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Details

Stereochemistry ABSOLUTE
Molecular Formula C26H44NO7S.K
Molecular Weight 553.793
Optical Activity UNSPECIFIED
Defined Stereocenters 11 / 11
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of POTASSIUM TAUROCHOLATE

SMILES

[K+].C[C@H](CCC(=O)NCCS([O-])(=O)=O)[C@H]1CC[C@H]2[C@@H]3[C@H](O)C[C@@H]4C[C@H](O)CC[C@]4(C)[C@H]3C[C@H](O)[C@]12C

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

Description

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

Targets

Targets

Primary TargetPharmacologyConditionPotency
4.95 µM [EC50]
Conditions
PubMed

PubMed

TitleDatePubMed
Alkaline phosphatase from rat liver and kidney is differentially modulated.
2001 Sep
Patents

Sample Use Guides

In Vivo Use Guide
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: Rectal, administered as an enema
In Vitro Use Guide
In primary murine intestinal cultures, Taurocholic acid (100 or 1000 umol/L) dose dependently increased GLP-1 release.
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 Tue Oct 22 06:23:43 UTC 2019 , Edited by admin on Tue Oct 22 06:23:43 UTC 2019
Code System Code Type Description
CAS
7487-77-6
Created by admin on Tue Oct 22 06:23:43 UTC 2019 , Edited by admin on Tue Oct 22 06:23:43 UTC 2019
PRIMARY
NCI_THESAURUS
C84101
Created by admin on Tue Oct 22 06:23:43 UTC 2019 , Edited by admin on Tue Oct 22 06:23:43 UTC 2019
PRIMARY
PUBCHEM
76963027
Created by admin on Tue Oct 22 06:23:43 UTC 2019 , Edited by admin on Tue Oct 22 06:23:43 UTC 2019
PRIMARY