A novel anti-HIV active integrase inhibitor with a favorable in vitro cytochrome P450 and uridine 5'-diphospho-glucuronosyltransferase metabolism profile

Antiviral Res. 2013 Jun;98(3):365-72. doi: 10.1016/j.antiviral.2013.04.005. Epub 2013 Apr 18.

Abstract

Research efforts on the human immunodeficiency virus (HIV) integrase have resulted in two approved drugs. However, co-infection of HIV with Mycobacterium tuberculosis and other microbial and viral agents has introduced added complications to this pandemic, requiring favorable drug-drug interaction profiles for antiviral therapeutics targeting HIV. Cytochrome P450 (CYP) and uridine 5'-diphospho-glucuronosyltransferase (UGT) are pivotal determining factors in the occurrence of adverse drug-drug interactions. For this reason, it is important that anti-HIV agents, such as integrase inhibitors, possess favorable profiles with respect to CYP and UGT. We have discovered a novel HIV integrase inhibitor (compound 1) that exhibits low nM antiviral activity against a diverse set of HIV-1 isolates, and against HIV-2 and the simian immunodeficiency virus (SIV). Compound 1 displays low in vitro cytotoxicity and its resistance and related drug susceptibility profiles are favorable. Data from in vitro studies revealed that compound 1 was not a substrate for UGT isoforms and that it was not an inhibitor or activator of key CYP isozymes.

Publication types

  • Research Support, N.I.H., Extramural
  • Research Support, Non-U.S. Gov't

MeSH terms

  • Cytochrome P-450 Enzyme System / metabolism*
  • Drug Evaluation, Preclinical
  • Drug Resistance, Viral
  • Glucuronosyltransferase / metabolism*
  • HIV Integrase / genetics
  • HIV Integrase / metabolism
  • HIV Integrase Inhibitors / chemical synthesis*
  • HIV Integrase Inhibitors / pharmacology
  • HIV-1 / drug effects*
  • HIV-1 / enzymology
  • HIV-2 / drug effects
  • HIV-2 / metabolism
  • HeLa Cells
  • Humans
  • Isoenzymes / metabolism
  • Leukocytes, Mononuclear / metabolism
  • Leukocytes, Mononuclear / virology
  • Microbial Sensitivity Tests
  • Microsomes, Liver / drug effects
  • Microsomes, Liver / metabolism
  • Molecular Docking Simulation
  • Mutation
  • Pyridines / chemical synthesis*
  • Pyridines / pharmacology
  • Pyrrolidines / chemical synthesis*
  • Pyrrolidines / pharmacology
  • Simian Immunodeficiency Virus / drug effects
  • Simian Immunodeficiency Virus / metabolism

Substances

  • (Z)-4-(5-(2,6-difluorobenzyl)-1-(2-fluorobenzyl)-2-oxo-1,2-dihydropyridin-3-yl)-4-hydroxy-2-oxo-N-(2-oxopyrrolidin-1-yl)but-3-enamide
  • HIV Integrase Inhibitors
  • Isoenzymes
  • Pyridines
  • Pyrrolidines
  • Cytochrome P-450 Enzyme System
  • Glucuronosyltransferase
  • HIV Integrase