POTASSIUM TAUROCHOLATE

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C26H44NO7S.K
Molecular Weight	553.7955
Optical Activity	UNSPECIFIED
Defined Stereocenters	11 / 11
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

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.[K+]

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

Molecular Formula	K
Molecular Weight	39.0983
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

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 5 Target ID: CHEMBL5409 Sources: https://www.ncbi.nlm.nih.gov/pubmed/26280129 \| https://www.ncbi.nlm.nih.gov/pubmed/18307294	Agonist 1109		4.95 µM [EC50]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Obesity 84 Sources: https://www.ncbi.nlm.nih.gov/pubmed/23181598 http://adisinsight.springer.com/drugs/800033000	Primary		Phase II 394	Unknown Approved Use Unknown
Type 2 diabetes mellitus 103 Sources: http://adisinsight.springer.com/drugs/800047529 https://clinicaltrials.gov/ct2/show/NCT02871882 https://www.ncbi.nlm.nih.gov/pubmed/23418316	Primary		Phase II 394	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
Temporary pancreatic duct occlusion by ethibloc: cause of microcirculatory shutdown, acute inflammation, and pancreas necrosis.	2001 Apr	11344393
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
Mechanisms for the transport of unconjugated bilirubin in human trophoblastic BeWo cells.	2001 Apr 20	11322954
Sinusoidal efflux of taurocholate is enhanced in Mrp2-deficient rat liver.	2001 Aug	11587482
Regulation of biliary cholesterol secretion is independent of hepatocyte canalicular membrane lipid composition: a study in the diosgenin-fed rat model.	2001 Aug	11580137
Tauroursodesoxycholate-induced choleresis involves p38(MAPK) activation and translocation of the bile salt export pump in rats.	2001 Aug	11487550
Identification of novel hypocholesterolemic peptides derived from bovine milk beta-lactoglobulin.	2001 Feb 16	11178953
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
Comparison of "type I" and "type II" organic cation transport by organic cation transporters and organic anion-transporting polypeptides.	2001 Jul	11408531
Influence of natural, electrically neutral lipids on the potentiometric responses of cation-selective polymeric membrane electrodes.	2001 Jul 15	11476216
Cell-specific basolateral membrane sorting of the human liver Na(+)-dependent bile acid cotransporter.	2001 Jun	11352825
Localized pancreatic NF-kappaB activation and inflammatory response in taurocholate-induced pancreatitis.	2001 Jun	11352813
Regulation of the dynamic localization of the rat Bsep gene-encoded bile salt export pump by anisoosmolarity.	2001 Mar	11230729
Differences in Ca(2+) signaling underlie age-specific effects of secretagogues on colonic Cl(-) transport.	2001 Mar	11171585
Abc protein transport of MRI contrast agents in canalicular rat liver plasma vesicles and yeast vacuoles.	2001 Mar 23	11263971
Transporters on demand: intrahepatic pools of canalicular ATP binding cassette transporters in rat liver.	2001 Mar 9	11113123
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
A new 5-aminosalicylic acid multi-unit dosage form for the therapy of ulcerative colitis.	2001 May	11343881
Identification and characterization of human organic anion transporter 3 expressing predominantly in the kidney.	2001 May	11306713
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
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
The utilization of sodium taurocholate in excystation of Cryptosporidium parvum and infection of tissue culture.	2001 Oct	11695421
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
Inhibition of inducible nitric oxide synthase reduces bacterial translocation in a rat model of acute pancreatitis.	2001 Oct	11590326
Alkaline phosphatase from rat liver and kidney is differentially modulated.	2001 Sep	11676975
Nuclear receptor-mediated repression of human cholesterol 7alpha-hydroxylase gene transcription by bile acids.	2001 Sep	11518759
Ischemic preconditioning, the most effective gastroprotective intervention: involvement of prostaglandins, nitric oxide, adenosine and sensory nerves.	2001 Sep 21	11567657

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 `Sat Jun 26 14:08:56 UTC 2021` Edited by `admin` on `Sat Jun 26 14:08:56 UTC 2021`
Record UNII	5ZU91PFW8G
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

POTASSIUM TAUROCHOLATE

Common Name

English

TAUROCHOLIC ACID POTASSIUM SALT

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C2140