Pleconaril
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| Systematic (IUPAC) name | |
| 3-{3,5-dimethyl-4-[3-(3-methylisoxazol-5-yl)propoxy] phenyl}-5-(trifluoromethyl)-1,2,4-oxadiazole |
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| Clinical data | |
| Pregnancy cat. | ? |
| Legal status | ? |
| Routes | Oral, intranasal |
| Pharmacokinetic data | |
| Bioavailability | 70% (oral) |
| Protein binding | >99% |
| Metabolism | Hepatic |
| Excretion | <1% excreted unchanged in urine |
| Identifiers | |
| CAS number | 153168-05-9  |
| ATC code | J05AX06 |
| PubChem | CID 1684 |
| DrugBank | DB08716 |
| ChemSpider | 1621  |
| UNII | 9H4570Q89D |
| ChEMBL | CHEMBL29609 |
| Chemical data | |
| Formula | C18H18F3N3O3 |
| Mol. mass | 381.35 g/mol |
| SMILES | eMolecules & PubChem |
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Pleconaril is an antiviral drug that was being developed by Schering-Plough for prevention of asthma exacerbations and common cold symptoms in asthmatic subjects exposed to picornavirus respiratory infections.[1] Although the formulation used by Schering-Plough was a nasal spray, pleconaril is orally bioavailable, and is active against viruses in the Picornaviridae family, including Enterovirus[2] and Rhinovirus.[3]
[edit] History
Pleconaril was originally developed by Sanofi-Aventis, and licensed to ViroPharma in 1997. ViroPharma developed it further, and submitted a New Drug Application to the United States Food and Drug Administration (FDA) in 2001. The application was rejected, citing safety concerns; and ViroPharma re-licensed it to Schering-Plough in 2003. The Phase II clinical trial was completed in 2007.[1]
[edit] Mechanism of action
Pleconaril binds to a hydrophobic pocket in VP1, the major protein which comprises the capsid (the outer "shell") of picornaviruses. In enteroviruses, this prevents the virus from exposing its RNA, and in rhinoviruses it also prevents the virus from attaching itself to the host cell.[4]
[edit] References
- ^ a b "Effects of Pleconaril Nasal Spray on Common Cold Symptoms and Asthma Exacerbations Following Rhinovirus Exposure (Study P04295AM2)". ClinicalTrials.gov. U.S. National Institutes of Health. March 2007. http://www.clinicaltrials.gov/ct/gui/show/NCT00394914. Retrieved 2007-04-10.
- ^ Pevear D, Tull T, Seipel M, Groarke J (1999). "Activity of pleconaril against enteroviruses". Antimicrob Agents Chemother 43 (9): 2109–15. PMC 89431. PMID 10471549. http://www.pubmedcentral.nih.gov/articlerender.fcgi?tool=pmcentrez&artid=89431.
- ^ Ronald B. Turner, J. Owen Hendley (2005). "Virucidal hand treatments for prevention of rhinovirus infection". J Antimicrob Chemother 56 (5): 805–807. doi:10.1093/jac/dki329. PMID 16159927.
- ^ Florea N, Maglio D, Nicolau D (2003). "Pleconaril, a novel antipicornaviral agent". Pharmacotherapy 23 (3): 339–48. doi:10.1592/phco.23.3.339.32099. PMID 12627933. Free full text with registration
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