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Rupintrivir

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Chemical compound Pharmaceutical compound
Rupintrivir
Clinical data
Trade namesRupintrivir
Legal status
Legal status
  • US: Investigational drug
Identifiers
IUPAC name
  • Ethyl (E,4S)-4--6-methyl-5--4-oxoheptanoyl]amino]-5-pent-2-enoate
CAS Number
PubChem CID
DrugBank
ChemSpider
UNII
KEGG
ChEMBL
Chemical and physical data
FormulaC31H39FN4O7
Molar mass598.672 g·mol
3D model (JSmol)
SMILES
  • CCOC(=O)/C=C/(C1CCNC1=O)NC(=O)(CC2=CC=C(C=C2)F)CC(=O)(C(C)C)NC(=O)C3=NOC(=C3)C
InChI
  • 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
  • Key:CAYJBRBGZBCZKO-BHGBQCOSSA-N

Rupintrivir (AG-7088, Rupinavir) is a peptidomimetic antiviral drug which acts as a 3C and 3CL protease inhibitor. It was developed for the treatment of rhinoviruses, and has subsequently been investigated for the treatment of other viral diseases including those caused by picornaviruses, norovirus, and coronaviruses, such as SARS and COVID-19.

See also

References

  1. Dragovich PS, Prins TJ, Zhou R, Webber SE, Marakovits JT, Fuhrman SA, et al. (April 1999). "Structure-based design, synthesis, and biological evaluation of irreversible human rhinovirus 3C protease inhibitors. 4. Incorporation of P1 lactam moieties as L-glutamine replacements". Journal of Medicinal Chemistry. 42 (7): 1213–24. doi:10.1021/jm9805384. PMID 10197965.
  2. Santos MM, Moreira R (October 2007). "Michael acceptors as cysteine protease inhibitors". Mini Reviews in Medicinal Chemistry. 7 (10): 1040–50. doi:10.2174/138955707782110105. PMID 17979807.
  3. Yuan S, Fan K, Chen Z, Sun Y, Hou H, Zhu L (February 2020). "Structure of the HRV-C 3C-Rupintrivir Complex Provides New Insights for Inhibitor Design". Virologica Sinica. 35 (4): 445–454. doi:10.1007/s12250-020-00196-4. PMC 7462945. PMID 32103448.
  4. Patick AK, Binford SL, Brothers MA, Jackson RL, Ford CE, Diem MD, et al. (October 1999). "In vitro antiviral activity of AG7088, a potent inhibitor of human rhinovirus 3C protease". Antimicrobial Agents and Chemotherapy. 43 (10): 2444–50. doi:10.1128/AAC.43.10.2444. PMC 89498. PMID 10508022.
  5. Jensen LM, Walker EJ, Jans DA, Ghildyal R (2015). "Proteases of human rhinovirus: role in infection". Rhinoviruses. Methods in Molecular Biology. Vol. 1221. pp. 129–41. doi:10.1007/978-1-4939-1571-2_10. ISBN 978-1-4939-1570-5. PMID 25261311.
  6. Barnard DL (2006). "Current status of anti-picornavirus therapies". Current Pharmaceutical Design. 12 (11): 1379–90. doi:10.2174/138161206776361129. PMID 16611122.
  7. De Palma AM, Vliegen I, De Clercq E, Neyts J (November 2008). "Selective inhibitors of picornavirus replication". Medicinal Research Reviews. 28 (6): 823–84. doi:10.1002/med.20125. PMID 18381747. S2CID 1575335.
  8. Rocha-Pereira J, Nascimento MS, Ma Q, Hilgenfeld R, Neyts J, Jochmans D (August 2014). "The enterovirus protease inhibitor rupintrivir exerts cross-genotypic anti-norovirus activity and clears cells from the norovirus replicon". Antimicrobial Agents and Chemotherapy. 58 (8): 4675–81. doi:10.1128/AAC.02546-13. PMC 4136040. PMID 24890597.
  9. Anand K, Ziebuhr J, Wadhwani P, Mesters JR, Hilgenfeld R (June 2003). "Coronavirus main proteinase (3CLpro) structure: basis for design of anti-SARS drugs". Science. 300 (5626): 1763–7. Bibcode:2003Sci...300.1763A. doi:10.1126/science.1085658. PMID 12746549.
  10. Liu C, Zhou Q, Li Y, Garner LV, Watkins SP, Carter LJ, et al. (2020). "Research and Development on Therapeutic Agents and Vaccines for COVID-19 and Related Human Coronavirus Diseases". ACS Central Science. 6 (3): 315–331. doi:10.1021/acscentsci.0c00272. PMC 7094090. PMID 32226821.


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