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
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
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
PubMed
Patents
Sample Use Guides
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