Rupintrivir
Basic information
- CAS
223537-30-2- Standard SMILES
CCOC(=O)/C=C/[C@H](C[C@@H]1CCNC1=O)NC(=O)[C@@H](CC(=O)[C@@H](NC(=O)c1cc(C)on1)C(C)C)Cc1ccc(F)cc1- InChIKey
CAYJBRBGZBCZKO-BHGBQCOSSA-N- Molecular formula
- C31H39FN4O7
- Average molar mass
- 598.7 g/mol
- Monoisotopic mass
- 598.28027776
Overview
Rupintrivir is a rhinovirus 3C protease inhibitor in development for use against human rhinoviral (HRV) infections. Rupintrivir was active against all 48 HRV serotypes tested in a cell protection assay in H1-HeLa cells. It is designed to combat colds caused by rhinovirus.
Names & identifiers
- Preferred name
- Rupintrivir
- IUPAC
- ethyl (E,4S)-4-[[(2R,5S)-2-[(4-fluorophenyl)methyl]-6-methyl-5-[(5-methyl-1,2-oxazole-3-carbonyl)amino]-4-oxoheptanoyl]amino]-5-[(3S)-2-oxopyrrolidin-3-yl]pent-2-enoate
- English name
- ethyl (E,4S)-4-[[(2R,5S)-2-[(4-fluorophenyl)methyl]-6-methyl-5-[(5-met hyloxazole-3-carbonyl)amino]-4-oxo-heptanoyl]amino]-5-[(3S)-2-oxopyrro lidin-3-yl]pent-2-enoate
- Molecular formula
- C31H39FN4O7
- Molecular weight
- 598.66
Names & synonyms
Rupintrivir223537-30-2RuprintrivirAG-7088RGE5K1Q5QWDTXSID201028116Ethyl (2E,4S)-4-(((2R,5S)-2-(4-fluorobenzyl)-6-methyl-5-(((5-methylisoxazol-3-yl)carbonyl)amino)-4-oxoheptanoyl)amino)-5-((3S)-2-oxopyrrolidin-3-yl)pent-2-enoaterupintrivirumethyl (2E,4S)-4-[((2R,5S)-2-(4-fluorobenzyl)-6-methyl-5-{[(5-methylisoxazol-3-yl)carbonyl]amino}-4-oxoheptanoyl)amino]-5-[(3S)-2-oxopyrrolidin-3-yl]pent-2-enoateEthyl (2E,4S)-4-[[(2R,5S)-2-(4-fluorobenzyl)-6-methyl-5-[[(5-methylisoxazol-3-yl)carbonyl]amino]-4-oxoheptanoyl]amino]-5-[(3S)-2-oxopyrrolidin-3-yl]pent-2-enoateRefChem:883978DTXCID101513693
Show more names
Aids121840Aids-121840Rupintrivir【PZ0315】Rupintrivir (AG7088)Rupintrivir, 10 mM in DMSOAG 7088 - Rupintrivir | Ruprintrivirethyl (E,4S)-4-[[(2R,5S)-2-[(4-fluorophenyl)methyl]-6-methyl-5-[(5-met hyloxazole-3-carbonyl)amino]-
Properties
Computed structural properties
- XLogP
- 3.1
- Topological polar surface area
- 157 Ų
- Hydrogen bond donors
- 3
- Hydrogen bond acceptors
- 9
- Rotatable bonds
- 16
- Heavy atoms
- 43
- Formal charge
- 0
- Complexity
- 1,010
Experimental & physicochemical properties
DrugsPharmaceuticals -> Listed in ZINC15
LogP2.8
Physicochemical properties
- Melting point
- 170 · 170-171°C
- Boiling point
- 866.7 · 866.7±65.0 °C(Predicted)
- Density
- 1.213 · 1.213
- storage temp.
- room temp
- solubility
- Chloroform (Slightly), Methanol (Slightly)
- pka
- 12.16 · 12.16±0.46(Predicted)
- form
- powder
- color
- white to beige
- optical activity
- 30 to · [α]/D +30 to +40°, c = 0.5 in chloroform-d
- InChIKey
- CAYJBRBGZBCZKO-BHGBQCOSSA-N
- SMILES
- C(OCC)(=O)/C=C/[C@@H](NC(=O)[C@H](CC1=CC=C(F)C=C1)CC(=O)[C@@H](NC(C1C=C(C)ON=1)=O)C(C)C)C[C@@H]1CCNC1=O
- FDA UNII
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
Safety data
- wgk
- WGK 3
- Storage Class
- 11 - Combustible Solids
Chemistry & industry
Pharmacology
Mechanism of ActionThe 3C protease (3CP) enzyme is central to rhinovirus replication. By binding to and inhibiting this enzyme, AG7088 prevents rhinovirus replication in cells of the respiratory tract and stops cold symptoms developing.
MeSH Pharmacological Classification
Agents used in the prophylaxis or therapy of VIRUS DISEASES. Some of the ways they may act include preventing viral replication by inhibiting viral DNA polymerase; binding to specific cell-surface receptors and inhibiting viral penetration or uncoating; inhibiting viral protein synthesis; or blocking late stages of virus assembly.
Compounds which inhibit or antagonize biosynthesis or actions of proteases (ENDOPEPTIDASES).
Applications
UsesLabelled Rupintrivir. Rupintrivir (formerly AG7088) is an irreversible inhibitor of the human rhinovirus (HRV) 3C protease that has been demonstrated to have in vitro activity against all HRVs tested, consistent with its interaction with a strictly conserved subset of amino acids in the 3C protease.
General DescriptionRupintrivir is an irreversible peptidomimetic inhibitor designed to target human rhinovirus (HRV). It was previously named as AG7088. It has been suggested that rupintrivir may be involved in vitro antiviral activity.
Related reactions
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Compound notes
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