SODIUM TAUROCHOLATE

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C26H44NO7S.Na
Molecular Weight	537.685
Optical Activity	UNSPECIFIED
Defined Stereocenters	11 / 11
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

[Na+].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=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	C26H44NO7S
Molecular Weight	514.695
Charge	-1
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	11 / 11
E/Z Centers	0
Optical Activity	UNSPECIFIED

Molecular Formula	Na
Molecular Weight	22.98976928
Charge	1
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

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 16 Target ID: CHEMBL5409 Sources: https://www.ncbi.nlm.nih.gov/pubmed/26280129 \| https://www.ncbi.nlm.nih.gov/pubmed/18307294	Agonist 2752		4.95 µM [EC50]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Obesity 206 Sources: https://www.ncbi.nlm.nih.gov/pubmed/23181598 http://adisinsight.springer.com/drugs/800033000	Primary		Phase II 1147	Unknown Approved Use Unknown
Type 2 diabetes mellitus 262 Sources: http://adisinsight.springer.com/drugs/800047529 https://clinicaltrials.gov/ct2/show/NCT02871882 https://www.ncbi.nlm.nih.gov/pubmed/23418316	Primary		Phase II 1147	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed
Ileal mucosal bile acid absorption is increased in Cftr knockout mice.	2001	11696242
Inhibitory effect of short-term bile duct ligation on hepatic cytochrome P450 of bile acid-depleted rats.	2001	11641615
Hydrophilic bile salts enhance differential distribution of sphingomyelin and phosphatidylcholine between micellar and vesicular phases: potential implications for their effects in vivo.	2001 Apr	11394647
The endothelin antagonist bosentan inhibits the canalicular bile salt export pump: a potential mechanism for hepatic adverse reactions.	2001 Apr	11309550
Cellular distribution and handling of liver-targeting preparations in human livers studied by a liver lobe perfusion.	2001 Apr	11259317
The bile acid taurocholate impairs rat cardiomyocyte function: a proposed mechanism for intra-uterine fetal death in obstetric cholestasis.	2001 Apr	11256973
Tauroursodesoxycholate-induced choleresis involves p38(MAPK) activation and translocation of the bile salt export pump in rats.	2001 Aug	11487550
Beneficial effects of growth hormone on bacterial translocation during the course of acute necrotizing pancreatitis in rats.	2001 Aug	11484917
Intracellular glutathione regulates taurocholate transport in HepG2 cells.	2001 Aug 1	11485381
Minor role of oxidative stress during intermediate phase of acute pancreatitis in rats.	2001 Feb 1	11165877
Interaction of bile salt and phospholipids with bovine submaxillary mucin.	2001 Jan	11336352
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
Attenuation of sepsis-related immunoparalysis by continuous veno-venous hemofiltration in experimental porcine pancreatitis.	2001 Jul	11445702
Optimization of culture conditions for determining hepatobiliary disposition of taurocholate in sandwich-cultured rat hepatocytes.	2001 Jun	11515972
The effect of glucagon-like peptide 2 on intestinal permeability and bacterial translocation in acute necrotizing pancreatitis.	2001 Jun	11513789
Long-term course in collagenous colitis and the impact of bile acid malabsorption and bile acid sequestrants on histopathology and clinical features.	2001 Jun	11424318
Colchicine inhibits taurodeoxycholate transport in pericentral but not in periportal hepatocytes.	2001 Jun 20	11420119
A simple method for measuring of intestinal solute transport in mucosal biopsy specimens.	2001 Mar	11318514
Regulation of the dynamic localization of the rat Bsep gene-encoded bile salt export pump by anisoosmolarity.	2001 Mar	11230729
Cyclosporin A reduces canalicular membrane fluidity and regulates transporter function in rats.	2001 Mar 15	11237863
Characterization of bile acid transport mediated by multidrug resistance associated protein 2 and bile salt export pump.	2001 Mar 9	11248200
Soluble receptors released during acute pancreatitis interfere with the detection of tumor necrosis factor-alpha.	2001 May	11378616
Taurocholic acid-induced secretion in normal and cystic fibrosis mouse ileum.	2001 May	11370710
Is a role of phospholipase A(2) in cholesterol gallstone formation phospholipid species-dependent?	2001 May 31	11420173
Interaction of 2,3-dimercapto-1-propane sulfonate with the human organic anion transporter hOAT1.	2001 Nov	11602689

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 `Mon Mar 31 17:35:59 GMT 2025` Edited by `admin` on `Mon Mar 31 17:35:59 GMT 2025`
Record UNII	M6N3TH81NO
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

SODIUM TAUROCHOLATE

Common Name

English

BILE SALTS [USP-RS]

Preferred Name

English

Sodium taurocholate [WHO-DD]

Common Name

English

Code System Code Type Description

FDA UNII

M6N3TH81NO