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Details

Stereochemistry ACHIRAL
Molecular Formula C18H18F3N3O3
Molecular Weight 381.349
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of PLECONARIL

SMILES

CC1=NOC(CCCOC2=C(C)C=C(C=C2C)C3=NOC(=N3)C(F)(F)F)=C1

InChI

InChIKey=KQOXLKOJHVFTRN-UHFFFAOYSA-N
InChI=1S/C18H18F3N3O3/c1-10-7-13(16-22-17(27-24-16)18(19,20)21)8-11(2)15(10)25-6-4-5-14-9-12(3)23-26-14/h7-9H,4-6H2,1-3H3

HIDE SMILES / InChI

Molecular Formula C18H18F3N3O3
Molecular Weight 381.349
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Description
Curator's Comment: The description was created based on several sources, including https://www.drugbank.ca/drugs/DB05105 | https://www.ncbi.nlm.nih.gov/pubmed/26169596

Pleconaril (Picovir) is an antiviral drug that was being developed by Schering-Plough for prevention of asthma exacerbations and common cold symptoms in patients exposed to picornavirus respiratory infections. Pleconaril binds to a hydrophobic pocket in viral protein 1, 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. The results of two randomized, double-blind, placebo studies found Pleconaril treatment could benefit patients suffering from colds due to picornaviruses. Participants in the studies were healthy adults from Canada and the United States, with self-diagnosed colds that had occurred within 24 hours of trial enrollment. Participants were randomly given a placebo or two 200 mg tablets to take three times daily for five days. To increase absorption it was recommended to be taken after a meal. To monitor the effectiveness of Pleconaril, Participants recorded the severity of their symptoms and nasal mucosal samples were obtained at enrollment, day 3, day 6 and day 18. The two studies had a total of 2096 participates and more than 90% (1945) completed the trial. The most common reason for a participant not finishing the trial was an adverse event. Pleconaril treatment showed a reduction in nose blowing, sleep disturbance, and less cold medication used. The U.S. Food and Drug Administration rejected pleconaril in 2002 due to the side effects. The most commonly reported side effects were mild to a moderate headache, diarrhea, and nausea.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Target ID: P03303|||Q84741|||Q89649
Gene ID: 1461213.0
Gene Symbol: NA
Target Organism: Human rhinovirus 14 (HRV-14)
58.0 nM [EC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown

Approved Use

Unknown
Primary
Unknown

Approved Use

Unknown
Curative
Unknown

Approved Use

Unknown
Curative
Unknown

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
Structure-based design, synthesis, and biological evaluation of irreversible human rhinovirus 3C protease inhibitors. 4. Incorporation of P1 lactam moieties as L-glutamine replacements.
1999 Apr 8
In vitro antiviral activity of AG7088, a potent inhibitor of human rhinovirus 3C protease.
1999 Oct
Antiviral agents for influenza, hepatitis C and herpesvirus, enterovirus and rhinovirus infections.
2001 Jul 16
Recent advances in the treatment of rhinovirus infections.
2001 Oct
Acute flaccid paralysis syndrome associated with echovirus 19, managed with pleconaril and intravenous immunoglobulin.
2001 Sep 1
Highlights in the development of new antiviral agents.
2002 Apr
Cold comfort.
2002 Jul
Severe Coxsackie virus B infection in preterm newborns treated with pleconaril.
2002 Sep
SPECT scans for monitoring response to pleconaril therapy in chronic enteroviral meningoencephalitis.
2003 Feb
Enteroviral infections in primary immunodeficiency (PID): a survey of morbidity and mortality.
2003 Jan
Efficacy and safety of oral pleconaril for treatment of colds due to picornaviruses in adults: results of 2 double-blind, randomized, placebo-controlled trials.
2003 Jun 15
Survival after pulmonary edema due to enterovirus 71 encephalitis.
2003 May 27
Gateways to clinical trials.
2003 Oct
Human rhinovirus capsid dynamics is controlled by canyon flexibility.
2003 Sep 15
Pleconaril--an advance in the treatment of enteroviral infection in immuno-compromised patients.
2005 Jan
[Rhinovirus diseases: pathogenesis, diagnostics and treatment].
2005 Sep-Oct
Current status of anti-picornavirus therapies.
2006
Gateways to clinical trials.
2006 Dec
Fatal coxsackievirus A-16 pneumonitis in adult.
2007 Jul
A case report of a premature infant with coxsackie B1 meningitis.
2007 Oct
Distinguishing molecular features and clinical characteristics of a putative new rhinovirus species, human rhinovirus C (HRV C).
2008 Apr 2
Selective inhibitors of picornavirus replication.
2008 Nov
MicroRNA antagonism of the picornaviral life cycle: alternative mechanisms of interference.
2010 Mar 19
Patents

Patents

Sample Use Guides

200 mg TID or 400 mg TID for 7 days
Route of Administration: Oral
Pleconaril’s antiviral activity was determined in a multicycle, virus-cell-based cytopathic effect (CPE) reduction assay in HeLa cells. The compound proved to be active against HRV strains from both the HRV-A (HRV09, HRV29, HRV85 and HRV89) and HRV-B group (HRV14, HRV70, and HRV86) with a 50 % effective concentrations (EC50’s) ranging from 0.01 μM to 15 μM.
Substance Class Chemical
Created
by admin
on Fri Dec 15 15:40:27 UTC 2023
Edited
by admin
on Fri Dec 15 15:40:27 UTC 2023
Record UNII
9H4570Q89D
Record Status Validated (UNII)
Record Version
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Name Type Language
PLECONARIL
INN   MART.   MI   USAN   WHO-DD  
INN   USAN  
Official Name English
PLECONARIL [MI]
Common Name English
pleconaril [INN]
Common Name English
VP-63843
Code English
VP63843
Code English
WIN63843
Code English
Pleconaril [WHO-DD]
Common Name English
PLECONARIL [MART.]
Common Name English
WIN-63843
Code English
PLECONARIL [USAN]
Common Name English
3-(4-(3-(3-METHYL-5-ISOXAZOLYL)PROPOXY)-3,5-XYLYL)-5-TRIFLUOROMETHYL)-1,2,4-OXADIZOLE
Common Name English
Classification Tree Code System Code
WHO-ATC J05AX06
Created by admin on Fri Dec 15 15:40:27 UTC 2023 , Edited by admin on Fri Dec 15 15:40:27 UTC 2023
NCI_THESAURUS C281
Created by admin on Fri Dec 15 15:40:27 UTC 2023 , Edited by admin on Fri Dec 15 15:40:27 UTC 2023
WHO-VATC QJ05AX06
Created by admin on Fri Dec 15 15:40:27 UTC 2023 , Edited by admin on Fri Dec 15 15:40:27 UTC 2023
FDA ORPHAN DRUG 457214
Created by admin on Fri Dec 15 15:40:27 UTC 2023 , Edited by admin on Fri Dec 15 15:40:27 UTC 2023
Code System Code Type Description
USAN
II-65
Created by admin on Fri Dec 15 15:40:27 UTC 2023 , Edited by admin on Fri Dec 15 15:40:27 UTC 2023
PRIMARY
DRUG CENTRAL
4690
Created by admin on Fri Dec 15 15:40:27 UTC 2023 , Edited by admin on Fri Dec 15 15:40:27 UTC 2023
PRIMARY
PUBCHEM
1684
Created by admin on Fri Dec 15 15:40:27 UTC 2023 , Edited by admin on Fri Dec 15 15:40:27 UTC 2023
PRIMARY
MERCK INDEX
m8918
Created by admin on Fri Dec 15 15:40:27 UTC 2023 , Edited by admin on Fri Dec 15 15:40:27 UTC 2023
PRIMARY Merck Index
NCI_THESAURUS
C81604
Created by admin on Fri Dec 15 15:40:27 UTC 2023 , Edited by admin on Fri Dec 15 15:40:27 UTC 2023
PRIMARY
CAS
153168-05-9
Created by admin on Fri Dec 15 15:40:27 UTC 2023 , Edited by admin on Fri Dec 15 15:40:27 UTC 2023
PRIMARY
DRUG BANK
DB05105
Created by admin on Fri Dec 15 15:40:27 UTC 2023 , Edited by admin on Fri Dec 15 15:40:27 UTC 2023
PRIMARY
MESH
C115201
Created by admin on Fri Dec 15 15:40:27 UTC 2023 , Edited by admin on Fri Dec 15 15:40:27 UTC 2023
PRIMARY
EPA CompTox
DTXSID8057649
Created by admin on Fri Dec 15 15:40:27 UTC 2023 , Edited by admin on Fri Dec 15 15:40:27 UTC 2023
PRIMARY
FDA UNII
9H4570Q89D
Created by admin on Fri Dec 15 15:40:27 UTC 2023 , Edited by admin on Fri Dec 15 15:40:27 UTC 2023
PRIMARY
EVMPD
SUB09957MIG
Created by admin on Fri Dec 15 15:40:27 UTC 2023 , Edited by admin on Fri Dec 15 15:40:27 UTC 2023
PRIMARY
SMS_ID
100000081912
Created by admin on Fri Dec 15 15:40:27 UTC 2023 , Edited by admin on Fri Dec 15 15:40:27 UTC 2023
PRIMARY
INN
7617
Created by admin on Fri Dec 15 15:40:27 UTC 2023 , Edited by admin on Fri Dec 15 15:40:27 UTC 2023
PRIMARY
ChEMBL
CHEMBL29609
Created by admin on Fri Dec 15 15:40:27 UTC 2023 , Edited by admin on Fri Dec 15 15:40:27 UTC 2023
PRIMARY
WIKIPEDIA
PLECONARIL
Created by admin on Fri Dec 15 15:40:27 UTC 2023 , Edited by admin on Fri Dec 15 15:40:27 UTC 2023
PRIMARY
Related Record Type Details
ACTIVE MOIETY