TAUROCHOLIC ACID

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 Search

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

Description
Sources: http://www.hmdb.ca/metabolites/HMDB00036 | http://adisinsight.springer.com/drugs/800033000 | https://www.ncbi.nlm.nih.gov/pubmed/23181598

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.

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
G-protein coupled bile acid receptor 1 15 Target ID: CHEMBL5409 Sources: https://www.ncbi.nlm.nih.gov/pubmed/26280129 \| https://www.ncbi.nlm.nih.gov/pubmed/18307294	Agonist 2662		4.95 µM [EC50]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Obesity 204 Sources: https://www.ncbi.nlm.nih.gov/pubmed/23181598 http://adisinsight.springer.com/drugs/800033000	Primary		Phase II 1144	Unknown Approved Use Unknown
Type 2 diabetes mellitus 256 Sources: http://adisinsight.springer.com/drugs/800047529 https://clinicaltrials.gov/ct2/show/NCT02871882 https://www.ncbi.nlm.nih.gov/pubmed/23418316	Primary		Phase II 1144	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed
Inhibitory effect of short-term bile duct ligation on hepatic cytochrome P450 of bile acid-depleted rats.	2001	11641615
Sinusoidal efflux of taurocholate is enhanced in Mrp2-deficient rat liver.	2001 Aug	11587482
Beneficial effects of growth hormone on bacterial translocation during the course of acute necrotizing pancreatitis in rats.	2001 Aug	11484917
Effects of internal biliary bypass on the regulation of hepatic cholesterol 7alpha-hydroxylase activity in rats.	2001 Aug	11430996
No effect of phenobarbital pretreatment of rats on methotrexate pharmacokinetics in the isolated liver perfused in a single-pass way.	2001 Feb	11174078
Identification of novel hypocholesterolemic peptides derived from bovine milk beta-lactoglobulin.	2001 Feb 16	11178953
Role of endogenous prostacyclin in gastric ulcerogenic and healing responses--a study using IP-receptor knockout mice.	2001 Jan-Dec	11595421
The effect of etodolac on bile salt and histamine-mediated gastric mucosal injury in the rat.	2001 Jan-Dec	11595417
Differential effects of caspase-1/interleukin-1beta-converting enzyme on acinar cell necrosis and apoptosis in severe acute experimental pancreatitis.	2001 Jul	11454989
Influence of natural, electrically neutral lipids on the potentiometric responses of cation-selective polymeric membrane electrodes.	2001 Jul 15	11476216
Improved in vitro gene transfer mediated by fluorinated lipoplexes in the presence of a bile salt surfactant.	2001 Jul-Aug	11529663
Modifying hepatic phospholipid synthesis associates with biliary phospholipid secretion rate in a transporter-independent manner in rats: relation to canalicular membrane fluidity.	2001 Jun	11414307
Oral delivery of synthetic eel calcitonin, elcatonin, in rats.	2001 Jun	11411554
Colchicine inhibits taurodeoxycholate transport in pericentral but not in periportal hepatocytes.	2001 Jun 20	11420119
Biochemical and physiological evidence that bile acids produced and released by lake char (Salvelinus namaycush) function as chemical signals.	2001 Mar	11302533
Interleukin-10 attenuates proinflammatory cytokine production and improves survival in lethal pancreatitis.	2001 Mar	11270881
Successful nonfreezing, subzero preservation of rat liver with 2,3-butanediol and type I antifreeze protein.	2001 Mar	11180993
Differences in Ca(2+) signaling underlie age-specific effects of secretagogues on colonic Cl(-) transport.	2001 Mar	11171585
Cyclosporin A reduces canalicular membrane fluidity and regulates transporter function in rats.	2001 Mar 15	11237863
Abc protein transport of MRI contrast agents in canalicular rat liver plasma vesicles and yeast vacuoles.	2001 Mar 23	11263971
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	11069906
Soluble receptors released during acute pancreatitis interfere with the detection of tumor necrosis factor-alpha.	2001 May	11378616
Identification and characterization of human organic anion transporter 3 expressing predominantly in the kidney.	2001 May	11306713
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	11278771
Is a role of phospholipase A(2) in cholesterol gallstone formation phospholipid species-dependent?	2001 May 31	11420173
Bile acid feeding increased proliferative activity and apical bile acid transporter expression in both small and large rat cholangiocytes.	2001 Nov	11679956
Increased matrix metalloproteinase expression and activation following experimental acute pancreatitis.	2001 Nov	11676550
Role of nonesterified fatty acids in necrotizing pancreatitis: an in vivo experimental study in rats.	2001 Nov	11668201
Interaction of 2,3-dimercapto-1-propane sulfonate with the human organic anion transporter hOAT1.	2001 Nov	11602689
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	11672435
Pericentral hepatocytes translocate hydrophilic bile acids more rapidly than hydrophobic ones.	2001 Oct	11680582
The effect of a functional group in penicillin derivatives on the interaction with bile salt micelles studied by micellar electrokinetic chromatography.	2001 Oct	11669544
Multispecific substrate recognition of kidney-specific organic anion transporters OAT-K1 and OAT-K2.	2001 Oct	11561088
Alkaline phosphatase from rat liver and kidney is differentially modulated.	2001 Sep	11676975

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: Other

In Vitro Use Guide

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

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Name

Type

Language

TAUROCHOLIC ACID

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