Characterization of efflux transporters involved in distribution and disposition of apixaban

Drug Metab Dispos. 2013 Apr;41(4):827-35. doi: 10.1124/dmd.112.050260. Epub 2013 Feb 4.

Abstract

The studies reported here were conducted to investigate the transport characteristics of apixaban (1-(4-methoxyphenyl)-7-oxo-6-(4-(2-oxopiperidin-1-yl)phenyl)-4,5,6,7-tetrahydro-1H-pyrazolo[3,4-c]pyridine-3-carboxamide) and to understand the impact of transporters on apixaban distribution and disposition. In human permeability glycoprotein (P-gp)- and breast cancer resistance protein (BCRP)-cDNA-transfected cell monolayers as well as Caco-2 cell monolayers, the apparent efflux ratio of basolateral-to-apical (PcB-A) versus apical-to-basolateral permeability (PcA-B) of apixaban was >10. The P-gp- and BCRP-facilitated transport of apixaban was concentration- and time-dependent and did not show saturation over a wide range of concentrations (1-100 μM). The efflux transport of apixaban was also demonstrated by the lower mucosal-to-serosal permeability than that of the serosal-to-mucosal direction in isolated rat jejunum segments. Apixaban did not inhibit digoxin transport in Caco-2 cells. Ketoconazole decreased the P-gp-mediated apixaban efflux in Caco-2 and the P-gp-cDNA-transfected cell monolayers, but did not affect the apixaban efflux to a meaningful extent in the BCRP-cDNA-transfected cell monolayers. Coincubation of a P-gp inhibitor (ketoconazole or cyclosporin A) and a BCRP inhibitor (Ko134) provided more complete inhibition of apixaban efflux in Caco-2 cells than separate inhibition by individual inhibitors. Naproxen inhibited apixaban efflux in Caco-2 cells but showed only a minimal effect on apixaban transport in the BCRP-transfected cells. Naproxen was the first nonsteroidal antiinflammatory drug that was demonstrated as a weak P-gp inhibitor. These results demonstrate that apixaban is a substrate for efflux transporters P-gp and BCRP, which can help explain its low brain penetration, and low fetal exposures and high milk excretion in rats.

MeSH terms

  • ATP Binding Cassette Transporter, Subfamily B, Member 1 / antagonists & inhibitors
  • ATP Binding Cassette Transporter, Subfamily B, Member 1 / metabolism*
  • ATP Binding Cassette Transporter, Subfamily G, Member 2
  • ATP-Binding Cassette Transporters / antagonists & inhibitors
  • ATP-Binding Cassette Transporters / metabolism*
  • Adenosine / analogs & derivatives
  • Adenosine / pharmacology
  • Animals
  • Biological Transport / drug effects
  • Caco-2 Cells / metabolism
  • Cell Line, Transformed
  • Cell Membrane Permeability / drug effects
  • Cyclosporine / pharmacology
  • Digoxin / pharmacokinetics
  • Diketopiperazines
  • Dose-Response Relationship, Drug
  • Drug Interactions
  • Fibrinolytic Agents / pharmacokinetics*
  • Heterocyclic Compounds, 4 or More Rings
  • Humans
  • Ketoconazole / pharmacology
  • Male
  • Naproxen / pharmacology
  • Neoplasm Proteins / antagonists & inhibitors
  • Neoplasm Proteins / metabolism*
  • Pyrazoles / pharmacokinetics*
  • Pyridones / pharmacokinetics*
  • Rats

Substances

  • 3-(6-isobutyl-9-methoxy-1,4-dioxo-1,2,3,4,6,7,12,12a-octahydropyrazino(1',2'-1,6)pyrido(3,4-b)indol-3-yl)propionic acid tert-butyl ester
  • ABCG2 protein, human
  • ATP Binding Cassette Transporter, Subfamily B, Member 1
  • ATP Binding Cassette Transporter, Subfamily G, Member 2
  • ATP-Binding Cassette Transporters
  • Diketopiperazines
  • Fibrinolytic Agents
  • Heterocyclic Compounds, 4 or More Rings
  • Neoplasm Proteins
  • Pyrazoles
  • Pyridones
  • apixaban
  • Naproxen
  • Digoxin
  • Cyclosporine
  • Adenosine
  • Ketoconazole