Involvement of the Transporters P-Glycoprotein and Breast Cancer Resistance Protein in Dermal Distribution of the Multikinase Inhibitor Regorafenib and Its Active Metabolites

J Pharm Sci. 2017 Sep;106(9):2632-2641. doi: 10.1016/j.xphs.2017.04.064. Epub 2017 May 4.

Abstract

Regorafenib is a multikinase inhibitor orally administered to colorectal cancer patients, and is known to often exhibit dermal toxicity. The purpose of this study is to clarify possible involvement of P-glycoprotein and breast cancer resistance protein (BCRP) in the dermal accumulation of regorafenib and its active metabolites M-2 and M-5. Following intravenous administration in triple knockout (Abcb1a/1b/bcrp-/-; TKO) and wild-type (WT) mice, delayed plasma clearance of M-2 and M-5, but not regorafenib, was observed in TKO mice compared to WT mice. Elacridar, an inhibitor of both transporters, also caused delayed clearance of M-2 and M-5, suggesting that these transporters are involved in their elimination. Skin-to-plasma concentration ratios of regorafenib, M-2, and M-5 were significantly higher in TKO mice than in WT mice. Elacridar increased skin-to-plasma and epidermis-to-plasma concentration ratios of regorafenib. Basal-to-apical transport of M-2 and M-5 was observed in LLC-PK1-Pgp and MDCKII/BCRP/PDZK1 cells, which was inhibited by elacridar and the BCRP inhibitor Ko143, respectively. The present findings thus indicate that P-glycoprotein and BCRP are involved in the accumulation of regorafenib and its active metabolites in the skin, by affecting either their systemic exposure or their plasma distribution in the circulating blood.

Keywords: ABC transporters; P-glycoprotein; skin; tissue partition; transporters.

MeSH terms

  • ATP Binding Cassette Transporter, Subfamily B / metabolism*
  • ATP Binding Cassette Transporter, Subfamily B, Member 1 / metabolism*
  • Acridines / chemistry
  • Acridines / metabolism
  • Acridines / pharmacology
  • Animals
  • Antineoplastic Agents / chemistry
  • Antineoplastic Agents / metabolism
  • Antineoplastic Agents / pharmacology*
  • Biological Transport
  • Breast Neoplasms / drug therapy
  • Breast Neoplasms / metabolism*
  • Diketopiperazines / chemistry
  • Diketopiperazines / metabolism
  • Diketopiperazines / pharmacology
  • Heterocyclic Compounds, 4 or More Rings / chemistry
  • Heterocyclic Compounds, 4 or More Rings / metabolism
  • Heterocyclic Compounds, 4 or More Rings / pharmacology
  • Humans
  • Male
  • Mice
  • Phenylurea Compounds / chemistry
  • Phenylurea Compounds / metabolism*
  • Phenylurea Compounds / toxicity
  • Protein Kinase Inhibitors / chemistry
  • Protein Kinase Inhibitors / pharmacology*
  • Pyridines / chemistry
  • Pyridines / metabolism*
  • Pyridines / toxicity
  • Skin / metabolism
  • Tetrahydroisoquinolines / chemistry
  • Tetrahydroisoquinolines / metabolism
  • Tetrahydroisoquinolines / pharmacology
  • Tissue Distribution

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
  • ATP Binding Cassette Transporter, Subfamily B
  • ATP Binding Cassette Transporter, Subfamily B, Member 1
  • Acridines
  • Antineoplastic Agents
  • Diketopiperazines
  • Heterocyclic Compounds, 4 or More Rings
  • Phenylurea Compounds
  • Protein Kinase Inhibitors
  • Pyridines
  • Tetrahydroisoquinolines
  • regorafenib
  • Elacridar