Pleconaril

Pleconaril

File:Pleconaril.svg
Clinical data
Routes of administration	Oral, intranasal
ATC code	J05AX06 (WHO)
Pharmacokinetic data
Bioavailability	70% (oral)
Protein binding	>99%
Identifiers
IUPAC name 3-{3,5-dimethyl-4-[3-(3-methylisoxazol-5-yl)propoxy] phenyl}-5-(trifluoromethyl)-1,2,4-oxadiazole
CAS Number	153168-05-09
PubChem CID	1684
E number	{{#property:P628}}
ECHA InfoCard	{{#property:P2566}}
Chemical and physical data
Formula	C18H18F3N3O3
Molar mass	381.35 g/mol
3D model (JSmol)	Interactive image
SMILES CC1=CC(=CC(=C1OCCCC2=CC(=NO2)C)C)C3=NOC(=N3)C(F)(F)F

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. 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 and Rhinovirus.

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. As of 2007, it is in Phase II clinical trials.

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.