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Substrate Report for: Remdesivir

Remdesivir is a prodrug of an adenosine triphosphate (ATP) analog, with potential antiviral activity against a variety of RNA viruses. Substrate of CES1 and inhibitor of CES2. Remdesivir was initially developed by Gilead Sciences as an anti-Ebola agent. Clinical trials were initiated and conducted to evaluate Remdesivir safety and efficacy in COVID-19 patients. The product of hydrolysis is GS-704277 which is next hydrolyzed to form its active form GS-441524 or phosphorylated into a nucleoside triphosphate for exerting antiviral effect. Redesivir can also be hydrolysed to a much lesser extent by cathepsin CTSA and AchE and BChE. The hydrolysis is inhibited by other drugs such as loperamide LPA or Boceprevir


General
Type Pro-Drug, Drug, Not A/B H target, Propionate, Triazine
Chemical_Nomenclature 2-ethylbutyl (2S)-2-[[[(2R,3S,4R,5R)-5-(4-aminopyrrolo[2,1-f][1,2,4]triazin-7-yl)-5-cyano-3,4-dihydroxyoxolan-2-yl]methoxy-phenoxyphosphoryl]amino]propanoate
Canonical SMILES CCC(CC)COC(=O)C(C)NP(=O)(OCC1C(C(C(O1)(C#N)C2=CC=C3N2N=CN=C3N)O)O)OC4=CC=CC=C4
InChI 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
InChIKey RWWYLEGWBNMMLJ-YSOARWBDSA-N
Other name(s) 3QKI37EEHE ; GS 5734 ; GS-5734 ; CHEMBL4065616 ; SCHEMBL17712225 ; CHEBI:145994
________________________________________________________________________________________________
MW|602.6
Formula|C27H35N6O8P
CAS_number|1809249-37-3
PubChem|121304016
UniChem|RWWYLEGWBNMMLJ-YSOARWBDSA-N
IUPHAR|
Wikipedia|

Target
Families | Remdesivir ligand of proteins in family: Carb_B_Chordata, Carboxypeptidase_S10
Protein | human-CES1, human-CTSA

References:
Search PubMed for references concerning: Remdesivir

5 more
    Title: Remdesivir potently inhibits carboxylesterase-2 through covalent modifications: signifying strong drug-drug interactions
    Shen Y, Eades W, Yan B
    Ref: Fundamental & Clinical Toxicology, 35:432, 2021 : PubMed

            

    Title: Comparative therapeutic efficacy of remdesivir and combination lopinavir, ritonavir, and interferon beta against MERS-CoV
    Sheahan TP, Sims AC, Leist SR, Schafer A, Won J, Brown AJ, Montgomery SA, Hogg A, Babusis D and Baric RS <9 more author(s)>
    Ref: Nat Commun, 11:222, 2020 : PubMed

            

    Title: Coronavirus Susceptibility to the Antiviral Remdesivir (GS-5734) Is Mediated by the Viral Polymerase and the Proofreading Exoribonuclease
    Agostini ML, Andres EL, Sims AC, Graham RL, Sheahan TP, Lu X, Smith EC, Case JB, Feng JY and Denison MR <7 more author(s)>
    Ref: MBio, 9:, 2018 : PubMed