IDOXURIDINE

/static/temp/default.svg Search structure
Trade Names
Synonyms
IDU
Status
Molecule Category UNKNOWN
ATC D06BB01 J05AB02 S01AD01
UNII LGP81V5245
EPA CompTox DTXSID2045238

Structure

InChI Key XQFRJNBWHJMXHO-RRKCRQDMSA-N
Smiles O=c1[nH]c(=O)n([C@H]2C[C@H](O)[C@@H](CO)O2)cc1I
InChI
InChI=1S/C9H11IN2O5/c10-4-2-12(9(16)11-8(4)15)7-1-5(14)6(3-13)17-7/h2,5-7,13-14H,1,3H2,(H,11,15,16)/t5-,6+,7+/m0/s1

Physicochemical Descriptors

Property Name Value
Molecular Formula C9H11IN2O5
Molecular Weight 354.1
AlogP -1.22
Hydrogen Bond Acceptor 6.0
Hydrogen Bond Donor 3.0
Number of Rotational Bond 2.0
Polar Surface Area 104.55
Molecular species NEUTRAL
Aromatic Rings 1.0
Heavy Atoms 17.0

Pharmacology

Mechanism of Action Action Reference
DNA inhibitor INHIBITOR DailyMed
Targets EC50(nM) IC50(nM) Kd(nM) Ki(nM) Inhibition(%)
Enzyme Transferase
- 1500 - 90 31
Assay Description Organism Bioactivity Reference
Inhibition of cellular DNA synthesis in BSCL cells at the dose of 0.8 ug/mL. Cercopithecidae 21.47 %
Tested for the 50% inhibitory concentration required to reduce TK+ Varicella-Zoster virus (TK+ VZV) strain YS plaque formation by 50% Homo sapiens 0.4 ug.mL-1
Tested for the inhibitory concentration required to reduce TK+ Varicella-Zoster virus (TK+ VZV) strain OKA plaque formation by 50%. Homo sapiens 0.17 ug.mL-1
Tested for the inhibitory concentration required to reduce cytomegalovirus (CMV) strain AD-169 plaque formation by 50%. Homo sapiens 20.0 ug.mL-1
Tested for the inhibitory concentration required to reduce cytomegalovirus (CMV) strain Davis plaque formation by 50%. Homo sapiens 50.0 ug.mL-1
Tested for the inhibitory concentration required to reduce thymidine kinase deficient Varicella-Zoster virus (TK- VZV) strain 07/1 plaque formation by 50%. Homo sapiens 4.0 ug.mL-1
Tested for the inhibitory concentration required to reduce thymidine kinase deficient Varicella-Zoster virus (TK- VZV) strain YS/R plaque formation by 50%. Homo sapiens 4.0 ug.mL-1
Growth inhibition against HSV-1 virus in BSCL cells at the dose of 0.8 ug/mL and 22h time of treatment. Human herpesvirus 1 71.3 %
Inhibition of viral DNA synthesis in HSV-1 virus at the dose of 0.8 ug/mL. Human herpesvirus 1 31.05 %
Inhibition constant against HSV-1 TK herpes simplex virus 90.0 nM
Percent inhibition of herpes simplex type-1 virus at the concentration of 50 uM Human herpesvirus 1 99.3 %
Concentration required to reduce HSV-1 (KOS strain) induced cytopathogenicity in NC-37 cells Homo sapiens 80.0 ug.mL-1
Compound was evaluated for antiviral activity in rabbit kidney cells infected with vaccinia virus Oryctolagus cuniculus 0.4 ug.mL-1
Concentration required to inhibit incorporation of [1,'2'-3H]dUrd into DNA of primary rabbit kidney (PRK) cells by 50% Oryctolagus cuniculus 0.3 ug.mL-1
Concentration required to inhibit incorporation of [Me-3H]-dThd into DNA of primary rabbit kidney (PRK) cells by 50% Oryctolagus cuniculus 1.0 ug.mL-1
Concentration required to reduce HSV-1 induced cytopathogenicity by 50% in primary rabbit kidney (PRK) cells Oryctolagus cuniculus 0.1 ug.mL-1
Concentration required to reduce HSV-2 induced cytopathogenicity by 50% in primary rabbit kidney (PRK) cells; 0.2-0.4 Oryctolagus cuniculus 0.2 ug.mL-1
Concentration required to reduce TK-HSV-1 (B2006) induced cytopathogenicity by 50% in primary rabbit kidney (PRK) cells Oryctolagus cuniculus 200.0 ug.mL-1
Kinetic inhibition constant against herpes simplex virus type I pyrimidine deoxyribonucleoside kinase was measured Human herpesvirus 1 400.0 nM
Binding affinity constant against HSV-1 thymidine kinase herpes simplex virus 90.0 nM
Inhibition constant was measured against Thymidine kinase None 100.0 Inhibition constant was measured against Thymidine kinase None 51.67
Antiviral activity against TK+ cowpox virus delta crmA in HFF cells Cowpox virus 400.0 nM
Antiviral activity against HSV1 2931 infected in African green monkey Vero cells assessed as inhibition of virus replication at 1 ug/ml after 24 hrs relative to control Human herpesvirus 1 90.0 %
Antiviral activity against HSV1 2931 infected in African green monkey Vero cells assessed as inhibition of virus replication at 10 ug/ml after 24 hrs relative to control Human herpesvirus 1 90.0 %
Antiviral activity against HSV1 2931 infected in African green monkey Vero cells assessed as inhibition of virus replication at 100 ug/ml after 24 hrs relative to control Human herpesvirus 1 100.0 %
Antiviral activity against HSV1 2931 infected in African green monkey Vero cells assessed as inhibition of virus replication at 0.01 ug/ml after 24 hrs relative to control Human herpesvirus 1 90.0 %
Antiviral activity against HSV1 2931 infected in African green monkey Vero cells assessed as inhibition of virus replication at 0.1 ug/ml after 24 hrs relative to control Human herpesvirus 1 90.0 %
Inhibition of thymidine kinase in BHK21 (C13) cells using [14C]thymidine at 0.19 mM after 10 mins by liquid scintillation spectrometer analysis relative to control in presence of Mg2+ Mesocricetus auratus 37.0 %
Inhibition of human mitochondrial thymidine kinase using [14C]thymidine at 0.19 mM after 10 mins by liquid scintillation spectrometer analysis relative to control in presence of Mg2+ Homo sapiens 31.0 %
Inhibition of human cytoplasmic thymidine kinase using [14C]thymidine at 0.19 mM after 10 mins by liquid scintillation spectrometer analysis relative to control in presence of Mg2+ Homo sapiens 56.0 %
Antiviral activity against HSV1 CL101 infected in African green monkey Vero cells assessed as inhibition of plaque formation at 50 uM after 40 hrs relative to control Herpes simplex virus (type 1 / strain CL101) 99.7 %
Antimicrobial activity against Streptococcus faecium assessed as growth inhibition at 400 uM after 15 to 17 hrs by turbidity assay in presence of 7 uM deoxythymidine Enterococcus faecium 12.0 %
Antimicrobial activity against Streptococcus faecium assessed as growth inhibition at 400 uM after 15 to 17 hrs by turbidity assay in presence of 4.53 nM folic acid Enterococcus faecium 71.0 %
Competitive inhibition of HSV-1 pyrimidine deoxythymidine kinase using 2-[14C]deoxythymidine as substrate Human herpesvirus 1 200.0 nM
Antiviral activity against HSV1 CL101 infected in African green monkey Vero cells assessed as plaque forming unit at 50 uM after 40 hrs relative to control Human herpesvirus 1 99.5 %
Cytotoxicity against African green monkey Vero cells at 50 uM after 3 days by haemocytometry Chlorocebus sabaeus 100.0 %
Cytotoxicity against mouse S180 cells at 50 uM after 18 to 42 hrs relative to control Mus musculus 100.0 %
PubChem BioAssay. VEGF stimulated ADSC/ECFC co-culture CD31-stained tube area decrease-IC50. (Class of assay: confirmatory) None 680.6 nM
Antiviral activity determined as inhibition of SARS-CoV-2 induced cytotoxicity of Caco-2 cells at 10 uM after 48 hours by high content imaging Homo sapiens 8.12 %
SARS-CoV-2 3CL-Pro protease inhibition percentage at 20µM by FRET kind of response from peptide substrate Severe acute respiratory syndrome coronavirus 2 13.41 % SARS-CoV-2 3CL-Pro protease inhibition percentage at 20µM by FRET kind of response from peptide substrate Severe acute respiratory syndrome coronavirus 2 -6.842 %
Antiviral activity determined as inhibition of SARS-CoV-2 induced cytotoxicity of VERO-6 cells at 10 uM after 48 hours exposure to 0.01 MOI SARS CoV-2 virus by high content imaging Chlorocebus sabaeus 0.28 % Antiviral activity determined as inhibition of SARS-CoV-2 induced cytotoxicity of VERO-6 cells at 10 uM after 48 hours exposure to 0.01 MOI SARS CoV-2 virus by high content imaging Chlorocebus sabaeus 0.25 % Antiviral activity determined as inhibition of SARS-CoV-2 induced cytotoxicity of VERO-6 cells at 10 uM after 48 hours exposure to 0.01 MOI SARS CoV-2 virus by high content imaging Chlorocebus sabaeus 0.25 % Antiviral activity determined as inhibition of SARS-CoV-2 induced cytotoxicity of VERO-6 cells at 10 uM after 48 hours exposure to 0.01 MOI SARS CoV-2 virus by high content imaging Chlorocebus sabaeus 0.28 %

Related Entries

Cross References

Resources Reference
ChEBI 147675
ChEMBL CHEMBL788
DrugBank DB00249
DrugCentral 1417
FDA SRS LGP81V5245
Human Metabolome Database HMDB0014394
KEGG D00342
PDB ID2
PharmGKB PA164781019
PubChem 5905
SureChEMBL SCHEMBL3683
ZINC ZINC000003834173
CONTENTS