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

Details

Stereochemistry ABSOLUTE
Molecular Formula C26H44NO7S.K
Molecular Weight 553.7955
Optical Activity UNSPECIFIED
Defined Stereocenters 11 / 11
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of POTASSIUM 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.[K+]

InChI

InChIKey=DMYWDAAJMXQHLP-IZYKLYLVSA-M
InChI=1S/C26H45NO7S.K/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 K
Molecular Weight 39.0983
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
Cloning and expression of murine sister of P-glycoprotein reveals a more discriminating transporter than MDR1/P-glycoprotein.
2000 Jan
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
The absorption of retinoic acids from the gastrointestinal tract is dependent upon chemical structure.
2001
Temporary pancreatic duct occlusion by ethibloc: cause of microcirculatory shutdown, acute inflammation, and pancreas necrosis.
2001 Apr
The endothelin antagonist bosentan inhibits the canalicular bile salt export pump: a potential mechanism for hepatic adverse reactions.
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
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
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
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
Attenuation of sepsis-related immunoparalysis by continuous veno-venous hemofiltration in experimental porcine 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
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
Regulation of the dynamic localization of the rat Bsep gene-encoded bile salt export pump by anisoosmolarity.
2001 Mar
Differences in Ca(2+) signaling underlie age-specific effects of secretagogues on colonic Cl(-) transport.
2001 Mar
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
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
Bile acid feeding increased proliferative activity and apical bile acid transporter expression in both small and large rat cholangiocytes.
2001 Nov
Increased matrix metalloproteinase expression and activation following experimental acute pancreatitis.
2001 Nov
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 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
Inhibition of inducible nitric oxide synthase reduces bacterial translocation in a rat model of acute pancreatitis.
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
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 14:08:56 UTC 2021
Edited
by admin
on Sat Jun 26 14:08:56 UTC 2021
Record UNII
5ZU91PFW8G
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
POTASSIUM TAUROCHOLATE
Common Name English
TAUROCHOLIC ACID POTASSIUM SALT
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C2140
Created by admin on Sat Jun 26 14:08:56 UTC 2021 , Edited by admin on Sat Jun 26 14:08:56 UTC 2021
Code System Code Type Description
CAS
7487-77-6
Created by admin on Sat Jun 26 14:08:56 UTC 2021 , Edited by admin on Sat Jun 26 14:08:56 UTC 2021
PRIMARY
FDA UNII
5ZU91PFW8G
Created by admin on Sat Jun 26 14:08:56 UTC 2021 , Edited by admin on Sat Jun 26 14:08:56 UTC 2021
PRIMARY
NCI_THESAURUS
C84101
Created by admin on Sat Jun 26 14:08:56 UTC 2021 , Edited by admin on Sat Jun 26 14:08:56 UTC 2021
PRIMARY
PUBCHEM
76963027
Created by admin on Sat Jun 26 14:08:56 UTC 2021 , Edited by admin on Sat Jun 26 14:08:56 UTC 2021
PRIMARY
Related Record Type Details
PARENT -> SALT/SOLVATE
Related Record Type Details
ACTIVE MOIETY