A prodrug form of GS-443902
Related Products
Active Metabolite(s)
30469GS-441524
Labeled Version(s)
30905Remdesivir-d4
Metabolite(s)
9003569GS-704277
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Remdesivir

Item No. 30354

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
N-[(S)-hydroxyphenoxyphosphinyl)-L-alanine, 2-ethylbutyl ester, 6-ester with 2-C-(4-aminopyrrolo[2,1-f][1,2,4]triazin-7-yl)-2,5-anhydro-D-altrononitrile
CAS Number
1809249-37-3
Synonyms
  • GS-5734
Molecular Formula
C27H35N6O8P
Formula Weight
602.6
Purity
≥98%
Formulation (Request formulation change)
A crystalline solid
Solubility(Learn about Variance in Solubility)
DMSO: soluble
λmax
246 nm
SMILES
O=[P@](N[C@@H](C)C(OCC(CC)CC)=O)(OC1=CC=CC=C1)OC[C@H]2O[C@](C3=CC=C4N3N=CN=C4N)(C#N)[C@H](O)[C@@H]2O
InChi Code
InChI=1S/C27H35N6O8P/c1-4-18(5-2)13-38-26(36)17(3)32-42(37,41-19-9-7-6-8-10-19)39-14-21-23(34)24(35)27(15-28,40-21)22-12-11-20-25(29)30-16-31-33(20)22/h6-12,16-18,21,23-24,34-35H,4-5,13-14H2,1-3H3,(H,32,37)(H2,29,30,31)/t17-,21+,23+,24+,27-,42-/m0/s1
InChi Key
RWWYLEGWBNMMLJ-YSOARWBDSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    Product Description

    Remdesivir is a prodrug form of the antiviral nucleotide analog GS-443902.1,2,3 Upon entry into cells, remdesivir is metabolized into the intermediate metabolite GS-441524 (Item No. 30469), which is then further metabolized to the active nucleotide triphosphate GS-443902 that induces RNA chain termination and inhibits viral polymerases.4 Remdesivir reduces viral titers in primary human airway epithelial (HAE) cells infected with Middle East respiratory syndrome coronavirus (MERS-CoV) or severe acute respiratory syndrome CoV (SARS-CoV; EC50s = 0.074 and 0.069 µM, respectively). It reduces infectious virus production in SARS-CoV-2-infected HAE cells (EC50 = 10 nM).5 In vivo, remdesivir (25 and 50 mg/kg) reduces lung viral titers and prevents weight loss in a mouse model of SARS-CoV infection.2 Remdesivir (25 mg/kg) also reduces lung viral titers and lung hemorrhage and improves pulmonary function in mice infected with a chimeric SARS-CoV encoding the SARS-CoV-2 RNA-dependent RNA polymerase (RdRp).5 Formulations containing remdesivir have been used in the treatment of COVID-19.

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Agostini, M.L., Andres, E.L., Sims, A.C., et al. Coronavirus susceptibility to the antiviral remdesivir (GS-5734) is mediated by the viral polymerase and the proofreading exoribonuclease. mBio 9(2), e00221-00218 (2018).

    2. Sheahan, T.P., Sims, A.C., Graham, R.L., et al. Broad-spectrum antiviral GS-5734 inhibits both epidemic and zoonotic coronaviruses. Sci. Transl. Med. 9(396), eaal3653 (2017).

    3. Cox, R.M., Wolf, J.D., Lieber, C.M., et al. Oral prodrug of remdesivir parent GS-441524 is efficacious against SARS-CoV-2 in ferrets. Nat. Commun. 12(1), 6415 (2021).

    4. Eastman, R.T., Roth, J.S., Brimacombe, K.R., et al. Remdesivir: A review of its discovery and development leading to emergency use authorization for treatment of COVID-19. ACS Cent. Sci. 6(5), 672-683 (2020).

    5. Pruijssers, A.J., George, A.S., Schäfer, A., et al. Remdesivir inhibits SARS-CoV-2 in human lung cells and chimeric SARS-CoV expressing the SARS-CoV-2 RNA polymerase in mice. Cell Rep. 32(3), 107940 (2020).

    Product Citations

    Li, J., de Melo Jorge, D.M., Wang, W., et al. Differential bioactivation profiles of different GS-441524 prodrugs in cell and mouse models: ProTide prodrugs with high cell permeability and susceptibility to cathepsin a are more efficient in delivering antiviral active metabolites to the lung. J. Med. Chem. (2024).