Pleconaril
File:Pleconaril.svg | |
Systematic (IUPAC) name | |
---|---|
3-{3,5-dimethyl-4-[3-(3-methylisoxazol-5-yl)propoxy] phenyl}-5-(trifluoromethyl)-1,2,4-oxadiazole | |
Clinical data | |
Routes of administration | 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 (WHO) |
PubChem | CID 1684 |
ChemSpider | 1621 |
Chemical data | |
Formula | C18H18F3N3O3 |
Molar mass | 381.35 g/mol[[Script error: No such module "String".]] |
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Pleconaril is an antiviral drug 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 is a nasal spray, pleconaril is orally bioavailable, and is active against viruses in the Picornaviridae family, including Enterovirus[2] and Rhinovirus.[3]
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]
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]
References
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- ↑ Pevear D, Tull T, Seipel M, Groarke J (1999). "Activity of pleconaril against enteroviruses". Antimicrob Agents Chemother. 43 (9): 2109–15. PMC 89431 Freely accessible. PMID 10471549.
- ↑ 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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