Details
Stereochemistry | ABSOLUTE |
Molecular Formula | C26H44NO7S.K |
Molecular Weight | 553.793 |
Optical Activity | UNSPECIFIED |
Defined Stereocenters | 11 / 11 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
[K+].[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])C[C@H](O)[C@]12C)[C@H](C)CCC(=O)NCCS([O-])(=O)=O
InChI
InChIKey=DMYWDAAJMXQHLP-IZYKLYLVSA-M
InChI=1S/C26H45NO7S.K/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);/q;+1/p-1/t15-,16+,17-,18-,19+,20+,21-,22+,24+,25+,26-;/m1./s1
Molecular Formula | K |
Molecular Weight | 39.0983 |
Charge | 1 |
Count |
|
Stereochemistry | ACHIRAL |
Additional Stereochemistry | No |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Optical Activity | NONE |
Molecular Formula | C26H44NO7S |
Molecular Weight | 514.695 |
Charge | -1 |
Count |
|
Stereochemistry | ABSOLUTE |
Additional Stereochemistry | No |
Defined Stereocenters | 10 / 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 |
---|---|---|
Ileal mucosal bile acid absorption is increased in Cftr knockout mice. | 2001 |
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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 |
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Sinusoidal efflux of taurocholate is enhanced in Mrp2-deficient rat liver. | 2001 Aug |
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Regulation of biliary cholesterol secretion is independent of hepatocyte canalicular membrane lipid composition: a study in the diosgenin-fed rat model. | 2001 Aug |
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Tauroursodesoxycholate-induced choleresis involves p38(MAPK) activation and translocation of the bile salt export pump in rats. | 2001 Aug |
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Beneficial effects of growth hormone on bacterial translocation during the course of acute necrotizing pancreatitis in rats. | 2001 Aug |
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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 |
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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 |
|
Analysis of the diffusion of bile salt/phospholipid micelles in rat intestinal mucin. | 2001 Jul |
|
Differential effects of caspase-1/interleukin-1beta-converting enzyme on acinar cell necrosis and apoptosis in severe acute experimental pancreatitis. | 2001 Jul |
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Anti-ICAM-1 antibody modulates late onset of acinar cell apoptosis and early necrosis in taurocholate-induced experimental acute pancreatitis. | 2001 Jul |
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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 |
|
Improved in vitro gene transfer mediated by fluorinated lipoplexes in the presence of a bile salt surfactant. | 2001 Jul-Aug |
|
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 |
|
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 |
|
Adaptive gastric cytoprotection is mediated by prostaglandin EP1 receptors: a study using rats and knockout mice. | 2001 Jun |
|
Human liver-specific organic anion transporter, LST-1, mediates uptake of pravastatin by human hepatocytes. | 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 |
|
Role of nonesterified fatty acids in necrotizing pancreatitis: an in vivo experimental study in rats. | 2001 Nov |
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Interaction of 2,3-dimercapto-1-propane sulfonate with the human organic anion transporter hOAT1. | 2001 Nov |
|
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 |
|
Common mechanisms of monoacylglycerol and fatty acid uptake by human intestinal Caco-2 cells. | 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 |
|
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
Sources: https://www.ncbi.nlm.nih.gov/pubmed/23181598
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 Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/26280129
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
Edited
Wed Jul 05 22:41:18 UTC 2023
by
admin
on
Wed Jul 05 22:41:18 UTC 2023
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Record UNII |
5ZU91PFW8G
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Record Status |
Validated (UNII)
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Record Version |
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NCI_THESAURUS |
C2140
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7487-77-6
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5ZU91PFW8G
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DTXSID70926945
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C84101
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76963027
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Related Record | Type | Details | ||
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PARENT -> SALT/SOLVATE |
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ACTIVE MOIETY |