Pleconaril
Identification
- Name
- Pleconaril
- Accession Number
- DB05105
- 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.
- Type
- Small Molecule
- Groups
- Investigational
- Structure
Structure for Pleconaril (DB05105)
- Weight
- Average: 381.349
Monoisotopic: 381.130026072 - Chemical Formula
- C18H18F3N3O3
- Synonyms
- Not Available
- External IDs
- VP 63843
- VP63843
- WIN 63843
Pharmacology
- Indication
Investigated for use/treatment in upper respiratory infection.
- Contraindications & Blackbox Warnings
Learn about our commercial Contraindications & Blackbox Warnings data.
Learn More- 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.
Target Actions Organism UPolyprotein Not Available Enterovirus 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
Learn about our commercial Adverse Effects data.
Learn More- Toxicity
- Not Available
- Affected organisms
- 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.
Drug Interaction Unlock Additional DataAdenovirus type 7 vaccine live The therapeutic efficacy of Adenovirus type 7 vaccine live can be decreased when used in combination with Pleconaril. Anthrax vaccine The therapeutic efficacy of Anthrax vaccine can be decreased when used in combination with Pleconaril. Bacillus calmette-guerin substrain connaught live antigen The therapeutic efficacy of Bacillus calmette-guerin substrain connaught live antigen can be decreased when used in combination with Pleconaril. Bacillus calmette-guerin substrain tice live antigen The therapeutic efficacy of Bacillus calmette-guerin substrain tice live antigen can be decreased when used in combination with Pleconaril. Human adenovirus e serotype 4 strain cl-68578 antigen The therapeutic efficacy of Human adenovirus e serotype 4 strain cl-68578 antigen can be decreased when used in combination with Pleconaril. Rubella virus vaccine The therapeutic efficacy of Rubella virus vaccine can be decreased when used in combination with Pleconaril. Typhoid Vaccine Live The 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. Vibrio cholerae CVD 103-HgR strain live antigen The therapeutic efficacy of Vibrio cholerae CVD 103-HgR strain live antigen can be decreased when used in combination with Pleconaril. Yellow Fever Vaccine The therapeutic efficacy of Yellow Fever Vaccine can be decreased when used in combination with Pleconaril. Additional Data Available- Extended DescriptionExtended DescriptionAvailable for Purchase
Extended description of the mechanism of action and particular properties of each drug interaction.
Learn more - SeveritySeverityAvailable for Purchase
A severity rating for each drug interaction, from minor to major.
Learn more - Evidence LevelEvidence LevelAvailable for Purchase
A rating for the strength of the evidence supporting each drug interaction.
Learn more - ActionActionAvailable for Purchase
An effect category for each drug interaction. Know how this interaction affects the subject drug.
Learn more
- Food Interactions
- Not Available
Products
Purchasing individual compounds or compound libraries for your research?
Learn More- 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
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
- Webster AD: Pleconaril--an advance in the treatment of enteroviral infection in immuno-compromised patients. J Clin Virol. 2005 Jan;32(1):1-6. [PubMed:15571999]
- Florea NR, Maglio D, Nicolau DP: Pleconaril, a novel antipicornaviral agent. Pharmacotherapy. 2003 Mar;23(3):339-48. [PubMed:12627933]
- External Links
- 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
Phase Status Purpose Conditions Count 2 Completed Prevention Acute Rhinitis / Asthma / Picornavirus Infection / Rhinovirus 1 2 Completed Treatment Enteroviral Sepsis 1
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
Property Value Source Water Solubility 0.0219 mg/mL 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 - Predicted ADMET Features
Property Value Probability Human Intestinal Absorption + 1.0 Blood Brain Barrier + 0.9707 Caco-2 permeable - 0.5395 P-glycoprotein substrate Non-substrate 0.7624 P-glycoprotein inhibitor I Non-inhibitor 0.8101 P-glycoprotein inhibitor II Non-inhibitor 0.727 Renal organic cation transporter Non-inhibitor 0.9064 CYP450 2C9 substrate Non-substrate 0.8199 CYP450 2D6 substrate Non-substrate 0.7861 CYP450 3A4 substrate Substrate 0.6055 CYP450 1A2 substrate Inhibitor 0.6447 CYP450 2C9 inhibitor Non-inhibitor 0.5778 CYP450 2D6 inhibitor Non-inhibitor 0.8948 CYP450 2C19 inhibitor Inhibitor 0.7046 CYP450 3A4 inhibitor Non-inhibitor 0.6775 CYP450 inhibitory promiscuity High CYP Inhibitory Promiscuity 0.7105 Ames test Non AMES toxic 0.5384 Carcinogenicity Non-carcinogens 0.7985 Biodegradation Not ready biodegradable 0.9923 Rat acute toxicity 2.6286 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.9566 hERG inhibition (predictor II) Non-inhibitor 0.7203
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Spectrum Spectrum Type Splash Key Predicted MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS Not Available
Targets
- 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 on October 21, 2007 16:23 / Updated on June 12, 2020 10:52
Are you a
new drug developer?
Contact us to learn more about our customized products and solutions.
![]({"CS-Molecular-Health-1.jpg":"/assets/ads/CS-Molecular-Health-1-19e76f023997d5ac198da2cb9976457f7b9ba733f0ea8a780fe21191c759e8fa.jpg","Drug-Dev-2.jpg":"/assets/ads/Drug-Dev-2-7c3039d93245f493c23278efbf759e4f933848a676262d579087d5cc516af179.jpg","Drug-Search-3.jpg":"/assets/ads/Drug-Search-3-7346c33d2133f62b46cbfbbe2b666e78f955c6847e242692c6081fec37c4d10d.jpg","PM-3.jpg":"/assets/ads/PM-3-13494ac4c996d71619127a11f685681418d4280832dec162c0b2c9c8bc2eda50.jpg","OD-Webinar-1.jpg":"/assets/ads/OD-Webinar-1-f9357f6d57fef5e411aa1c0439ef46c86d9151214434659d096eeed6407b799b.jpg","DDI-3.jpg":"/assets/ads/DDI-3-12808cf864d540ad43757b10b08fc52ae93e793b0c6e81345555187b2840ad09.jpg","EMR-2.jpg":"/assets/ads/EMR-2-adacf8de3f42cb06d6676d06fce611c29781db6ad30776cd18b72a7d8e69f0c8.jpg","Covid.jpg":"/assets/ads/Covid-eed8f17668b0308db62ce3c656f5e2f562376e9185ae08dda5ce6ed9ab0bbd1f.jpg","CS-Molecular-Health-2.jpg":"/assets/ads/CS-Molecular-Health-2-22f41f94b3f87e44a1dcaa8f6c03dc411ab69558efd4f3148ff9bb6adaa956dc.jpg","PM-5.jpg":"/assets/ads/PM-5-d0dc031e0fa0d0097d912eff07b7e80b27b867264dd5b055e379a57bfa2a8723.jpg","DDI-4.jpg":"/assets/ads/DDI-4-313b9c374b937fd78bb2ade652b9b030abb9e6cb90efd35833f793e384e8185b.jpg","Discover-1.jpg":"/assets/ads/Discover-1-b48ae6a3872eeb442f4c22a9a1d867428c83a917ec78a8c3ff4e02f84c5d4fef.jpg","Discover-2.jpg":"/assets/ads/Discover-2-6e7759998ee0fdc234cd84eea962f2480f0c7dafadabd785924918420decb102.jpg","Repurpose-1.jpg":"/assets/ads/Repurpose-1-265fbec40f0eac18d51d3ec4f558c10cb623d834ea75e0296259e458b72ee6d4.jpg","Repurpose-2.jpg":"/assets/ads/Repurpose-2-d12bd1d18b92d36eab60e71e6fd59acf04ef60a53783570e11eef397a0e0f4f5.jpg","PM-6.jpg":"/assets/ads/PM-6-3ae66e41f7ae1e851a0910be89141cf2533509b46df6379464efc885d5ee2f07.jpg","Drug-Search-4.jpg":"/assets/ads/Drug-Search-4-2a9102bd41f16e8c40c9d8044d1dcb6f206ff80107cc269aa83d02ea683bc829.jpg","DDI-5.jpg":"/assets/ads/DDI-5-fa1c287946f4044094c723161577cb5ac631f9cd1217446e510dc79ace6cb94e.jpg","TH-1.jpg":"/assets/ads/TH-1-55a9077bb39e8c38a68c67b555b8091d21a9d41b1c21c7daed3fe53e6f9f3c97.jpg","TH-2.jpg":"/assets/ads/TH-2-1d488747fa4af00ab970a48dba0b228b054d166aa22c1760a310e2b72dd22589.jpg"})
Stay in the know!
As part of our commitment to providing the most up-to-date drug information, we will be releasing #DrugBankUpdates with our newly added curated drug pages.
#DrugBankUpdates