SODIUM TAUROCHOLATE

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

Structure Search

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

HIDE SMILES / InChI

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

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 2470		4.95 µM [EC50]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Obesity 194 Sources: https://www.ncbi.nlm.nih.gov/pubmed/23181598 http://adisinsight.springer.com/drugs/800033000	Primary		Phase II 1101	Unknown Approved Use Unknown
Type 2 diabetes mellitus 240 Sources: http://adisinsight.springer.com/drugs/800047529 https://clinicaltrials.gov/ct2/show/NCT02871882 https://www.ncbi.nlm.nih.gov/pubmed/23418316	Primary		Phase II 1101	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed
Ileal mucosal bile acid absorption is increased in Cftr knockout mice.	2001	11696242
Inhibitory effect of short-term bile duct ligation on hepatic cytochrome P450 of bile acid-depleted rats.	2001	11641615
Temporary pancreatic duct occlusion by ethibloc: cause of microcirculatory shutdown, acute inflammation, and pancreas necrosis.	2001 Apr	11344393
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
Intracellular glutathione regulates taurocholate transport in HepG2 cells.	2001 Aug 1	11485381
No effect of phenobarbital pretreatment of rats on methotrexate pharmacokinetics in the isolated liver perfused in a single-pass way.	2001 Feb	11174078
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
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
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
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
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
Human liver-specific organic anion transporter, LST-1, mediates uptake of pravastatin by human hepatocytes.	2001 Jun	11356905
Differences in Ca(2+) signaling underlie age-specific effects of secretagogues on colonic Cl(-) transport.	2001 Mar	11171585
Characterization of bile acid transport mediated by multidrug resistance associated protein 2 and bile salt export pump.	2001 Mar 9	11248200
Taurocholic acid-induced secretion in normal and cystic fibrosis mouse ileum.	2001 May	11370710
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
Transbuccal peptide delivery: stability and in vitro permeation studies on endomorphin-1.	2001 May 18	11337057
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
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
Inhibition of inducible nitric oxide synthase reduces bacterial translocation in a rat model of acute pancreatitis.	2001 Oct	11590326
Multispecific substrate recognition of kidney-specific organic anion transporters OAT-K1 and OAT-K2.	2001 Oct	11561088
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
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 `Sat Jun 26 10:40:24 UTC 2021` Edited by `admin` on `Sat Jun 26 10:40:24 UTC 2021`
Record UNII	M6N3TH81NO
Record Status	`Validated (UNII)`
Record Version

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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