ContaminantDB: Pleconaril

Identification Taxonomy Biological Properties Physical Properties Toxicity Profile Spectra Concentrations Links References XML

Record Information

Version

1.0

Creation Date

2016-05-22 07:17:53 UTC

Update Date

2016-11-09 01:16:14 UTC

Accession Number

CHEM020648

Identification

Common Name

Pleconaril

Class

Small Molecule

Description

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.

Contaminant Sources

ToxCast & Tox21 Chemicals

Contaminant Type

Not Available

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
Picovir	MeSH
3-(3,5-Dimethyl-4((3-(3-methyl-5-isoxazolyl)propyl)phenyl)-5-trifluoromethyl)-1,2,4-oxadiazole	MeSH

Chemical Formula

C₁₈H₁₈F₃N₃O₃

Average Molecular Mass

381.349 g/mol

Monoisotopic Mass

381.130 g/mol

CAS Registry Number

153168-05-9

IUPAC Name

3-{3,5-dimethyl-4-[3-(3-methyl-1,2-oxazol-5-yl)propoxy]phenyl}-5-(trifluoromethyl)-1,2,4-oxadiazole

Traditional Name

pleconaril

SMILES

CC1=NOC(CCCOC2=C(C)C=C(C=C2C)C2=NOC(=N2)C(F)(F)F)=C1

InChI Identifier

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

InChI Key

KQOXLKOJHVFTRN-UHFFFAOYSA-N

Chemical Taxonomy

Description

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

Substituents

Phenyl-1,2,4-oxadiazole
Phenoxy compound
Phenol ether
Xylene
M-xylene
Alkyl aryl ether
Monocyclic benzene moiety
Benzenoid
Heteroaromatic compound
Isoxazole
Oxacycle
Azacycle
Ether
Alkyl fluoride
Organic oxygen compound
Organooxygen compound
Organonitrogen compound
Organofluoride
Organohalogen compound
Organic nitrogen compound
Alkyl halide
Hydrocarbon derivative
Organopnictogen compound
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

Not Available

Biological Properties

Status

Detected and Not Quantified

Origin

Not Available

Cellular Locations

Not Available

Biofluid Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Applications

Not Available

Biological Roles

Not Available

Chemical Roles

Not Available

Physical Properties

State

Not Available

Appearance

Not Available

Experimental Properties

Property	Value
Melting Point	Not Available
Boiling Point	Not Available
Solubility	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	0.022 g/L	ALOGPS
logP	4.7	ALOGPS
logP	5.04	ChemAxon
logS	-4.2	ALOGPS
pKa (Strongest Basic)	1.64	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	74.18 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	104.12 m³·mol⁻¹	ChemAxon
Polarizability	37.46 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0a4j-6692000000-9a838755be95ff5a45fa	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-001i-0119000000-5e32691eedc2eb627a23	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-00ei-1698000000-4bbf2713217e39bb32f0	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-06di-8930000000-4a868e2ab123c2e3b903	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-001i-0039000000-4ba847560df799c339c4	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0bu0-3297000000-c8497e2ceca8788a6cd4	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0006-3690000000-5464f370262665fa2022	Spectrum

Toxicity Profile

Route of Exposure

Not Available

Mechanism of Toxicity

Not Available

Metabolism

Not Available

Toxicity Values

Not Available

Lethal Dose

Not Available

Carcinogenicity (IARC Classification)

Not Available

Uses/Sources

Not Available

Minimum Risk Level

Not Available

Health Effects

Not Available

Symptoms

Not Available

Treatment

Not Available

Concentrations

Not Available

External Links

DrugBank ID

DB05105

HMDB ID

HMDB0256637

FooDB ID

Not Available

Phenol Explorer ID

Not Available

KNApSAcK ID

Not Available

BiGG ID

Not Available

BioCyc ID

Not Available

METLIN ID

Not Available

PDB ID

Not Available

Wikipedia Link

Pleconaril

Chemspider ID

1621

ChEBI ID

Not Available

PubChem Compound ID

Not Available

Kegg Compound ID

Not Available

YMDB ID

Not Available

ECMDB ID

Not Available

References

Synthesis Reference

Not Available

MSDS

Not Available

General References

Not Available

Pleconaril (CHEM020648)

Structure for CHEM020648: Pleconaril