Rupintrivir

Names

[ Name ]:
Rupintrivir

[Synonym ]:
ag7088
UNII-RGE5K1Q5QW
Ruprintrivir
Rupintrivir

Biological Activity

[Description]:

Rupintrivirvr (AG7088), an antiviral drug, is a potent, selective and irreversible inhibitor of human rhinovirus (HRV) 3C protease. Rupintrivirvr inhibits replication of a panel of 48 different HRV serotypes in H1-HeLA and MRC-5 cell protection assays, with a mean EC50 of 0.023 μM. Rupintrivirvr shows immune-modulatory effect[1][2].

[Related Catalog]:

Research Areas >> Infection

Research Areas >> Inflammation/Immunology

[In Vitro]

In H1-HeLa and MRC-5 cell protection assays, Rupintrivirvr (AG7088) inhibited the replication of all HRV serotypes (48 of 48) tested with a mean 50% effective concentration (EC50) of 0.023 μM (range, 0.003 to 0.081 μM) and a mean EC90 of 0.082 μM (range, 0.018 to 0.261 μM) as well as that of related picornaviruses including coxsackieviruses A21 and B3, enterovirus 70, and echovirus 11[1].

[In Vivo]

Rupintrivirvr (AG7088) reduces RV-induced TH-2 cytokine IL-4 in precision-cut lung slices (PCLS) of HDM-sensitized mice ex vivo[2].

[References]

[1]. Patick AK, et al. In vitro antiviral activity of AG7088, a potent inhibitor of human rhinovirus 3C protease. Antimicrob Agents Chemother. 1999 Oct;43(10):2444-50.

[2]. Danov O, et al. Rupintrivir reduces RV-induced TH-2 cytokine IL-4 in precision-cut lung slices (PCLS) of HDM-sensitized mice ex vivo. Respir Res. 2019 Oct 22;20(1):228.

[3]. Dragovich PS, et al. Structure-based design, synthesis, and biological evaluation of irreversible human rhinovirus 3C protease inhibitors. 3. Structure-activity studies of ketomethylene-containing peptidomimetics. J Med Chem. 1999 Apr 8;42(7):1203-12.

Chemical & Physical Properties

[ Density]:
1.213g/cm3

[ Boiling Point ]:
866.7ºC at 760mmHg

[ Melting Point ]:
170-171°C

[ Molecular Formula ]:
C₃₁H₃₉FN₄O₇

[ Molecular Weight ]:
598.66200

[ Flash Point ]:
477.9ºC

[ Exact Mass ]:
598.28000

[ PSA ]:
156.70000

[ LogP ]:
3.93550

[ Vapour Pressure ]:
1.87E-30mmHg at 25°C

[ Index of Refraction ]:
1.537

Safety Information

[ RIDADR ]:
NONH for all modes of transport

Articles

Crystal structures of enterovirus 71 3C protease complexed with rupintrivir reveal the roles of catalytically important residues.

J. Virol. 85(19) , 10021-30, (2011)

EV71 is the primary pathogenic cause of hand-foot-mouth disease (HFMD), but an effective antiviral drug currently is unavailable. Rupintrivir, an inhibitor against human rhinovirus (HRV), has potent a...

Conservation of amino acids in human rhinovirus 3C protease correlates with broad-spectrum antiviral activity of rupintrivir, a novel human rhinovirus 3C protease inhibitor.

Antimicrob. Agents Chemother. 49(2) , 619-26, (2005)

The picornavirus 3C protease is required for the majority of proteolytic cleavages that occur during the viral life cycle. Comparisons of published amino acid sequences from 6 human rhinoviruses (HRV)...