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Analysis of the Structural Diversity, Substitution Patterns, and Frequency of Nitrogen Heterocycles among U.S. FDA Approved Pharmaceuticals: Miniperspective

Vitaku, Edon, Smith, David T., Njardarson, Jon T.·2014·Journal of Medicinal Chemistry

Abstract

Nitrogen heterocycles are among the most significant structural components of pharmaceuticals. Analysis of our database of U.S. FDA approved drugs reveals that 59% of unique small-molecule drugs contain a nitrogen heterocycle. In this review we report on the top 25 most commonly utilized nitrogen heterocycles found in pharmaceuticals. The main part of our analysis is divided into seven sections: (1) three- and four-membered heterocycles, (2) five-, (3) six-, and (4) seven- and eight-membered heterocycles, as well as (5) fused, (6) bridged bicyclic, and (7) macrocyclic nitrogen heterocycles. Each section reveals the top nitrogen heterocyclic structures and their relative impact for that ring type. For the most commonly used nitrogen heterocycles, we report detailed substitution patterns, highlight common architectural cores, and discuss unusual or rare structures.

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Metadata

Authors
Vitaku, E., Smith, D. T., & Njardarson, J. T.
Venue
Journal of Medicinal Chemistry
Published
2014-10-07
Volume
57
Issue
24
Pages
10257-10274
ISSN
  • 0022-2623 (ISSN-L)
  • 1520-4804
OpenAlex
W2407040666
Cited by
6,418
References
1
FWCI
154.40
Type
journal article
Language
en
Open access
closed

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Contains information from the Semantic Scholar Academic Graph Datasets, made available under the ODC Attribution License (ODC-BY 1.0).

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