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 2678		4.95 µM [EC50]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Obesity 203 Sources: https://www.ncbi.nlm.nih.gov/pubmed/23181598 http://adisinsight.springer.com/drugs/800033000	Primary		Phase II 1132	Unknown Approved Use Unknown
Type 2 diabetes mellitus 259 Sources: http://adisinsight.springer.com/drugs/800047529 https://clinicaltrials.gov/ct2/show/NCT02871882 https://www.ncbi.nlm.nih.gov/pubmed/23418316	Primary		Phase II 1132	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed
Cloning and expression of murine sister of P-glycoprotein reveals a more discriminating transporter than MDR1/P-glycoprotein.	2000 Jan	10617675
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
The absorption of retinoic acids from the gastrointestinal tract is dependent upon chemical structure.	2001	11221958
Differential oxidative injury in extrapancreatic tissues during experimental pancreatitis: modification of lung proteins by 4-hydroxynonenal.	2001 Apr	11330437
The endothelin antagonist bosentan inhibits the canalicular bile salt export pump: a potential mechanism for hepatic adverse reactions.	2001 Apr	11309550
Mechanisms for the transport of unconjugated bilirubin in human trophoblastic BeWo cells.	2001 Apr 20	11322954
Interrelationship between colonic muscularis mucosae activity and changes in transmucosal potential difference.	2001 Aug	11447028
Effects of internal biliary bypass on the regulation of hepatic cholesterol 7alpha-hydroxylase activity in rats.	2001 Aug	11430996
Minor role of oxidative stress during intermediate phase of acute pancreatitis in rats.	2001 Feb 1	11165877
V-PYRRO/NO: an hepato-selective nitric oxide donor improves porcine liver hemodynamics and function after ischemia reperfusion.	2001 Jan 27	11213058
Role of endogenous prostacyclin in gastric ulcerogenic and healing responses--a study using IP-receptor knockout mice.	2001 Jan-Dec	11595421
Anti-ICAM-1 antibody modulates late onset of acinar cell apoptosis and early necrosis in taurocholate-induced experimental acute pancreatitis.	2001 Jul	11451152
Influence of natural, electrically neutral lipids on the potentiometric responses of cation-selective polymeric membrane electrodes.	2001 Jul 15	11476216
Gastric preconditioning induced by short ischemia: the role of prostaglandins, nitric oxide and adenosine.	2001 Jul-Aug	11433185
Cellular distribution and handling of liver-targeting preparations in human livers studied by a liver lobe perfusion.	2001 Jun	11353741
Localized pancreatic NF-kappaB activation and inflammatory response in taurocholate-induced pancreatitis.	2001 Jun	11352813
Biochemical and physiological evidence that bile acids produced and released by lake char (Salvelinus namaycush) function as chemical signals.	2001 Mar	11302533
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
Bile salt hydrolase activity of Enterococci isolated from food: screening and quantitative determination.	2001 May	11348009
A new 5-aminosalicylic acid multi-unit dosage form for the therapy of ulcerative colitis.	2001 May	11343881
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
Changes in the activity of lysosomal enzymes in rat kidneys in the course of acute pancreatitis.	2001 Nov-Dec	11687729
The utilization of sodium taurocholate in excystation of Cryptosporidium parvum and infection of tissue culture.	2001 Oct	11695421
The effect of a functional group in penicillin derivatives on the interaction with bile salt micelles studied by micellar electrokinetic chromatography.	2001 Oct	11669544
Single amino acid substitution of rat MRP2 results in acquired transport activity for taurocholate.	2001 Oct	11557524
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 `Fri Dec 15 18:25:35 GMT 2023` Edited by `admin` on `Fri Dec 15 18:25:35 GMT 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