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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
Ileal mucosal bile acid absorption is increased in Cftr knockout mice.
2001
Inhibitory effect of short-term bile duct ligation on hepatic cytochrome P450 of bile acid-depleted rats.
2001
Hydrophilic bile salts enhance differential distribution of sphingomyelin and phosphatidylcholine between micellar and vesicular phases: potential implications for their effects in vivo.
2001 Apr
Design and properties of hepatitis C virus antisense oligonucleotides for liver specific drug targeting.
2001 Apr-Jul
Sinusoidal efflux of taurocholate is enhanced in Mrp2-deficient rat liver.
2001 Aug
Regulation of biliary cholesterol secretion is independent of hepatocyte canalicular membrane lipid composition: a study in the diosgenin-fed rat model.
2001 Aug
Beneficial effects of growth hormone on bacterial translocation during the course of acute necrotizing pancreatitis 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
Effects of internal biliary bypass on the regulation of hepatic cholesterol 7alpha-hydroxylase activity in rats.
2001 Aug
Intracellular glutathione regulates taurocholate transport in HepG2 cells.
2001 Aug 1
Role of endogenous prostacyclin in gastric ulcerogenic and healing responses--a study using IP-receptor knockout mice.
2001 Jan-Dec
The effect of etodolac on bile salt and histamine-mediated gastric mucosal injury in the rat.
2001 Jan-Dec
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
Attenuation of sepsis-related immunoparalysis by continuous veno-venous hemofiltration in experimental porcine pancreatitis.
2001 Jul
Synthesis and properties of bile acid phosphoramidites 5'-tethered to antisense oligodeoxynucleotides against HCV.
2001 Jul
Characterization of the efflux transport of 17beta-estradiol-D-17beta-glucuronide from the brain across the blood-brain barrier.
2001 Jul
Comparison of "type I" and "type II" organic cation transport by organic cation transporters and organic anion-transporting polypeptides.
2001 Jul
Influence of natural, electrically neutral lipids on the potentiometric responses of cation-selective polymeric membrane electrodes.
2001 Jul 15
Gastric preconditioning induced by short ischemia: the role of prostaglandins, nitric oxide and adenosine.
2001 Jul-Aug
Optimization of culture conditions for determining hepatobiliary disposition of taurocholate in sandwich-cultured rat hepatocytes.
2001 Jun
The effect of glucagon-like peptide 2 on intestinal permeability and bacterial translocation in acute necrotizing pancreatitis.
2001 Jun
Obesity increases the severity of acute experimental pancreatitis in the rat.
2001 Jun
Long-term course in collagenous colitis and the impact of bile acid malabsorption and bile acid sequestrants on histopathology and clinical features.
2001 Jun
Modifying hepatic phospholipid synthesis associates with biliary phospholipid secretion rate in a transporter-independent manner in rats: relation to canalicular membrane fluidity.
2001 Jun
Characterization of model bile using fluorescence energy transfer from dehydroergosterol to dansylated lecithin.
2001 Jun
Colchicine inhibits taurodeoxycholate transport in pericentral but not in periportal hepatocytes.
2001 Jun 20
Soluble receptors released during acute pancreatitis interfere with the detection of tumor necrosis factor-alpha.
2001 May
Taurocholic acid-induced secretion in normal and cystic fibrosis mouse ileum.
2001 May
Is a role of phospholipase A(2) in cholesterol gallstone formation phospholipid species-dependent?
2001 May 31
Bile acid feeding increased proliferative activity and apical bile acid transporter expression in both small and large rat cholangiocytes.
2001 Nov
Increased matrix metalloproteinase expression and activation following experimental acute pancreatitis.
2001 Nov
Role of nonesterified fatty acids in necrotizing pancreatitis: an in vivo experimental study in rats.
2001 Nov
Interaction of 2,3-dimercapto-1-propane sulfonate with the human organic anion transporter hOAT1.
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
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
Hydrocortisone treatment of early SIRS in acute experimental pancreatitis.
2001 Oct
Pericentral hepatocytes translocate hydrophilic bile acids more rapidly than hydrophobic ones.
2001 Oct
The effect of a functional group in penicillin derivatives on the interaction with bile salt micelles studied by micellar electrokinetic chromatography.
2001 Oct
Inhibition of inducible nitric oxide synthase reduces bacterial translocation in a rat model of acute pancreatitis.
2001 Oct
Regulation of sterol regulatory element-binding proteins by cholesterol flux in CaCo-2 cells.
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
Alkaline phosphatase from rat liver and kidney is differentially modulated.
2001 Sep
Ezetimibe selectively inhibits intestinal cholesterol absorption in rodents in the presence and absence of exocrine pancreatic function.
2001 Sep
Nuclear receptor-mediated repression of human cholesterol 7alpha-hydroxylase gene transcription by bile acids.
2001 Sep
Ischemic preconditioning, the most effective gastroprotective intervention: involvement of prostaglandins, nitric oxide, adenosine and sensory nerves.
2001 Sep 21
Toxicity and uptake mechanism of cylindrospermopsin and lophyrotomin in primary rat hepatocytes.
2002 Feb
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