Details
| Stereochemistry | ACHIRAL |
| Molecular Formula | C21H27N3O3 |
| Molecular Weight | 369.4574 |
| Optical Activity | NONE |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
CCOC(=O)C1=CC=C(OCCC2CCN(CC2)C3=NN=C(C)C=C3)C=C1
InChI
InChIKey=KCHIOGFOPPOUJC-UHFFFAOYSA-N
InChI=1S/C21H27N3O3/c1-3-26-21(25)18-5-7-19(8-6-18)27-15-12-17-10-13-24(14-11-17)20-9-4-16(2)22-23-20/h4-9,17H,3,10-15H2,1-2H3
Pirodavir (R77975) (ethyl 4-[2-(1-[6-methyl-3-pyridazinyl]-4-piperidinyl)ethoxy]benzoate) and its predecessor (R61837) belong to a series of pyridazine analogues developed by the Janssen Research Foundation. Compared to R61837, pirodavir was 500-fold more potent as an antiviral in vitro, inhibiting 80% of 100 rhinovirus serotypes tested at concentration of 0.064 mg/mL or less. Pirodavir acts at an early stage of the viral replication cycle (up to 40 min after infection) and reduces the yield of selected rhinoviruses 1,000- to 100,000-fold in a single round of replication. The mode of action appears to be serotype specific, since pirodavir was able to inhibit the adsorption of human rhinovirus 9 but not that of human rhinovirus 1A. Pirodavir is a novel capsid-binding antipicornavirus agent with potent in vitro activity against both group A and group B rhinovirus serotypes.
Originator
Approval Year
Doses
| Dose | Population | Adverse events |
|---|---|---|
2 mg 6 times / day multiple, intranasal Studied dose Dose: 2 mg, 6 times / day Route: intranasal Route: multiple Dose: 2 mg, 6 times / day Sources: Page: p.293 |
unhealthy, 20±1 n = 53 Health Status: unhealthy Condition: Rhinovirus colds Age Group: 20±1 Sex: M+F Population Size: 53 Sources: Page: p.293 |
PubMed
| Title | Date | PubMed |
|---|---|---|
| Structure-based design, synthesis, and biological evaluation of irreversible human rhinovirus 3C protease inhibitors. 6. Structure-activity studies of orally bioavailable, 2-pyridone-containing peptidomimetics. | 2002 Apr 11 |
|
| Synthesis of new 3-methylthio-5-aryl-4-isothiazolecarbonitriles with broad antiviral spectrum. | 2002 Aug |
|
| An orally bioavailable oxime ether capsid binder with potent activity against human rhinovirus. | 2003 Jul 17 |
|
| Isothiazole derivatives as antiviral agents. | 2007 |
Sample Use Guides
Intranasal spray (Pirodavir 5 mg/ml in an aqueous solution containing saccharin and 10% hydroxypropyl-beta-cyclodextrin). Each treatment (or dose) consisted of two sprays per nostril (100 uL per spray), so that a single treatment administered 2 mg of pirodavir. Four doses of the first day of the study were given and continued six times daily over the next three days, with three doses on the fifth day (total of 25 doses).
Route of Administration:
Nasal
Virus was used at a multiplicity of infection (MOI) of 0.001 to 0.01. Compound was added at the appropriate concentration to near-confluent cell monolayers in 96 –well tissue culture plates, immediately followed by the addition of an equal volume of virus. Pirodavir was very potent in a virus yield reduction assay (IC90 = 2.3 nM). None of the compounds physically disrupted the virus or apparently prevented binding of the virus to the cell at the concentrations tested (including pirodavir, 27,000 nM), as determined by a virucidal assay.
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ACTIVE MOIETY
