U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

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

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
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
0.3 mg/L
50 mg single, oral
dose: 50 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
PLECONARIL plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FED
0.44 mg/L
100 mg single, oral
dose: 100 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
PLECONARIL plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FED
1.66 mg/L
200 mg single, oral
dose: 200 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
PLECONARIL plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FED
2.03 mg/L
400 mg single, oral
dose: 400 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
PLECONARIL plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FED
3.39 mg/L
600 mg single, oral
dose: 600 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
PLECONARIL plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FED
4.3 mg/L
800 mg single, oral
dose: 800 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
PLECONARIL plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FED
5.25 mg/L
1000 mg single, oral
dose: 1000 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
PLECONARIL plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FED
1.14 mg/L
200 mg single, oral
dose: 200 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
PLECONARIL plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FED
0.46 mg/L
200 mg single, oral
dose: 200 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
PLECONARIL plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FASTED
1272.5 ng/mL
5 mg/kg single, oral
dose: 5 mg/kg
route of administration: Oral
experiment type: SINGLE
co-administered:
PLECONARIL plasma
Homo sapiens
population: UNHEALTHY
age: CHILD
sex: FEMALE / MALE
food status: FED
836 ng/mL
8.5 mg/kg 3 times / day steady-state, oral
dose: 8.5 mg/kg
route of administration: Oral
experiment type: STEADY-STATE
co-administered:
PLECONARIL plasma
Homo sapiens
population: UNHEALTHY
age: NEWBORN
sex: FEMALE / MALE
food status: UNKNOWN
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
3.2 mg × h/mL
50 mg single, oral
dose: 50 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
PLECONARIL plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FED
3.67 mg × h/mL
100 mg single, oral
dose: 100 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
PLECONARIL plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FED
8.76 mg × h/mL
200 mg single, oral
dose: 200 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
PLECONARIL plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FED
16.21 mg × h/mL
400 mg single, oral
dose: 400 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
PLECONARIL plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FED
19.11 mg × h/mL
600 mg single, oral
dose: 600 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
PLECONARIL plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FED
31.14 mg × h/mL
800 mg single, oral
dose: 800 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
PLECONARIL plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FED
49.3 mg × h/mL
1000 mg single, oral
dose: 1000 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
PLECONARIL plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FED
9.08 mg × h/L
200 mg single, oral
dose: 200 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
PLECONARIL plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FED
4.08 mg × h/L
200 mg single, oral
dose: 200 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
PLECONARIL plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FASTED
8131.2 ng × h/mL
5 mg/kg single, oral
dose: 5 mg/kg
route of administration: Oral
experiment type: SINGLE
co-administered:
PLECONARIL plasma
Homo sapiens
population: UNHEALTHY
age: CHILD
sex: FEMALE / MALE
food status: FED
6824 ng × h/mL
8.5 mg/kg 3 times / day steady-state, oral
dose: 8.5 mg/kg
route of administration: Oral
experiment type: STEADY-STATE
co-administered:
PLECONARIL plasma
Homo sapiens
population: UNHEALTHY
age: NEWBORN
sex: FEMALE / MALE
food status: UNKNOWN
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
34 h
50 mg single, oral
dose: 50 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
PLECONARIL plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FED
18 h
100 mg single, oral
dose: 100 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
PLECONARIL plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FED
19.9 h
200 mg single, oral
dose: 200 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
PLECONARIL plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FED
35.2 h
400 mg single, oral
dose: 400 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
PLECONARIL plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FED
22.3 h
600 mg single, oral
dose: 600 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
PLECONARIL plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FED
28.2 h
800 mg single, oral
dose: 800 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
PLECONARIL plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FED
27 h
1000 mg single, oral
dose: 1000 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
PLECONARIL plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FED
6.74 h
200 mg single, oral
dose: 200 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
PLECONARIL plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FED
4.38 h
200 mg single, oral
dose: 200 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
PLECONARIL plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FASTED
5.7 h
5 mg/kg single, oral
dose: 5 mg/kg
route of administration: Oral
experiment type: SINGLE
co-administered:
PLECONARIL plasma
Homo sapiens
population: UNHEALTHY
age: CHILD
sex: FEMALE / MALE
food status: FED
22.8 h
8.5 mg/kg 3 times / day steady-state, oral
dose: 8.5 mg/kg
route of administration: Oral
experiment type: STEADY-STATE
co-administered:
PLECONARIL plasma
Homo sapiens
population: UNHEALTHY
age: NEWBORN
sex: FEMALE / MALE
food status: UNKNOWN
Funbound

Funbound

ValueDoseCo-administeredAnalytePopulation
1%
PLECONARIL unknown
Homo sapiens
Doses

Doses

DosePopulationAdverse events​
1000 mg single, oral
Highest studied dose
Dose: 1000 mg
Route: oral
Route: single
Dose: 1000 mg
Sources:
healthy, ADULT
Health Status: healthy
Age Group: ADULT
Sex: M
Food Status: FED
Sources:
Other AEs: Syncope...
Other AEs:
Syncope (grade 1, 12.5%)
Sources:
400 mg 3 times / day multiple, oral
Highest studied dose
Dose: 400 mg, 3 times / day
Route: oral
Route: multiple
Dose: 400 mg, 3 times / day
Sources:
unhealthy, ADULT
Health Status: unhealthy
Age Group: ADULT
Sex: M+F
Food Status: FED
Sources:
Other AEs: Headache, Diarrhea...
Other AEs:
Headache (grade 1-2, 22%)
Diarrhea (grade 1-2, 9%)
Nausea (grade 1-2, 6%)
Bronchitis (grade 1-2, 3%)
Rhinitis (grade 1-2, 2%)
Sinusitis (grade 1-2, 3%)
Sources:
AEs

AEs

AESignificanceDosePopulation
Syncope grade 1, 12.5%
1000 mg single, oral
Highest studied dose
Dose: 1000 mg
Route: oral
Route: single
Dose: 1000 mg
Sources:
healthy, ADULT
Health Status: healthy
Age Group: ADULT
Sex: M
Food Status: FED
Sources:
Rhinitis grade 1-2, 2%
400 mg 3 times / day multiple, oral
Highest studied dose
Dose: 400 mg, 3 times / day
Route: oral
Route: multiple
Dose: 400 mg, 3 times / day
Sources:
unhealthy, ADULT
Health Status: unhealthy
Age Group: ADULT
Sex: M+F
Food Status: FED
Sources:
Headache grade 1-2, 22%
400 mg 3 times / day multiple, oral
Highest studied dose
Dose: 400 mg, 3 times / day
Route: oral
Route: multiple
Dose: 400 mg, 3 times / day
Sources:
unhealthy, ADULT
Health Status: unhealthy
Age Group: ADULT
Sex: M+F
Food Status: FED
Sources:
Bronchitis grade 1-2, 3%
400 mg 3 times / day multiple, oral
Highest studied dose
Dose: 400 mg, 3 times / day
Route: oral
Route: multiple
Dose: 400 mg, 3 times / day
Sources:
unhealthy, ADULT
Health Status: unhealthy
Age Group: ADULT
Sex: M+F
Food Status: FED
Sources:
Sinusitis grade 1-2, 3%
400 mg 3 times / day multiple, oral
Highest studied dose
Dose: 400 mg, 3 times / day
Route: oral
Route: multiple
Dose: 400 mg, 3 times / day
Sources:
unhealthy, ADULT
Health Status: unhealthy
Age Group: ADULT
Sex: M+F
Food Status: FED
Sources:
Nausea grade 1-2, 6%
400 mg 3 times / day multiple, oral
Highest studied dose
Dose: 400 mg, 3 times / day
Route: oral
Route: multiple
Dose: 400 mg, 3 times / day
Sources:
unhealthy, ADULT
Health Status: unhealthy
Age Group: ADULT
Sex: M+F
Food Status: FED
Sources:
Diarrhea grade 1-2, 9%
400 mg 3 times / day multiple, oral
Highest studied dose
Dose: 400 mg, 3 times / day
Route: oral
Route: multiple
Dose: 400 mg, 3 times / day
Sources:
unhealthy, ADULT
Health Status: unhealthy
Age Group: ADULT
Sex: M+F
Food Status: FED
Sources:
PubMed

PubMed

TitleDatePubMed
The need for treatment against human parechoviruses: how, why and when?
2010-12
Assessment of oral midazolam limited sampling strategies to predict area under the concentration time curve (AUC) during cytochrome P450 (CYP) 3A baseline, inhibition and induction or activation.
2010-12
Clinical features, diagnosis, and management of enterovirus 71.
2010-11
An RNA replication-center assay for high content image-based quantifications of human rhinovirus and coxsackievirus infections.
2010-10-11
Viral meningoencephalitis: a review of diagnostic methods and guidelines for management.
2010-08
Enterovirus genotype EV-104 in humans, Italy, 2008-2009.
2010-06
Rhinovirus genome evolution during experimental human infection.
2010-05-11
Enterovirus 71 infection: An experience in Korea, 2009.
2010-05
Anti-human rhinovirus activity of raoulic acid from Raoulia australis.
2010-04
MicroRNA antagonism of the picornaviral life cycle: alternative mechanisms of interference.
2010-03-19
Human rhinovirus C: a newly discovered human rhinovirus species.
2010
Antiviral treatments reduce severity of diabetes in Ljungan virus-infected CD-1 mice and delay onset in diabetes-prone BB rats.
2009-10
Role of rhinovirus C in apparently life-threatening events in infants, Spain.
2009-09
Limited duration of vaccine poliovirus and other enterovirus excretion among human immunodeficiency virus infected children in Kenya.
2009-08-23
New perspectives of infections in cardiovascular disease.
2009-05
New pleconaril and [(biphenyloxy)propyl]isoxazole derivatives with substitutions in the central ring exhibit antiviral activity against pleconaril-resistant coxsackievirus B3.
2009-01
Frequency and clinical relevance of human bocavirus infection in acute exacerbations of chronic obstructive pulmonary disease.
2009
Novel human rhinoviruses and exacerbation of asthma in children.
2008-11
Selective inhibitors of picornavirus replication.
2008-11
Iota-Carrageenan is a potent inhibitor of rhinovirus infection.
2008-09-26
Distinguishing molecular features and clinical characteristics of a putative new rhinovirus species, human rhinovirus C (HRV C).
2008-04-02
Potential use of antiviral agents in polio eradication.
2008-04
Treatment of viral myocarditis caused by coxsackievirus B.
2008-01-15
Enterovirus-associated hemophagocytic syndrome in children with malignancy: report of three cases and review of the literature.
2008-01
A case report of a premature infant with coxsackie B1 meningitis.
2007-10
WITHDRAWN: Antivirals for the common cold.
2007-07-18
Fatal coxsackievirus A-16 pneumonitis in adult.
2007-07
Sufficiently important difference for common cold: severity reduction.
2007-06-06
Characterisation of a newly identified human rhinovirus, HRV-QPM, discovered in infants with bronchiolitis.
2007-06
Genome-wide diversity and selective pressure in the human rhinovirus.
2007-05-03
Antiviral treatment of Coxsackie B virus infection in human pancreatic islets.
2007-04
Enteroviral infections in children with malignant disease: a 5-year study in a single institution.
2007-04
Gateways to clinical trials.
2006-12
An experimental model of rhinovirus induced chronic obstructive pulmonary disease exacerbations: a pilot study.
2006-09-06
Gateways to clinical trials.
2006-06
Duration of pleconaril effect on cytochrome P450 3A activity in healthy adults using the oral biomarker midazolam.
2006-05
Investigation of treatment failure in neonatal echovirus 7 infection.
2006-03
The effect of oral pleconaril on hepatic cytochrome P450 3A activity in healthy adults using intravenous midazolam as a probe.
2006-01
Current status of anti-picornavirus therapies.
2006
Insights into the genetic basis for natural phenotypic resistance of human rhinoviruses to pleconaril.
2005-12
[Rhinovirus diseases: pathogenesis, diagnostics and treatment].
2005-11-11
Susceptibility of coxsackievirus B3 laboratory strains and clinical isolates to the capsid function inhibitor pleconaril: antiviral studies with virus chimeras demonstrate the crucial role of amino acid 1092 in treatment.
2005-10
Pharmacokinetics of antivirals in neonate.
2005-09
Coxsackievirus-induced myocarditis: new trends in treatment.
2005-08
Viral encephalitis: a review of diagnostic methods and guidelines for management.
2005-05
Using benefit harm tradeoffs to estimate sufficiently important difference: the case of the common cold.
2005-01-28
Pleconaril--an advance in the treatment of enteroviral infection in immuno-compromised patients.
2005-01
Failure to clear persistent vaccine-derived neurovirulent poliovirus infection in an immunodeficient man.
2004-05-08
Neonatal coxsackie B virus infection-a treatable disease?
2004-04
Presentation, diagnosis, and management of enterovirus infections in neonates.
2004
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.
Name Type Language
VP-63843
Preferred Name English
PLECONARIL
INN   MART.   MI   USAN   WHO-DD  
INN   USAN  
Official Name English
PLECONARIL [MI]
Common Name English
pleconaril [INN]
Common Name 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 Mon Mar 31 18:05:04 GMT 2025 , Edited by admin on Mon Mar 31 18:05:04 GMT 2025
NCI_THESAURUS C281
Created by admin on Mon Mar 31 18:05:04 GMT 2025 , Edited by admin on Mon Mar 31 18:05:04 GMT 2025
WHO-VATC QJ05AX06
Created by admin on Mon Mar 31 18:05:04 GMT 2025 , Edited by admin on Mon Mar 31 18:05:04 GMT 2025
FDA ORPHAN DRUG 457214
Created by admin on Mon Mar 31 18:05:04 GMT 2025 , Edited by admin on Mon Mar 31 18:05:04 GMT 2025
Code System Code Type Description
USAN
II-65
Created by admin on Mon Mar 31 18:05:04 GMT 2025 , Edited by admin on Mon Mar 31 18:05:04 GMT 2025
PRIMARY
DRUG CENTRAL
4690
Created by admin on Mon Mar 31 18:05:04 GMT 2025 , Edited by admin on Mon Mar 31 18:05:04 GMT 2025
PRIMARY
PUBCHEM
1684
Created by admin on Mon Mar 31 18:05:04 GMT 2025 , Edited by admin on Mon Mar 31 18:05:04 GMT 2025
PRIMARY
MERCK INDEX
m8918
Created by admin on Mon Mar 31 18:05:04 GMT 2025 , Edited by admin on Mon Mar 31 18:05:04 GMT 2025
PRIMARY Merck Index
NCI_THESAURUS
C81604
Created by admin on Mon Mar 31 18:05:04 GMT 2025 , Edited by admin on Mon Mar 31 18:05:04 GMT 2025
PRIMARY
CAS
153168-05-9
Created by admin on Mon Mar 31 18:05:04 GMT 2025 , Edited by admin on Mon Mar 31 18:05:04 GMT 2025
PRIMARY
DRUG BANK
DB05105
Created by admin on Mon Mar 31 18:05:04 GMT 2025 , Edited by admin on Mon Mar 31 18:05:04 GMT 2025
PRIMARY
MESH
C115201
Created by admin on Mon Mar 31 18:05:04 GMT 2025 , Edited by admin on Mon Mar 31 18:05:04 GMT 2025
PRIMARY
EPA CompTox
DTXSID8057649
Created by admin on Mon Mar 31 18:05:04 GMT 2025 , Edited by admin on Mon Mar 31 18:05:04 GMT 2025
PRIMARY
FDA UNII
9H4570Q89D
Created by admin on Mon Mar 31 18:05:04 GMT 2025 , Edited by admin on Mon Mar 31 18:05:04 GMT 2025
PRIMARY
EVMPD
SUB09957MIG
Created by admin on Mon Mar 31 18:05:04 GMT 2025 , Edited by admin on Mon Mar 31 18:05:04 GMT 2025
PRIMARY
SMS_ID
100000081912
Created by admin on Mon Mar 31 18:05:04 GMT 2025 , Edited by admin on Mon Mar 31 18:05:04 GMT 2025
PRIMARY
INN
7617
Created by admin on Mon Mar 31 18:05:04 GMT 2025 , Edited by admin on Mon Mar 31 18:05:04 GMT 2025
PRIMARY
ChEMBL
CHEMBL29609
Created by admin on Mon Mar 31 18:05:04 GMT 2025 , Edited by admin on Mon Mar 31 18:05:04 GMT 2025
PRIMARY
WIKIPEDIA
PLECONARIL
Created by admin on Mon Mar 31 18:05:04 GMT 2025 , Edited by admin on Mon Mar 31 18:05:04 GMT 2025
PRIMARY