Details
| Stereochemistry | ABSOLUTE |
| Molecular Formula | C26H45NO7S |
| Molecular Weight | 515.703 |
| Optical Activity | UNSPECIFIED |
| Defined Stereocenters | 11 / 11 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
C[C@H](CCC(=O)NCCS(O)(=O)=O)[C@H]1CC[C@H]2[C@@H]3[C@H](O)C[C@@H]4C[C@H](O)CC[C@]4(C)[C@H]3C[C@H](O)[C@]12C
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
| Molecular Formula | C26H45NO7S |
| Molecular Weight | 515.703 |
| 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.
Originator
Approval Year
PubMed
| Title | Date | PubMed |
|---|---|---|
| Toxicity and uptake mechanism of cylindrospermopsin and lophyrotomin in primary rat hepatocytes. | 2002-02 |
|
| Changes in the activity of lysosomal enzymes in rat kidneys in the course of acute pancreatitis. | 2001-11-01 |
|
| Bile-salt hydrophobicity is a key factor regulating rat liver plasma-membrane communication: relation to bilayer structure, fluidity and transporter expression and function. | 2001-11-01 |
|
| Bile acid feeding increased proliferative activity and apical bile acid transporter expression in both small and large rat cholangiocytes. | 2001-11 |
|
| Increased matrix metalloproteinase expression and activation following experimental acute pancreatitis. | 2001-11 |
|
| Role of nonesterified fatty acids in necrotizing pancreatitis: an in vivo experimental study in rats. | 2001-11 |
|
| Interaction of 2,3-dimercapto-1-propane sulfonate with the human organic anion transporter hOAT1. | 2001-11 |
|
| Role of endogenous prostacyclin in gastric ulcerogenic and healing responses--a study using IP-receptor knockout mice. | 2001-10-12 |
|
| The effect of etodolac on bile salt and histamine-mediated gastric mucosal injury in the rat. | 2001-10-12 |
|
| 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. | 2001-10-05 |
|
| The utilization of sodium taurocholate in excystation of Cryptosporidium parvum and infection of tissue culture. | 2001-10 |
|
| Hydrocortisone treatment of early SIRS in acute experimental pancreatitis. | 2001-10 |
|
| Pericentral hepatocytes translocate hydrophilic bile acids more rapidly than hydrophobic ones. | 2001-10 |
|
| The effect of a functional group in penicillin derivatives on the interaction with bile salt micelles studied by micellar electrokinetic chromatography. | 2001-10 |
|
| Inhibition of inducible nitric oxide synthase reduces bacterial translocation in a rat model of acute pancreatitis. | 2001-10 |
|
| Regulation of sterol regulatory element-binding proteins by cholesterol flux in CaCo-2 cells. | 2001-10 |
|
| Multispecific substrate recognition of kidney-specific organic anion transporters OAT-K1 and OAT-K2. | 2001-10 |
|
| Single amino acid substitution of rat MRP2 results in acquired transport activity for taurocholate. | 2001-10 |
|
| Common mechanisms of monoacylglycerol and fatty acid uptake by human intestinal Caco-2 cells. | 2001-10 |
|
| Ischemic preconditioning, the most effective gastroprotective intervention: involvement of prostaglandins, nitric oxide, adenosine and sensory nerves. | 2001-09-21 |
|
| Design and properties of hepatitis C virus antisense oligonucleotides for liver specific drug targeting. | 2001-09-21 |
|
| Improved in vitro gene transfer mediated by fluorinated lipoplexes in the presence of a bile salt surfactant. | 2001-09-01 |
|
| Alkaline phosphatase from rat liver and kidney is differentially modulated. | 2001-09 |
|
| Ezetimibe selectively inhibits intestinal cholesterol absorption in rodents in the presence and absence of exocrine pancreatic function. | 2001-09 |
|
| Nuclear receptor-mediated repression of human cholesterol 7alpha-hydroxylase gene transcription by bile acids. | 2001-09 |
|
| Intracellular glutathione regulates taurocholate transport in HepG2 cells. | 2001-08-01 |
|
| Sinusoidal efflux of taurocholate is enhanced in Mrp2-deficient rat liver. | 2001-08 |
|
| Regulation of biliary cholesterol secretion is independent of hepatocyte canalicular membrane lipid composition: a study in the diosgenin-fed rat model. | 2001-08 |
|
| Tauroursodesoxycholate-induced choleresis involves p38(MAPK) activation and translocation of the bile salt export pump in rats. | 2001-08 |
|
| Beneficial effects of growth hormone on bacterial translocation during the course of acute necrotizing pancreatitis in rats. | 2001-08 |
|
| Interrelationship between colonic muscularis mucosae activity and changes in transmucosal potential difference. | 2001-08 |
|
| Bile salt export pump is highly conserved during vertebrate evolution and its expression is inhibited by PFIC type II mutations. | 2001-08 |
|
| Effects of internal biliary bypass on the regulation of hepatic cholesterol 7alpha-hydroxylase activity in rats. | 2001-08 |
|
| Influence of natural, electrically neutral lipids on the potentiometric responses of cation-selective polymeric membrane electrodes. | 2001-07-15 |
|
| Gastric preconditioning induced by short ischemia: the role of prostaglandins, nitric oxide and adenosine. | 2001-07-04 |
|
| Analysis of the diffusion of bile salt/phospholipid micelles in rat intestinal mucin. | 2001-07 |
|
| Differential effects of caspase-1/interleukin-1beta-converting enzyme on acinar cell necrosis and apoptosis in severe acute experimental pancreatitis. | 2001-07 |
|
| Anti-ICAM-1 antibody modulates late onset of acinar cell apoptosis and early necrosis in taurocholate-induced experimental acute pancreatitis. | 2001-07 |
|
| Attenuation of sepsis-related immunoparalysis by continuous veno-venous hemofiltration in experimental porcine pancreatitis. | 2001-07 |
|
| Synthesis and properties of bile acid phosphoramidites 5'-tethered to antisense oligodeoxynucleotides against HCV. | 2001-07 |
|
| Colchicine inhibits taurodeoxycholate transport in pericentral but not in periportal hepatocytes. | 2001-06-20 |
|
| Optimization of culture conditions for determining hepatobiliary disposition of taurocholate in sandwich-cultured rat hepatocytes. | 2001-06 |
|
| The effect of glucagon-like peptide 2 on intestinal permeability and bacterial translocation in acute necrotizing pancreatitis. | 2001-06 |
|
| Obesity increases the severity of acute experimental pancreatitis in the rat. | 2001-06 |
|
| Long-term course in collagenous colitis and the impact of bile acid malabsorption and bile acid sequestrants on histopathology and clinical features. | 2001-06 |
|
| Modifying hepatic phospholipid synthesis associates with biliary phospholipid secretion rate in a transporter-independent manner in rats: relation to canalicular membrane fluidity. | 2001-06 |
|
| Oral delivery of synthetic eel calcitonin, elcatonin, in rats. | 2001-06 |
|
| Is a role of phospholipase A(2) in cholesterol gallstone formation phospholipid species-dependent? | 2001-05-31 |
|
| 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 |
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
| Substance Class |
Chemical
Created
by
admin
on
Edited
Mon Mar 31 19:12:14 GMT 2025
by
admin
on
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| Record UNII |
5E090O0G3Z
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| Record Status |
Validated (UNII)
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| Related Record | Type | Details | ||
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SALT/SOLVATE -> PARENT | |||
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TRANSPORTER -> SUBSTRATE | |||
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TRANSPORTER -> SUBSTRATE | |||
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TRANSPORTER -> INHIBITOR | |||
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LABELED -> NON-LABELED | |||
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TRANSPORTER -> SUBSTRATE | |||
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TRANSPORTER -> INHIBITOR | |||
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SALT/SOLVATE -> PARENT |
| Related Record | Type | Details | ||
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ACTIVE MOIETY |
