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
Cloning and expression of murine sister of P-glycoprotein reveals a more discriminating transporter than MDR1/P-glycoprotein.
2000 Jan
Hydrophilic bile salts enhance differential distribution of sphingomyelin and phosphatidylcholine between micellar and vesicular phases: potential implications for their effects in vivo.
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
The endothelin antagonist bosentan inhibits the canalicular bile salt export pump: a potential mechanism for hepatic adverse reactions.
2001 Apr
Carrier-mediated hepatobiliary transport of a novel antifolate, N-[4-[(2,4-dianninopteridine-6-yl)methyl]-3,4-dihydro-2H-1,4-benzothiazin-7-yl]carbonyl-L-homoglutamic acid, in rats.
2001 Apr
Cellular distribution and handling of liver-targeting preparations in human livers studied by a liver lobe perfusion.
2001 Apr
The bile acid taurocholate impairs rat cardiomyocyte function: a proposed mechanism for intra-uterine fetal death in obstetric cholestasis.
2001 Apr
Mechanisms for the transport of unconjugated bilirubin in human trophoblastic BeWo cells.
2001 Apr 20
Regulation of biliary cholesterol secretion is independent of hepatocyte canalicular membrane lipid composition: a study in the diosgenin-fed rat model.
2001 Aug
Identification of novel hypocholesterolemic peptides derived from bovine milk beta-lactoglobulin.
2001 Feb 16
Urinary excretion of trypsinogen activation peptide (TAP) in taurocholate-induced pancreatitis in rats.
2001 Jan
Kinetics characterization of taurocholic transport in Lactobacillus reuteri.
2001 Jan
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
Anti-ICAM-1 antibody modulates late onset of acinar cell apoptosis and early necrosis in taurocholate-induced experimental acute pancreatitis.
2001 Jul
Attenuation of sepsis-related immunoparalysis by continuous veno-venous hemofiltration in experimental porcine pancreatitis.
2001 Jul
Synthesis and properties of bile acid phosphoramidites 5'-tethered to antisense oligodeoxynucleotides against HCV.
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
Optimization of culture conditions for determining hepatobiliary disposition of taurocholate in sandwich-cultured rat hepatocytes.
2001 Jun
Obesity increases the severity of acute experimental pancreatitis in the rat.
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
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
A simple method for measuring of intestinal solute transport in mucosal biopsy specimens.
2001 Mar
Biochemical and physiological evidence that bile acids produced and released by lake char (Salvelinus namaycush) function as chemical signals.
2001 Mar
Regulation of the dynamic localization of the rat Bsep gene-encoded bile salt export pump by anisoosmolarity.
2001 Mar
The rat liver Na(+)/bile acid cotransporter. Importance of the cytoplasmic tail to function and plasma membrane targeting.
2001 Mar 2
Abc protein transport of MRI contrast agents in canalicular rat liver plasma vesicles and yeast vacuoles.
2001 Mar 23
Transporters on demand: intrahepatic pools of canalicular ATP binding cassette transporters in rat liver.
2001 Mar 9
Identification of the bile acid-binding site of the ileal lipid-binding protein by photoaffinity labeling, matrix-assisted laser desorption ionization-mass spectrometry, and NMR structure.
2001 Mar 9
Taurocholic acid-induced secretion in normal and cystic fibrosis mouse ileum.
2001 May
A new 5-aminosalicylic acid multi-unit dosage form for the therapy of ulcerative colitis.
2001 May
Increased matrix metalloproteinase expression and activation following experimental acute pancreatitis.
2001 Nov
Hydrocortisone treatment of early SIRS in acute experimental pancreatitis.
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
Alkaline phosphatase from rat liver and kidney is differentially modulated.
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 Wed Jul 05 22:33:59 UTC 2023
Edited
by admin
on Wed Jul 05 22:33:59 UTC 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 Wed Jul 05 22:33:59 UTC 2023 , Edited by admin on Wed Jul 05 22:33:59 UTC 2023
PRIMARY
CHEBI
36276
Created by admin on Wed Jul 05 22:33:59 UTC 2023 , Edited by admin on Wed Jul 05 22:33:59 UTC 2023
PRIMARY
DRUG BANK
DBSALT002887
Created by admin on Wed Jul 05 22:33:59 UTC 2023 , Edited by admin on Wed Jul 05 22:33:59 UTC 2023
PRIMARY
ECHA (EC/EINECS)
205-653-7
Created by admin on Wed Jul 05 22:33:59 UTC 2023 , Edited by admin on Wed Jul 05 22:33:59 UTC 2023
PRIMARY
CAS
145-42-6
Created by admin on Wed Jul 05 22:33:59 UTC 2023 , Edited by admin on Wed Jul 05 22:33:59 UTC 2023
PRIMARY
EPA CompTox
DTXSID80274181
Created by admin on Wed Jul 05 22:33:59 UTC 2023 , Edited by admin on Wed Jul 05 22:33:59 UTC 2023
PRIMARY
EVMPD
SUB15328MIG
Created by admin on Wed Jul 05 22:33:59 UTC 2023 , Edited by admin on Wed Jul 05 22:33:59 UTC 2023
PRIMARY
SMS_ID
100000078145
Created by admin on Wed Jul 05 22:33:59 UTC 2023 , Edited by admin on Wed Jul 05 22:33:59 UTC 2023
PRIMARY
PUBCHEM
23666345
Created by admin on Wed Jul 05 22:33:59 UTC 2023 , Edited by admin on Wed Jul 05 22:33:59 UTC 2023
PRIMARY
Related Record Type Details
PARENT -> SALT/SOLVATE
SOLVATE->ANHYDROUS
LABELED -> NON-LABELED
Related Record Type Details
ACTIVE MOIETY