Details
Stereochemistry | ABSOLUTE |
Molecular Formula | C31H39FN4O7 |
Molecular Weight | 598.6624 |
Optical Activity | UNSPECIFIED |
Defined Stereocenters | 4 / 4 |
E/Z Centers | 1 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
[H][C@@]3(C[C@H](NC(=O)[C@@H](CC(=O)[C@@H](NC(=O)C1=NOC(C)=C1)C(C)C)CC2=CC=C(F)C=C2)\C=C\C(=O)OCC)CCNC3=O
InChI
InChIKey=CAYJBRBGZBCZKO-BHGBQCOSSA-N
InChI=1S/C31H39FN4O7/c1-5-42-27(38)11-10-24(16-21-12-13-33-29(21)39)34-30(40)22(15-20-6-8-23(32)9-7-20)17-26(37)28(18(2)3)35-31(41)25-14-19(4)43-36-25/h6-11,14,18,21-22,24,28H,5,12-13,15-17H2,1-4H3,(H,33,39)(H,34,40)(H,35,41)/b11-10+/t21-,22+,24+,28-/m0/s1
Rupintrivir is a peptide aldehyde that targets the human rhinovirus (HRV) 3C proteinase enzyme and has the potential for the treatment of the common cold. Rupintrivir is derived from AG-6084 - in order to develop human rhinovirus 3C protease inhibitors with improved pharmacological properties, Agouron replaced the backbone amide moiety of the series which yielded AG-6084, with a ketomethylene isostere. A phase II efficacy study has been completed in healthy patients infected with the rhinovirus. Ruprintrivir was well tolerated; blood-tinged mucus and nasal passage irritation were the most common adverse effects reported. Pharmacokinetic analysis of plasma and nasal ruprintrivir concentrations revealed intranasal drug residence with minimal systemic absorption. The fact that rupintrivir is active against noroviruses belonging to genogroup I (Norwalk virus), genogroup V (murine norovirus), and the recombinant 3C-like protease of a GII norovirus suggests that the drug exerts cross-genotypic anti-norovirus activity and will thus most likely be effective against the clinically relevant human norovirus strains. Rupintrivir is also a high affinity inhibitor of Enterovirus-71 3C protease.
Originator
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: HRV-14 3C protease |
0.005 µM [EC50] | ||
Target ID: EV-A71 3C protease |
7.3 µM [IC50] | ||
Target ID: GII norovirus 3C-like protease Sources: https://www.ncbi.nlm.nih.gov/pubmed/24890597 |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
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Primary | Unknown Approved UseUnknown |
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Primary | Unknown Approved UseUnknown |
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Primary | Unknown Approved UseUnknown |
PubMed
Title | Date | PubMed |
---|---|---|
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 Apr 8 |
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Design and synthesis of peptidomimetic severe acute respiratory syndrome chymotrypsin-like protease inhibitors. | 2005 Nov 3 |
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Inhibition of the severe acute respiratory syndrome 3CL protease by peptidomimetic alpha,beta-unsaturated esters. | 2005 Sep 1 |
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In vitro resistance study of rupintrivir, a novel inhibitor of human rhinovirus 3C protease. | 2007 Dec |
Patents
Sample Use Guides
In Vivo Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/14638501
8 mg two or five times daily for 5 days.
Route of Administration:
Nasal
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/10508022
In H1-HeLa or MRC-5 cell protection assays, AG7088 was active against all four picornaviruses tested (CAV 21, CVB 3, EV 11, ETV 70), with EC50 ranging from 0.007 to 0.183 uM and EC90 ranging from 0.033 to 0.340 uM.
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NCI_THESAURUS |
C783
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C281
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223537-30-2
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MM-65
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6440352
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C82255
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Rupintrivir
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RGE5K1Q5QW
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CHEMBL20210
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DTXSID201028116
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8308
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DB05102
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ACTIVE MOIETY