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

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	514.695
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 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
Inhibitory effect of short-term bile duct ligation on hepatic cytochrome P450 of bile acid-depleted rats.	2001	11641615
The endothelin antagonist bosentan inhibits the canalicular bile salt export pump: a potential mechanism for hepatic adverse reactions.	2001 Apr	11309550
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
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
Interrelationship between colonic muscularis mucosae activity and changes in transmucosal potential difference.	2001 Aug	11447028
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
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
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
Cell-specific basolateral membrane sorting of the human liver Na(+)-dependent bile acid cotransporter.	2001 Jun	11352825
A simple method for measuring of intestinal solute transport in mucosal biopsy specimens.	2001 Mar	11318514
Successful nonfreezing, subzero preservation of rat liver with 2,3-butanediol and type I antifreeze protein.	2001 Mar	11180993
Characterization of bile acid transport mediated by multidrug resistance associated protein 2 and bile salt export pump.	2001 Mar 9	11248200
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
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
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
The effect of a functional group in penicillin derivatives on the interaction with bile salt micelles studied by micellar electrokinetic chromatography.	2001 Oct	11669544
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
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
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 `Fri Dec 15 15:01:55 GMT 2023` Edited by `admin` on `Fri Dec 15 15:01:55 GMT 2023`
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