Details
Stereochemistry | ABSOLUTE |
Molecular Formula | C26H44NO7S.Na |
Molecular Weight | 537.685 |
Optical Activity | UNSPECIFIED |
Defined Stereocenters | 11 / 11 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
[Na+].[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=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
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 |
---|---|---|
Hydrophilic bile salts enhance differential distribution of sphingomyelin and phosphatidylcholine between micellar and vesicular phases: potential implications for their effects in vivo. | 2001 Apr |
|
Distribution and properties of neutral ceramidase activity in rat intestinal tract. | 2001 Apr |
|
The effect of absorption enhancers on the initial degradation kinetics of insulin by alpha-chymotrypsin. | 2001 Apr 17 |
|
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 |
|
Bile salt export pump is highly conserved during vertebrate evolution and its expression is inhibited by PFIC type II mutations. | 2001 Aug |
|
Interaction of bile salt and phospholipids with bovine submaxillary mucin. | 2001 Jan |
|
Urinary excretion of trypsinogen activation peptide (TAP) in taurocholate-induced pancreatitis in rats. | 2001 Jan |
|
Kinetics characterization of taurocholic transport in Lactobacillus reuteri. | 2001 Jan |
|
Analysis of the diffusion of bile salt/phospholipid micelles in rat intestinal mucin. | 2001 Jul |
|
Synthesis and properties of bile acid phosphoramidites 5'-tethered to antisense oligodeoxynucleotides against HCV. | 2001 Jul |
|
Human liver-specific organic anion transporter, LST-1, mediates uptake of pravastatin by human hepatocytes. | 2001 Jun |
|
Cellular distribution and handling of liver-targeting preparations in human livers studied by a liver lobe perfusion. | 2001 Jun |
|
Hemodynamic and metabolic variables predict porcine ex vivo liver function. | 2001 Mar |
|
Successful nonfreezing, subzero preservation of rat liver with 2,3-butanediol and type I antifreeze protein. | 2001 Mar |
|
Differences in Ca(2+) signaling underlie age-specific effects of secretagogues on colonic Cl(-) transport. | 2001 Mar |
|
Transporters on demand: intrahepatic pools of canalicular ATP binding cassette transporters in rat liver. | 2001 Mar 9 |
|
Identification of the bile acid-binding site of the ileal lipid-binding protein by photoaffinity labeling, matrix-assisted laser desorption ionization-mass spectrometry, and NMR structure. | 2001 Mar 9 |
|
Bile salt hydrolase activity of Enterococci isolated from food: screening and quantitative determination. | 2001 May |
|
Transbuccal peptide delivery: stability and in vitro permeation studies on endomorphin-1. | 2001 May 18 |
|
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 |
|
Ezetimibe selectively inhibits intestinal cholesterol absorption in rodents in the presence and absence of exocrine pancreatic function. | 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.
Name | Type | Language | ||
---|---|---|---|---|
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English |
Code System | Code | Type | Description | ||
---|---|---|---|---|---|
|
M6N3TH81NO
Created by
admin on Fri Dec 15 15:01:56 GMT 2023 , Edited by admin on Fri Dec 15 15:01:56 GMT 2023
|
PRIMARY | |||
|
36276
Created by
admin on Fri Dec 15 15:01:56 GMT 2023 , Edited by admin on Fri Dec 15 15:01:56 GMT 2023
|
PRIMARY | |||
|
DBSALT002887
Created by
admin on Fri Dec 15 15:01:56 GMT 2023 , Edited by admin on Fri Dec 15 15:01:56 GMT 2023
|
PRIMARY | |||
|
205-653-7
Created by
admin on Fri Dec 15 15:01:56 GMT 2023 , Edited by admin on Fri Dec 15 15:01:56 GMT 2023
|
PRIMARY | |||
|
145-42-6
Created by
admin on Fri Dec 15 15:01:56 GMT 2023 , Edited by admin on Fri Dec 15 15:01:56 GMT 2023
|
PRIMARY | |||
|
DTXSID80274181
Created by
admin on Fri Dec 15 15:01:56 GMT 2023 , Edited by admin on Fri Dec 15 15:01:56 GMT 2023
|
PRIMARY | |||
|
SUB15328MIG
Created by
admin on Fri Dec 15 15:01:56 GMT 2023 , Edited by admin on Fri Dec 15 15:01:56 GMT 2023
|
PRIMARY | |||
|
100000078145
Created by
admin on Fri Dec 15 15:01:56 GMT 2023 , Edited by admin on Fri Dec 15 15:01:56 GMT 2023
|
PRIMARY | |||
|
23666345
Created by
admin on Fri Dec 15 15:01:56 GMT 2023 , Edited by admin on Fri Dec 15 15:01:56 GMT 2023
|
PRIMARY |
ACTIVE MOIETY
SUBSTANCE RECORD