PIRODAVIR

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

Structure Search

SMILES

CCOC(=O)C1=CC=C(OCCC2CCN(CC2)C3=CC=C(C)N=N3)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

HIDE SMILES / InChI

Molecular Formula	C21H27N3O3
Molecular Weight	369.4574
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/1317142

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

Targets

Primary Target	Pharmacology	Condition	Potency
viral genome replication 4 Target ID: GO:0019079 Sources: https://www.ncbi.nlm.nih.gov/pubmed/1317142	Inhibitor 8504

Conditions

Condition	Modality	Targets	Highest Phase	Product
Rhinovirus cold 2 Sources: https://www.ncbi.nlm.nih.gov/pubmed/	Primary		Phase II 1147	Unknown Approved Use Unknown
Rhinovirus infection 1 Sources: https://www.ncbi.nlm.nih.gov/pubmed/1503435	Curative		Phase II 1147	Unknown Approved Use Unknown

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: https://pubmed.ncbi.nlm.nih.gov/7726484	unhealthy, 20±1 Health Status: unhealthy Age Group: 20±1 Sex: M+F Sources: https://pubmed.ncbi.nlm.nih.gov/7726484	Sources: https://pubmed.ncbi.nlm.nih.gov/7726484

Sourcing

Vendor/Aggregator	ID	URL
001 Chemical	DY442825	https://www.001chemical.com/chem/search?q=DY442825
1PlusChem LLC	1P000MHA	https://www.1pchem.com/search?query=1P000MHA
A2B Chem	AA28334	http://a2bchem.com/prod/AA28334
Aceschem	ACS019620	https://www.aceschem.com/catalog/search.do?q=ACS019620
AK Scientific	X5608	https://aksci.com/item_detail.php?cat=X5608
AKOS	AKOS025117571	http://akoscompounds.de/catalogue/AKosSamplesiSSretrieval.php?GUID=4e4caa52-3dca-4da0-b75a-caeae59e1096&IDNUMBERS=AKOS025117571
Angene	AGN-PC-0PHTRT	http://www.angenechemical.com/productshow/AGN-PC-0PHTRT.html
AstaTech	40907	http://astatechinc.com/CPSResult.php?CRNO=40907
BLD Pharm	BD148330	http://www.bldpharm.com/search/Search.html?keyword=BD148330
BOC Sciences	124436-59-5	http://www.bocsci.com/description.asp?cas=124436-59-5
Capot Chemical	33829	https://www.capotchem.com/search.do?q=33829
ChemShuttle	111941	https://www.chemshuttle.com/catalogsearch/result/?q=111941
Debye Scientific	DA-46799	https://www.debyesci.com/index.php?id=product&ext[cno]=DA-46799
eMolecules	46013927	https://orderbb.emolecules.com/search/#?query=46013927
eNovation Chemicals	D372484	https://www.enovationchem.com/Products.asp?SEARCHTEXT=D372484&searchbtn.x=0&searchbtn.y=0
Excenen	EX-A218	http://www.excenen.com/searchresultlist.php?id=EX-A218
Hairui	HR32761	http://www.hairuichem.com/en/product/search.do?q=HR32761
KeyOrganics	AS-73886	http://www.keyorganicsinc.com/bionet/catalogsearch/result?q=AS-73886
Lab Network	LN01311165	https://labnetwork.com/frontend-app/p/#!/moleculedetails/LN01311165
Lab Seeker	SC-74202	http://www.labseeker.com/search.php?keywords=SC-74202&category=0
LabSeeker	SC-74202	http://www.labseeker.com/search.php?keywords=SC-74202&category=0
Matrix Scientific	147266	http://www.matrixscientific.com/147266.html
mcule	MCULE-5940471072	https://mcule.com/MCULE-5940471072/
MedChem Express	HY-13784	https://www.medchemexpress.com/search.html?q=HY-13784&ft=&fa=&fp=
Molcore	MC442825	http://www.molcore.com/CatMC442825.html
Molnova	M10990	https://www.molnova.com/en/serch-list.html?keywords=M10990
MolPort	MolPort-028-599-985	https://www.molport.com/shop/molecule-link/MolPort-028-599-985
MuseChem	I000970	https://www.musechem.com/product/I000970.html
ShangHai Biochempartner	BCP000825	http://www.biochempartner.com/search_BCP000825
ShangHai Biochempartner	BCP07399	http://www.biochempartner.com/search_BCP07399
Sigma Aldrich	SML1818	http://www.sigmaaldrich.com/catalog/search?term=SML1818&interface=All&N=0&mode=match%20partialmax&lang=en®ion=US&focus=product
TargetMol	T1750	https://www.targetmol.com/search?keyword=T1750

PubMed

Title	Date	PubMed
Isothiazole derivatives as antiviral agents.	2007	18046960
In vitro activity of expanded-spectrum pyridazinyl oxime ethers related to pirodavir: novel capsid-binding inhibitors with potent antipicornavirus activity.	2004-05	15105133
An orally bioavailable oxime ether capsid binder with potent activity against human rhinovirus.	2003-07-17	12852746
Synthesis of new 3-methylthio-5-aryl-4-isothiazolecarbonitriles with broad antiviral spectrum.	2002-08	12103435
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.	2002-04-11	11931615
In vitro antiviral activity of AG7088, a potent inhibitor of human rhinovirus 3C protease.	1999-10	10508022
Structure-based design, synthesis, and biological evaluation of irreversible human rhinovirus 3C protease inhibitors. 4. Incorporation of P1 lactam moieties as L-glutamine replacements.	1999-04-08	10197965
In vitro studies of the antirhinovirus activity of soluble intercellular adhesion molecule-1.	1992-06	1358025
In vitro activity of pirodavir (R 77975), a substituted phenoxy-pyridazinamine with broad-spectrum antipicornaviral activity.	1992-01	1317142

Sample Use Guides

In Vivo Use Guide

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

In Vitro Use Guide

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.

Substance Class	Chemical Created by `admin` on `Mon Mar 31 18:11:00 GMT 2025` Edited by `admin` on `Mon Mar 31 18:11:00 GMT 2025`
Record UNII	BML697718K
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

R-77975

Preferred Name

English

PIRODAVIR

Official Name

English

R77975

Code

English

PIRODAVIR [MART.]

Common Name

English

BENZOIC ACID, 4-(2-(1-(6-METHYL-3-PYRIDAZINYL)-4-PIPERIDINYL)ETHOXY)-, ETHYL ESTER

Common Name

English

PIRODAVIR [USAN]

Common Name

English

ETHYL P-(2-(1-(6-METHYL-3-PYRIDAZINYL)-4-PIPERIDYL)ETHOXY)BENZOATE

Common Name

English

pirodavir [INN]

Common Name

English

Code System Code Type Description

DRUG BANK

DB08012