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Glyco-obeticholic acid-[d4]

General Information
Catalog: BLP-006873
Molecular Formula: C28H42D5NO5
Molecular Weight: 481.71
Chemical Structure
Glyco-obeticholic acid-[d4]
Description Glyco-obeticholic acid-[d4] is the isotope labelled analog of Glyco-obeticholic acid. Glyco-obeticholic acid is an active metabolite of obeticholic acid, which is a farnesoid X receptor (FXR) agonist and semisynthetic derivative of chenodeoxycholic acid.
Synonyms N-​[(3α,​5β,​6α,​7α)​-​6-Eethyl-​3,​7-​dihydroxy-​24-​oxocholan-​24-​yl]​glycine-d4; Obeticholic Acid Glycine Conjugate-d4
IUPAC Name 2-[[(4R)-4-[(3R,5S,6R,7R,8S,9S,10S,13R,14S,17R)-2,2,4,4-tetradeuterio-6-ethyl-3,7-dihydroxy-10,13-dimethyl-3,5,6,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-17-yl]pentanoyl]amino]acetic acid
Related CAS 863239-60-5 (unlabelled)
Canonical SMILES CCC1C2CC(CCC2(C3CCC4(C(C3C1O)CCC4C(C)CCC(=O)NCC(=O)O)C)C)O
InChI InChI=1S/C28H47NO5/c1-5-18-22-14-17(30)10-12-28(22,4)21-11-13-27(3)19(7-8-20(27)25(21)26(18)34)16(2)6-9-23(31)29-15-24(32)33/h16-22,25-26,30,34H,5-15H2,1-4H3,(H,29,31)(H,32,33)/t16-,17-,18-,19-,20+,21+,22+,25+,26-,27-,28-/m1/s1/i10D2,14D2
InChI Key MTLPUOZJBFHNSO-JNTBFLEXSA-N

Glyco-obeticholic acid-[d4] is a deuterated derivative of glyco-obeticholic acid used in research and clinical monitoring. Here are some key applications of Glyco-obeticholic acid-[d4]:

Pharmacokinetics Studies: Glyco-obeticholic acid-[d4] is utilized in pharmacokinetic research to track and understand the absorption, distribution, metabolism, and excretion of glyco-obeticholic acid in the body. The deuterium-labeling allows for precise monitoring via mass spectrometry, distinguishing it from endogenous compounds. This is crucial for developing effective dosage regimens and ensuring safety in drug development.

Liver Disease Research: In the study of liver diseases, Glyco-obeticholic acid-[d4] serves as an important tool to investigate bile acid pathways in hepatic conditions such as primary biliary cholangitis. By using this labeled compound, researchers can gain detailed insights into the altered metabolism of bile acids in diseased versus healthy states. This assists in elucidating disease mechanisms and evaluating therapeutic interventions.

Biochemical Assays: Glyco-obeticholic acid-[d4] is employed in biochemical assays to accurately quantify the presence of glyco-obeticholic acid in biological samples. Its stable isotope labeling provides a reliable internal standard, enhancing the specificity and precision of analytical results. This application is vital for both research purposes and in clinical settings for therapeutic monitoring.

Metabolic Pathway Elucidation: This compound aids in the elucidation of metabolic pathways involving bile acids. By tracking the labeled Glyco-obeticholic acid through various metabolic routes, researchers can identify active pathways and potential sites of metabolic regulation. This knowledge is fundamental for advancing understanding in fields like hepatology and gastroenterology, potentially leading to new therapeutic targets.

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