The DOI matches its Crossref record; 3 of the 3 references it cites were found in a registry or an index.
Macrocyclic Drugs and Clinical Candidates: What Can Medicinal Chemists Learn from Their Properties?
Abstract
Macrocycles are ideal in efforts to tackle "difficult" targets, but our understanding of what makes them cell permeable and orally bioavailable is limited. Analysis of approximately 100 macrocyclic drugs and clinical candidates revealed that macrocycles are predominantly used for infectious disease and in oncology and that most belong to the macrolide or cyclic peptide class. A significant number (N = 34) of these macrocycles are administered orally, revealing that oral bioavailability can be obtained at molecular weights up to and above 1 kDa and polar surface areas ranging toward 250 Å(2). Moreover, insight from a group of "de novo designed" oral macrocycles in clinical studies and understanding of how cyclosporin A and model cyclic hexapeptides cross cell membranes may unlock wider opportunities in drug discovery. However, the number of oral macrocycles is still low and it remains to be seen if they are outliers or if macrocycles will open up novel oral druggable space.
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Cites
Molecular properties that influence the oral bioavailability of drug candidates
Veber, D. F., Johnson, S. R., Cheng, H.-Y., Smith, B. R., Ward, K. W., & Kopple, K. D. (2002) · Journal of Medicinal Chemistry · doi:10.1021/jm020017n · Cited by 8,420
Diagnosing the decline in pharmaceutical R&D efficiency
Scannell, J. W., Blanckley, A., Boldon, H., & Warrington, B. (2012) · Nature Reviews Drug Discovery · doi:10.1038/nrd3681 · Cited by 1,981
Structural Biology and Drug Discovery of Difficult Targets: The Limits of Ligandability
Surade, S., & Blundell, T. L. (2012) · Chemistry & Biology · doi:10.1016/j.chembiol.2011.12.013 · Cited by 230
Cited by
Counting on natural products for drug design
Rodrigues, T., Reker, D., Schneider, P., & Schneider, G. (2016) · Nature Chemistry · doi:10.1038/nchem.2479 · Cited by 1,250
Oral Druggable Space beyond the Rule of 5: Insights from Drugs and Clinical Candidates
Doak, B. C., Over, B., Giordanetto, F., & Kihlberg, J. (2014) · Chemistry & Biology · doi:10.1016/j.chembiol.2014.08.013 · Cited by 835
Self-citationA Survey of the Role of Noncovalent Sulfur Interactions in Drug Design
Beno, B. R., Yeung, K.-S., Bartberger, M. D., Pennington, L. D., & Meanwell, N. A. (2015) · Journal of Medicinal Chemistry · doi:10.1021/jm501853m · Cited by 772
Johnson, T. W., Richardson, P. F., Bailey, S., Brooun, A., Burke, B. J., Collins, M. R., Cui, J. J., Deal, J. G., Deng, Y.-L., Dinh, D., et al. (2014) · Journal of Medicinal Chemistry · doi:10.1021/jm500261q · Cited by 594
Theranostic Fluorescent Probes
Sharma, A., Verwilst, P., Li, M., Ma, D., Singh, N., Yoo, J., Kim, Y., Yang, Y., Zhu, J.-H., Huang, H., et al. (2024) · Chemical Reviews · doi:10.1021/acs.chemrev.3c00778 · Cited by 499
Metadata
- Authors
- Giordanetto, F., & Kihlberg, J.
- Venue
- Journal of Medicinal Chemistry
- Publisher
- American Chemical Society (ACS)
- Published
- 2013-09-17
- Volume
- 57
- Issue
- 2
- Pages
- 278-295
- ISSN
- 0022-2623 (ISSN-L)
- 1520-4804
- OpenAlex
- W1968711897
- Cited by
- 563
- References
- 3
- FWCI
- 19.10
- Type
- journal article
- Language
- en
- Open access
- closed
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