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Synthesis of unlabelled and stable‐isotope–labelled glucuronide metabolites of dapagliflozin and synthesis of stable‐isotope–labelled dapagliflozin
Author(s) -
Cao Kai,
Brailsford John A.,
Yao Ming,
CaceresCortes Janet,
Espina Robert,
Bonacorsi Samuel J.
Publication year - 2017
Publication title -
journal of labelled compounds and radiopharmaceuticals
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.432
H-Index - 47
eISSN - 1099-1344
pISSN - 0362-4803
DOI - 10.1002/jlcr.3484
Subject(s) - chemistry , dapagliflozin , urine , heteronuclear molecule , glucuronide , metabolite , chromatography , isotope , stable isotope ratio , stereochemistry , nuclear magnetic resonance spectroscopy , biochemistry , medicine , physics , quantum mechanics , type 2 diabetes , diabetes mellitus , endocrinology
Two regioisomeric glucuronide metabolites of dapagliflozin (BMS‐512148) were synthesized and used to elucidate the structures of dapagliflozin metabolites observed in human urine samples. The structures of the synthetic metabolites were assigned by heteronuclear multiple‐bond correlation, ROESY, and total correlation spectroscopy experiments. Analogues of these metabolites containing carbon‐13 as a stable label were also prepared for use as internal standards for the analysis of urine samples obtained from patients participating in clinical studies.