Importance of tautomerism in drugs

Prasad V Bharatam; Omkar R Valanju; Aabid A Wani; Devendra K Dhaked

doi:10.1016/j.drudis.2023.103494

Importance of tautomerism in drugs

Drug Discov Today. 2023 Apr;28(4):103494. doi: 10.1016/j.drudis.2023.103494. Epub 2023 Jan 18.

Authors

Prasad V Bharatam¹, Omkar R Valanju², Aabid A Wani², Devendra K Dhaked³

Affiliations

¹ Department of Medicinal Chemistry, National Institute of Pharmaceutical Education and Research (NIPER), Sector 67, S.A.S. Nagar, Punjab 160062, India. Electronic address: pvbharatam@niper.ac.in.
² Department of Medicinal Chemistry, National Institute of Pharmaceutical Education and Research (NIPER), Sector 67, S.A.S. Nagar, Punjab 160062, India.
³ Department of Pharmacoinformatics, National Institute of Pharmaceutical Education and Research (NIPER)-Kolkata, Chunilal Bhawan, 168 Maniktala Main Road, Kolkata, West Bengal 700054, India.

PMID: 36681235
DOI: 10.1016/j.drudis.2023.103494

Abstract

Tautomerism is an important phenomenon exhibited by many drugs. As we discuss in this review, identifying the different tautomers of drugs and exploring their importance in the mechanisms of drug action are integral components of current drug discovery. Nuclear magnetic resonance (NMR), infrared (IR), ultraviolet (UV), Raman, and terahertz spectroscopic techniques, as well as X-ray diffraction, are useful for exploring drug tautomerism. Quantum chemical methods, in association with pharmacoinformatics tools, are being used to evaluate tautomeric preferences in terms of energy effects. Desmotropy (i.e., tautomeric polymorphism) of the drugs is particularly important in drug delivery studies.

Keywords: CADD; NMR; desmotropy; polymorphism; quantum chemical studies; tautomerism.

Publication types

Review
Research Support, Non-U.S. Gov't

MeSH terms

Magnetic Resonance Spectroscopy
Pharmaceutical Preparations*

Substances

Pharmaceutical Preparations