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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
In vitro antiviral activity of AG7088, a potent inhibitor of human rhinovirus 3C protease.
1999 Oct
In vitro activity of pleconaril and AG7088 against selected serotypes and clinical isolates of human rhinoviruses.
2000 Sep
Gateways to Clinical Trials.
2002 Apr
Design, synthesis, and structure-activity relationship of pyridyl imidazolidinones: a novel class of potent and selective human enterovirus 71 inhibitors.
2002 Apr 11
Enterovirus infections: diagnosis and treatment.
2002 Jan
Management of viral infections in immunocompromised cancer patients.
2002 Jul 13
Severe Coxsackie virus B infection in preterm newborns treated with pleconaril.
2002 Sep
Double blind placebo-controlled trial of pleconaril in infants with enterovirus meningitis.
2003 Apr
SPECT scans for monitoring response to pleconaril therapy in chronic enteroviral meningoencephalitis.
2003 Feb
A fatal case of coxsackievirus B4 meningoencephalitis.
2003 Jan
Enteroviral infections in primary immunodeficiency (PID): a survey of morbidity and mortality.
2003 Jan
Gateways to clinical trials.
2003 Jun
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
Pleconaril, a novel antipicornaviral agent.
2003 Mar
Diagnosis and treatment of rhinovirus respiratory infections.
2003 May
Nucleotide variation in Sabin type 2 poliovirus from an immunodeficient patient with poliomyelitis.
2003 May
Survival after pulmonary edema due to enterovirus 71 encephalitis.
2003 May 27
Gateways to clinical trials.
2003 Oct
Neonatal coxsackie B virus infection-a treatable disease?
2004 Apr
Failure to clear persistent vaccine-derived neurovirulent poliovirus infection in an immunodeficient man.
2004 May 8
Gateways to clinical trials.
2006 Dec
The effect of oral pleconaril on hepatic cytochrome P450 3A activity in healthy adults using intravenous midazolam as a probe.
2006 Jan
Investigation of treatment failure in neonatal echovirus 7 infection.
2006 Mar
Antiviral treatment of Coxsackie B virus infection in human pancreatic islets.
2007 Apr
Enteroviral infections in children with malignant disease: a 5-year study in a single institution.
2007 Apr
A case report of a premature infant with coxsackie B1 meningitis.
2007 Oct
Enterovirus-associated hemophagocytic syndrome in children with malignancy: report of three cases and review of the literature.
2008 Jan
Limited duration of vaccine poliovirus and other enterovirus excretion among human immunodeficiency virus infected children in Kenya.
2009 Aug 23
Human rhinovirus C: a newly discovered human rhinovirus species.
2010
Clinical features, diagnosis, and management of enterovirus 71.
2010 Nov
An RNA replication-center assay for high content image-based quantifications of human rhinovirus and coxsackievirus infections.
2010 Oct 11
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 GMT 2023
Edited
by admin
on Fri Dec 15 15:40:27 GMT 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 GMT 2023 , Edited by admin on Fri Dec 15 15:40:27 GMT 2023
NCI_THESAURUS C281
Created by admin on Fri Dec 15 15:40:27 GMT 2023 , Edited by admin on Fri Dec 15 15:40:27 GMT 2023
WHO-VATC QJ05AX06
Created by admin on Fri Dec 15 15:40:27 GMT 2023 , Edited by admin on Fri Dec 15 15:40:27 GMT 2023
FDA ORPHAN DRUG 457214
Created by admin on Fri Dec 15 15:40:27 GMT 2023 , Edited by admin on Fri Dec 15 15:40:27 GMT 2023
Code System Code Type Description
USAN
II-65
Created by admin on Fri Dec 15 15:40:27 GMT 2023 , Edited by admin on Fri Dec 15 15:40:27 GMT 2023
PRIMARY
DRUG CENTRAL
4690
Created by admin on Fri Dec 15 15:40:27 GMT 2023 , Edited by admin on Fri Dec 15 15:40:27 GMT 2023
PRIMARY
PUBCHEM
1684
Created by admin on Fri Dec 15 15:40:27 GMT 2023 , Edited by admin on Fri Dec 15 15:40:27 GMT 2023
PRIMARY
MERCK INDEX
m8918
Created by admin on Fri Dec 15 15:40:27 GMT 2023 , Edited by admin on Fri Dec 15 15:40:27 GMT 2023
PRIMARY Merck Index
NCI_THESAURUS
C81604
Created by admin on Fri Dec 15 15:40:27 GMT 2023 , Edited by admin on Fri Dec 15 15:40:27 GMT 2023
PRIMARY
CAS
153168-05-9
Created by admin on Fri Dec 15 15:40:27 GMT 2023 , Edited by admin on Fri Dec 15 15:40:27 GMT 2023
PRIMARY
DRUG BANK
DB05105
Created by admin on Fri Dec 15 15:40:27 GMT 2023 , Edited by admin on Fri Dec 15 15:40:27 GMT 2023
PRIMARY
MESH
C115201
Created by admin on Fri Dec 15 15:40:27 GMT 2023 , Edited by admin on Fri Dec 15 15:40:27 GMT 2023
PRIMARY
EPA CompTox
DTXSID8057649
Created by admin on Fri Dec 15 15:40:27 GMT 2023 , Edited by admin on Fri Dec 15 15:40:27 GMT 2023
PRIMARY
FDA UNII
9H4570Q89D
Created by admin on Fri Dec 15 15:40:27 GMT 2023 , Edited by admin on Fri Dec 15 15:40:27 GMT 2023
PRIMARY
EVMPD
SUB09957MIG
Created by admin on Fri Dec 15 15:40:27 GMT 2023 , Edited by admin on Fri Dec 15 15:40:27 GMT 2023
PRIMARY
SMS_ID
100000081912
Created by admin on Fri Dec 15 15:40:27 GMT 2023 , Edited by admin on Fri Dec 15 15:40:27 GMT 2023
PRIMARY
INN
7617
Created by admin on Fri Dec 15 15:40:27 GMT 2023 , Edited by admin on Fri Dec 15 15:40:27 GMT 2023
PRIMARY
ChEMBL
CHEMBL29609
Created by admin on Fri Dec 15 15:40:27 GMT 2023 , Edited by admin on Fri Dec 15 15:40:27 GMT 2023
PRIMARY
WIKIPEDIA
PLECONARIL
Created by admin on Fri Dec 15 15:40:27 GMT 2023 , Edited by admin on Fri Dec 15 15:40:27 GMT 2023
PRIMARY
Related Record Type Details
ACTIVE MOIETY