Synthesis of isotopically labeled daclatasvir for use in human clinical studies

J Labelled Comp Radiopharm. 2016 Apr;59(4):164-70. doi: 10.1002/jlcr.3386. Epub 2016 Mar 10.

Abstract

Daclatasvir is a novel hepatitis C virus NS5A inhibitor developed by Bristol-Myers Squibb and marketed as Daklinza®. The need to support the development of daclatasvir required the synthesis of carbon-14 labeled material for use in human absorption, distribution, metabolism, and excretion studies. A total of 7.53 mCi of [(14) C]-daclatasvir was synthesized in eight steps from commercially available [(14) C]-copper cyanide. The radiochemical purity was 99.6%, and specific activity was 3.86 μCi/mg. To support a human absolute bioavailability study, 5.56 g of [(13) C2 , (15) N4 ]-daclatasvir was synthesized in four steps.

Keywords: HCV; carbon-14; daclatasvir; hepatitis C virus; stable isotope synthesis.

MeSH terms

  • Biological Availability
  • Carbamates
  • Chemistry Techniques, Synthetic
  • Humans
  • Imidazoles / chemical synthesis*
  • Imidazoles / chemistry
  • Imidazoles / metabolism
  • Imidazoles / pharmacokinetics*
  • Isotope Labeling
  • Pyrrolidines
  • RNA-Dependent RNA Polymerase / antagonists & inhibitors
  • Teprotide / chemical synthesis
  • Teprotide / chemistry
  • Teprotide / metabolism
  • Teprotide / pharmacokinetics
  • Valine / analogs & derivatives
  • Viral Nonstructural Proteins / antagonists & inhibitors

Substances

  • Carbamates
  • Imidazoles
  • Pyrrolidines
  • Viral Nonstructural Proteins
  • Teprotide
  • NS-5 protein, hepatitis C virus
  • RNA-Dependent RNA Polymerase
  • Valine
  • daclatasvir