Quantum chemical calculation of intrinsic reaction coordinates from trans to cis structure of fluvoxamine

Kei Odai, Tohru Sugimoto, Etsuro Ito

Research output: Contribution to journalArticlepeer-review

Abstract

Fluvoxamine is a selective serotonin reuptake inhibitor. Its trans-isomer [(E)-isomer] is pharmacologically active, whereas its cis-isomer [(Z)-isomer] loses its activity. It is a pharmaceutical interest whether the structural change from the (E)-isomer to the (Z)-isomer spontaneously occurs in aqueous solutions without ultraviolet (UV) irradiation. In the present study, the transition state of fluvoxamine was determined by quantum chemical calculation using density functional theory (DFT), and the intrinsic reaction coordinates (IRCs) from the (E)-isomer to the (Z)-isomer were calculated using UB3LYP/6-311++G(d,p) with the integral equation formalism-polarizable continuum model (IEF-PCM). The activation energy of isomerization from the (E)-isomer to the (Z)-isomer was estimated to be 55 kcal/mol. Further, the absorption spectra, the nuclear magnetic resonance chemical shift values, the Raman spectra and the infrared spectra were calculated for the (E) and (Z)-isomers obtained from the reaction coordinate calculation, and these results were in good agreement with the experimental values. The geometrical structures of the (E) and (Z)-isomers proposed in the present study can be used as theoretical models of fluvoxamine for molecular dynamics calculations in future.

Original languageEnglish
Article number113051
JournalComputational and Theoretical Chemistry
Volume1192
DOIs
Publication statusPublished - 2020 Dec 15

Keywords

  • DFT
  • Fluvoxamine
  • Intrinsic reaction coordinate
  • Isomerization
  • Transition state

ASJC Scopus subject areas

  • Biochemistry
  • Condensed Matter Physics
  • Physical and Theoretical Chemistry

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