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
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
Molecular Formula | C18H18F3N3O3 |
Molecular Weight | 381.349 |
Charge | 0 |
Count |
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Stereochemistry | ACHIRAL |
Additional Stereochemistry | No |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Optical Activity | NONE |
DescriptionCurator'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
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.
CNS Activity
Originator
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
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Target ID: P03303|||Q84741|||Q89649 Gene ID: 1461213.0 Gene Symbol: NA Target Organism: Human rhinovirus 14 (HRV-14) |
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Target ID: CHEMBL2857 Sources: https://www.ncbi.nlm.nih.gov/pubmed/11931615 |
58.0 nM [EC50] |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
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Primary | Unknown Approved UseUnknown |
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Primary | Unknown Approved UseUnknown |
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Curative | Unknown Approved UseUnknown |
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Curative | Unknown Approved UseUnknown |
PubMed
Title | Date | PubMed |
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In vitro antiviral activity of AG7088, a potent inhibitor of human rhinovirus 3C protease. | 1999 Oct |
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In vitro activity of pleconaril and AG7088 against selected serotypes and clinical isolates of human rhinoviruses. | 2000 Sep |
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Gateways to Clinical Trials. | 2002 Apr |
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Design, synthesis, and structure-activity relationship of pyridyl imidazolidinones: a novel class of potent and selective human enterovirus 71 inhibitors. | 2002 Apr 11 |
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Enterovirus infections: diagnosis and treatment. | 2002 Jan |
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Management of viral infections in immunocompromised cancer patients. | 2002 Jul 13 |
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Severe Coxsackie virus B infection in preterm newborns treated with pleconaril. | 2002 Sep |
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Double blind placebo-controlled trial of pleconaril in infants with enterovirus meningitis. | 2003 Apr |
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SPECT scans for monitoring response to pleconaril therapy in chronic enteroviral meningoencephalitis. | 2003 Feb |
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A fatal case of coxsackievirus B4 meningoencephalitis. | 2003 Jan |
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Enteroviral infections in primary immunodeficiency (PID): a survey of morbidity and mortality. | 2003 Jan |
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Gateways to clinical trials. | 2003 Jun |
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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 |
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Pleconaril, a novel antipicornaviral agent. | 2003 Mar |
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Diagnosis and treatment of rhinovirus respiratory infections. | 2003 May |
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Nucleotide variation in Sabin type 2 poliovirus from an immunodeficient patient with poliomyelitis. | 2003 May |
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Survival after pulmonary edema due to enterovirus 71 encephalitis. | 2003 May 27 |
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Gateways to clinical trials. | 2003 Oct |
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Neonatal coxsackie B virus infection-a treatable disease? | 2004 Apr |
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Failure to clear persistent vaccine-derived neurovirulent poliovirus infection in an immunodeficient man. | 2004 May 8 |
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Gateways to clinical trials. | 2006 Dec |
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The effect of oral pleconaril on hepatic cytochrome P450 3A activity in healthy adults using intravenous midazolam as a probe. | 2006 Jan |
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Investigation of treatment failure in neonatal echovirus 7 infection. | 2006 Mar |
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Antiviral treatment of Coxsackie B virus infection in human pancreatic islets. | 2007 Apr |
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Enteroviral infections in children with malignant disease: a 5-year study in a single institution. | 2007 Apr |
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A case report of a premature infant with coxsackie B1 meningitis. | 2007 Oct |
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Enterovirus-associated hemophagocytic syndrome in children with malignancy: report of three cases and review of the literature. | 2008 Jan |
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Limited duration of vaccine poliovirus and other enterovirus excretion among human immunodeficiency virus infected children in Kenya. | 2009 Aug 23 |
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Human rhinovirus C: a newly discovered human rhinovirus species. | 2010 |
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Clinical features, diagnosis, and management of enterovirus 71. | 2010 Nov |
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An RNA replication-center assay for high content image-based quantifications of human rhinovirus and coxsackievirus infections. | 2010 Oct 11 |
Patents
Sample Use Guides
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/26169596
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
Edited
Fri Dec 15 15:40:27 GMT 2023
by
admin
on
Fri Dec 15 15:40:27 GMT 2023
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Record UNII |
9H4570Q89D
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Record Status |
Validated (UNII)
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Record Version |
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WHO-ATC |
J05AX06
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NCI_THESAURUS |
C281
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WHO-VATC |
QJ05AX06
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FDA ORPHAN DRUG |
457214
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II-65
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4690
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1684
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m8918
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C81604
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153168-05-9
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DB05105
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C115201
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DTXSID8057649
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9H4570Q89D
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SUB09957MIG
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100000081912
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7617
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CHEMBL29609
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PLECONARIL
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Related Record | Type | Details | ||
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ACTIVE MOIETY |
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