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Syntheses of isotope‐labeled SGLT2 inhibitor canagliflozin ( JNJ ‐28431754)
Author(s) -
Lin Ronghui,
Hoerr David C.,
Weaner Larry E.,
Salter Rhys
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.3542
Subject(s) - canagliflozin , chemistry , sodium , type 2 diabetes , diabetes mellitus , organic chemistry , endocrinology , medicine
Canagliflozin (Invokana, JNJ‐28431754) is an orally bioavailable and selective SGLT2 (subtype 2 sodium‐glucose transport protein) inhibitor approved for the treatment of type 2 diabetes. Herein, we report the synthesis of 13 C and 14 C‐labeled canagliflozin. Stable isotope‐labeled [ 13 C 6 ]canagliflozin was synthesized in 4 steps starting from [ 13 C 6 ]‐labeled glucose. The [ 14 C]‐Labeled canagliflozin was synthesized by incorporation of [ 14 C] into the benzylic position between the thiophene and benzene rings of the compound. Detailed synthesis of the isotope‐labeled compounds is reported.