SODIUM TAUROCHOLATE

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

Structure Search

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

HIDE SMILES / InChI

Description
Sources: http://www.hmdb.ca/metabolites/HMDB00036 | http://adisinsight.springer.com/drugs/800033000 | https://www.ncbi.nlm.nih.gov/pubmed/23181598

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

Targets

Primary Target	Pharmacology	Condition	Potency
G-protein coupled bile acid receptor 1 15 Target ID: CHEMBL5409 Sources: https://www.ncbi.nlm.nih.gov/pubmed/26280129 \| https://www.ncbi.nlm.nih.gov/pubmed/18307294	Agonist 2678		4.95 µM [EC50]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Obesity 203 Sources: https://www.ncbi.nlm.nih.gov/pubmed/23181598 http://adisinsight.springer.com/drugs/800033000	Primary		Phase II 1132	Unknown Approved Use Unknown
Type 2 diabetes mellitus 259 Sources: http://adisinsight.springer.com/drugs/800047529 https://clinicaltrials.gov/ct2/show/NCT02871882 https://www.ncbi.nlm.nih.gov/pubmed/23418316	Primary		Phase II 1132	Unknown Approved Use Unknown

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	11394647
Distribution and properties of neutral ceramidase activity in rat intestinal tract.	2001 Apr	11330410
The effect of absorption enhancers on the initial degradation kinetics of insulin by alpha-chymotrypsin.	2001 Apr 17	11292547
Design and properties of hepatitis C virus antisense oligonucleotides for liver specific drug targeting.	2001 Apr-Jul	11563018
Sinusoidal efflux of taurocholate is enhanced in Mrp2-deficient rat liver.	2001 Aug	11587482
Regulation of biliary cholesterol secretion is independent of hepatocyte canalicular membrane lipid composition: a study in the diosgenin-fed rat model.	2001 Aug	11580137
Bile salt export pump is highly conserved during vertebrate evolution and its expression is inhibited by PFIC type II mutations.	2001 Aug	11447010
Interaction of bile salt and phospholipids with bovine submaxillary mucin.	2001 Jan	11336352
Urinary excretion of trypsinogen activation peptide (TAP) in taurocholate-induced pancreatitis in rats.	2001 Jan	11138966
Kinetics characterization of taurocholic transport in Lactobacillus reuteri.	2001 Jan	11116391
Analysis of the diffusion of bile salt/phospholipid micelles in rat intestinal mucin.	2001 Jul	11518575
Synthesis and properties of bile acid phosphoramidites 5'-tethered to antisense oligodeoxynucleotides against HCV.	2001 Jul	11425584
Human liver-specific organic anion transporter, LST-1, mediates uptake of pravastatin by human hepatocytes.	2001 Jun	11356905
Cellular distribution and handling of liver-targeting preparations in human livers studied by a liver lobe perfusion.	2001 Jun	11353741
Hemodynamic and metabolic variables predict porcine ex vivo liver function.	2001 Mar	11181004
Successful nonfreezing, subzero preservation of rat liver with 2,3-butanediol and type I antifreeze protein.	2001 Mar	11180993
Differences in Ca(2+) signaling underlie age-specific effects of secretagogues on colonic Cl(-) transport.	2001 Mar	11171585
Transporters on demand: intrahepatic pools of canalicular ATP binding cassette transporters in rat liver.	2001 Mar 9	11113123
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	11069906
Bile salt hydrolase activity of Enterococci isolated from food: screening and quantitative determination.	2001 May	11348009
Transbuccal peptide delivery: stability and in vitro permeation studies on endomorphin-1.	2001 May 18	11337057
Interaction of 2,3-dimercapto-1-propane sulfonate with the human organic anion transporter hOAT1.	2001 Nov	11602689
Inhibition of inducible nitric oxide synthase reduces bacterial translocation in a rat model of acute pancreatitis.	2001 Oct	11590326
Ezetimibe selectively inhibits intestinal cholesterol absorption in rodents in the presence and absence of exocrine pancreatic function.	2001 Sep	11564660
Ischemic preconditioning, the most effective gastroprotective intervention: involvement of prostaglandins, nitric oxide, adenosine and sensory nerves.	2001 Sep 21	11567657
Toxicity and uptake mechanism of cylindrospermopsin and lophyrotomin in primary rat hepatocytes.	2002 Feb	11689242

Patents

Sample Use Guides

In Vivo Use Guide

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

In primary murine intestinal cultures, Taurocholic acid (100 or 1000 umol/L) dose dependently increased GLP-1 release.

Name

Type

Language

SODIUM TAUROCHOLATE

Common Name

English

BILE SALTS [USP-RS]

Common Name

English

Sodium taurocholate [WHO-DD]

Common Name

English

Code System Code Type Description

FDA UNII

M6N3TH81NO