TAUROCHOLIC ACID

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

Structure Search

SMILES

[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=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

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
Ileal mucosal bile acid absorption is increased in Cftr knockout mice.	2001	11696242
In vitro taurocholate-induced segmentation and clustering of Mesocestoides vogae (syn. corti) tetrathyridia (Cestoda)--inhibition byh cestocidal drugs.	2001 Apr	11355676
Temporary pancreatic duct occlusion by ethibloc: cause of microcirculatory shutdown, acute inflammation, and pancreas necrosis.	2001 Apr	11344393
Carrier-mediated hepatobiliary transport of a novel antifolate, N-[4-[(2,4-dianninopteridine-6-yl)methyl]-3,4-dihydro-2H-1,4-benzothiazin-7-yl]carbonyl-L-homoglutamic acid, in rats.	2001 Apr	11259322
Cellular distribution and handling of liver-targeting preparations in human livers studied by a liver lobe perfusion.	2001 Apr	11259317
The bile acid taurocholate impairs rat cardiomyocyte function: a proposed mechanism for intra-uterine fetal death in obstetric cholestasis.	2001 Apr	11256973
Mechanisms for the transport of unconjugated bilirubin in human trophoblastic BeWo cells.	2001 Apr 20	11322954
Design and properties of hepatitis C virus antisense oligonucleotides for liver specific drug targeting.	2001 Apr-Jul	11563018
Beneficial effects of growth hormone on bacterial translocation during the course of acute necrotizing pancreatitis in rats.	2001 Aug	11484917
Effect of bile acids on the uptake of irinotecan and its active metabolite, SN-38, by intestinal cells.	2001 Feb 16	11342261
Identification of novel hypocholesterolemic peptides derived from bovine milk beta-lactoglobulin.	2001 Feb 16	11178953
Interaction of bile salt and phospholipids with bovine submaxillary mucin.	2001 Jan	11336352
Enhancement of jejunal absorption of conjugated bile acid by neurotensin in rats.	2001 Jan	11208724
Kinetics characterization of taurocholic transport in Lactobacillus reuteri.	2001 Jan	11116391
Role of endogenous prostacyclin in gastric ulcerogenic and healing responses--a study using IP-receptor knockout mice.	2001 Jan-Dec	11595421
The effect of etodolac on bile salt and histamine-mediated gastric mucosal injury in the rat.	2001 Jan-Dec	11595417
Differential effects of caspase-1/interleukin-1beta-converting enzyme on acinar cell necrosis and apoptosis in severe acute experimental pancreatitis.	2001 Jul	11454989
Anti-ICAM-1 antibody modulates late onset of acinar cell apoptosis and early necrosis in taurocholate-induced experimental acute pancreatitis.	2001 Jul	11451152
Synthesis and properties of bile acid phosphoramidites 5'-tethered to antisense oligodeoxynucleotides against HCV.	2001 Jul	11425584
Characterization of the efflux transport of 17beta-estradiol-D-17beta-glucuronide from the brain across the blood-brain barrier.	2001 Jul	11408557
Optimization of culture conditions for determining hepatobiliary disposition of taurocholate in sandwich-cultured rat hepatocytes.	2001 Jun	11515972
Obesity increases the severity of acute experimental pancreatitis in the rat.	2001 Jun	11424327
Modifying hepatic phospholipid synthesis associates with biliary phospholipid secretion rate in a transporter-independent manner in rats: relation to canalicular membrane fluidity.	2001 Jun	11414307
Oral delivery of synthetic eel calcitonin, elcatonin, in rats.	2001 Jun	11411554
Characterization of model bile using fluorescence energy transfer from dehydroergosterol to dansylated lecithin.	2001 Jun	11369800
Colchicine inhibits taurodeoxycholate transport in pericentral but not in periportal hepatocytes.	2001 Jun 20	11420119
A simple method for measuring of intestinal solute transport in mucosal biopsy specimens.	2001 Mar	11318514
Interleukin-10 attenuates proinflammatory cytokine production and improves survival in lethal pancreatitis.	2001 Mar	11270881
Cholestatic potential of troglitazone as a possible factor contributing to troglitazone-induced hepatotoxicity: in vivo and in vitro interaction at the canalicular bile salt export pump (Bsep) in the rat.	2001 Mar	11179459
Cyclosporin A reduces canalicular membrane fluidity and regulates transporter function in rats.	2001 Mar 15	11237863
Characterization of bile acid transport mediated by multidrug resistance associated protein 2 and bile salt export pump.	2001 Mar 9	11248200
Bile salt hydrolase activity of Enterococci isolated from food: screening and quantitative determination.	2001 May	11348009
A new 5-aminosalicylic acid multi-unit dosage form for the therapy of ulcerative colitis.	2001 May	11343881
Identification and characterization of human organic anion transporter 3 expressing predominantly in the kidney.	2001 May	11306713
Transbuccal peptide delivery: stability and in vitro permeation studies on endomorphin-1.	2001 May 18	11337057
Is a role of phospholipase A(2) in cholesterol gallstone formation phospholipid species-dependent?	2001 May 31	11420173
Bile acid feeding increased proliferative activity and apical bile acid transporter expression in both small and large rat cholangiocytes.	2001 Nov	11679956
Increased matrix metalloproteinase expression and activation following experimental acute pancreatitis.	2001 Nov	11676550
Bile-salt hydrophobicity is a key factor regulating rat liver plasma-membrane communication: relation to bilayer structure, fluidity and transporter expression and function.	2001 Nov 1	11672435
Changes in the activity of lysosomal enzymes in rat kidneys in the course of acute pancreatitis.	2001 Nov-Dec	11687729
The utilization of sodium taurocholate in excystation of Cryptosporidium parvum and infection of tissue culture.	2001 Oct	11695421
Hydrocortisone treatment of early SIRS in acute experimental pancreatitis.	2001 Oct	11680590
Pericentral hepatocytes translocate hydrophilic bile acids more rapidly than hydrophobic ones.	2001 Oct	11680582
Common mechanisms of monoacylglycerol and fatty acid uptake by human intestinal Caco-2 cells.	2001 Oct	11546646
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	11557132
Alkaline phosphatase from rat liver and kidney is differentially modulated.	2001 Sep	11676975
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

TAUROCHOLIC ACID

Common Name

English

CHOLYLTAURINE

Common Name

English

3.BETA.-HYDROXYDINOR-5-CHOLENIC ACID

Systematic Name

English

CHOLAIC ACID

Common Name

English

TAUROCHOLIC ACID [HSDB]

Common Name

English

2-(((3.ALPHA.,5.BETA.,7.ALPHA.,12.ALPHA.)-3,7,12-TRIHYDROXY-24-OXOCHOLAN-24-YL)AMINO)ETHANESULFONIC ACID

Common Name

English

NSC-25505

Code

English

TAUROCHOLIC ACID [MI]

Common Name

English

N-CHOLOYLTAURINE

Common Name

English

Code System Code Type Description

FDA UNII

5E090O0G3Z