Details
Stereochemistry | ABSOLUTE |
Molecular Formula | C26H44NO7S.Na |
Molecular Weight | 537.6869 |
Optical Activity | UNSPECIFIED |
Defined Stereocenters | 11 / 11 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
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.[Na+]
InChI
InChIKey=JAJWGJBVLPIOOH-IZYKLYLVSA-M
InChI=1S/C26H45NO7S.Na/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 | Na |
Molecular Weight | 22.9898 |
Charge | 1 |
Count |
|
Stereochemistry | ACHIRAL |
Additional Stereochemistry | No |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Optical Activity | NONE |
Molecular Formula | C26H44NO7S |
Molecular Weight | 514.6971 |
Charge | -1 |
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 |
---|---|---|
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 |
|
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 |
|
Regulation of biliary cholesterol secretion is independent of hepatocyte canalicular membrane lipid composition: a study in the diosgenin-fed rat model. | 2001 Aug |
|
Tauroursodesoxycholate-induced choleresis involves p38(MAPK) activation and translocation of the bile salt export pump in rats. | 2001 Aug |
|
Beneficial effects of growth hormone on bacterial translocation during the course of acute necrotizing pancreatitis in rats. | 2001 Aug |
|
Intracellular glutathione regulates taurocholate transport in HepG2 cells. | 2001 Aug 1 |
|
No effect of phenobarbital pretreatment of rats on methotrexate pharmacokinetics in the isolated liver perfused in a single-pass way. | 2001 Feb |
|
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 |
|
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 |
|
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 |
|
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 |
|
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 |
|
Human liver-specific organic anion transporter, LST-1, mediates uptake of pravastatin by human hepatocytes. | 2001 Jun |
|
Differences in Ca(2+) signaling underlie age-specific effects of secretagogues on colonic Cl(-) transport. | 2001 Mar |
|
Characterization of bile acid transport mediated by multidrug resistance associated protein 2 and bile salt export pump. | 2001 Mar 9 |
|
Taurocholic acid-induced secretion in normal and cystic fibrosis mouse ileum. | 2001 May |
|
Bile salt hydrolase activity of Enterococci isolated from food: screening and quantitative determination. | 2001 May |
|
A new 5-aminosalicylic acid multi-unit dosage form for the therapy of ulcerative colitis. | 2001 May |
|
Transbuccal peptide delivery: stability and in vitro permeation studies on endomorphin-1. | 2001 May 18 |
|
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 |
|
Interaction of 2,3-dimercapto-1-propane sulfonate with the human organic anion transporter hOAT1. | 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 |
|
Inhibition of inducible nitric oxide synthase reduces bacterial translocation in a rat model of acute pancreatitis. | 2001 Oct |
|
Multispecific substrate recognition of kidney-specific organic anion transporters OAT-K1 and OAT-K2. | 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 |
|
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
Sat Jun 26 10:40:24 UTC 2021
by
admin
on
Sat Jun 26 10:40:24 UTC 2021
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Record UNII |
M6N3TH81NO
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Record Status |
Validated (UNII)
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Record Version |
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-
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DBSALT002887
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LABELED -> NON-LABELED |
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ACTIVE MOIETY |