An inhibitor of HRV 3C protease
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Rupintrivir

Item No. 41543

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
(2E,4S)-4-[[(2R,5S)-2-[(4-fluorophenyl)methyl]-6-methyl-5-[[(5-methyl-3-isoxazolyl)carbonyl]amino]-1,4-dioxoheptyl]amino]-5-[(3S)-2-oxo-3-pyrrolidinyl]-2-pentenoic acid, ethyl ester
CAS Number
223537-30-2
Synonyms
  • AG-7088
  • Rupinavir
Molecular Formula
C31H39FN4O7
Formula Weight
598.7
Purity
≥98%
Formulation (Request formulation change)
A solid
Solubility(Learn about Variance in Solubility)
Acetonitrile: Slightly soluble: 0.1-1 mg/mlDMSO: Sparingly soluble: 1-10 mg/ml
SMILES
O=C(N[C@H](/C=C/C(OCC)=O)C[C@@H]1CCNC1=O)[C@@H](CC([C@H](C(C)C)NC(C2=NOC(C)=C2)=O)=O)CC(C=C3)=CC=C3F
InChi Code
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
InChi Key
CAYJBRBGZBCZKO-BHGBQCOSSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    Cayman Chemical
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    Product Description

    Rupintrivir is an inhibitor of human rhinovirus (HRV) 3C protease.1 It inhibits HRV 3C protease-induced proteolysis of HRV-14 precursor polyproteins in HRV-14-infected H1HeLa cells when used at a concentration of 2 µM. Rupintrivir inhibits the replication of 49 serotypes of HRV in HRV-infected H1HeLa cells (mean EC50 = 0.023 µM). It also inhibits the replication of coxsackievirus 21, coxsackievirus B3, echovirus type 11, and enterovirus 70 in virus-infected MRC-5 cells (EC50s = 0.147, 0.183, 0.014, and 0.007 µM, respectively). Rupintrivir (10 µM) decreases the number of HRV-2 plaque forming units (PFUs) in, and IL-8 and IL-6 secretion by, HRV-2-infected BEAS-2B bronchial epithelial cells.2 In vivo, rupintrivir (0.1 mg/kg per day) inhibits enterovirus 71-induced limb paralysis and decreases in survival, as well as reduces intestinal, lung, brain stem, and cardiac muscle viral loads, in enterovirus-71-infected neonatal mice.3

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Patick, A.K., Binford, S.L., Brothers, M.A., et al. In vitro antiviral activity of AG7088, a potent inhibitor of human rhinovirus 3C protease. Antimicrob. Agents Chemother. 43(10), 2444-2450 (1999).

    2. Zalman, L.S., Brothers, M.A., Dragovich, P.S., et al. Inhibition of human rhinovirus-induced cytokine production by AG7088, a human rhinovirus 3C protease inhibitor. Antimicrob. Agents Chemother. 44(5), 1236-1241 (2000).

    3. Zhang, X., Song, Z., Qin, B., et al. Rupintrivir is a promising candidate for treating severe cases of enterovirus-71 infection: Evaluation of antiviral efficacy in a murine infection model. Antiviral Res. 97(3), 264-269 (2013).