REMDESIVIR

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Synonyms
Status
Molecule Category Free-form
UNII 3QKI37EEHE

Structure

InChI Key RWWYLEGWBNMMLJ-YSOARWBDSA-N
Smiles CCC(CC)COC(=O)[C@H](C)N[P@](=O)(OC[C@H]1O[C@@](C#N)(c2ccc3c(N)ncnn23)[C@H](O)[C@@H]1O)Oc1ccccc1
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

Physicochemical Descriptors

Property Name Value
Molecular Formula C27H35N6O8P
Molecular Weight 602.59
AlogP 2.31
Hydrogen Bond Acceptor 13.0
Hydrogen Bond Donor 4.0
Number of Rotational Bond 13.0
Polar Surface Area 203.55
Molecular species NEUTRAL
Aromatic Rings 3.0
Heavy Atoms 42.0

Bioactivity

Mechanism of Action Action Reference
RNA-directed RNA polymerase L inhibitor INHIBITOR PubMed PubMed Other FDA
Assay Description Organism Bioactivity Reference
Antiviral activity against Ebolavirus Kikwit infected in human HeLa cells assessed as reduction in viral glycoprotein levels preincubated with cells for 2 hrs followed by viral infection measured after 48 hrs by immunostaining based assay Ebolavirus 100.0 nM
Antiviral activity against GFP-fused Ebolavirus infected in TERT-immortalized HMVEC assessed as reduction in viral replication preincubated with cells followed by viral infection measured after 3 to 4 days by fluorescence assay Ebolavirus 53.0 nM
Antiviral activity against Respiratory syncytial virus A2 infected in human Hep2 cells assessed as reduction of virus-induced cytopathic effect after 4 days by Cell-Titer Glo assay Human respiratory syncytial virus A2 15.0 nM
Antiviral activity against Hepatitis C virus genotype 1b infected in human HuH7 cells preincubated with cells for 3 days followed by viral infection by luciferase assay Hepatitis C virus subtype 1b 57.0 nM
Antiviral activity against Ebolavirus Kikwit infected in human macrophages preincubated with cells for 2 hrs followed by viral infection measured after 48 hrs Ebolavirus 86.0 nM
Antiviral activity against Ebolavirus infected in human primary macrophages after 48 hrs by immuno-staining assay Ebolavirus 86.0 nM
Antiviral activity against Ebolavirus infected in human HeLa cells after 48 hrs by immuno-staining assay Ebolavirus 140.0 nM
Antiviral activity against Ebolavirus infected in human HuH7 cells after 3 days by end point dilution assay Ebolavirus 70.0 nM
Determination of IC50 values for inhibition of SARS-CoV-2 induced cytotoxicity of Caco-2 cells after 48 hours by high content imaging Homo sapiens 760.0 nM
Determination of antiviral efficacy in high-content imaging assay in Vero E6 cells infected with SARS-CoV-2 (USA-WA1/2020 isolate) at MOI 0.75 after 24 hrs Chlorocebus sabaeus 620.0 nM
Antiviral activity against SARS coronavirus infected in primary HAE cells SARS coronavirus 69.0 nM
Antiviral activity against Middle East respiratory syndrome coronavirus infected in primary HAE cells Middle East respiratory syndrome coronavirus 74.0 nM
Antiviral activity against 2019-nCoV BetaCoV/Wuhan/WIV04/2019 infected in African green monkey VeroE6 cells assessed as reduction in viral yield preincubated with virus for 1 hr followed by cell infection and measured after 2 hrs by qRT-PCR method Severe acute respiratory syndrome coronavirus 2 770.0 nM
Antiviral activity against wild type HCoV-OC43 infected in human Huh-7 cells preincubated for 1 hrs followed by overlaying with reduced-serum Medium and measured after 72 hrs ELISpot assay Human coronavirus OC43 150.0 nM
Antiviral activity against HCoV-229E infected in human Huh7 cells assessed as reduction in virus induced cytopathic effect incubated for 6 days by cellTiter-Glo assay Human coronavirus 229E 24.0 nM
Antiviral activity against SARS-CoV expressing green fluorescent protein infected in human airway epithelial cells incubated for 48 hrs by RT-PCR method Severe acute respiratory syndrome-related coronavirus 60.0 nM
Antiviral activity against RSV A2 infected in HEp-2 cells assessed as reduction in virus-induced cytopathic effect after 4 days by CellTiter Glo viability assay Human respiratory syncytial virus 15.0 nM
Antiviral activity against RSV infected in NHBE cells after 3 days by ONE-Glo luciferase assay Respiratory syncytial virus 49.0 nM
Drug metabolism in human HEp-2 cells assessed as 1-NTP metabolite concentration at EC50 over 48 hrs by LC-MS/MS analysis Homo sapiens 110.0 nM
Drug metabolism in NHBE cells assessed as 1-NTP metabolite concentration at EC50 over 48 hrs by LC-MS/MS analysis Homo sapiens 140.0 nM
Antiviral activity against SARS-CoV-2 infected in 16HBE14o- cells assessed as inhibition of viral replication after 1 day by Nano-Glo luciferase assay Severe acute respiratory syndrome coronavirus 2 590.0 nM
Antiviral activity against SARS-CoV-2 infected in Vero E6 cells assessed as inhibition of viral replication measured after 48 hrs by qRT-PCR method Severe acute respiratory syndrome coronavirus 2 770.0 nM
Antiviral activity against SARS-CoV-2 nCoV-2019BetaCoV/Wuhan/WIV04/ infected in African green monkey Vero E6 cells assessed as inhibition of viral replication at 5 uM when host cells were pretreated for 1 hr followed by viral infection then followed by removal of infected supernatant and subsequent culture addition with fresh compounds and measured after 24 hrs by qRT-PCR method relative to control Severe acute respiratory syndrome coronavirus 2 65.0 %
Antiviral activity against HCoV-OC43 infected in HCT-8 cells assessed as reduction in viral replication treated 1 hr post infection and measured after 120 hrs post infection by MTS cell proliferation colorimetric assay Human coronavirus OC43 700.0 nM
Antiviral activity against SARS-COV 2 infected in human Huh-7 cells assessed as inhibition of viral replication at MOI of 0.01 and incubated after 2 hrs post infection for 48 hrs by direct yield reduction assay Severe acute respiratory syndrome coronavirus 2 4.0 nM
Antiviral activity against SARS-COV 2 infected in human Caco-2 cells assessed as inhibition of viral replication at MOI of 0.01 and incubated after 2 hrs post infection for 48 hrs by immunodetection assay Severe acute respiratory syndrome coronavirus 2 10.0 nM
Antiviral activity against SARS-COV 2 infected in human Calu-3 cells assessed as inhibition of viral replication at MOI of 0.01 and incubated after 2 hrs post infection for 48 hrs by direct yield reduction assay Severe acute respiratory syndrome coronavirus 2 110.0 nM
Antiviral activity against SARS-COV 2 infected in human Huh-7 cells Severe acute respiratory syndrome coronavirus 2 2.0 nM
Antiviral activity against SARS-COV 2 infected in human Caco-2 cells Severe acute respiratory syndrome coronavirus 2 380.0 nM
Antiviral activity against SARS-CoV-2 C-Tan-nCoV Wuhan strain 01 infected in African green monkey Vero cells assessed as inhibition of viral replication measured after 48 hrs by RT-qPCR method Severe acute respiratory syndrome coronavirus 2 800.0 nM
Antiviral activity against SARS Cov-2 USA/WA1/2020 infected in Vero E6 cells assessed as reduction in virus-induced cytopathic effect preincubated for 1 hr followed by viral infection and measured after 48 hrs post infection Severe acute respiratory syndrome coronavirus 2 850.0 nM
Antiviral activity against SARS coronavirus 2 USA/WA1/2020 infected in Calu-3 cells assessed as reduction in virus-induced cytopathic effect preincubated for 1 hr followed by viral infection and measured after 48 hrs Severe acute respiratory syndrome coronavirus 2 60.0 nM
Antiviral activity against Ebola virus trVLP infected in human Huh-7 cells pretreated for 1 hrs followed by viral infection and measured after 24 hrs by dual luciferase reporter assay Ebolavirus 320.0 nM
Antiviral activity against SARS-CoV-2 nCoV-2019 BetaCoV/Wuhan/WIV04/2019 infected in African green monkey VeroE6 cells incubated for 48 hrs by qRT-PCR method Severe acute respiratory syndrome coronavirus 2 770.0 nM
Antiviral activity against SARS Cov-2 USA_WA1/2020 infected in human Calu-3 cells measured upto 72 hrs by qRT-PCR method Severe acute respiratory syndrome coronavirus 2 280.0 nM
Antiviral activity against SARS Cov-2 USA_WA1/2020 infected in HAE cells measured upto 72 hrs by qRT-PCR method Severe acute respiratory syndrome coronavirus 2 10.0 nM
Antiviral activity against SARS-CoV-2/NL/2020 infected in African green monkey Vero E6 cells assessed as inhibition of plaque formation measured after 3 days by Plaque reduction assay Severe acute respiratory syndrome coronavirus 2 150.0 nM
Antiviral activity against SARS-COV2/Padova/2020 infected in African green monkey Vero E6 cells assessed as inhibition of plaque formation measured after 3 days by Plaque reduction assay Severe acute respiratory syndrome coronavirus 2 250.0 nM
Antiviral activity against Severe acute respiratory syndrome coronavirus 2 UC-1074 infected in African green monkey Vero cells assessed as reduction in plaque formation measured after 5 days by microscopic analysis Severe acute respiratory syndrome coronavirus 2 870.0 nM
Antiviral activity against Severe acute respiratory syndrome coronavirus 2 UC-1075 infected in African green monkey Vero cells assessed as reduction in plaque formation measured after 5 days by microscopic analysis Severe acute respiratory syndrome coronavirus 2 610.0 nM

Related Entries

Cross References

Resources Reference
ChEBI 145994
ChEMBL CHEMBL4065616
DrugBank DB14761
DrugCentral 5376
FDA SRS 3QKI37EEHE
Guide to Pharmacology 10715
PubChem 121304016
SureChEMBL SCHEMBL17712225
CONTENTS