The DOI matches its Crossref record; 242 of the 242 references it cites were found in a registry or an index.
Metabolic and Pharmaceutical Aspects of Fluorinated Compounds
Open accessAbstract
The applications of fluorine in drug design continue to expand, facilitated by an improved understanding of its effects on physicochemical properties and the development of synthetic methodologies that are providing access to new fluorinated motifs. In turn, studies of fluorinated molecules are providing deeper insights into the effects of fluorine on metabolic pathways, distribution, and disposition. Despite the high strength of the C-F bond, the departure of fluoride from metabolic intermediates can be facile. This reactivity has been leveraged in the design of mechanism-based enzyme inhibitors and has influenced the metabolic fate of fluorinated compounds. In this Perspective, we summarize the literature associated with the metabolism of fluorinated molecules, focusing on examples where the presence of fluorine influences the metabolic profile. These studies have revealed potentially problematic outcomes with some fluorinated motifs and are enhancing our understanding of how fluorine should be deployed.
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1 retracted
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RetractedFluorine in Pharmaceuticals: Looking Beyond Intuition
Müller, K., Faeh, C., & Diederich, F. (2007) · Science · doi:10.1126/science.1131943 · Cited by 6,596
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O'Hagan, D. (2008) · Chem. Soc. Rev. · doi:10.1039/b711844a · Cited by 4,045
Applications of Fluorine in Medicinal Chemistry
Gillis, E. P., Eastman, K. J., Hill, M. D., Donnelly, D. J., & Meanwell, N. A. (2015) · Journal of Medicinal Chemistry · doi:10.1021/acs.jmedchem.5b00258 · Cited by 3,618
Self-citationThe Many Roles for Fluorine in Medicinal Chemistry
Hagmann, W. K. (2008) · Journal of Medicinal Chemistry · doi:10.1021/jm800219f · Cited by 3,578
Bond Dissociation Energies of Organic Molecules
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Fluorine and Fluorinated Motifs in the Design and Application of Bioisosteres for Drug Design
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Self-citationIntroduction of Fluorine and Fluorine‐Containing Functional Groups
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Cited by
U.S. FDA Approved Drugs from 2015–June 2020: A Perspective
Bhutani, P., Joshi, G., Raja, N., Bachhav, N., Rajanna, P. K., Bhutani, H., Paul, A. T., & Kumar, R. (2021) · Journal of Medicinal Chemistry · doi:10.1021/acs.jmedchem.0c01786 · Cited by 815
Dekant, W., & Dekant, R. (2023) · Archives of Toxicology · doi:10.1007/s00204-023-03454-y · Cited by 55
Yue, Y., Fan, J., Xin, G., Huang, Q., Wang, J.-B., Li, Y., Zhang, Q., & Wang, W. (2021) · Environmental Science & Technology · doi:10.1021/acs.est.0c08811 · Cited by 50
Metadata
- Authors
- Johnson, B. M., Shu, Y.-Z., Zhuo, X., & Meanwell, N. A.
- Venue
- Journal of Medicinal Chemistry
- Publisher
- American Chemical Society (ACS)
- Published
- 2020-03-17
- Volume
- 63
- Issue
- 12
- Pages
- 6315-6386
- ISSN
- 0022-2623 (ISSN-L)
- 1520-4804
- OpenAlex
- W3011890716
- Cited by
- 719
- References
- 242
- FWCI
- 68.14
- Type
- journal article
- Language
- en
- Open access
- green
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Bibliographic data: Semantic Scholar, OpenAlex, Crossref.
Contains information from the Semantic Scholar Academic Graph Datasets, made available under the ODC Attribution License (ODC-BY 1.0).
Semantic Scholar’s data is described in: Kinney, R., et al. (2023). The Semantic Scholar Open Data Platform. arXiv:2301.10140.
