Metabolism and Disposition of Pan-Genotypic Inhibitor of Hepatitis C Virus NS5A Ombitasvir in Humans

Drug Metab Dispos. 2016 Aug;44(8):1148-57. doi: 10.1124/dmd.115.067496. Epub 2016 May 13.

Abstract

Ombitasvir (also known as ABT-267) is a potent inhibitor of hepatitis C virus (HCV) nonstructural protein 5A (NS5A), which has been developed in combination with paritaprevir/ritonavir and dasabuvir in a three direct-acting antiviral oral regimens for the treatment of patients infected with HCV genotype 1. This article describes the mass balance, metabolism, and disposition of ombitasvir in humans without coadministration of paritaprevir/ritonavir and dasabuvir. Following the administration of a single 25-mg oral dose of [(14)C]ombitasvir to four healthy male volunteers, the mean total percentage of the administered radioactive dose recovered was 92.1% over the 192-hour sample collection in the study. The recovery from the individual subjects ranged from 91.4 to 93.1%. Ombitasvir and corresponding metabolites were primarily eliminated in feces (90.2% of dose), mainly as unchanged parent drug (87.8% of dose), but minimally through renal excretion (1.9% of dose). Biotransformation of ombitasvir in human involves enzymatic amide hydrolysis to form M23 (dianiline), which is further metabolized through cytochrome P450-mediated oxidative metabolism (primarily by CYP2C8) at the tert-butyl group to generate oxidative and/or C-desmethyl metabolites. [(14)C]Ombitasvir, M23, M29, M36, and M37 are the main components in plasma, representing about 93% of total plasma radioactivity. The steady-state concentration measurement of ombitasvir metabolites by liquid chromatography-mass spectrometry analysis in human plasma following multiple doses of ombitasvir, in combination with paritaprevir/ritonavir and dasabuvir, confirmed that ombitasvir is the main component (51.9% of all measured drug-related components), whereas M29 (19.9%) and M36 (13.1%) are the major circulating metabolites. In summary, the study characterized ombitasvir metabolites in circulation, the metabolic pathways, and the elimination routes of the drug.

MeSH terms

  • Administration, Oral
  • Anilides / administration & dosage
  • Anilides / blood
  • Anilides / pharmacokinetics*
  • Antiviral Agents / administration & dosage
  • Antiviral Agents / blood
  • Antiviral Agents / pharmacokinetics*
  • Biotransformation
  • Carbamates / administration & dosage
  • Carbamates / blood
  • Carbamates / pharmacokinetics*
  • Chromatography, High Pressure Liquid
  • Cytochrome P-450 CYP2C8 / metabolism
  • Drug Administration Schedule
  • Feces / chemistry
  • Healthy Volunteers
  • Hepacivirus / drug effects*
  • Hepacivirus / enzymology
  • Humans
  • Hydrolysis
  • Male
  • Oxidation-Reduction
  • Proline
  • Tandem Mass Spectrometry
  • Tissue Distribution
  • Valine
  • Viral Nonstructural Proteins / antagonists & inhibitors*
  • Viral Nonstructural Proteins / metabolism

Substances

  • Anilides
  • Antiviral Agents
  • Carbamates
  • Viral Nonstructural Proteins
  • ombitasvir
  • Proline
  • CYP2C8 protein, human
  • Cytochrome P-450 CYP2C8
  • NS-5 protein, hepatitis C virus
  • Valine