Page last updated: 2024-11-06

disoxaril

Description Research Excerpts Clinical Trials Roles Classes Pathways Study Profile Bioassays Related Drugs Related Conditions Protein Interactions Research Growth Market Indicators

Description

disoxaril: antipicornavirus agent [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Cross-References

ID SourceID
PubMed CID55717
CHEMBL ID283639
CHEBI ID3846
SCHEMBL ID147146
MeSH IDM0133430

Synonyms (37)

Synonym
3-methyl-5-(7-(p-2-oxazolin-2-ylphenoxy)heptyl)isoxazole
isoxazole, 5-(7-(4-(4,5-dihydro-2-oxazolyl)phenoxy)heptyl)-3-methyl-
win-51711
brn 3626820
disoxaril [usan:inn]
disoxarilum [latin]
disoxarilo [spanish]
D03874
disoxaril (usan/inn)
87495-31-6
win 51711
5-[7-[4-(4,5-dihydrooxazol-2-yl)phenoxy]heptyl]-3-methyl-isoxazole
isoxazole, 5-[7-[4-(4,5-dihydro-2-oxazolyl)phenoxy]heptyl]-3-methyl-
5-(7-(4-(4,5-dihydro-2-oxazolyl)phenoxy)heptyl)-3-methylisoxazole
compound iv
disoxaril
C06496
5-(7-(4-(4,5-dihydro-2-oxazolyl)phenoxy)heptyl)-3-methyl isoxazole
win 51,711
CHEMBL283639
chebi:3846 ,
DB08726
5-{7-[4-(4,5-dihydro-2-oxazolyl)phenoxy]heptyl}-3-methylisoxazole
FKLJPTJMIBLJAV-UHFFFAOYSA-N
5-[7-[4-(4,5-dihydro-1,3-oxazol-2-yl)phenoxy]heptyl]-3-methyl-1,2-oxazole
unii-fx8q9pi4vp
disoxarilo
fx8q9pi4vp ,
disoxarilum
disoxaril [inn]
disoxaril [usan]
SCHEMBL147146
AKOS028110949
DTXSID70236354
5-{7-[4-(4,5-dihydro-1,3-oxazol-2-yl)phenoxy]heptyl}-3-methylisoxazole
Q27097911
5-(7-(4-(4,5-dihydrooxazol-2-yl)phenoxy)heptyl)-3-methylisoxazole

Research Excerpts

Overview

Disoxaril is a hydrophobic antiviral compound that blocks picornavirus uncoating.

ExcerptReferenceRelevance
"Disoxaril is a hydrophobic antiviral compound that blocks picornavirus uncoating."( Clearance of a persistent human enterovirus infection of the mouse central nervous system by the antiviral agent disoxaril.
Guidinger, PL; Jubelt, B; McKinlay, MA; Ropka, SL; Wilson, AK, 1989
)
1.21

Treatment

ExcerptReferenceRelevance
"Treatment with disoxaril (a WIN compound binding to the hydrophobic pocket within the enterovirus VP1 capsid protein) in newborn mice infected with Coxsackie B1 virus, for 10 days post virus inoculation at a daily subcutaneous dose of 25mg/kg decreased the virus titer in the mouse brain till day 7. "( Development of resistance to disoxaril in Coxsackie B1 virus-infected newborn mice.
Galabov, AS; Nikolova, I, 2003
)
0.96

Dosage Studied

ExcerptRelevanceReference
" An oral four times a day dosage regimen initiated 48 h postinfection with WIN 51711 doses as low as 12."( Oral efficacy of WIN 51711 in mice infected with human poliovirus.
McKinlay, MA; Steinberg, BA, 1986
)
0.27
" Oral administration of WIN 51711 twice daily beginning 72 hr after infection was the most-effective dosage regimen, with doses as low as 3 mg/kg preventing paralysis in 75% of the animals."( Use of WIN 51711 to prevent echovirus type 9-induced paralysis in suckling mice.
Benziger, DP; Frank, JA; McKinlay, MA; Steinberg, BA, 1986
)
0.27
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Drug Classes (1)

ClassDescription
aromatic etherAny ether in which the oxygen is attached to at least one aryl substituent.
[compound class information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Bioassays (56)

Assay IDTitleYearJournalArticle
AID124292In vivo antiviral activity at 4 mg/kg oral dose in mice infected with Poliovirus1985Journal of medicinal chemistry, Dec, Volume: 28, Issue:12
[[(4,5-Dihydro-2-oxazolyl)phenoxy]alkyl]isoxazoles. Inhibitors of picornavirus uncoating.
AID111324Prevention of Echo-9-Induced Paralysis in Suckling mice with Placebo; expressed as no. nonparalyzed/total 0/301985Journal of medicinal chemistry, Dec, Volume: 28, Issue:12
[[(4,5-Dihydro-2-oxazolyl)phenoxy]alkyl]isoxazoles. Inhibitors of picornavirus uncoating.
AID84552Compound concentration which inhibits 80% of serotypes tested, was reported.1995Journal of medicinal chemistry, Mar-03, Volume: 38, Issue:5
[[[(Thienylcarbonyl)alkyl]oxy]phenyl]- and [[[(pyrrylcarbonyl)alkyl]oxy]phenyl]oxazoline derivatives with potent and selective antihuman rhinovirus activity.
AID1287134Selectivity index, ratio of CC50 for african green monkey Vero cells to EC50 for Enterovirus 712016Journal of medicinal chemistry, Mar-10, Volume: 59, Issue:5
Identification and Structure-Activity Relationships of Diarylhydrazides as Novel Potent and Selective Human Enterovirus Inhibitors.
AID342767Selectivity index, CC50 for human FL cells to IC50 for Echovirus 132008Bioorganic & medicinal chemistry, Aug-01, Volume: 16, Issue:15
Cinnamoyl- and hydroxycinnamoyl amides of glaucine and their antioxidative and antiviral activities.
AID1562980Antiviral activity against Human rhinovirus A22019European journal of medicinal chemistry, Sep-15, Volume: 178Back to the future: Advances in development of broad-spectrum capsid-binding inhibitors of enteroviruses.
AID1287145Induction of stabilization of Human enterovirus 71 capsid protein assessed as increase in temperature for achieving equal staining of viral genome at 50 ug/ml by SYBR green fluorescent assay2016Journal of medicinal chemistry, Mar-10, Volume: 59, Issue:5
Identification and Structure-Activity Relationships of Diarylhydrazides as Novel Potent and Selective Human Enterovirus Inhibitors.
AID111318Prevention of Echo-9-Induced Paralysis in Suckling mice by intraperitoneal administration at dose 10 mg/kg; expressed as no. nonparalyzed/total 19/301985Journal of medicinal chemistry, Dec, Volume: 28, Issue:12
[[(4,5-Dihydro-2-oxazolyl)phenoxy]alkyl]isoxazoles. Inhibitors of picornavirus uncoating.
AID84907Antirhinovirus activity was assessed and the maximum testable concentration that causes no apparent effects on the cell monolayers was determined against HRV-2 virus in vitro.1987Journal of medicinal chemistry, Feb, Volume: 30, Issue:2
Structure-activity studies of 5-[[4-(4,5-dihydro-2-oxazolyl) phenoxy]alkyl]-3-methylisoxazoles: inhibitors of picornavirus uncoating.
AID123023In vivo antiviral activity at 4 mg/kg oral dose in mice infected with Poliovirus; 8/201985Journal of medicinal chemistry, Dec, Volume: 28, Issue:12
[[(4,5-Dihydro-2-oxazolyl)phenoxy]alkyl]isoxazoles. Inhibitors of picornavirus uncoating.
AID1287131Cytotoxicity against african green monkey Vero cells assessed as reduction in cell viability after 24 to 36 hrs by MTS-based CPE reduction assay2016Journal of medicinal chemistry, Mar-10, Volume: 59, Issue:5
Identification and Structure-Activity Relationships of Diarylhydrazides as Novel Potent and Selective Human Enterovirus Inhibitors.
AID1287148Inhibition of human enterovirus 71 capsid assessed as reduction in viral replication at early stages infected in human RD cells at 20 ug/ml2016Journal of medicinal chemistry, Mar-10, Volume: 59, Issue:5
Identification and Structure-Activity Relationships of Diarylhydrazides as Novel Potent and Selective Human Enterovirus Inhibitors.
AID342764Selectivity index, CC50 for human FL cells to IC50 for Coxsackievirus B12008Bioorganic & medicinal chemistry, Aug-01, Volume: 16, Issue:15
Cinnamoyl- and hydroxycinnamoyl amides of glaucine and their antioxidative and antiviral activities.
AID111323Prevention of Echo-9-Induced Paralysis in Suckling mice with Placebo; Expressed as % nonparalyzed1985Journal of medicinal chemistry, Dec, Volume: 28, Issue:12
[[(4,5-Dihydro-2-oxazolyl)phenoxy]alkyl]isoxazoles. Inhibitors of picornavirus uncoating.
AID93742In vitro minimum inhibitory concentration against human rhinovirus-14 (HRV-14)1988Journal of medicinal chemistry, Mar, Volume: 31, Issue:3
Enantiomeric effects of homologues of disoxaril on the inhibitory activity against human rhinovirus-14.
AID88357In vitro concentration required to achieve 50% protection of HeLa cells from HRV-14 induced cytopathic effect1995Journal of medicinal chemistry, Mar-03, Volume: 38, Issue:5
[[[(Thienylcarbonyl)alkyl]oxy]phenyl]- and [[[(pyrrylcarbonyl)alkyl]oxy]phenyl]oxazoline derivatives with potent and selective antihuman rhinovirus activity.
AID124291In vivo antiviral activity at 32 mg/kg oral dose in mice infected with Poliovirus1985Journal of medicinal chemistry, Dec, Volume: 28, Issue:12
[[(4,5-Dihydro-2-oxazolyl)phenoxy]alkyl]isoxazoles. Inhibitors of picornavirus uncoating.
AID111208Prevention of Echo-9-Induced Paralysis in Suckling mice by intraperitoneal administration at dose 1 mg/kg; Expressed as % nonparalyzed1985Journal of medicinal chemistry, Dec, Volume: 28, Issue:12
[[(4,5-Dihydro-2-oxazolyl)phenoxy]alkyl]isoxazoles. Inhibitors of picornavirus uncoating.
AID111320Prevention of Echo-9-Induced Paralysis in Suckling mice by intraperitoneal administration at dose 3.3 mg/kg; expressed as no. nonparalyzed/total 6/301985Journal of medicinal chemistry, Dec, Volume: 28, Issue:12
[[(4,5-Dihydro-2-oxazolyl)phenoxy]alkyl]isoxazoles. Inhibitors of picornavirus uncoating.
AID1562974Antiviral activity against Human poliovirus 22019European journal of medicinal chemistry, Sep-15, Volume: 178Back to the future: Advances in development of broad-spectrum capsid-binding inhibitors of enteroviruses.
AID1287139Selectivity index, ratio of CC50 for human RD cells to EC50 for Enterovirus 712016Journal of medicinal chemistry, Mar-10, Volume: 59, Issue:5
Identification and Structure-Activity Relationships of Diarylhydrazides as Novel Potent and Selective Human Enterovirus Inhibitors.
AID342762Antiviral activity against Coxsackievirus B1 in human FL cells2008Bioorganic & medicinal chemistry, Aug-01, Volume: 16, Issue:15
Cinnamoyl- and hydroxycinnamoyl amides of glaucine and their antioxidative and antiviral activities.
AID124294In vivo antiviral activity of the compound in Placebo treated mice infected with Poliovirus1985Journal of medicinal chemistry, Dec, Volume: 28, Issue:12
[[(4,5-Dihydro-2-oxazolyl)phenoxy]alkyl]isoxazoles. Inhibitors of picornavirus uncoating.
AID123021In vivo antiviral activity at 16 mg/kg oral dose in mice infected with Poliovirus;13/201985Journal of medicinal chemistry, Dec, Volume: 28, Issue:12
[[(4,5-Dihydro-2-oxazolyl)phenoxy]alkyl]isoxazoles. Inhibitors of picornavirus uncoating.
AID111322Prevention of Echo-9-Induced Paralysis in Suckling mice by intraperitoneal administration at dose 33 mg/kg; expressed as no. nonparalyzed/total 29/301985Journal of medicinal chemistry, Dec, Volume: 28, Issue:12
[[(4,5-Dihydro-2-oxazolyl)phenoxy]alkyl]isoxazoles. Inhibitors of picornavirus uncoating.
AID124293In vivo antiviral activity at 8 mg/kg oral dose in mice infected with Poliovirus1985Journal of medicinal chemistry, Dec, Volume: 28, Issue:12
[[(4,5-Dihydro-2-oxazolyl)phenoxy]alkyl]isoxazoles. Inhibitors of picornavirus uncoating.
AID1287132Antiviral activity against Human enterovirus 71 infected in monkey African green Vero cells by MTS-based CPE reduction assay2016Journal of medicinal chemistry, Mar-10, Volume: 59, Issue:5
Identification and Structure-Activity Relationships of Diarylhydrazides as Novel Potent and Selective Human Enterovirus Inhibitors.
AID84901Antiviral activity determined by ability to inhibit the HRV-2( human rhinovirus type -2) virus by plaque reduction assay in vitro1987Journal of medicinal chemistry, Feb, Volume: 30, Issue:2
Structure-activity studies of 5-[[4-(4,5-dihydro-2-oxazolyl) phenoxy]alkyl]-3-methylisoxazoles: inhibitors of picornavirus uncoating.
AID222916In vitro minimum inhibitory concentration for the inhibition of human rhinovirus-14 replication.1990Journal of medicinal chemistry, May, Volume: 33, Issue:5
A model for compounds active against human rhinovirus-14 based on X-ray crystallography data.
AID342758Cytotoxicity against human FL cells after 24 hrs2008Bioorganic & medicinal chemistry, Aug-01, Volume: 16, Issue:15
Cinnamoyl- and hydroxycinnamoyl amides of glaucine and their antioxidative and antiviral activities.
AID111316Prevention of Echo-9-Induced Paralysis in Suckling mice by intraperitoneal administration at dose 1 mg/kg; expressed as no. nonparalyzed/total 2/301985Journal of medicinal chemistry, Dec, Volume: 28, Issue:12
[[(4,5-Dihydro-2-oxazolyl)phenoxy]alkyl]isoxazoles. Inhibitors of picornavirus uncoating.
AID123024In vivo antiviral activity at 8 mg/kg oral dose in mice infected with Poliovirus; 9/201985Journal of medicinal chemistry, Dec, Volume: 28, Issue:12
[[(4,5-Dihydro-2-oxazolyl)phenoxy]alkyl]isoxazoles. Inhibitors of picornavirus uncoating.
AID111317Prevention of Echo-9-Induced Paralysis in Suckling mice by intraperitoneal administration at dose 10 mg/kg; Expressed as % nonparalyzed1985Journal of medicinal chemistry, Dec, Volume: 28, Issue:12
[[(4,5-Dihydro-2-oxazolyl)phenoxy]alkyl]isoxazoles. Inhibitors of picornavirus uncoating.
AID124290In vivo antiviral activity at 16 mg/kg oral dose in mice infected with Poliovirus1985Journal of medicinal chemistry, Dec, Volume: 28, Issue:12
[[(4,5-Dihydro-2-oxazolyl)phenoxy]alkyl]isoxazoles. Inhibitors of picornavirus uncoating.
AID84720Compound was tested for minimum inhibitory concentration against human rhinovirus 14 (HRV14)1998Journal of medicinal chemistry, Jan-15, Volume: 41, Issue:2
Modeling RNA-ligand interactions: the Rev-binding element RNA-aminoglycoside complex.
AID1287138Cytotoxicity against human RD cells assessed as reduction in cell viability after 24 to 36 hrs by MTS-based CPE reduction assay2016Journal of medicinal chemistry, Mar-10, Volume: 59, Issue:5
Identification and Structure-Activity Relationships of Diarylhydrazides as Novel Potent and Selective Human Enterovirus Inhibitors.
AID222913Mean of MIC's was determined for the five types of virus like HRV-2, HRV-1A,HRV-22,HRV-41 and HRV-501987Journal of medicinal chemistry, Feb, Volume: 30, Issue:2
Structure-activity studies of 5-[[4-(4,5-dihydro-2-oxazolyl) phenoxy]alkyl]-3-methylisoxazoles: inhibitors of picornavirus uncoating.
AID1287137Antiviral activity against Enterovirus 71 infected in human RD cells after 24 to 36 hrs by MTS-based CPE reduction assay2016Journal of medicinal chemistry, Mar-10, Volume: 59, Issue:5
Identification and Structure-Activity Relationships of Diarylhydrazides as Novel Potent and Selective Human Enterovirus Inhibitors.
AID111319Prevention of Echo-9-Induced Paralysis in Suckling mice by intraperitoneal administration at dose 3.3 mg/kg; Expressed as % nonparalyzed1985Journal of medicinal chemistry, Dec, Volume: 28, Issue:12
[[(4,5-Dihydro-2-oxazolyl)phenoxy]alkyl]isoxazoles. Inhibitors of picornavirus uncoating.
AID342759Antiviral activity against Poliovirus type 1 Lsc-2ab in human FL cells2008Bioorganic & medicinal chemistry, Aug-01, Volume: 16, Issue:15
Cinnamoyl- and hydroxycinnamoyl amides of glaucine and their antioxidative and antiviral activities.
AID88358In vitro concentration required to achieve 50% protection of HeLa cells from HRV-2 induced cytopathic effect1995Journal of medicinal chemistry, Mar-03, Volume: 38, Issue:5
[[[(Thienylcarbonyl)alkyl]oxy]phenyl]- and [[[(pyrrylcarbonyl)alkyl]oxy]phenyl]oxazoline derivatives with potent and selective antihuman rhinovirus activity.
AID88190Compound concentration required to reduce the viability of mock-infected HeLa cells by 50%, was reported.1995Journal of medicinal chemistry, Mar-03, Volume: 38, Issue:5
[[[(Thienylcarbonyl)alkyl]oxy]phenyl]- and [[[(pyrrylcarbonyl)alkyl]oxy]phenyl]oxazoline derivatives with potent and selective antihuman rhinovirus activity.
AID111321Prevention of Echo-9-Induced Paralysis in Suckling mice by intraperitoneal administration at dose 33 mg/kg; Expressed as % nonparalyzed1985Journal of medicinal chemistry, Dec, Volume: 28, Issue:12
[[(4,5-Dihydro-2-oxazolyl)phenoxy]alkyl]isoxazoles. Inhibitors of picornavirus uncoating.
AID199858In vitro antiviral activity against Rhinovirus type-21985Journal of medicinal chemistry, Dec, Volume: 28, Issue:12
[[(4,5-Dihydro-2-oxazolyl)phenoxy]alkyl]isoxazoles. Inhibitors of picornavirus uncoating.
AID342761Selectivity index, CC50 for human FL cells to IC50 for Poliovirus type 1 Lsc-2ab2008Bioorganic & medicinal chemistry, Aug-01, Volume: 16, Issue:15
Cinnamoyl- and hydroxycinnamoyl amides of glaucine and their antioxidative and antiviral activities.
AID342769Cytotoxicity against human HeLa Ohio-1 cells2008Bioorganic & medicinal chemistry, Aug-01, Volume: 16, Issue:15
Cinnamoyl- and hydroxycinnamoyl amides of glaucine and their antioxidative and antiviral activities.
AID115931In vitro antiviral activity against mice infected intracerebrally with Poliovirus type-21985Journal of medicinal chemistry, Dec, Volume: 28, Issue:12
[[(4,5-Dihydro-2-oxazolyl)phenoxy]alkyl]isoxazoles. Inhibitors of picornavirus uncoating.
AID342770Selectivity index, CC50 for human HeLa Ohio-1 cells to IC50 for Human rhinovirus type 142008Bioorganic & medicinal chemistry, Aug-01, Volume: 16, Issue:15
Cinnamoyl- and hydroxycinnamoyl amides of glaucine and their antioxidative and antiviral activities.
AID342765Antiviral activity against Echovirus 13 in human FL cells2008Bioorganic & medicinal chemistry, Aug-01, Volume: 16, Issue:15
Cinnamoyl- and hydroxycinnamoyl amides of glaucine and their antioxidative and antiviral activities.
AID123022In vivo antiviral activity at 32 mg/kg oral dose in mice infected with Poliovirus; 15/201985Journal of medicinal chemistry, Dec, Volume: 28, Issue:12
[[(4,5-Dihydro-2-oxazolyl)phenoxy]alkyl]isoxazoles. Inhibitors of picornavirus uncoating.
AID392156Inhibition of Cryptosporidium hominis TS-DHFR by spectroscopic assay2009Bioorganic & medicinal chemistry letters, Jan-15, Volume: 19, Issue:2
Novel non-active site inhibitor of Cryptosporidium hominis TS-DHFR identified by a virtual screen.
AID123025In vivo antiviral activity of the compound in Placebo treated mice infected with Poliovirus; 4/201985Journal of medicinal chemistry, Dec, Volume: 28, Issue:12
[[(4,5-Dihydro-2-oxazolyl)phenoxy]alkyl]isoxazoles. Inhibitors of picornavirus uncoating.
AID342768Antiviral activity against Human rhinovirus type 14 in human HeLa Ohio-1 cells2008Bioorganic & medicinal chemistry, Aug-01, Volume: 16, Issue:15
Cinnamoyl- and hydroxycinnamoyl amides of glaucine and their antioxidative and antiviral activities.
AID115948MIC at the Maximal testable level in mice was evaluated1985Journal of medicinal chemistry, Dec, Volume: 28, Issue:12
[[(4,5-Dihydro-2-oxazolyl)phenoxy]alkyl]isoxazoles. Inhibitors of picornavirus uncoating.
AID85207Negative logarithm of minimal inhibitory concentration against human rhinovirus 141993Journal of medicinal chemistry, Jan-08, Volume: 36, Issue:1
On the prediction of binding properties of drug molecules by comparative molecular field analysis.
AID1562979Antiviral activity against Rhinovirus2019European journal of medicinal chemistry, Sep-15, Volume: 178Back to the future: Advances in development of broad-spectrum capsid-binding inhibitors of enteroviruses.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (55)

TimeframeStudies, This Drug (%)All Drugs %
pre-199017 (30.91)18.7374
1990's25 (45.45)18.2507
2000's9 (16.36)29.6817
2010's4 (7.27)24.3611
2020's0 (0.00)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 17.98

According to the monthly volume, diversity, and competition of internet searches for this compound, as well the volume and growth of publications, there is estimated to be moderate demand-to-supply ratio for research on this compound.

MetricThis Compound (vs All)
Research Demand Index17.98 (24.57)
Research Supply Index4.04 (2.92)
Research Growth Index4.39 (4.65)
Search Engine Demand Index15.26 (26.88)
Search Engine Supply Index2.00 (0.95)

This Compound (17.98)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Reviews2 (3.57%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other54 (96.43%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]