Minor role of oxidative stress during intermediate phase of acute pancreatitis in rats.
2001 Feb 1
Effect of bile acids on the uptake of irinotecan and its active metabolite, SN-38, by intestinal cells.
2001 Feb 16
Identification of novel hypocholesterolemic peptides derived from bovine milk beta-lactoglobulin.
2001 Feb 16
Differential effects of caspase-1/interleukin-1beta-converting enzyme on acinar cell necrosis and apoptosis in severe acute experimental pancreatitis.
2001 Jul
Anti-ICAM-1 antibody modulates late onset of acinar cell apoptosis and early necrosis in taurocholate-induced experimental acute pancreatitis.
2001 Jul
Characterization of the efflux transport of 17beta-estradiol-D-17beta-glucuronide from the brain across the blood-brain barrier.
2001 Jul
Influence of natural, electrically neutral lipids on the potentiometric responses of cation-selective polymeric membrane electrodes.
2001 Jul 15
Improved in vitro gene transfer mediated by fluorinated lipoplexes in the presence of a bile salt surfactant.
2001 Jul-Aug
Oral delivery of synthetic eel calcitonin, elcatonin, in rats.
2001 Jun
Characterization of model bile using fluorescence energy transfer from dehydroergosterol to dansylated lecithin.
2001 Jun
Interleukin-10 attenuates proinflammatory cytokine production and improves survival in lethal pancreatitis.
2001 Mar
Regulation of the dynamic localization of the rat Bsep gene-encoded bile salt export pump by anisoosmolarity.
2001 Mar
Successful nonfreezing, subzero preservation of rat liver with 2,3-butanediol and type I antifreeze protein.
2001 Mar
Identification and characterization of human organic anion transporter 3 expressing predominantly in the kidney.
2001 May
Increased matrix metalloproteinase expression and activation following experimental acute pancreatitis.
2001 Nov
Changes in the activity of lysosomal enzymes in rat kidneys in the course of acute pancreatitis.
2001 Nov-Dec
The utilization of sodium taurocholate in excystation of Cryptosporidium parvum and infection of tissue culture.
2001 Oct
Multispecific substrate recognition of kidney-specific organic anion transporters OAT-K1 and OAT-K2.
2001 Oct
Single amino acid substitution of rat MRP2 results in acquired transport activity for taurocholate.
2001 Oct
Troglitazone-induced intrahepatic cholestasis by an interference with the hepatobiliary export of bile acids in male and female rats. Correlation with the gender difference in troglitazone sulfate formation and the inhibition of the canalicular bile salt export pump (Bsep) by troglitazone and troglitazone sulfate.
2001 Oct 5
Ezetimibe selectively inhibits intestinal cholesterol absorption in rodents in the presence and absence of exocrine pancreatic function.
2001 Sep
Patents

Sample Use Guides

In Vivo Use Guide
Curator's Comment:: In 10 healthy male subjects rectal administration of TCA promptly stimulated secretion of both GLP-1 and PYY, and increased fullness, in a dose-dependent manner.
A 20 ml aqueous gel (1% carboxymethyl cellulose) containing 1500 or 3500 mg Taurocholic acid (TCA), or vehicle only, was infused into the rectum using a syringe and 10 cm soft cannula over 2 min.
Route of Administration: Other
In primary murine intestinal cultures, Taurocholic acid (100 or 1000 umol/L) dose dependently increased GLP-1 release.
Substance Class Chemical
Created
by admin
on Sat Jun 26 01:06:18 UTC 2021
Edited
by admin
on Sat Jun 26 01:06:18 UTC 2021
Record UNII
5E090O0G3Z
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
TAUROCHOLIC ACID
HSDB   MI  
Common Name English
CHOLYLTAURINE
Common Name English
3.BETA.-HYDROXYDINOR-5-CHOLENIC ACID
Systematic Name English
CHOLAIC ACID
Common Name English
TAUROCHOLIC ACID [HSDB]
Common Name English
2-(((3.ALPHA.,5.BETA.,7.ALPHA.,12.ALPHA.)-3,7,12-TRIHYDROXY-24-OXOCHOLAN-24-YL)AMINO)ETHANESULFONIC ACID
Common Name English
NSC-25505
Code English
TAUROCHOLIC ACID [MI]
Common Name English
N-CHOLOYLTAURINE
Common Name English
Code System Code Type Description
FDA UNII
5E090O0G3Z
Created by admin on Sat Jun 26 01:06:18 UTC 2021 , Edited by admin on Sat Jun 26 01:06:18 UTC 2021
PRIMARY
MESH
D013656
Created by admin on Sat Jun 26 01:06:18 UTC 2021 , Edited by admin on Sat Jun 26 01:06:18 UTC 2021
PRIMARY
PUBCHEM
6675
Created by admin on Sat Jun 26 01:06:18 UTC 2021 , Edited by admin on Sat Jun 26 01:06:18 UTC 2021
PRIMARY
MERCK INDEX
M10482
Created by admin on Sat Jun 26 01:06:18 UTC 2021 , Edited by admin on Sat Jun 26 01:06:18 UTC 2021
PRIMARY Merck Index
WIKIPEDIA
TAUROCHOLIC ACID
Created by admin on Sat Jun 26 01:06:18 UTC 2021 , Edited by admin on Sat Jun 26 01:06:18 UTC 2021
PRIMARY
CAS
81-24-3
Created by admin on Sat Jun 26 01:06:18 UTC 2021 , Edited by admin on Sat Jun 26 01:06:18 UTC 2021
PRIMARY
DRUG BANK
DB04348
Created by admin on Sat Jun 26 01:06:18 UTC 2021 , Edited by admin on Sat Jun 26 01:06:18 UTC 2021
PRIMARY
ECHA (EC/EINECS)
201-336-2
Created by admin on Sat Jun 26 01:06:18 UTC 2021 , Edited by admin on Sat Jun 26 01:06:18 UTC 2021
PRIMARY
HSDB
832
Created by admin on Sat Jun 26 01:06:18 UTC 2021 , Edited by admin on Sat Jun 26 01:06:18 UTC 2021
PRIMARY
Related Record Type Details
SALT/SOLVATE -> PARENT
TRANSPORTER -> INHIBITOR
TRANSPORTER -> SUBSTRATE
TRANSPORTER -> SUBSTRATE
LABELED -> NON-LABELED
TRANSPORTER -> SUBSTRATE
TRANSPORTER -> INHIBITOR
SALT/SOLVATE -> PARENT
Related Record Type Details
ACTIVE MOIETY