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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 of SODIUM TAUROCHOLATE

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

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.

Approval Year

PubMed

PubMed

TitleDatePubMed
Ileal mucosal bile acid absorption is increased in Cftr knockout mice.
2001
Inhibitory effect of short-term bile duct ligation on hepatic cytochrome P450 of bile acid-depleted rats.
2001
Temporary pancreatic duct occlusion by ethibloc: cause of microcirculatory shutdown, acute inflammation, and pancreas necrosis.
2001 Apr
Sinusoidal efflux of taurocholate is enhanced in Mrp2-deficient rat liver.
2001 Aug
Regulation of biliary cholesterol secretion is independent of hepatocyte canalicular membrane lipid composition: a study in the diosgenin-fed rat model.
2001 Aug
Tauroursodesoxycholate-induced choleresis involves p38(MAPK) activation and translocation of the bile salt export pump in rats.
2001 Aug
Beneficial effects of growth hormone on bacterial translocation during the course of acute necrotizing pancreatitis in rats.
2001 Aug
Intracellular glutathione regulates taurocholate transport in HepG2 cells.
2001 Aug 1
No effect of phenobarbital pretreatment of rats on methotrexate pharmacokinetics in the isolated liver perfused in a single-pass way.
2001 Feb
Effect of bile acids on the uptake of irinotecan and its active metabolite, SN-38, by intestinal cells.
2001 Feb 16
Identification of novel hypocholesterolemic peptides derived from bovine milk beta-lactoglobulin.
2001 Feb 16
Role of endogenous prostacyclin in gastric ulcerogenic and healing responses--a study using IP-receptor knockout mice.
2001 Jan-Dec
The effect of etodolac on bile salt and histamine-mediated gastric mucosal injury in the rat.
2001 Jan-Dec
Analysis of the diffusion of bile salt/phospholipid micelles in rat intestinal mucin.
2001 Jul
Differential effects of caspase-1/interleukin-1beta-converting enzyme on acinar cell necrosis and apoptosis in severe acute experimental pancreatitis.
2001 Jul
Comparison of "type I" and "type II" organic cation transport by organic cation transporters and organic anion-transporting polypeptides.
2001 Jul
Influence of natural, electrically neutral lipids on the potentiometric responses of cation-selective polymeric membrane electrodes.
2001 Jul 15
Improved in vitro gene transfer mediated by fluorinated lipoplexes in the presence of a bile salt surfactant.
2001 Jul-Aug
Optimization of culture conditions for determining hepatobiliary disposition of taurocholate in sandwich-cultured rat hepatocytes.
2001 Jun
The effect of glucagon-like peptide 2 on intestinal permeability and bacterial translocation in acute necrotizing pancreatitis.
2001 Jun
Oral delivery of synthetic eel calcitonin, elcatonin, in rats.
2001 Jun
Characterization of model bile using fluorescence energy transfer from dehydroergosterol to dansylated lecithin.
2001 Jun
Human liver-specific organic anion transporter, LST-1, mediates uptake of pravastatin by human hepatocytes.
2001 Jun
Differences in Ca(2+) signaling underlie age-specific effects of secretagogues on colonic Cl(-) transport.
2001 Mar
Characterization of bile acid transport mediated by multidrug resistance associated protein 2 and bile salt export pump.
2001 Mar 9
Taurocholic acid-induced secretion in normal and cystic fibrosis mouse ileum.
2001 May
Bile salt hydrolase activity of Enterococci isolated from food: screening and quantitative determination.
2001 May
A new 5-aminosalicylic acid multi-unit dosage form for the therapy of ulcerative colitis.
2001 May
Transbuccal peptide delivery: stability and in vitro permeation studies on endomorphin-1.
2001 May 18
Bile acid feeding increased proliferative activity and apical bile acid transporter expression in both small and large rat cholangiocytes.
2001 Nov
Role of nonesterified fatty acids in necrotizing pancreatitis: an in vivo experimental study in rats.
2001 Nov
Interaction of 2,3-dimercapto-1-propane sulfonate with the human organic anion transporter hOAT1.
2001 Nov
Changes in the activity of lysosomal enzymes in rat kidneys in the course of acute pancreatitis.
2001 Nov-Dec
The utilization of sodium taurocholate in excystation of Cryptosporidium parvum and infection of tissue culture.
2001 Oct
Inhibition of inducible nitric oxide synthase reduces bacterial translocation in a rat model of acute pancreatitis.
2001 Oct
Multispecific substrate recognition of kidney-specific organic anion transporters OAT-K1 and OAT-K2.
2001 Oct
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
Ezetimibe selectively inhibits intestinal cholesterol absorption in rodents in the presence and absence of exocrine pancreatic function.
2001 Sep
Nuclear receptor-mediated repression of human cholesterol 7alpha-hydroxylase gene transcription by bile acids.
2001 Sep
Ischemic preconditioning, the most effective gastroprotective intervention: involvement of prostaglandins, nitric oxide, adenosine and sensory nerves.
2001 Sep 21
Toxicity and uptake mechanism of cylindrospermopsin and lophyrotomin in primary rat hepatocytes.
2002 Feb
Patents

Sample Use Guides

In Vivo Use Guide
Curator's Comment:: In 10 healthy male subjects rectal administration of TCA promptly stimulated secretion of both GLP-1 and PYY, and increased fullness, in a dose-dependent manner.
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 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
WHO-DD  
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
Created by admin on Sat Jun 26 10:40:25 UTC 2021 , Edited by admin on Sat Jun 26 10:40:25 UTC 2021
PRIMARY
DRUG BANK
DBSALT002887
Created by admin on Sat Jun 26 10:40:25 UTC 2021 , Edited by admin on Sat Jun 26 10:40:25 UTC 2021
PRIMARY
ECHA (EC/EINECS)
205-653-7
Created by admin on Sat Jun 26 10:40:25 UTC 2021 , Edited by admin on Sat Jun 26 10:40:25 UTC 2021
PRIMARY
CAS
145-42-6
Created by admin on Sat Jun 26 10:40:25 UTC 2021 , Edited by admin on Sat Jun 26 10:40:25 UTC 2021
PRIMARY
EPA CompTox
145-42-6
Created by admin on Sat Jun 26 10:40:25 UTC 2021 , Edited by admin on Sat Jun 26 10:40:25 UTC 2021
PRIMARY
EVMPD
SUB15328MIG
Created by admin on Sat Jun 26 10:40:25 UTC 2021 , Edited by admin on Sat Jun 26 10:40:25 UTC 2021
PRIMARY
PUBCHEM
23666345
Created by admin on Sat Jun 26 10:40:25 UTC 2021 , Edited by admin on Sat Jun 26 10:40:25 UTC 2021
PRIMARY
Related Record Type Details
PARENT -> SALT/SOLVATE
LABELED -> NON-LABELED
Related Record Type Details
ACTIVE MOIETY