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Details

Stereochemistry ABSOLUTE
Molecular Formula C26H44NO7S.Na.H2O
Molecular Weight 555.7
Optical Activity UNSPECIFIED
Defined Stereocenters 11 / 11
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of SODIUM TAUROCHOLATE MONOHYDRATE

SMILES

O.[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=RDAJAQDLEFHVNR-NEMAEHQESA-M
InChI=1S/C26H45NO7S.Na.H2O/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);;1H2/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 H2O
Molecular Weight 18.0153
Charge 0
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 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
Cloning and expression of murine sister of P-glycoprotein reveals a more discriminating transporter than MDR1/P-glycoprotein.
2000 Jan
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
Design and properties of hepatitis C virus antisense oligonucleotides for liver specific drug targeting.
2001 Apr-Jul
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
Intracellular glutathione regulates taurocholate transport in HepG2 cells.
2001 Aug 1
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
Interaction of bile salt and phospholipids with bovine submaxillary mucin.
2001 Jan
Enhancement of jejunal absorption of conjugated bile acid by neurotensin in rats.
2001 Jan
V-PYRRO/NO: an hepato-selective nitric oxide donor improves porcine liver hemodynamics and function after ischemia reperfusion.
2001 Jan 27
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
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
Human liver-specific organic anion transporter, LST-1, mediates uptake of pravastatin by human hepatocytes.
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
Cholestatic potential of troglitazone as a possible factor contributing to troglitazone-induced hepatotoxicity: in vivo and in vitro interaction at the canalicular bile salt export pump (Bsep) in the rat.
2001 Mar
Differences in Ca(2+) signaling underlie age-specific effects of secretagogues on colonic Cl(-) transport.
2001 Mar
Cyclosporin A reduces canalicular membrane fluidity and regulates transporter function in rats.
2001 Mar 15
Abc protein transport of MRI contrast agents in canalicular rat liver plasma vesicles and yeast vacuoles.
2001 Mar 23
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
Soluble receptors released during acute pancreatitis interfere with the detection of tumor necrosis factor-alpha.
2001 May
Bile salt hydrolase activity of Enterococci isolated from food: screening and quantitative determination.
2001 May
Identification and characterization of human organic anion transporter 3 expressing predominantly in the kidney.
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
Regulation of sterol regulatory element-binding proteins by cholesterol flux in CaCo-2 cells.
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
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
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 Thu Jul 06 21:06:43 UTC 2023
Edited
by admin
on Thu Jul 06 21:06:43 UTC 2023
Record UNII
WOX5F63THK
Record Status Validated (UNII)
Record Version
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Name Type Language
SODIUM TAUROCHOLATE MONOHYDRATE
Common Name English
ETHANESULFONIC ACID, 2-(((3.ALPHA.,5.BETA.,7.ALPHA.,12.ALPHA.)-3,7,12-TRIHYDROXY-24-OXOCHOLAN-24-YL)AMINO)-, SODIUM SALT, HYDRATE (1:1:1)
Systematic Name English
Code System Code Type Description
FDA UNII
WOX5F63THK
Created by admin on Thu Jul 06 21:06:43 UTC 2023 , Edited by admin on Thu Jul 06 21:06:43 UTC 2023
PRIMARY
CAS
345909-26-4
Created by admin on Thu Jul 06 21:06:43 UTC 2023 , Edited by admin on Thu Jul 06 21:06:43 UTC 2023
NON-SPECIFIC STOICHIOMETRY
CAS
312693-83-7
Created by admin on Thu Jul 06 21:06:43 UTC 2023 , Edited by admin on Thu Jul 06 21:06:43 UTC 2023
PRIMARY
PUBCHEM
23687511
Created by admin on Thu Jul 06 21:06:43 UTC 2023 , Edited by admin on Thu Jul 06 21:06:43 UTC 2023
PRIMARY
EPA CompTox
DTXSID101017419
Created by admin on Thu Jul 06 21:06:43 UTC 2023 , Edited by admin on Thu Jul 06 21:06:43 UTC 2023
PRIMARY
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ANHYDROUS->SOLVATE
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ACTIVE MOIETY