Identification

Generic Name
Pleconaril
DrugBank Accession Number
DB05105
Background

Pleconaril is an antiviral drug from viral capsid inhibitor class, manufactured by Schering-Plough and intended for the prevention of acute asthma exacerbations and common cold symptoms in asthmatic patients who have had exposure to picornavirus. It acts by inhibiting viral replication. The use of pleconaril has not gained approval by the U.S. Food and Drug Administration (FDA) due to the fact that it has been found to induce CYP3A enzyme activity, therefore increasing the risk for serious drug interactions.

Type
Small Molecule
Groups
Investigational
Structure
Thumb
Weight
Average: 381.349
Monoisotopic: 381.130026072
Chemical Formula
C18H18F3N3O3
Synonyms
  • Pleconaril
External IDs
  • VP 63843
  • VP63843
  • WIN 63843

Pharmacology

Indication

Investigated for use/treatment in upper respiratory infection.

Pharmacology
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Contraindications & Blackbox Warnings
Contraindications
Avoid life-threatening adverse drug events
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Pharmacodynamics

Not Available

Mechanism of action

Pleconaril binds to a hydrophobic pocket in viral protein 1, the major protein which makes up the capsid (shell) of picornaviruses. This renders the viral capsid rigid and compressed and prevents the uncoating of its RNA. As a result, the virus is stopped from attaching to the host cell and causing infection.

TargetActionsOrganism
UPolyproteinNot AvailableEnterovirus J
Absorption

70% (oral)

Volume of distribution

Not Available

Protein binding

>99%

Metabolism
Not Available
Route of elimination

Not Available

Half-life

Not Available

Clearance

Not Available

Adverse Effects
Adverseeffects
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Toxicity

Not Available

Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
DrugInteraction
Adenovirus type 7 vaccine liveThe therapeutic efficacy of Adenovirus type 7 vaccine live can be decreased when used in combination with Pleconaril.
Anthrax vaccineThe therapeutic efficacy of Anthrax vaccine can be decreased when used in combination with Pleconaril.
Bacillus calmette-guerin substrain connaught live antigenThe therapeutic efficacy of Bacillus calmette-guerin substrain connaught live antigen can be decreased when used in combination with Pleconaril.
Bacillus calmette-guerin substrain russian BCG-I live antigenThe therapeutic efficacy of Bacillus calmette-guerin substrain russian BCG-I live antigen can be decreased when used in combination with Pleconaril.
Bacillus calmette-guerin substrain tice live antigenThe therapeutic efficacy of Bacillus calmette-guerin substrain tice live antigen can be decreased when used in combination with Pleconaril.
BCG vaccineThe therapeutic efficacy of BCG vaccine can be decreased when used in combination with Pleconaril.
Human adenovirus e serotype 4 strain cl-68578 antigenThe therapeutic efficacy of Human adenovirus e serotype 4 strain cl-68578 antigen can be decreased when used in combination with Pleconaril.
Rubella virus vaccineThe therapeutic efficacy of Rubella virus vaccine can be decreased when used in combination with Pleconaril.
Typhoid Vaccine LiveThe therapeutic efficacy of Typhoid Vaccine Live can be decreased when used in combination with Pleconaril.
Varicella zoster vaccine (live/attenuated)The therapeutic efficacy of Varicella zoster vaccine (live/attenuated) can be decreased when used in combination with Pleconaril.
Interactions
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Food Interactions
Not Available

Products

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International/Other Brands
Picovir

Categories

ATC Codes
J05AX06 — Pleconaril
Drug Categories
Chemical TaxonomyProvided by Classyfire
Description
This compound belongs to the class of organic compounds known as phenyloxadiazoles. These are polycyclic aromatic compounds containing a benzene ring linked to a 1,2,4-oxadiazole ring through a CC or CN bond.
Kingdom
Organic compounds
Super Class
Organoheterocyclic compounds
Class
Azoles
Sub Class
Oxadiazoles
Direct Parent
Phenyloxadiazoles
Alternative Parents
m-Xylenes / Phenoxy compounds / Phenol ethers / Alkyl aryl ethers / Isoxazoles / Heteroaromatic compounds / Oxacyclic compounds / Azacyclic compounds / Organopnictogen compounds / Organonitrogen compounds
show 3 more
Substituents
Alkyl aryl ether / Alkyl fluoride / Alkyl halide / Aromatic heteromonocyclic compound / Azacycle / Benzenoid / Ether / Heteroaromatic compound / Hydrocarbon derivative / Isoxazole
show 14 more
Molecular Framework
Aromatic heteromonocyclic compounds
External Descriptors
Not Available
Affected organisms
Not Available

Chemical Identifiers

UNII
9H4570Q89D
CAS number
153168-05-9
InChI Key
KQOXLKOJHVFTRN-UHFFFAOYSA-N
InChI
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
IUPAC Name
3-{3,5-dimethyl-4-[3-(3-methyl-1,2-oxazol-5-yl)propoxy]phenyl}-5-(trifluoromethyl)-1,2,4-oxadiazole
SMILES
CC1=NOC(CCCOC2=C(C)C=C(C=C2C)C2=NOC(=N2)C(F)(F)F)=C1

References

General References
  1. Webster AD: Pleconaril--an advance in the treatment of enteroviral infection in immuno-compromised patients. J Clin Virol. 2005 Jan;32(1):1-6. [Article]
  2. Florea NR, Maglio D, Nicolau DP: Pleconaril, a novel antipicornaviral agent. Pharmacotherapy. 2003 Mar;23(3):339-48. [Article]
PubChem Compound
1684
PubChem Substance
175426946
ChemSpider
1621
BindingDB
50111469
ChEMBL
CHEMBL29609
ZINC
ZINC000001537619
PDBe Ligand
W11
Wikipedia
Pleconaril
PDB Entries
1c8m / 1na1 / 1ncq / 1ncr / 1nd3 / 4wm7

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
2CompletedPreventionAsthma / Common Cold / Picornavirus Infection / Rhinovirus1
2CompletedTreatmentEnteroviral Sepsis1
2CompletedTreatmentEnterovirus / Type 1 Diabetes Mellitus1

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage Forms
Not Available
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.0219 mg/mLALOGPS
logP4.7ALOGPS
logP5.04ChemAxon
logS-4.2ALOGPS
pKa (Strongest Basic)1.64ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area74.18 Å2ChemAxon
Rotatable Bond Count7ChemAxon
Refractivity104.12 m3·mol-1ChemAxon
Polarizability37.46 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveNoChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+1.0
Blood Brain Barrier+0.9707
Caco-2 permeable-0.5395
P-glycoprotein substrateNon-substrate0.7624
P-glycoprotein inhibitor INon-inhibitor0.8101
P-glycoprotein inhibitor IINon-inhibitor0.727
Renal organic cation transporterNon-inhibitor0.9064
CYP450 2C9 substrateNon-substrate0.8199
CYP450 2D6 substrateNon-substrate0.7861
CYP450 3A4 substrateSubstrate0.6055
CYP450 1A2 substrateInhibitor0.6447
CYP450 2C9 inhibitorNon-inhibitor0.5778
CYP450 2D6 inhibitorNon-inhibitor0.8948
CYP450 2C19 inhibitorInhibitor0.7046
CYP450 3A4 inhibitorNon-inhibitor0.6775
CYP450 inhibitory promiscuityHigh CYP Inhibitory Promiscuity0.7105
Ames testNon AMES toxic0.5384
CarcinogenicityNon-carcinogens0.7985
BiodegradationNot ready biodegradable0.9923
Rat acute toxicity2.6286 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9566
hERG inhibition (predictor II)Non-inhibitor0.7203
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available

Targets

Drugtargets2
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Kind
Protein
Organism
Enterovirus J
Pharmacological action
Unknown
General Function
Structural molecule activity
Specific Function
Not Available
Gene Name
Not Available
Uniprot ID
Q8V397
Uniprot Name
Genome polyprotein
Molecular Weight
241285.765 Da

Drug created at October 21, 2007 22:23 / Updated at February 21, 2021 18:51