U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

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 of SODIUM TAUROCHOLATE

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

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
In vitro taurocholate-induced segmentation and clustering of Mesocestoides vogae (syn. corti) tetrathyridia (Cestoda)--inhibition byh cestocidal drugs.
2001 Apr
Temporary pancreatic duct occlusion by ethibloc: cause of microcirculatory shutdown, acute inflammation, and pancreas necrosis.
2001 Apr
Differential oxidative injury in extrapancreatic tissues during experimental pancreatitis: modification of lung proteins by 4-hydroxynonenal.
2001 Apr
Distribution and properties of neutral ceramidase activity in rat intestinal tract.
2001 Apr
Mechanisms for the transport of unconjugated bilirubin in human trophoblastic BeWo cells.
2001 Apr 20
Design and properties of hepatitis C virus antisense oligonucleotides for liver specific drug targeting.
2001 Apr-Jul
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
Interrelationship between colonic muscularis mucosae activity and changes in transmucosal potential difference.
2001 Aug
Bile salt export pump is highly conserved during vertebrate evolution and its expression is inhibited by PFIC type II mutations.
2001 Aug
Effect of bile acids on the uptake of irinotecan and its active metabolite, SN-38, by intestinal cells.
2001 Feb 16
Interaction of bile salt and phospholipids with bovine submaxillary mucin.
2001 Jan
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
Anti-ICAM-1 antibody modulates late onset of acinar cell apoptosis and early necrosis in taurocholate-induced experimental acute pancreatitis.
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
Gastric preconditioning induced by short ischemia: the role of prostaglandins, nitric oxide and adenosine.
2001 Jul-Aug
The effect of glucagon-like peptide 2 on intestinal permeability and bacterial translocation in acute necrotizing pancreatitis.
2001 Jun
Long-term course in collagenous colitis and the impact of bile acid malabsorption and bile acid sequestrants on histopathology and clinical features.
2001 Jun
Modifying hepatic phospholipid synthesis associates with biliary phospholipid secretion rate in a transporter-independent manner in rats: relation to canalicular membrane fluidity.
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
Adaptive gastric cytoprotection is mediated by prostaglandin EP1 receptors: a study using rats and knockout mice.
2001 Jun
Cellular distribution and handling of liver-targeting preparations in human livers studied by a liver lobe perfusion.
2001 Jun
Cell-specific basolateral membrane sorting of the human liver Na(+)-dependent bile acid cotransporter.
2001 Jun
Localized pancreatic NF-kappaB activation and inflammatory response in taurocholate-induced pancreatitis.
2001 Jun
Colchicine inhibits taurodeoxycholate transport in pericentral but not in periportal hepatocytes.
2001 Jun 20
Soluble receptors released during acute pancreatitis interfere with the detection of tumor necrosis factor-alpha.
2001 May
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
The utilization of sodium taurocholate in excystation of Cryptosporidium parvum and infection of tissue culture.
2001 Oct
Pericentral hepatocytes translocate hydrophilic bile acids more rapidly than hydrophobic ones.
2001 Oct
The effect of a functional group in penicillin derivatives on the interaction with bile salt micelles studied by micellar electrokinetic chromatography.
2001 Oct
Multispecific substrate recognition of kidney-specific organic anion transporters OAT-K1 and OAT-K2.
2001 Oct
Single amino acid substitution of rat MRP2 results in acquired transport activity for taurocholate.
2001 Oct
Common mechanisms of monoacylglycerol and fatty acid uptake by human intestinal Caco-2 cells.
2001 Oct
Ezetimibe selectively inhibits intestinal cholesterol absorption in rodents in the presence and absence of exocrine pancreatic function.
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 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
  • Download
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 Fri Dec 15 15:01:56 GMT 2023 , Edited by admin on Fri Dec 15 15:01:56 GMT 2023
PRIMARY
CHEBI
36276
Created by admin on Fri Dec 15 15:01:56 GMT 2023 , Edited by admin on Fri Dec 15 15:01:56 GMT 2023
PRIMARY
DRUG BANK
DBSALT002887
Created by admin on Fri Dec 15 15:01:56 GMT 2023 , Edited by admin on Fri Dec 15 15:01:56 GMT 2023
PRIMARY
ECHA (EC/EINECS)
205-653-7
Created by admin on Fri Dec 15 15:01:56 GMT 2023 , Edited by admin on Fri Dec 15 15:01:56 GMT 2023
PRIMARY
CAS
145-42-6
Created by admin on Fri Dec 15 15:01:56 GMT 2023 , Edited by admin on Fri Dec 15 15:01:56 GMT 2023
PRIMARY
EPA CompTox
DTXSID80274181
Created by admin on Fri Dec 15 15:01:56 GMT 2023 , Edited by admin on Fri Dec 15 15:01:56 GMT 2023
PRIMARY
EVMPD
SUB15328MIG
Created by admin on Fri Dec 15 15:01:56 GMT 2023 , Edited by admin on Fri Dec 15 15:01:56 GMT 2023
PRIMARY
SMS_ID
100000078145
Created by admin on Fri Dec 15 15:01:56 GMT 2023 , Edited by admin on Fri Dec 15 15:01:56 GMT 2023
PRIMARY
PUBCHEM
23666345
Created by admin on Fri Dec 15 15:01:56 GMT 2023 , Edited by admin on Fri Dec 15 15:01:56 GMT 2023
PRIMARY
Related Record Type Details
PARENT -> SALT/SOLVATE
SOLVATE->ANHYDROUS
LABELED -> NON-LABELED
Related Record Type Details
ACTIVE MOIETY