POTASSIUM TAUROCHOLATE

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

Structure Search

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

HIDE SMILES / InChI

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

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 2662		4.95 µM [EC50]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Obesity 204 Sources: https://www.ncbi.nlm.nih.gov/pubmed/23181598 http://adisinsight.springer.com/drugs/800033000	Primary		Phase II 1144	Unknown Approved Use Unknown
Type 2 diabetes mellitus 256 Sources: http://adisinsight.springer.com/drugs/800047529 https://clinicaltrials.gov/ct2/show/NCT02871882 https://www.ncbi.nlm.nih.gov/pubmed/23418316	Primary		Phase II 1144	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed
Ileal mucosal bile acid absorption is increased in Cftr knockout mice.	2001	11696242
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
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
Tauroursodesoxycholate-induced choleresis involves p38(MAPK) activation and translocation of the bile salt export pump in rats.	2001 Aug	11487550
Beneficial effects of growth hormone on bacterial translocation during the course of acute necrotizing pancreatitis in rats.	2001 Aug	11484917
Interrelationship between colonic muscularis mucosae activity and changes in transmucosal potential difference.	2001 Aug	11447028
Bile salt export pump is highly conserved during vertebrate evolution and its expression is inhibited by PFIC type II mutations.	2001 Aug	11447010
Effects of internal biliary bypass on the regulation of hepatic cholesterol 7alpha-hydroxylase activity in rats.	2001 Aug	11430996
Intracellular glutathione regulates taurocholate transport in HepG2 cells.	2001 Aug 1	11485381
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
Analysis of the diffusion of bile salt/phospholipid micelles in rat intestinal mucin.	2001 Jul	11518575
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
Attenuation of sepsis-related immunoparalysis by continuous veno-venous hemofiltration in experimental porcine pancreatitis.	2001 Jul	11445702
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
Comparison of "type I" and "type II" organic cation transport by organic cation transporters and organic anion-transporting polypeptides.	2001 Jul	11408531
Influence of natural, electrically neutral lipids on the potentiometric responses of cation-selective polymeric membrane electrodes.	2001 Jul 15	11476216
Improved in vitro gene transfer mediated by fluorinated lipoplexes in the presence of a bile salt surfactant.	2001 Jul-Aug	11529663
Gastric preconditioning induced by short ischemia: the role of prostaglandins, nitric oxide and adenosine.	2001 Jul-Aug	11433185
Optimization of culture conditions for determining hepatobiliary disposition of taurocholate in sandwich-cultured rat hepatocytes.	2001 Jun	11515972
The effect of glucagon-like peptide 2 on intestinal permeability and bacterial translocation in acute necrotizing pancreatitis.	2001 Jun	11513789
Obesity increases the severity of acute experimental pancreatitis in the rat.	2001 Jun	11424327
Long-term course in collagenous colitis and the impact of bile acid malabsorption and bile acid sequestrants on histopathology and clinical features.	2001 Jun	11424318
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
Adaptive gastric cytoprotection is mediated by prostaglandin EP1 receptors: a study using rats and knockout mice.	2001 Jun	11356942
Human liver-specific organic anion transporter, LST-1, mediates uptake of pravastatin by human hepatocytes.	2001 Jun	11356905
Colchicine inhibits taurodeoxycholate transport in pericentral but not in periportal hepatocytes.	2001 Jun 20	11420119
Soluble receptors released during acute pancreatitis interfere with the detection of tumor necrosis factor-alpha.	2001 May	11378616
Taurocholic acid-induced secretion in normal and cystic fibrosis mouse ileum.	2001 May	11370710
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
Role of nonesterified fatty acids in necrotizing pancreatitis: an in vivo experimental study in rats.	2001 Nov	11668201
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
Regulation of sterol regulatory element-binding proteins by cholesterol flux in CaCo-2 cells.	2001 Oct	11590226
Multispecific substrate recognition of kidney-specific organic anion transporters OAT-K1 and OAT-K2.	2001 Oct	11561088
Single amino acid substitution of rat MRP2 results in acquired transport activity for taurocholate.	2001 Oct	11557524
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
Ezetimibe selectively inhibits intestinal cholesterol absorption in rodents in the presence and absence of exocrine pancreatic function.	2001 Sep	11564660
Nuclear receptor-mediated repression of human cholesterol 7alpha-hydroxylase gene transcription by bile acids.	2001 Sep	11518759
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.

Substance Class	Chemical Created by `admin` on `Wed Jul 05 22:41:18 UTC 2023` Edited by `admin` on `Wed Jul 05 22:41:18 UTC 2023`
Record UNII	5ZU91PFW8G
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

POTASSIUM TAUROCHOLATE

Common Name

English

TAUROCHOLIC ACID POTASSIUM SALT

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C2140