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Details

Stereochemistry ABSOLUTE
Molecular Formula C26H45NO7S
Molecular Weight 515.703
Optical Activity UNSPECIFIED
Defined Stereocenters 11 / 11
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of TAUROCHOLIC ACID

SMILES

[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=WBWWGRHZICKQGZ-HZAMXZRMSA-N
InChI=1S/C26H45NO7S/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)/t15-,16+,17-,18-,19+,20+,21-,22+,24+,25+,26-/m1/s1

HIDE SMILES / InChI

Molecular Formula C26H45NO7S
Molecular Weight 515.703
Charge 0
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
Hydrophilic bile salts enhance differential distribution of sphingomyelin and phosphatidylcholine between micellar and vesicular phases: potential implications for their effects in vivo.
2001 Apr
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
The endothelin antagonist bosentan inhibits the canalicular bile salt export pump: a potential mechanism for hepatic adverse reactions.
2001 Apr
Regulation of biliary cholesterol secretion is independent of hepatocyte canalicular membrane lipid composition: a study in the diosgenin-fed rat model.
2001 Aug
Beneficial effects of growth hormone on bacterial translocation during the course of acute necrotizing pancreatitis in rats.
2001 Aug
Bile salt export pump is highly conserved during vertebrate evolution and its expression is inhibited by PFIC type II mutations.
2001 Aug
No effect of phenobarbital pretreatment of rats on methotrexate pharmacokinetics in the isolated liver perfused in a single-pass way.
2001 Feb
Minor role of oxidative stress during intermediate phase of acute pancreatitis in rats.
2001 Feb 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
Enhancement of jejunal absorption of conjugated bile acid by neurotensin in rats.
2001 Jan
Role of endogenous prostacyclin in gastric ulcerogenic and healing responses--a study using IP-receptor knockout mice.
2001 Jan-Dec
Comparison of "type I" and "type II" organic cation transport by organic cation transporters and organic anion-transporting polypeptides.
2001 Jul
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
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
Interleukin-10 attenuates proinflammatory cytokine production and improves survival in lethal pancreatitis.
2001 Mar
Regulation of the dynamic localization of the rat Bsep gene-encoded bile salt export pump by anisoosmolarity.
2001 Mar
Hemodynamic and metabolic variables predict porcine ex vivo liver function.
2001 Mar
Successful nonfreezing, subzero preservation of rat liver with 2,3-butanediol and type I antifreeze protein.
2001 Mar
Differences in Ca(2+) signaling underlie age-specific effects of secretagogues on colonic Cl(-) transport.
2001 Mar
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
Identification and characterization of human organic anion transporter 3 expressing predominantly in the kidney.
2001 May
Down-regulation of cholesterol 7alpha-hydroxylase (CYP7A1) gene expression by bile acids in primary rat hepatocytes is mediated by the c-Jun N-terminal kinase pathway.
2001 May 11
Transbuccal peptide delivery: stability and in vitro permeation studies on endomorphin-1.
2001 May 18
Is a role of phospholipase A(2) in cholesterol gallstone formation phospholipid species-dependent?
2001 May 31
Role of nonesterified fatty acids in necrotizing pancreatitis: an in vivo experimental study in rats.
2001 Nov
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
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
Common mechanisms of monoacylglycerol and fatty acid uptake by human intestinal Caco-2 cells.
2001 Oct
Alkaline phosphatase from rat liver and kidney is differentially modulated.
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 01:39:07 UTC 2023
Edited
by admin
on Thu Jul 06 01:39:07 UTC 2023
Record UNII
5E090O0G3Z
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
TAUROCHOLIC ACID
HSDB   MI  
Common Name English
CHOLYLTAURINE
Common Name English
3.BETA.-HYDROXYDINOR-5-CHOLENIC ACID
Systematic Name English
CHOLAIC ACID
Common Name English
TAUROCHOLIC ACID [HSDB]
Common Name English
2-(((3.ALPHA.,5.BETA.,7.ALPHA.,12.ALPHA.)-3,7,12-TRIHYDROXY-24-OXOCHOLAN-24-YL)AMINO)ETHANESULFONIC ACID
Common Name English
NSC-25505
Code English
TAUROCHOLIC ACID [MI]
Common Name English
N-CHOLOYLTAURINE
Common Name English
Code System Code Type Description
FDA UNII
5E090O0G3Z
Created by admin on Thu Jul 06 01:39:07 UTC 2023 , Edited by admin on Thu Jul 06 01:39:07 UTC 2023
PRIMARY
CHEBI
28865
Created by admin on Thu Jul 06 01:39:07 UTC 2023 , Edited by admin on Thu Jul 06 01:39:07 UTC 2023
PRIMARY
NSC
25505
Created by admin on Thu Jul 06 01:39:07 UTC 2023 , Edited by admin on Thu Jul 06 01:39:07 UTC 2023
PRIMARY
MESH
D013656
Created by admin on Thu Jul 06 01:39:07 UTC 2023 , Edited by admin on Thu Jul 06 01:39:07 UTC 2023
PRIMARY
PUBCHEM
6675
Created by admin on Thu Jul 06 01:39:07 UTC 2023 , Edited by admin on Thu Jul 06 01:39:07 UTC 2023
PRIMARY
MERCK INDEX
M10482
Created by admin on Thu Jul 06 01:39:07 UTC 2023 , Edited by admin on Thu Jul 06 01:39:07 UTC 2023
PRIMARY Merck Index
WIKIPEDIA
TAUROCHOLIC ACID
Created by admin on Thu Jul 06 01:39:07 UTC 2023 , Edited by admin on Thu Jul 06 01:39:07 UTC 2023
PRIMARY
CAS
81-24-3
Created by admin on Thu Jul 06 01:39:07 UTC 2023 , Edited by admin on Thu Jul 06 01:39:07 UTC 2023
PRIMARY
EPA CompTox
DTXSID00883259
Created by admin on Thu Jul 06 01:39:07 UTC 2023 , Edited by admin on Thu Jul 06 01:39:07 UTC 2023
PRIMARY
DRUG BANK
DB04348
Created by admin on Thu Jul 06 01:39:07 UTC 2023 , Edited by admin on Thu Jul 06 01:39:07 UTC 2023
PRIMARY
ECHA (EC/EINECS)
201-336-2
Created by admin on Thu Jul 06 01:39:07 UTC 2023 , Edited by admin on Thu Jul 06 01:39:07 UTC 2023
PRIMARY
HSDB
832
Created by admin on Thu Jul 06 01:39:07 UTC 2023 , Edited by admin on Thu Jul 06 01:39:07 UTC 2023
PRIMARY
Related Record Type Details
TRANSPORTER -> INHIBITOR
SALT/SOLVATE -> PARENT
TRANSPORTER -> SUBSTRATE
TRANSPORTER -> SUBSTRATE
TRANSPORTER -> INHIBITOR
LABELED -> NON-LABELED
TRANSPORTER -> SUBSTRATE
SALT/SOLVATE -> PARENT
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ACTIVE MOIETY