Page last updated: 2024-11-13

GS-443902

Description Research Excerpts Clinical Trials Roles Classes Pathways Study Profile Bioassays Related Drugs Related Conditions Protein Interactions Research Growth Market Indicators

Description

GS-441524 triphosphate: intracellular active metabolite of remdesivir [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

GS-443902 : An organic triphosphate that is GS-441524 in which the 5'-hydroxy group has been replaced by a triphosphate group. It is the active metabolite of remdesivir. [Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Cross-References

ID SourceID
PubMed CID56832906
CHEMBL ID2016761
CHEBI ID150869
SCHEMBL ID10120881

Synonyms (32)

Synonym
rdv-tp
((2r,3s,4r,5r)-5-(4-aminopyrrolo[2,1-f][1,2,4]triazin-7-yl)-5-cyano-3,4-dihydroxytetrahydrofuran-2-yl)methyl tetrahydrogen triphosphate ,
gs-443902
gs-441524 triphosphate
1355149-45-9
remdesivir triphosphate
CHEBI:150869
CHEMBL2016761 ,
SCHEMBL10120881
((2r,3s,4r,5r)-5-(4-aminopyrrolo[2,1-f][1,2,4]triazin-7-yl)-5-cyano-3,4-dihydroxytetrahydrofuran-2-yl)methyl tetrahydrogentriphosphate
r-32-gs-441524
bdbm50236025
EX-A3055
remdesivir tp
gs443902;gs 443902;gs-441524 triphosphate; remdesivir metabolite;gs441524 triphosphate
BCP32801
unii-ael0yed4su
ael0yed4su ,
d-altrononitrile, 2-c-(4-aminopyrrolo(2,1-f)(1,2,4)triazin-7-yl)-2,5-anhydro-, 6-(tetrahydrogen triphosphate)
((2r,3s,4r,5r)-5-(4-aminopyrrolo[2,1-f][1,2,4]triazin-7-yl)-5-cyano-3,4-dihydroxytetrahydrofuran-2-yl)methyl tetrahydrogen (s)-triphosphate
(s)-((2r,3s,4r,5r)-5-(4-aminopyrrolo[2,1-f][1,2,4]triazin-7-yl)-5-cyano-3,4-dihydroxytetrahydrofuran-2-yl)methyl tetrahydrogen triphosphate
CS-0101780
HY-126303
[[(2r,3s,4r,5r)-5-(4-aminopyrrolo[2,1-f][1,2,4]triazin-7-yl)-5-cyano-3,4-dihydroxyoxolan-2-yl]methoxy-hydroxyphosphoryl] phosphono hydrogen phosphate
remdesivir metabolite
[[(2~{r},3~{s},4~{r},5~{r})-5-(4-azanylpyrrolo[2,1-f][1,2,4]triazin-7-yl)-5-cyano-3,4-bis(oxidanyl)oxolan-2-yl]methoxy-oxidanyl-phosphoryl] phosphono hydrogen phosphate
NWX ,
A937234
(((2r,3s,4r,5r)-5-(4-aminopyrrolo[2,1-f][1,2,4]triazin-7-yl)-5-cyano-3,4-dihydroxytetrahydrofuran-2-yl)methyl)triphosphoric acid
gtpl11899
AKOS040758773
F90242

Research Excerpts

Pharmacokinetics

ExcerptReferenceRelevance
"We report the first pharmacokinetic evaluation of remdesivir and GS-441524 in recovered COVID-19 patients."( Pharmacokinetics of remdesivir and GS-441524 in two critically ill patients who recovered from COVID-19.
Agrati, C; Ascoli Bartoli, T; Avataneo, V; Capobianchi, MR; Caputi, P; Castilletti, C; D'Avolio, A; Forini, O; Ippolito, G; Lalle, E; Marchioni, L; Nicastri, E; Notari, S; Scorzolini, L; Tempestilli, M, 2020
)
0.56
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Roles (3)

RoleDescription
drug metabolitenull
antiviral drugA substance used in the prophylaxis or therapy of virus diseases.
anticoronaviral agentAny antiviral agent which inhibits the activity of coronaviruses.
[role information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Drug Classes (5)

ClassDescription
C-nucleoside
aromatic amineAn amino compound in which the amino group is linked directly to an aromatic system.
nitrileA compound having the structure RC#N; thus a C-substituted derivative of hydrocyanic acid, HC#N. In systematic nomenclature, the suffix nitrile denotes the triply bound #N atom, not the carbon atom attached to it.
pyrrolotriazineAny organic heterobicyclic compound containing ortho-fused pyrrolidine and triazine rings.
organic triphosphateAn organic phosphate ester formed by condensation of triphosphoric acid with one or more alcohols.
[compound class information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Protein Targets (3)

Inhibition Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
DNA polymerase betaHomo sapiens (human)IC50 (µMol)200.00001.40006.56679.0000AID1440666
DNA polymerase alpha catalytic subunitHomo sapiens (human)IC50 (µMol)200.00001.00002.74294.3000AID1440665
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Biological Processes (35)

Processvia Protein(s)Taxonomy
DNA replication, synthesis of primerDNA-directed RNA polymerase, mitochondrialHomo sapiens (human)
mitochondrial transcriptionDNA-directed RNA polymerase, mitochondrialHomo sapiens (human)
transcription initiation at mitochondrial promoterDNA-directed RNA polymerase, mitochondrialHomo sapiens (human)
nucleotide-excision repair, DNA gap fillingDNA polymerase betaHomo sapiens (human)
in utero embryonic developmentDNA polymerase betaHomo sapiens (human)
DNA-templated DNA replicationDNA polymerase betaHomo sapiens (human)
DNA repairDNA polymerase betaHomo sapiens (human)
base-excision repairDNA polymerase betaHomo sapiens (human)
base-excision repair, gap-fillingDNA polymerase betaHomo sapiens (human)
pyrimidine dimer repairDNA polymerase betaHomo sapiens (human)
inflammatory responseDNA polymerase betaHomo sapiens (human)
DNA damage responseDNA polymerase betaHomo sapiens (human)
salivary gland morphogenesisDNA polymerase betaHomo sapiens (human)
intrinsic apoptotic signaling pathway in response to DNA damageDNA polymerase betaHomo sapiens (human)
response to gamma radiationDNA polymerase betaHomo sapiens (human)
somatic hypermutation of immunoglobulin genesDNA polymerase betaHomo sapiens (human)
response to ethanolDNA polymerase betaHomo sapiens (human)
lymph node developmentDNA polymerase betaHomo sapiens (human)
spleen developmentDNA polymerase betaHomo sapiens (human)
homeostasis of number of cellsDNA polymerase betaHomo sapiens (human)
neuron apoptotic processDNA polymerase betaHomo sapiens (human)
response to hyperoxiaDNA polymerase betaHomo sapiens (human)
immunoglobulin heavy chain V-D-J recombinationDNA polymerase betaHomo sapiens (human)
DNA biosynthetic processDNA polymerase betaHomo sapiens (human)
double-strand break repair via nonhomologous end joiningDNA polymerase betaHomo sapiens (human)
DNA repairDNA polymerase alpha catalytic subunitHomo sapiens (human)
nucleotide-excision repairDNA polymerase alpha catalytic subunitHomo sapiens (human)
DNA synthesis involved in UV-damage excision repairDNA polymerase alpha catalytic subunitHomo sapiens (human)
DNA synthesis involved in DNA repairDNA polymerase alpha catalytic subunitHomo sapiens (human)
DNA replicationDNA polymerase alpha catalytic subunitHomo sapiens (human)
DNA replication, synthesis of primerDNA polymerase alpha catalytic subunitHomo sapiens (human)
DNA replication initiationDNA polymerase alpha catalytic subunitHomo sapiens (human)
DNA strand elongation involved in DNA replicationDNA polymerase alpha catalytic subunitHomo sapiens (human)
leading strand elongationDNA polymerase alpha catalytic subunitHomo sapiens (human)
lagging strand elongationDNA polymerase alpha catalytic subunitHomo sapiens (human)
DNA repairDNA polymerase alpha catalytic subunitHomo sapiens (human)
double-strand break repair via nonhomologous end joiningDNA polymerase alpha catalytic subunitHomo sapiens (human)
regulation of type I interferon productionDNA polymerase alpha catalytic subunitHomo sapiens (human)
mitotic DNA replication initiationDNA polymerase alpha catalytic subunitHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Molecular Functions (23)

Processvia Protein(s)Taxonomy
3'-5'-RNA exonuclease activityDNA-directed RNA polymerase, mitochondrialHomo sapiens (human)
RNA bindingDNA-directed RNA polymerase, mitochondrialHomo sapiens (human)
DNA primase activityDNA-directed RNA polymerase, mitochondrialHomo sapiens (human)
DNA-directed 5'-3' RNA polymerase activityDNA-directed RNA polymerase, mitochondrialHomo sapiens (human)
protein bindingDNA-directed RNA polymerase, mitochondrialHomo sapiens (human)
sequence-specific DNA bindingDNA-directed RNA polymerase, mitochondrialHomo sapiens (human)
mitochondrial promoter sequence-specific DNA bindingDNA-directed RNA polymerase, mitochondrialHomo sapiens (human)
damaged DNA bindingDNA polymerase betaHomo sapiens (human)
DNA-directed DNA polymerase activityDNA polymerase betaHomo sapiens (human)
DNA-(apurinic or apyrimidinic site) endonuclease activityDNA polymerase betaHomo sapiens (human)
protein bindingDNA polymerase betaHomo sapiens (human)
microtubule bindingDNA polymerase betaHomo sapiens (human)
lyase activityDNA polymerase betaHomo sapiens (human)
enzyme bindingDNA polymerase betaHomo sapiens (human)
metal ion bindingDNA polymerase betaHomo sapiens (human)
5'-deoxyribose-5-phosphate lyase activityDNA polymerase betaHomo sapiens (human)
class I DNA-(apurinic or apyrimidinic site) endonuclease activityDNA polymerase betaHomo sapiens (human)
nucleotide bindingDNA polymerase alpha catalytic subunitHomo sapiens (human)
DNA bindingDNA polymerase alpha catalytic subunitHomo sapiens (human)
chromatin bindingDNA polymerase alpha catalytic subunitHomo sapiens (human)
DNA-directed DNA polymerase activityDNA polymerase alpha catalytic subunitHomo sapiens (human)
protein bindingDNA polymerase alpha catalytic subunitHomo sapiens (human)
zinc ion bindingDNA polymerase alpha catalytic subunitHomo sapiens (human)
protein kinase bindingDNA polymerase alpha catalytic subunitHomo sapiens (human)
DNA replication origin bindingDNA polymerase alpha catalytic subunitHomo sapiens (human)
single-stranded DNA bindingDNA polymerase alpha catalytic subunitHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Ceullar Components (16)

Processvia Protein(s)Taxonomy
mitochondrionDNA-directed RNA polymerase, mitochondrialHomo sapiens (human)
mitochondrial matrixDNA-directed RNA polymerase, mitochondrialHomo sapiens (human)
mitochondrial nucleoidDNA-directed RNA polymerase, mitochondrialHomo sapiens (human)
protein-containing complexDNA-directed RNA polymerase, mitochondrialHomo sapiens (human)
mitochondrial DNA-directed RNA polymerase complexDNA-directed RNA polymerase, mitochondrialHomo sapiens (human)
nucleusDNA polymerase betaHomo sapiens (human)
nucleoplasmDNA polymerase betaHomo sapiens (human)
cytoplasmDNA polymerase betaHomo sapiens (human)
microtubuleDNA polymerase betaHomo sapiens (human)
spindle microtubuleDNA polymerase betaHomo sapiens (human)
protein-containing complexDNA polymerase betaHomo sapiens (human)
nucleusDNA polymerase betaHomo sapiens (human)
nucleusDNA polymerase alpha catalytic subunitHomo sapiens (human)
nuclear envelopeDNA polymerase alpha catalytic subunitHomo sapiens (human)
nucleoplasmDNA polymerase alpha catalytic subunitHomo sapiens (human)
alpha DNA polymerase:primase complexDNA polymerase alpha catalytic subunitHomo sapiens (human)
nucleolusDNA polymerase alpha catalytic subunitHomo sapiens (human)
cytosolDNA polymerase alpha catalytic subunitHomo sapiens (human)
nuclear matrixDNA polymerase alpha catalytic subunitHomo sapiens (human)
chromatinDNA polymerase alpha catalytic subunitHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (18)

Assay IDTitleYearJournalArticle
AID1440695Drug level in TERT-immortalized HMVEC treated with (2S)-2-ethylbutyl 2-((((2R,3S,4R,5R)-5-(4-aminopyrrolo[1,2-f][1,2,4]triazin-7-yl)-5-cyano-3,4-dihydroxytetrahydrofuran-2-yl)methoxy)(phenoxy)phosphorylamino)propanoate at 1 uM after 2 to 72 hrs2017Journal of medicinal chemistry, 03-09, Volume: 60, Issue:5
Discovery and Synthesis of a Phosphoramidate Prodrug of a Pyrrolo[2,1-f][triazin-4-amino] Adenine C-Nucleoside (GS-5734) for the Treatment of Ebola and Emerging Viruses.
AID1661023Cytotoxic activity in HAE cells2020ACS medicinal chemistry letters, Jul-09, Volume: 11, Issue:7
Advantages of the Parent Nucleoside GS-441524 over Remdesivir for Covid-19 Treatment.
AID1440663Inhibition of human mitochondrial RNA polymerase after 30 mins in presence of [33P]GTP2017Journal of medicinal chemistry, 03-09, Volume: 60, Issue:5
Discovery and Synthesis of a Phosphoramidate Prodrug of a Pyrrolo[2,1-f][triazin-4-amino] Adenine C-Nucleoside (GS-5734) for the Treatment of Ebola and Emerging Viruses.
AID1440664Inhibition of RNA polymerase 2 in human HeLa cells preincubated for 5 mins with dATP/dGTP/dTTP as substrate followed by addition of cell extract measured after 1 hr by SDS-PAGE method2017Journal of medicinal chemistry, 03-09, Volume: 60, Issue:5
Discovery and Synthesis of a Phosphoramidate Prodrug of a Pyrrolo[2,1-f][triazin-4-amino] Adenine C-Nucleoside (GS-5734) for the Treatment of Ebola and Emerging Viruses.
AID1440662Inhibition of Hepatitis C virus genotype 1b NS5B RNA-dependent-RNA polymerase preincubated for 5 mins followed by [alpha-33P]GTP addition measured after 90 mins by phosphorimaging assay2017Journal of medicinal chemistry, 03-09, Volume: 60, Issue:5
Discovery and Synthesis of a Phosphoramidate Prodrug of a Pyrrolo[2,1-f][triazin-4-amino] Adenine C-Nucleoside (GS-5734) for the Treatment of Ebola and Emerging Viruses.
AID1661024Antiviral activity against Feline corona virus infected in CRFK cells2020ACS medicinal chemistry letters, Jul-09, Volume: 11, Issue:7
Advantages of the Parent Nucleoside GS-441524 over Remdesivir for Covid-19 Treatment.
AID1440667Inhibition of recombinant human DNA polymerase gamma preincubated with enzyme followed by addition of dATP/dGTP/TTP as substrate in presence of [gamma-33P]TTP by phosphorimaging assay2017Journal of medicinal chemistry, 03-09, Volume: 60, Issue:5
Discovery and Synthesis of a Phosphoramidate Prodrug of a Pyrrolo[2,1-f][triazin-4-amino] Adenine C-Nucleoside (GS-5734) for the Treatment of Ebola and Emerging Viruses.
AID1440696Drug level in human HeLa cells treated with (2S)-2-ethylbutyl 2-((((2R,3S,4R,5R)-5-(4-aminopyrrolo[1,2-f][1,2,4]triazin-7-yl)-5-cyano-3,4-dihydroxytetrahydrofuran-2-yl)methoxy)(phenoxy)phosphorylamino)propanoate at 1 uM after 2 to 72 hrs2017Journal of medicinal chemistry, 03-09, Volume: 60, Issue:5
Discovery and Synthesis of a Phosphoramidate Prodrug of a Pyrrolo[2,1-f][triazin-4-amino] Adenine C-Nucleoside (GS-5734) for the Treatment of Ebola and Emerging Viruses.
AID1440677Drug level in rhesus monkey PBMC treated with (S)-2-Ethylbutyl 2-(((S)-(((2R,3S,4R,5R)-5-(4-Aminopyrrolo-[2,1-f][1,2,4]triazin-7-yl)-5-cyano-3,4-dihydroxytetrahydrofuran-2-yl)methoxy)(phenoxy)phosphoryl)amino)propanoate at 10 mg/kg, iv administered as sin2017Journal of medicinal chemistry, 03-09, Volume: 60, Issue:5
Discovery and Synthesis of a Phosphoramidate Prodrug of a Pyrrolo[2,1-f][triazin-4-amino] Adenine C-Nucleoside (GS-5734) for the Treatment of Ebola and Emerging Viruses.
AID1440665Inhibition of recombinant human DNA polymerase alpha preincubated with enzyme followed by addition of dATP/dGTP/TTP as substrate in presence of [gamma-33P]TTP by phosphorimaging assay2017Journal of medicinal chemistry, 03-09, Volume: 60, Issue:5
Discovery and Synthesis of a Phosphoramidate Prodrug of a Pyrrolo[2,1-f][triazin-4-amino] Adenine C-Nucleoside (GS-5734) for the Treatment of Ebola and Emerging Viruses.
AID656940Inhibition of Hepatitis C virus genotype 1b NS5B RNA-dependent RNA polymerase using [33P]ATP after 90 mins by phosphoimaging2012Bioorganic & medicinal chemistry letters, Apr-15, Volume: 22, Issue:8
Synthesis and antiviral activity of a series of 1'-substituted 4-aza-7,9-dideazaadenosine C-nucleosides.
AID1661022Antiviral activity against SARS coronavirus infected in primary HAE cells2020ACS medicinal chemistry letters, Jul-09, Volume: 11, Issue:7
Advantages of the Parent Nucleoside GS-441524 over Remdesivir for Covid-19 Treatment.
AID1440697Drug level in human macrophages treated with (2S)-2-ethylbutyl 2-((((2R,3S,4R,5R)-5-(4-aminopyrrolo[1,2-f][1,2,4]triazin-7-yl)-5-cyano-3,4-dihydroxytetrahydrofuran-2-yl)methoxy)(phenoxy)phosphorylamino)propanoate at 1 uM after 2 to 72 hrs2017Journal of medicinal chemistry, 03-09, Volume: 60, Issue:5
Discovery and Synthesis of a Phosphoramidate Prodrug of a Pyrrolo[2,1-f][triazin-4-amino] Adenine C-Nucleoside (GS-5734) for the Treatment of Ebola and Emerging Viruses.
AID1440661Inhibition of Respiratory syncytial virus A2 RNA-dependent-RNA polymerase assessed as reduction in RNP transcriptional activity after 90 mins in presence of [gamma-32P]ATP by agarose gel based phosphorimaging assay2017Journal of medicinal chemistry, 03-09, Volume: 60, Issue:5
Discovery and Synthesis of a Phosphoramidate Prodrug of a Pyrrolo[2,1-f][triazin-4-amino] Adenine C-Nucleoside (GS-5734) for the Treatment of Ebola and Emerging Viruses.
AID1440669Inhibition of recombinant human DNA polymerase gamma assessed as single nucleotide incorporation rate after 5 to 90 mins in presence of [32P]-D19/D36 as primer/template by PAGE based phosphorimaging assay2017Journal of medicinal chemistry, 03-09, Volume: 60, Issue:5
Discovery and Synthesis of a Phosphoramidate Prodrug of a Pyrrolo[2,1-f][triazin-4-amino] Adenine C-Nucleoside (GS-5734) for the Treatment of Ebola and Emerging Viruses.
AID1440666Inhibition of recombinant human DNA polymerase beta preincubated with enzyme followed by addition of dATP/dGTP/TTP as substrate in presence of [gamma-33P]TTP by phosphorimaging assay2017Journal of medicinal chemistry, 03-09, Volume: 60, Issue:5
Discovery and Synthesis of a Phosphoramidate Prodrug of a Pyrrolo[2,1-f][triazin-4-amino] Adenine C-Nucleoside (GS-5734) for the Treatment of Ebola and Emerging Viruses.
AID1440668Inhibition of human mitochondrial RNA polymerase assessed as single nucleotide incorporation rate in presence of 5'-[32P]-R12/D18 as primer/template by PAGE based phosphorimaging assay2017Journal of medicinal chemistry, 03-09, Volume: 60, Issue:5
Discovery and Synthesis of a Phosphoramidate Prodrug of a Pyrrolo[2,1-f][triazin-4-amino] Adenine C-Nucleoside (GS-5734) for the Treatment of Ebola and Emerging Viruses.
AID1661025Antiviral activity against Middle East respiratory syndrome coronavirus infected in primary HAE cells2020ACS medicinal chemistry letters, Jul-09, Volume: 11, Issue:7
Advantages of the Parent Nucleoside GS-441524 over Remdesivir for Covid-19 Treatment.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (13)

TimeframeStudies, This Drug (%)All Drugs %
pre-19900 (0.00)18.7374
1990's0 (0.00)18.2507
2000's0 (0.00)29.6817
2010's2 (15.38)24.3611
2020's11 (84.62)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 21.31

According to the monthly volume, diversity, and competition of internet searches for this compound, as well the volume and growth of publications, there is estimated to be moderate demand-to-supply ratio for research on this compound.

MetricThis Compound (vs All)
Research Demand Index21.31 (24.57)
Research Supply Index2.64 (2.92)
Research Growth Index4.65 (4.65)
Search Engine Demand Index18.60 (26.88)
Search Engine Supply Index2.00 (0.95)

This Compound (21.31)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Reviews1 (7.69%)6.00%
Case Studies2 (15.38%)4.05%
Observational0 (0.00%)0.25%
Other10 (76.92%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]