Compounds > n(4)-hydroxycytidine
Page last updated: 2024-12-08

n(4)-hydroxycytidine

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

Description

N(4)-hydroxycytidine : A nucleoside analogue that is cytidine which carries a hydroxy group at the N(4)-positon. It has broad-spectrum antiviral activity against influenza, SARS-CoV , SARS-CoV-2 and MERS-CoV. [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 CID197020
CHEMBL ID2178720
CHEBI ID180654
SCHEMBL ID5190819
SCHEMBL ID24780346
MeSH IDM0056481

Synonyms (42)

Synonym
n-hydroxycytidine
4-oxime uridine
eidd 1931
n-hydroxy-3,4-dihydrocytidine
CHEBI:180654
1-[(2r,3r,4s,5r)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl]-4-(hydroxyimino)-3,4-dihydropyrimidin-2(1h)-one
beta-d-n(4)-hydroxycytidine
3258-02-4
eidd-1931
1-((2r,3r,4s,5r)-3,4-dihydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl)-4-hydroxyamino-1h-pyrimidin-2-one
1-[(2r,3r,4s,5r)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl]-4-(hydroxyamino)pyrimidin-2-one
4-n-hydroxycytidine
n4-hydroxycytidine
cytidine, n-hydroxy-
n-4-hydroxycytidine
uridine, 4-oxime
ccris 1074
n(4)-hydroxycytidine
1-[(2r,3r,4s,5r)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-4-(hydroxyamino)pyrimidin-2-one
CHEMBL2178720
beta-d-n4-hydroxycytidine
c3d11pv2o4 ,
unii-c3d11pv2o4
SCHEMBL5190819
DTXSID20186274
gtpl10735
mfcd01675695
BS-47105
CS-0088698
HY-125033
AT13085
1-((2r,3r,4s,5r)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)-4-(hydroxyimino)-3,4-dihydropyrimidin-2(1h)-one
1-((2r,3r,4s,5r)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)-4-(hydroxyamino)pyrimidin-2(1h)-one
eidd1931
EX-A3655
1-[(2r,3r,4s,5r)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-4-(hydroxyamino)-1,2-dihydropyrimidin-2-one
bdbm430624
EN300-7534996
1-[(2r,3r,4s,5r)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-4-(hydroxyimino)-1,2,3,4-tetrahydropyrimidin-2-one
SCHEMBL24780346
(e)-1-((2r,3r,4s,5r)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)-4-(hydroxyimino)-3,4-dihydropyrimidin-2(1h)-one
Z4171362498

Research Excerpts

Pharmacokinetics

ExcerptReferenceRelevance
"The pharmacokinetic alteration of an antimicrobial medication leading to sub-therapeutic plasma level can aid in the emergence of resistance, a global threat nowadays."( Impact of Disease States on the Oral Pharmacokinetics of EIDD-1931 (an Active Form of Molnupiravir) in Rats for Implication in the Dose Adjustment.
Ahmed, A; Bhardwaj, M; Dhiman, S; Gour, A; Khajuria, P; Manhas, D; Mukherjee, D; Nandi, U; Wazir, P, 2023)		0.91
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Roles (4)

RoleDescription
drug metabolitenull
human xenobiotic metaboliteAny human metabolite produced by metabolism of a xenobiotic compound in humans.
anticoronaviral agentAny antiviral agent which inhibits the activity of coronaviruses.
antiviral agentA substance that destroys or inhibits replication of viruses.
[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 (2)

ClassDescription
nucleoside analogueAn analogue of a nucleoside, being an N-glycosyl compound in which the nitrogen-containing moiety is a modified nucleotide base. They are commonly used as antiviral products to prevent viral replication in infected cells.
ketoximeOximes of ketones R2C=NOH (where R =/= H).
[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 (1)

Inhibition Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Replicase polyprotein 1abSevere acute respiratory syndrome coronavirus 2IC50 (µMol)0.15670.00022.45859.9600AID1804169; AID1804170
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Molecular Functions (10)

Processvia Protein(s)Taxonomy
3'-5'-RNA exonuclease activityReplicase polyprotein 1abSevere acute respiratory syndrome coronavirus 2
RNA-dependent RNA polymerase activityReplicase polyprotein 1abSevere acute respiratory syndrome coronavirus 2
cysteine-type endopeptidase activityReplicase polyprotein 1abSevere acute respiratory syndrome coronavirus 2
mRNA 5'-cap (guanine-N7-)-methyltransferase activityReplicase polyprotein 1abSevere acute respiratory syndrome coronavirus 2
mRNA (nucleoside-2'-O-)-methyltransferase activityReplicase polyprotein 1abSevere acute respiratory syndrome coronavirus 2
mRNA guanylyltransferase activityReplicase polyprotein 1abSevere acute respiratory syndrome coronavirus 2
RNA endonuclease activity, producing 3'-phosphomonoestersReplicase polyprotein 1abSevere acute respiratory syndrome coronavirus 2
ISG15-specific peptidase activityReplicase polyprotein 1abSevere acute respiratory syndrome coronavirus 2
5'-3' RNA helicase activityReplicase polyprotein 1abSevere acute respiratory syndrome coronavirus 2
protein guanylyltransferase activityReplicase polyprotein 1abSevere acute respiratory syndrome coronavirus 2
[Information is prepared from geneontology information from the June-17-2024 release]

Ceullar Components (1)

Processvia Protein(s)Taxonomy
double membrane vesicle viral factory outer membraneReplicase polyprotein 1abSevere acute respiratory syndrome coronavirus 2
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (34)

Assay IDTitleYearJournalArticle
AID1782690Cytotoxicity in African green monkey Vero cells assessed as reduction in cell viability measured after 5 days by resazurin dye based assay2021European journal of medicinal chemistry, Aug-05, Volume: 220Phenoxazine nucleoside derivatives with a multiple activity against RNA and DNA viruses.
AID1857883Cytotoxicity against HEK293T cells transfected with ACE2 and TMPRSS2 assessed as reduction in cell viability2022Journal of medicinal chemistry, 10-27, Volume: 65, Issue:20
Discovery of Chlorofluoroacetamide-Based Covalent Inhibitors for Severe Acute Respiratory Syndrome Coronavirus 2 3CL Protease.
AID1881749Oral bioavailability in CD1 mouse at 150 mg/kg administered as single dose by LC-MS/MS analysis2022Journal of medicinal chemistry, 02-24, Volume: 65, Issue:4
Targeting SARS-CoV-2 Proteases and Polymerase for COVID-19 Treatment: State of the Art and Future Opportunities.
AID1857880Antiviral activity against SARS CoV-2 delta TY11-927 infected in HEK293T cells transfected with ACE2 and TMPRSS2 assessed as inhibition of virus induced cytopathic effect incubated for 2 to 3 days by MTT assay2022Journal of medicinal chemistry, 10-27, Volume: 65, Issue:20
Discovery of Chlorofluoroacetamide-Based Covalent Inhibitors for Severe Acute Respiratory Syndrome Coronavirus 2 3CL Protease.
AID1881748Oral bioavailability in CD1 mouse at 50 mg/kg administered as single dose by LC-MS/MS analysis2022Journal of medicinal chemistry, 02-24, Volume: 65, Issue:4
Targeting SARS-CoV-2 Proteases and Polymerase for COVID-19 Treatment: State of the Art and Future Opportunities.
AID1881752Half life in CD1 mouse at 150 mg/kg, po administered as single dose by LC-MS/MS analysis2022Journal of medicinal chemistry, 02-24, Volume: 65, Issue:4
Targeting SARS-CoV-2 Proteases and Polymerase for COVID-19 Treatment: State of the Art and Future Opportunities.
AID1857882Antiviral activity against SARS CoV-2 omicron TY38-873 BA.2 variant infected in HEK293T cells transfected with ACE2 and TMPRSS2 assessed as inhibition of virus induced cytopathic effect incubated for 2 to 3 days by MTT assay2022Journal of medicinal chemistry, 10-27, Volume: 65, Issue:20
Discovery of Chlorofluoroacetamide-Based Covalent Inhibitors for Severe Acute Respiratory Syndrome Coronavirus 2 3CL Protease.
AID1881753Half life in CD1 mouse at 500 mg/kg, po administered as single dose by LC-MS/MS analysis2022Journal of medicinal chemistry, 02-24, Volume: 65, Issue:4
Targeting SARS-CoV-2 Proteases and Polymerase for COVID-19 Treatment: State of the Art and Future Opportunities.
AID1857878Antiviral activity against wild type SARS CoV-2 infected in HEK293T cells transfected with ACE2 and TMPRSS2 assessed as inhibition of virus induced cytopathic effect incubated for 2 to 3 days by MTT assay2022Journal of medicinal chemistry, 10-27, Volume: 65, Issue:20
Discovery of Chlorofluoroacetamide-Based Covalent Inhibitors for Severe Acute Respiratory Syndrome Coronavirus 2 3CL Protease.
AID1881746Cytotoxicity against African green monkey Vero E6 cells infected with SARS CoV-2 clinical isolate 2019-nCoV/USA-WA1/2020 incubated for 48 hrs by CellTiter-Glo assay2022Journal of medicinal chemistry, 02-24, Volume: 65, Issue:4
Targeting SARS-CoV-2 Proteases and Polymerase for COVID-19 Treatment: State of the Art and Future Opportunities.
AID1857885Antiviral activity against wild type SARS CoV-2 infected in Vero E6 cells transfected with TMPRSS2 assessed as inhibition of virus induced cytopathic effect incubated for 2 to 3 days in presence of P-gp inhibitor CP-100356 by MTT assay2022Journal of medicinal chemistry, 10-27, Volume: 65, Issue:20
Discovery of Chlorofluoroacetamide-Based Covalent Inhibitors for Severe Acute Respiratory Syndrome Coronavirus 2 3CL Protease.
AID1782697Antiviral activity against SARS COV-2 infected in monkey vero cells assessed as reduction in virus-induced cytopathic effect preincubated with virus for 1 hr followed by cell infection and measured after 5 days by microscopic analysis2021European journal of medicinal chemistry, Aug-05, Volume: 220Phenoxazine nucleoside derivatives with a multiple activity against RNA and DNA viruses.
AID1857889Antiviral activity against HCoV-OC43 infected in HEK293T cells transfected with ACE2 and TMPRSS2 assessed as inhibition of virus induced cytopathic effect incubated for 2 to 3 days by MTT assay2022Journal of medicinal chemistry, 10-27, Volume: 65, Issue:20
Discovery of Chlorofluoroacetamide-Based Covalent Inhibitors for Severe Acute Respiratory Syndrome Coronavirus 2 3CL Protease.
AID1881745Antiviral activity against SARS CoV-2 clinical isolate 2019-nCoV/USA-WA1/2020 infected in African green monkey Vero E6 cells incubated for 48 hrs by CellTiter-Glo assay2022Journal of medicinal chemistry, 02-24, Volume: 65, Issue:4
Targeting SARS-CoV-2 Proteases and Polymerase for COVID-19 Treatment: State of the Art and Future Opportunities.
AID1881754Drug distribution in CD1 mouse liver at 150 to 500 mg/kg, po measured after 8 hrs by LC-MS/MS analysis2022Journal of medicinal chemistry, 02-24, Volume: 65, Issue:4
Targeting SARS-CoV-2 Proteases and Polymerase for COVID-19 Treatment: State of the Art and Future Opportunities.
AID1653791Substrate activity at human mARC1 expressed in Escherichia coli assessed as turnover rates at 3 mM pre-incubated for 3 mins followed by NADH addition and measured after 15 mins by UV-Visible spectroscopy based NADH assay2020Journal of medicinal chemistry, 06-25, Volume: 63, Issue:12
Drug Metabolism by the Mitochondrial Amidoxime Reducing Component (mARC): Rapid Assay and Identification of New Substrates.
AID1881747Antiviral activity against SARS CoV-2 clinical isolate 2019-nCoV/USA-WA1/2020 infected in human Calu-3 cells measured after 72 hrs by plaque assay2022Journal of medicinal chemistry, 02-24, Volume: 65, Issue:4
Targeting SARS-CoV-2 Proteases and Polymerase for COVID-19 Treatment: State of the Art and Future Opportunities.
AID1857884Antiviral activity against wild type SARS CoV-2 infected in Vero E6 cells transfected with TMPRSS2 assessed as inhibition of virus induced cytopathic effect incubated for 2 to 3 days by MTT assay2022Journal of medicinal chemistry, 10-27, Volume: 65, Issue:20
Discovery of Chlorofluoroacetamide-Based Covalent Inhibitors for Severe Acute Respiratory Syndrome Coronavirus 2 3CL Protease.
AID1653796Substrate activity at human mARC2 expressed in Escherichia coli assessed as turnover rates at 3 mM pre-incubated for 3 mins followed by NADH addition and measured after 15 mins by UV-Visible spectroscopy based NADH assay2020Journal of medicinal chemistry, 06-25, Volume: 63, Issue:12
Drug Metabolism by the Mitochondrial Amidoxime Reducing Component (mARC): Rapid Assay and Identification of New Substrates.
AID1653806Substrate activity at human mARC2 expressed in Escherichia coli assessed as turnover rates at 3 mM pre-incubated for 3 mins followed by NADH addition and measured after 15 mins by LC-MS analysis based assay2020Journal of medicinal chemistry, 06-25, Volume: 63, Issue:12
Drug Metabolism by the Mitochondrial Amidoxime Reducing Component (mARC): Rapid Assay and Identification of New Substrates.
AID1857879Antiviral activity against SARS CoV-2 alpha QK002 infected in HEK293T cells transfected with ACE2 and TMPRSS2 assessed as inhibition of virus induced cytopathic effect incubated for 2 to 3 days by MTT assay2022Journal of medicinal chemistry, 10-27, Volume: 65, Issue:20
Discovery of Chlorofluoroacetamide-Based Covalent Inhibitors for Severe Acute Respiratory Syndrome Coronavirus 2 3CL Protease.
AID1881756Antiviral activity against SARS CoV clinical isolate 2019-nCoV/USA-WA1/2020 infected in HAE cells incubated for 48 hrs by qRT-PCR analysis2022Journal of medicinal chemistry, 02-24, Volume: 65, Issue:4
Targeting SARS-CoV-2 Proteases and Polymerase for COVID-19 Treatment: State of the Art and Future Opportunities.
AID1857881Antiviral activity against SARS CoV-2 omicron TY38-873 BA.1 variant infected in HEK293T cells transfected with ACE2 and TMPRSS2 assessed as inhibition of virus induced cytopathic effect incubated for 2 to 3 days by MTT assay2022Journal of medicinal chemistry, 10-27, Volume: 65, Issue:20
Discovery of Chlorofluoroacetamide-Based Covalent Inhibitors for Severe Acute Respiratory Syndrome Coronavirus 2 3CL Protease.
AID1881751Half life in CD1 mouse at 50 mg/kg, po administered as single dose by LC-MS/MS analysis2022Journal of medicinal chemistry, 02-24, Volume: 65, Issue:4
Targeting SARS-CoV-2 Proteases and Polymerase for COVID-19 Treatment: State of the Art and Future Opportunities.
AID707243Antimalarial activity against Plasmodium falciparum incubated for 48 hrs by fluorescence-based SYBR-green assay2012Journal of medicinal chemistry, Nov-26, Volume: 55, Issue:22
Novel cytidine-based orotidine-5'-monophosphate decarboxylase inhibitors with an unusual twist.
AID1653801Substrate activity at human mARC1 expressed in Escherichia coli assessed as turnover rates at 3 mM pre-incubated for 3 mins followed by NADH addition and measured after 15 mins by LC-MS analysis based assay2020Journal of medicinal chemistry, 06-25, Volume: 63, Issue:12
Drug Metabolism by the Mitochondrial Amidoxime Reducing Component (mARC): Rapid Assay and Identification of New Substrates.
AID1881757Antiviral activity against MERS CoV clinical isolate 2019-nCoV/USA-WA1/2020 infected in HAE cells incubated for 48 hrs by qRT-PCR analysis2022Journal of medicinal chemistry, 02-24, Volume: 65, Issue:4
Targeting SARS-CoV-2 Proteases and Polymerase for COVID-19 Treatment: State of the Art and Future Opportunities.
AID1857887Antiviral activity against SARS CoV infected in HEK293T cells transfected with ACE2 and TMPRSS2 assessed as inhibition of virus induced cytopathic effect incubated for 2 to 3 days by MTT assay2022Journal of medicinal chemistry, 10-27, Volume: 65, Issue:20
Discovery of Chlorofluoroacetamide-Based Covalent Inhibitors for Severe Acute Respiratory Syndrome Coronavirus 2 3CL Protease.
AID1881750Oral bioavailability in CD1 mouse at 500 mg/kg administered as single dose by LC-MS/MS analysis2022Journal of medicinal chemistry, 02-24, Volume: 65, Issue:4
Targeting SARS-CoV-2 Proteases and Polymerase for COVID-19 Treatment: State of the Art and Future Opportunities.
AID1857886Cytotoxicity against African green monkey Vero E6 cells transfected with TMPRSS2 assessed as reduction in cell viability2022Journal of medicinal chemistry, 10-27, Volume: 65, Issue:20
Discovery of Chlorofluoroacetamide-Based Covalent Inhibitors for Severe Acute Respiratory Syndrome Coronavirus 2 3CL Protease.
AID1857888Antiviral activity against MERS-CoV EMC2012 infected in HEK293T cells transfected with DPP4 assessed as inhibition of virus induced cytopathic effect incubated for 2 to 3 days by MTT assay2022Journal of medicinal chemistry, 10-27, Volume: 65, Issue:20
Discovery of Chlorofluoroacetamide-Based Covalent Inhibitors for Severe Acute Respiratory Syndrome Coronavirus 2 3CL Protease.
AID1804170SARS-CoV-2 in Calu-3 from Article 10.1126/scitranslmed.abb5883: \\An orally bioavailable broad-spectrum antiviral inhibits SARS-CoV-2 in human airway epithelial cell cultures and multiple coronaviruses in mice.\\2020Science translational medicine, 04-29, Volume: 12, Issue:541
An orally bioavailable broad-spectrum antiviral inhibits SARS-CoV-2 in human airway epithelial cell cultures and multiple coronaviruses in mice.
AID1804168MERS-CoV nLUC in Calu-3 from Article 10.1126/scitranslmed.abb5883: \\An orally bioavailable broad-spectrum antiviral inhibits SARS-CoV-2 in human airway epithelial cell cultures and multiple coronaviruses in mice.\\2020Science translational medicine, 04-29, Volume: 12, Issue:541
An orally bioavailable broad-spectrum antiviral inhibits SARS-CoV-2 in human airway epithelial cell cultures and multiple coronaviruses in mice.
AID1804169SARS-CoV-2 in Vero E6 from Article 10.1126/scitranslmed.abb5883: \\An orally bioavailable broad-spectrum antiviral inhibits SARS-CoV-2 in human airway epithelial cell cultures and multiple coronaviruses in mice.\\2020Science translational medicine, 04-29, Volume: 12, Issue:541
An orally bioavailable broad-spectrum antiviral inhibits SARS-CoV-2 in human airway epithelial cell cultures and multiple coronaviruses in mice.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (42)

TimeframeStudies, This Drug (%)All Drugs %
pre-19904 (9.52)18.7374
1990's1 (2.38)18.2507
2000's5 (11.90)29.6817
2010's7 (16.67)24.3611
2020's25 (59.52)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 16.82

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 Index16.82 (24.57)
Research Supply Index3.78 (2.92)
Research Growth Index5.43 (4.65)
Search Engine Demand Index10.37 (26.88)
Search Engine Supply Index2.00 (0.95)

This Compound (16.82)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials1 (2.38%)5.53%
Reviews2 (4.76%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other39 (92.86%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]
SubstanceRelationship StrengthStudiesTrialsClassesRoles
adenine
[no description available]		2.42206-aminopurines;
purine nucleobase		Daphnia magna metabolite;
Escherichia coli metabolite;
human metabolite;
mouse metabolite;
Saccharomyces cerevisiae metabolite
cytosine
[no description available]		2.0710aminopyrimidine;
pyrimidine nucleobase;
pyrimidone		Escherichia coli metabolite;
human metabolite;
mouse metabolite;
Saccharomyces cerevisiae metabolite
lactic acid
Lactic Acid: A normal intermediate in the fermentation (oxidation, metabolism) of sugar. The concentrated form is used internally to prevent gastrointestinal fermentation. (From Stedman, 26th ed). 2-hydroxypropanoic acid : A 2-hydroxy monocarboxylic acid that is propanoic acid in which one of the alpha-hydrogens is replaced by a hydroxy group.		2.25102-hydroxy monocarboxylic acidalgal metabolite;
Daphnia magna metabolite
ebselen
ebselen : A benzoselenazole that is 1,2-benzoselenazol-3-one carrying an additional phenyl substituent at position 2. Acts as a mimic of glutathione peroxidase.		3.5110benzoselenazoleanti-inflammatory drug;
antibacterial agent;
anticoronaviral agent;
antifungal agent;
antineoplastic agent;
antioxidant;
apoptosis inducer;
EC 1.13.11.33 (arachidonate 15-lipoxygenase) inhibitor;
EC 1.13.11.34 (arachidonate 5-lipoxygenase) inhibitor;
EC 1.3.1.8 [acyl-CoA dehydrogenase (NADP(+))] inhibitor;
EC 1.8.1.12 (trypanothione-disulfide reductase) inhibitor;
EC 2.5.1.7 (UDP-N-acetylglucosamine 1-carboxyvinyltransferase) inhibitor;
EC 2.7.10.1 (receptor protein-tyrosine kinase) inhibitor;
EC 3.1.3.25 (inositol-phosphate phosphatase) inhibitor;
EC 3.4.22.69 (SARS coronavirus main proteinase) inhibitor;
EC 3.5.4.1 (cytosine deaminase) inhibitor;
EC 5.1.3.2 (UDP-glucose 4-epimerase) inhibitor;
enzyme mimic;
ferroptosis inhibitor;
genotoxin;
hepatoprotective agent;
neuroprotective agent;
radical scavenger
hydroxyurea
[no description available]		2.2510one-carbon compound;
ureas		antimetabolite;
antimitotic;
antineoplastic agent;
DNA synthesis inhibitor;
EC 1.17.4.1 (ribonucleoside-diphosphate reductase) inhibitor;
genotoxin;
immunomodulator;
radical scavenger;
teratogenic agent
leflunomide
Leflunomide: An isoxazole derivative that inhibits dihydroorotate dehydrogenase, the fourth enzyme in the pyrimidine biosynthetic pathway. It is used an immunosuppressive agent in the treatment of RHEUMATOID ARTHRITIS and PSORIATIC ARTHRITIS.. leflunomide : A monocarboxylic acid amide obtained by formal condensation of the carboxy group of 5-methyl-1,2-oxazole-4-carboxylic acid with the anilino group of 4-(trifluoromethyl)aniline. The prodrug of teriflunomide.		2.2510(trifluoromethyl)benzenes;
isoxazoles;
monocarboxylic acid amide		antineoplastic agent;
antiparasitic agent;
EC 1.3.98.1 [dihydroorotate oxidase (fumarate)] inhibitor;
EC 3.1.3.16 (phosphoprotein phosphatase) inhibitor;
hepatotoxic agent;
immunosuppressive agent;
non-steroidal anti-inflammatory drug;
prodrug;
pyrimidine synthesis inhibitor;
tyrosine kinase inhibitor
zonisamide
Zonisamide: A benzisoxazole and sulfonamide derivative that acts as a CALCIUM CHANNEL blocker. It is used primarily as an adjunctive antiepileptic agent for the treatment of PARTIAL SEIZURES, with or without secondary generalization.. zonisamide : A 1,2-benzoxazole compound having a sulfamoylmethyl substituent at the 3-position.		2.25101,2-benzoxazoles;
sulfonamide		anticonvulsant;
antioxidant;
central nervous system drug;
protective agent;
T-type calcium channel blocker
azauridine
Azauridine: A triazine nucleoside used as an antineoplastic antimetabolite. It interferes with pyrimidine biosynthesis thereby preventing formation of cellular nucleic acids. As the triacetate, it is also effective as an antipsoriatic.		2.0310N-glycosyl-1,2,4-triazineantimetabolite;
antineoplastic agent;
drug metabolite
alanine
Alanine: A non-essential amino acid that occurs in high levels in its free state in plasma. It is produced from pyruvate by transamination. It is involved in sugar and acid metabolism, increases IMMUNITY, and provides energy for muscle tissue, BRAIN, and the CENTRAL NERVOUS SYSTEM.. alanine : An alpha-amino acid that consists of propionic acid bearing an amino substituent at position 2.		3.4550alanine zwitterion;
alanine;
L-alpha-amino acid;
proteinogenic amino acid;
pyruvate family amino acid		EC 4.3.1.15 (diaminopropionate ammonia-lyase) inhibitor;
fundamental metabolite
uridine monophosphate
Uridine Monophosphate: 5'-Uridylic acid. A uracil nucleotide containing one phosphate group esterified to the sugar moiety in the 2', 3' or 5' position.. uridine 5'-monophosphate : A pyrimidine ribonucleoside 5'-monophosphate having uracil as the nucleobase.		2.0710pyrimidine ribonucleoside 5'-monophosphate;
uridine 5'-phosphate		Escherichia coli metabolite;
human metabolite;
mouse metabolite
adenosine monophosphate
Adenosine Monophosphate: Adenine nucleotide containing one phosphate group esterified to the sugar moiety in the 2'-, 3'-, or 5'-position.		3.4550adenosine 5'-phosphate;
purine ribonucleoside 5'-monophosphate		adenosine A1 receptor agonist;
cofactor;
EC 3.1.3.1 (alkaline phosphatase) inhibitor;
EC 3.1.3.11 (fructose-bisphosphatase) inhibitor;
fundamental metabolite;
micronutrient;
nutraceutical
leucine
Leucine: An essential branched-chain amino acid important for hemoglobin formation.. leucine : A branched-chain amino acid that consists of glycine in which one of the hydrogens attached to the alpha-carbon is substituted by an isobutyl group.		2.4110amino acid zwitterion;
L-alpha-amino acid;
leucine;
proteinogenic amino acid;
pyruvate family amino acid		algal metabolite;
Escherichia coli metabolite;
human metabolite;
mouse metabolite;
plant metabolite;
Saccharomyces cerevisiae metabolite
cytidine monophosphate
Cytidine Monophosphate: Cytidine (dihydrogen phosphate). A cytosine nucleotide containing one phosphate group esterified to the sugar moiety in the 2', 3' or 5' position.. cytidine 5'-monophosphate : A pyrimidine ribonucleoside 5'-monophosphate having cytosine as the nucleobase.		2.0710cytidine 5'-phosphate;
pyrimidine ribonucleoside 5'-monophosphate		Escherichia coli metabolite;
human metabolite;
mouse metabolite
cytidine
[no description available]		8.24311cytidinesEscherichia coli metabolite;
human metabolite;
mouse metabolite;
Saccharomyces cerevisiae metabolite
pyrazines
Pyrazines: A heterocyclic aromatic organic compound with the chemical formula C4H4N2.. pyrazine : A diazine that is benzene in which the carbon atoms at positions 1 and 4 have been replaced by nitrogen atoms.		3.5110diazine;
pyrazines		Daphnia magna metabolite
2-aminopurine
2-Aminopurine: A purine that is an isomer of ADENINE (6-aminopurine).. aminopurine : Any purine having at least one amino substituent.. 2-aminopurine : The parent compound of the 2-aminopurines, comprising a purine core carrying an amino substituent at the 2-position.		2102-aminopurines;
nucleobase analogue		antimetabolite
deoxycytidine
[no description available]		2.0710pyrimidine 2'-deoxyribonucleosideEscherichia coli metabolite;
human metabolite;
mouse metabolite;
Saccharomyces cerevisiae metabolite
deoxyuridine
[no description available]		420pyrimidine 2'-deoxyribonucleosideEscherichia coli metabolite;
human metabolite;
mouse metabolite;
Saccharomyces cerevisiae metabolite
6-hydroxyadenosine
[no description available]		2.2510
amitriptyline n-oxide
[no description available]		2.2510organic tricyclic compound
zidovudine
Zidovudine: A dideoxynucleoside compound in which the 3'-hydroxy group on the sugar moiety has been replaced by an azido group. This modification prevents the formation of phosphodiester linkages which are needed for the completion of nucleic acid chains. The compound is a potent inhibitor of HIV replication, acting as a chain-terminator of viral DNA during reverse transcription. It improves immunologic function, partially reverses the HIV-induced neurological dysfunction, and improves certain other clinical abnormalities associated with AIDS. Its principal toxic effect is dose-dependent suppression of bone marrow, resulting in anemia and leukopenia.. zidovudine : A pyrimidine 2',3'-dideoxyribonucleoside compound having a 3'-azido substituent and thymine as the nucleobase.		2.2510azide;
pyrimidine 2',3'-dideoxyribonucleoside		antimetabolite;
antiviral drug;
HIV-1 reverse transcriptase inhibitor
ribavirin
Rebetron: Rebetron is tradename		4.2401-ribosyltriazole;
aromatic amide;
monocarboxylic acid amide;
primary carboxamide		anticoronaviral agent;
antiinfective agent;
antimetabolite;
antiviral agent;
EC 2.7.7.49 (RNA-directed DNA polymerase) inhibitor
4-(n-methyl-n-nitrosamino)-1-(3-pyridyl)-1-butanone
4-(N-methyl-N-nitrosamino)-1-(3-pyridyl)-1-butanone: structure; from tobacco smoke		2.2510nitrosamine;
pyridines
zileuton
[no description available]		2.25101-benzothiophenes;
ureas		anti-asthmatic drug;
EC 1.13.11.34 (arachidonate 5-lipoxygenase) inhibitor;
ferroptosis inhibitor;
leukotriene antagonist;
non-steroidal anti-inflammatory drug
cidofovir anhydrous
Cidofovir: An acyclic nucleoside phosphonate that acts as a competitive inhibitor of viral DNA polymerases. It is used in the treatment of RETINITIS caused by CYTOMEGALOVIRUS INFECTIONS and may also be useful for treating HERPESVIRUS INFECTIONS.. cidofovir anhydrous : Cytosine substituted at the 1 position by a 3-hydroxy-2-(phosphonomethoxy)propyl group (S configuration). A nucleoside analogue, it is an injectable antiviral used for the treatment of cytomegalovirus (CMV) retinitis in AIDS patients.		2.3110phosphonic acids;
pyrimidone		anti-HIV agent;
antineoplastic agent;
antiviral drug;
photosensitizing agent
lamivudine
[no description available]		2.0710monothioacetal;
nucleoside analogue;
oxacycle;
primary alcohol		allergen;
anti-HBV agent;
antiviral drug;
EC 2.7.7.49 (RNA-directed DNA polymerase) inhibitor;
HIV-1 reverse transcriptase inhibitor;
prodrug
ziprasidone
ziprasidone: a benzisothiazoylpiperazine derivative; has combined dopamine and serotonin receptor antagonist activity; structurally related to tiospirone. ziprasidone : A piperazine compound having 1,2-benzothiazol-3-yl- and 2-(6-chloro-1,3-dihydro-2-oxindol-5-yl)ethyl substituents attached to the nitrogen atoms.		2.25101,2-benzisothiazole;
indolones;
organochlorine compound;
piperazines		antipsychotic agent;
dopaminergic antagonist;
histamine antagonist;
muscarinic antagonist;
psychotropic drug;
serotonergic antagonist
adenosine
quinquefolan B: isolated from roots of Panax quinquefolium L.; RN not in Chemline 10/87; RN from Toxlit		2.4110adenosines;
purines D-ribonucleoside		analgesic;
anti-arrhythmia drug;
fundamental metabolite;
human metabolite;
vasodilator agent
baicalin
[no description available]		3.5110dihydroxyflavone;
glucosiduronic acid;
glycosyloxyflavone;
monosaccharide derivative		antiatherosclerotic agent;
antibacterial agent;
anticoronaviral agent;
antineoplastic agent;
antioxidant;
cardioprotective agent;
EC 2.7.7.48 (RNA-directed RNA polymerase) inhibitor;
EC 3.4.21.26 (prolyl oligopeptidase) inhibitor;
ferroptosis inhibitor;
neuroprotective agent;
non-steroidal anti-inflammatory drug;
plant metabolite;
prodrug
nicotinamide n-oxide
[no description available]		2.2510pyridines
2-amino-n(6)-hydroxyadenine
2-amino-N(6)-hydroxyadenine: mutagen & bacterial growth inhibitor; structure in first source. 2-amino-6-hydroxyaminopurine : A 2,6-diaminopurine that is the N(6)-hydroxy derivative of 2,6-diamino-3H-purine.		2.07102,6-diaminopurines;
hydroxylamines;
nucleobase analogue		mutagen;
teratogenic agent
proline
Proline: A non-essential amino acid that is synthesized from GLUTAMIC ACID. It is an essential component of COLLAGEN and is important for proper functioning of joints and tendons.. proline : An alpha-amino acid that is pyrrolidine bearing a carboxy substituent at position 2.		2.4110amino acid zwitterion;
glutamine family amino acid;
L-alpha-amino acid;
proline;
proteinogenic amino acid		algal metabolite;
compatible osmolytes;
Escherichia coli metabolite;
micronutrient;
mouse metabolite;
nutraceutical;
Saccharomyces cerevisiae metabolite
n(4)-hydroxycytosine
[no description available]		2.0710
brivudine
brivudine: anti-herpes agent		2.3110
gs 4071
GS 4071: The acid form.. oseltamivir acid : A cyclohexenecarboxylic acid that is cyclohex-1-ene-1-carboxylic acid which is substituted at positions 3, 4, and 5 by pentan-3-yloxy, acetamido, and amino groups, respectively (the 3R,4R,5S enantiomer). An antiviral drug, it is used as the corresponding ethyl ester prodrug, oseltamivir, to slow the spread of influenza.		2.3110acetate ester;
amino acid;
cyclohexenecarboxylic acid;
primary amino compound		antiviral drug;
EC 3.2.1.18 (exo-alpha-sialidase) inhibitor;
marine xenobiotic metabolite
favipiravir
favipiravir : A member of the class of pyrazines that is pyrazine substituted by aminocarbonyl, hydroxy and fluoro groups at positions 2, 3 and 6, respectively. It is an anti-viral agent that inhibits RNA-dependent RNA polymerase of several RNA viruses and is approved for the treatment of influenza in Japan.		4.4320hydroxypyrazine;
organofluorine compound;
primary carboxamide		anticoronaviral agent;
antiviral drug;
EC 2.7.7.48 (RNA-directed RNA polymerase) inhibitor
cf 1743
[no description available]		2.3110
5-(2-chloroethyl)-2'-deoxyuridine
5-(2-chloroethyl)-2'-deoxyuridine: inhibitor of herpes viruses; structure given in first source		3.5110pyrimidine 2'-deoxyribonucleoside
fosmidomycin monosodium salt
[no description available]		2.2510
baicalein
[no description available]		3.5110trihydroxyflavoneangiogenesis inhibitor;
anti-inflammatory agent;
antibacterial agent;
anticoronaviral agent;
antifungal agent;
antineoplastic agent;
antioxidant;
apoptosis inducer;
EC 1.13.11.31 (arachidonate 12-lipoxygenase) inhibitor;
EC 1.13.11.33 (arachidonate 15-lipoxygenase) inhibitor;
EC 3.4.21.26 (prolyl oligopeptidase) inhibitor;
EC 3.4.22.69 (SARS coronavirus main proteinase) inhibitor;
EC 4.1.1.17 (ornithine decarboxylase) inhibitor;
ferroptosis inhibitor;
geroprotector;
hormone antagonist;
plant metabolite;
prostaglandin antagonist;
radical scavenger
N-[(5-methyl-1,2-oxazol-3-yl)carbonyl]-L-alanyl-L-valyl-N-{(2S,3E)-5-(benzyloxy)-5-oxo-1-[(3S)-2-oxopyrrolidin-3-yl]pent-3-en-2-yl}-L-leucinamide
N-[(5-methyl-1,2-oxazol-3-yl)carbonyl]-L-alanyl-L-valyl-N-{(2S,3E)-5-(benzyloxy)-5-oxo-1-[(3S)-2-oxopyrrolidin-3-yl]pent-3-en-2-yl}-L-leucinamide : A tripeptide resulting from the formal condensation of the carboxy group of N-[(5-methyl-1,2-oxazol-3-yl)carbonyl]-L-alanyl-L-valine with the amino group of benzyl (2E,4S)-4-(L-leucylamino)-5-[(3S)-2-oxopyrrolidin-3-yl]pent-2-enoate. It is an inhibitor of the main protease of SARS-CoV-2.		3.5110benzyl ester;
isoxazoles;
pyrrolidin-2-ones;
tripeptide		anticoronaviral agent;
antiviral agent;
EC 3.4.22.69 (SARS coronavirus main proteinase) inhibitor
psi 6130
2'-deoxy-2'-fluoro-2'-C-methylcytidine: PSI-6130 is the (beta-D)-isomer; has antiviral activity against hepatitis C virus; structure in first source		2.0710
benzamidoxime
benzamidoxime: structure given in first source. benzamidoxime : A member of the class of amidoximes obtained by formal condensation of the carbonyl group of benzamide with hydroxylamine.		2.2510amidoximebacterial metabolite;
genotoxin;
mammalian metabolite
guanoxabenz
[no description available]		2.2510
upamostat
[no description available]		2.2510
galidesivir
[no description available]		3.5110
PF-00835231
PF-00835231 : A primary alcohol resulting from the cleavage of the phosphate group of the prodrug PF-07304814. It is an inhibitor of SARS-CoV-1 and -2 main protease (3CLpro) and exhibits potent in vitro antiviral activity.		2.4110aromatic ether;
indolecarboxamide;
L-leucine derivative;
primary alcohol;
pyrrolidin-2-ones;
secondary carboxamide		anticoronaviral agent;
drug metabolite;
EC 3.4.22.69 (SARS coronavirus main proteinase) inhibitor
4-amino-1-(3,4-dihydroxy-5-(hydroxymethyl)-3-methyltetrahydrofuran-2-yl)pyrimidin-2(1h)-one
4-amino-1-(3,4-dihydroxy-5-(hydroxymethyl)-3-methyltetrahydrofuran-2-yl)pyrimidin-2(1H)-one: has antiviral activity		2.0710
n(4)-aminocytidine
[no description available]		210
oligonucleotides
[no description available]		210
GRL-0617
GRL-0617 : A benzamide resulting from the formal condensation of the carboxy group of 5-amino-2-methylbenzoic acid with the amino group of (1R)-1-(naphthalen-1-yl)ethan-1-amine. It is a potent noncovalent inhibitor (IC50 = 600 nM) of severe acute respiratory syndrome-coronavirus papain-like protease (SARS-CoV PLpro).		3.5110benzamides;
naphthalenes;
secondary carboxamide;
substituted aniline		anticoronaviral agent;
protease inhibitor
GS-441524
[no description available]		2.4110aromatic amine;
C-nucleoside;
nitrile;
pyrrolotriazine		anticoronaviral agent;
antiviral agent;
drug metabolite
s 8932
[no description available]		4.7160aromatic amine;
C-nucleoside;
carboxylic ester;
nitrile;
phosphoramidate ester;
pyrrolotriazine		anticoronaviral agent;
antiviral drug;
prodrug
acyclovir
Acyclovir: A GUANOSINE analog that acts as an antimetabolite. Viruses are especially susceptible. Used especially against herpes.. acyclovir : An oxopurine that is guanine substituted by a (2-hydroxyethoxy)methyl substituent at position 9. Used in the treatment of viral infections.		2.31102-aminopurines;
oxopurine		antimetabolite;
antiviral drug
rifampin
Rifampin: A semisynthetic antibiotic produced from Streptomyces mediterranei. It has a broad antibacterial spectrum, including activity against several forms of Mycobacterium. In susceptible organisms it inhibits DNA-dependent RNA polymerase activity by forming a stable complex with the enzyme. It thus suppresses the initiation of RNA synthesis. Rifampin is bactericidal, and acts on both intracellular and extracellular organisms. (From Gilman et al., Goodman and Gilman's The Pharmacological Basis of Therapeutics, 9th ed, p1160)		1.9610cyclic ketal;
hydrazone;
N-iminopiperazine;
N-methylpiperazine;
rifamycins;
semisynthetic derivative;
zwitterion		angiogenesis inhibitor;
antiamoebic agent;
antineoplastic agent;
antitubercular agent;
DNA synthesis inhibitor;
EC 2.7.7.6 (RNA polymerase) inhibitor;
Escherichia coli metabolite;
geroprotector;
leprostatic drug;
neuroprotective agent;
pregnane X receptor agonist;
protein synthesis inhibitor
ganciclovir
[no description available]		2.31102-aminopurines;
oxopurine		antiinfective agent;
antiviral drug
molnupiravir
molnupiravir: prodrug that’s metabolized into N4-hydroxycytidine (NHC), a ribonucleoside analog. molnupiravir : A nucleoside analogue that is N(4)-hydroxycytidine in which the 5'-hydroxy group is replaced by a (2-methylpropanoyl)oxy group. It is the prodrug of the active antiviral ribonucleoside analog N(4)-hydroxycytidine (EIDD-1931), has activity against a number of RNA viruses including SARS-CoV-2, MERS-CoV, and seasonal and pandemic influenza viruses. It is currently in phase III trials for the treatment of patients with COVID-19.		7.75131isopropyl ester;
ketoxime;
nucleoside analogue		anticoronaviral agent;
antiviral drug;
prodrug
3-fluoro-Nalpha-(1H-indol-2-ylcarbonyl)-N-{(2S)-1-oxo-3-[(3S)-2-oxopyrrolidin-3-yl]propan-2-yl}-L-phenylalaninamide
3-fluoro-Nalpha-(1H-indol-2-ylcarbonyl)-N-{(2S)-1-oxo-3-[(3S)-2-oxopyrrolidin-3-yl]propan-2-yl}-L-phenylalaninamide : A secondary carboxamide resulting from the formal condensation of the carboxy group of 1H-indole-2-carboxylic acid with the primary amino group of 3-fluoro-N-{(2S)-1-oxo-3-[(3S)-2-oxopyrrolidin-3-yl]propan-2-yl}-L-phenylalaninamide. It is an inhibitor of SARS coronavirus main proteinase and inhibits SARS-CoV-2 replication in cell culture (EC50 = 0.72 muM).		3.5110aldehyde;
indolecarboxamide;
monofluorobenzenes;
oligopeptide;
pyrrolidin-2-ones;
secondary carboxamide		anticoronaviral agent;
EC 3.4.22.69 (SARS coronavirus main proteinase) inhibitor
nirmatrelvir
nirmatrelvir: component of COVID-19 drug Paxlovid. Paxlovid : A mixture containing nirmatrelvir and ritonavir. It is co-administered in tablet form for the treatment and post-exposure prophylaxis of COVID-19.. nirmatrelvir : An azabicyclohexane that is (1R,5S)-3-azabicyclo[3.1.0]hexane substituted by {(1S)-1-cyano-2-[(3S)-2-oxopyrrolidin-3-yl]ethyl}aminoacyl, 3-methyl-N-(trifluoroacetyl)-L-valinamide, methyl and methyl groups at positions 2S, 3, 6 and 6, respectively. It is the first orally administered inhibitor of SARS-CoV-2 main protease developed by Pfizer and used in combination with ritonavir for the treatment of COVID-19.		2.8220azabicyclohexane;
nitrile;
organofluorine compound;
pyrrolidin-2-ones;
pyrrolidinecarboxamide;
secondary carboxamide;
tertiary carboxamide		anticoronaviral agent;
EC 3.4.22.69 (SARS coronavirus main proteinase) inhibitor
ConditionIndicatedRelationship StrengthStudiesTrials
Plasmodium falciparum Malaria
[description not available]		02.0710
Malaria, Falciparum
Malaria caused by PLASMODIUM FALCIPARUM. This is the severest form of malaria and is associated with the highest levels of parasites in the blood. This disease is characterized by irregularly recurring febrile paroxysms that in extreme cases occur with acute cerebral, renal, or gastrointestinal manifestations.		02.0710
Infections, Coronavirus
[description not available]		02.830
2019 Novel Coronavirus Disease
[description not available]		05.38140
Disease Models, Animal
Naturally-occurring or experimentally-induced animal diseases with pathological processes analogous to human diseases.		02.6620
Pneumonia, Viral
Inflammation of the lung parenchyma that is caused by a viral infection.		02.2510
Coronavirus Infections
Virus diseases caused by the CORONAVIRUS genus. Some specifics include transmissible enteritis of turkeys (ENTERITIS, TRANSMISSIBLE, OF TURKEYS); FELINE INFECTIOUS PERITONITIS; and transmissible gastroenteritis of swine (GASTROENTERITIS, TRANSMISSIBLE, OF SWINE).		02.830
Infections, RNA Virus
[description not available]		02.4110
Enterovirus Infections
Diseases caused by ENTEROVIRUS.		02.4110
Ebola Hemorrhagic Fever
[description not available]		04.2190
Hemorrhagic Fever, Ebola
A highly fatal, acute hemorrhagic fever caused by EBOLAVIRUS.		04.2190
Coronaviridae Infections
Virus diseases caused by CORONAVIRIDAE.		02.2110
Grippe
[description not available]		02.2510
Influenza, Human
An acute viral infection in humans involving the respiratory tract. It is marked by inflammation of the NASAL MUCOSA; the PHARYNX; and conjunctiva, and by headache and severe, often generalized, myalgia.		02.2510
Gastroenteritis
INFLAMMATION of any segment of the GASTROINTESTINAL TRACT from ESOPHAGUS to RECTUM. Causes of gastroenteritis are many including genetic, infection, HYPERSENSITIVITY, drug effects, and CANCER.		02.0710
Respiratory Syndrome, Acute, Severe
[description not available]		02.0210
Severe Acute Respiratory Syndrome
A viral disorder characterized by high FEVER, dry COUGH, shortness of breath (DYSPNEA) or breathing difficulties, and atypical PNEUMONIA. A virus in the genus CORONAVIRUS is the suspected agent.		02.0210