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Details

Stereochemistry ABSOLUTE
Molecular Formula C26H44NO7S.Na
Molecular Weight 537.6869
Optical Activity UNSPECIFIED
Defined Stereocenters 11 / 11
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of SODIUM 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.[Na+]

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 514.6971
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
Temporary pancreatic duct occlusion by ethibloc: cause of microcirculatory shutdown, acute inflammation, and pancreas necrosis.
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
Minor role of oxidative stress during intermediate phase of acute pancreatitis in rats.
2001 Feb 1
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
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
Influence of natural, electrically neutral lipids on the potentiometric responses of cation-selective polymeric membrane electrodes.
2001 Jul 15
The effect of glucagon-like peptide 2 on intestinal permeability and bacterial translocation in acute necrotizing pancreatitis.
2001 Jun
Characterization of model bile using fluorescence energy transfer from dehydroergosterol to dansylated lecithin.
2001 Jun
Differences in Ca(2+) signaling underlie age-specific effects of secretagogues on colonic Cl(-) transport.
2001 Mar
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
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
Changes in the activity of lysosomal enzymes in rat kidneys in the course of acute pancreatitis.
2001 Nov-Dec
The effect of a functional group in penicillin derivatives on the interaction with bile salt micelles studied by micellar electrokinetic chromatography.
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
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 10:40:24 UTC 2021
Edited
by admin
on Sat Jun 26 10:40:24 UTC 2021
Record UNII
M6N3TH81NO
Record Status Validated (UNII)
Record Version
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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 Sat Jun 26 10:40:25 UTC 2021 , Edited by admin on Sat Jun 26 10:40:25 UTC 2021
PRIMARY
DRUG BANK
DBSALT002887
Created by admin on Sat Jun 26 10:40:25 UTC 2021 , Edited by admin on Sat Jun 26 10:40:25 UTC 2021
PRIMARY
ECHA (EC/EINECS)
205-653-7
Created by admin on Sat Jun 26 10:40:25 UTC 2021 , Edited by admin on Sat Jun 26 10:40:25 UTC 2021
PRIMARY
CAS
145-42-6
Created by admin on Sat Jun 26 10:40:25 UTC 2021 , Edited by admin on Sat Jun 26 10:40:25 UTC 2021
PRIMARY
EPA CompTox
145-42-6
Created by admin on Sat Jun 26 10:40:25 UTC 2021 , Edited by admin on Sat Jun 26 10:40:25 UTC 2021
PRIMARY
EVMPD
SUB15328MIG
Created by admin on Sat Jun 26 10:40:25 UTC 2021 , Edited by admin on Sat Jun 26 10:40:25 UTC 2021
PRIMARY
PUBCHEM
23666345
Created by admin on Sat Jun 26 10:40:25 UTC 2021 , Edited by admin on Sat Jun 26 10:40:25 UTC 2021
PRIMARY
Related Record Type Details
PARENT -> SALT/SOLVATE
LABELED -> NON-LABELED
Related Record Type Details
ACTIVE MOIETY