Pleconaril

drugbox
IUPAC_name = 3-{3,5-dimethyl-4- [3-(3-methylisoxazol-5-yl)propoxy]
phenyl}-5-(trifluoromethyl)-1,2,4-oxadiazole

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CAS_number = 153168-05-09
ATC_prefix = J05
ATC_suffix = AX06
PubChem = 1684
ChemSpiderID = 1621
DrugBank =
C=18|H=18|F=3|N=3|O=3
molecular_weight = 381.35 g/mol
smiles = CC1=CC(=CC(=C1OCCCC2=CC(=NO2)C)C)C3=NOC(=N3)C(F)(F)F
bioavailability = 70% (oral)
protein_bound = >99%
metabolism =
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pregnancy_AU =
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routes_of_administration = Oral, intranasal

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.cite web | url = http://www.clinicaltrials.gov/ct/gui/show/NCT00394914 | title = Effects of Pleconaril Nasal Spray on Common Cold Symptoms and Asthma Exacerbations Following Rhinovirus Exposure (Study P04295AM2) | month = March | year = 2007 | accessdate = 2007-04-10 | publisher = U.S. National Institutes of Health | work = ClinicalTrials.gov] 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" [cite journal |author=Pevear D, Tull T, Seipel M, Groarke J |title=Activity of pleconaril against enteroviruses |journal=Antimicrob Agents Chemother |volume=43 |issue=9 |pages=2109–15 |year=1999 |pmid=10471549] and "Rhinovirus". [cite journal |author=Ronald B. Turner, J. Owen Hendley|title=Virucidal hand treatments for prevention of rhinovirus infection |journal=J Antimicrob Chemother |volume=56 |issue=5 |pages=805–807 |year=2005 |pmid=16159927|doi=10.1093/jac/dki329]

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, and ViroPharma re-licensed it to Schering-Plough in 2003. The Phase II clinical trial was completed in 2007.

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. [cite journal |author=Florea N, Maglio D, Nicolau D |title=Pleconaril, a novel antipicornaviral agent |journal=Pharmacotherapy |volume=23 |issue=3 |pages=339–48 |year=2003 |pmid=12627933 |doi=10.1592/phco.23.3.339.32099 [http://www.medscape.com/viewarticle/451846 Free full text with registration] ]

References