ZALCITABINE

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Trade Names
Synonyms
Status
Molecule Category UNKNOWN
ATC J05AF03
UNII 6L3XT8CB3I
EPA CompTox DTXSID0023747

Structure

InChI Key WREGKURFCTUGRC-POYBYMJQSA-N
Smiles Nc1ccn([C@H]2CC[C@@H](CO)O2)c(=O)n1
InChI
InChI=1S/C9H13N3O3/c10-7-3-4-12(9(14)11-7)8-2-1-6(5-13)15-8/h3-4,6,8,13H,1-2,5H2,(H2,10,11,14)/t6-,8+/m0/s1

Physicochemical Descriptors

Property Name Value
Molecular Formula C9H13N3O3
Molecular Weight 211.22
AlogP -0.5
Hydrogen Bond Acceptor 6.0
Hydrogen Bond Donor 2.0
Number of Rotational Bond 2.0
Polar Surface Area 90.37
Molecular species NEUTRAL
Aromatic Rings 1.0
Heavy Atoms 15.0

Metabolites Network

visNetwork

Bioactivity

Mechanism of Action Action Reference
Human immunodeficiency virus type 1 reverse transcriptase inhibitor INHIBITOR FDA
Targets EC50(nM) IC50(nM) Kd(nM) Ki(nM) Inhibition(%)
Enzyme Hydrolase
31 - - 51 -
Membrane receptor Family A G protein-coupled receptor Peptide receptor (family A GPCR) Chemokine receptor CXC chemokine receptor
88 - - - -
Secreted protein
- - 44000 - -
Assay Description Organism Bioactivity Reference
Ability to inhibit the episomal HBV-DNA in 2.2.15 cells. Homo sapiens 2.1 ug.mL-1
Antiviral activity against HIV-1 (RF strain) in C8166 cells Homo sapiens 125.0 nM
Concentration of compound required to inhibit the synthesis of mitochondrial DNA (mt DNA) in human CCRF-CEM T-lymphoblastic leukemia cells Homo sapiens 22.0 nM
Effective concentration required to achieve 50% inhibition of HIV-1 LAI replication in human T4 lymphoblastoid CEM-SS cells. Human immunodeficiency virus 1 31.0 nM
Concentration required to achieve 50% protection of CEM-SS cells against the cytopathic effect of HIV-1. Human immunodeficiency virus 1 190.0 nM
Anti-HIV activity against HIV-I RFII strain in CEM cell line Homo sapiens 189.0 nM
Compound was evaluated for the antiviral activity against HIV-1 strain IIIB in CEM-SS cells Homo sapiens 20.0 nM
Compound was evaluated for the antiviral activity against HIV-1 strain RF in CEM-SS cells Homo sapiens 50.0 nM
Compound was evaluated for the antiviral activity against HIV-1 strain SK1 in CEM-SS cells Homo sapiens 50.0 nM
Compound was evaluated for the antiviral activity against SIV delta in CEM-SS cells Homo sapiens 190.0 nM
Effect on HIV-induced cytopathogenesis in CEM cells. Homo sapiens 300.0 nM
Compound was tested for its inhibitory activity against HIV replication in CEM cells. Homo sapiens 0.05 ug.mL-1
Inhibitory concentration against mitochondrial DNA synthesis CEM cells Homo sapiens 70.0 nM
Inhibition of HIV-1 replication in H9 lymphocytic cells. Human immunodeficiency virus 1 30.0 nM
Effective concentration required to achieve 50% protection of MT-4 cells against the cytopathic effect of HIV-1 (HTLV-IIIB). Human immunodeficiency virus 300.0 nM
Concentration required to protect 50% of HIV-1 infected MT-4 cells against viral cytopathicity. Human immunodeficiency virus 1 910.0 nM
Concentration required to protect 50% of HIV-2 infected MT-4 cells against viral cytopathicity. Human immunodeficiency virus 2 690.0 nM
Effective concentration that increases formazan production in infected MT-2 cells Homo sapiens 0.29 ug.mL-1
Compound was tested for its inhibitory activity against HIV replication in MT-2 cells. Homo sapiens 0.44 ug.mL-1
Inhibitory concentration that reduces formazan production in infected MT-2 cells. Homo sapiens 44.0 ug.mL-1
Effective concentration for 50% protection of HIV-induced cytopathogenicity in MT-4 cells on the MTT assay None 88.0 nM
AntiHIV-1 activity measured in MT-4 cells at 5 to 6 different concentrations, using the P24 antigen enzyme-linked immunosorbent assay (ELISA). Homo sapiens 236.0 nM
AntiHIV-1 activity measured in MT-4 cells at 5 to 6 different concentrations, using the reverse transcriptase (RT) assay Homo sapiens 240.0 nM
Anti-HIV activity against HIV-I A17 strain in MT2 cell line Homo sapiens 331.0 nM
Anti-HIV activity against HIV-I G910-6 strain in MT2 cell line Homo sapiens 994.0 nM
Anti-HIV activity against HIV-I IIIB strain in MT2 cell line Homo sapiens 900.0 nM
Concentration required to achieve 50% protection of MT-4 cells against cytopathic effect of HIV-1 Homo sapiens 300.0 nM
Effective conc. required to achieve 50% inhibition of HIV-1 IIIB multiplication in PBM (peripheral blood mononuclear) cells Homo sapiens 16.0 nM
Effective conc. required to achieve 50% inhibition of HIV-2 D194 multiplication in PBM (peripheral blood mononuclear) cells Homo sapiens 70.0 nM
Inhibition of Tomioka strain of herpes simplex virus( Tomioka strain of HSV-1) by quantitative CPE reduction assay in vero cells Human herpesvirus 1 0.02 ug.mL-1
Inhibitory constant against HIV-1 reverse transcriptase Human immunodeficiency virus 1 51.0 nM
Effective concentration to inhibit 50% of human immunodeficiency virus replication in a cell culture model None 800.0 nM
Antimycobacterial activity against Mycobacterium tuberculosis H37Ra at 100 uM by microplate alamar blue assay Mycobacterium tuberculosis 0.0 %
Antimycobacterial activity against Mycobacterium bovis BCG at 100 uM by microplate alamar blue assay Mycobacterium bovis BCG 0.0 %
Antimycobacterial activity against Mycobacterium avium ATCC 25291 at 100 uM by microplate alamar blue assay Mycobacterium avium 0.0 %
Antiviral activity against HIV1 3B infected in human MT4 cells assessed as inhibition of virus-induced cytopathic effect after 5 days by MTT assay Human immunodeficiency virus 1 0.1 ug.mL-1
Antiviral activity against HIV2 ROD infected in human MT4 cells assessed as inhibition of virus-induced cytopathic effect after 5 days by MTT assay Human immunodeficiency virus 2 0.1 ug.mL-1
Antiviral activity against HIV1 3B in human H9 cells assessed as inhibition of virus-induced cytopathic effect by formazan-based conventional colorimetric technique Human immunodeficiency virus 1 1.0 nM
Antiviral activity against HIV1 RF in human H9 cells assessed as inhibition of virus-induced cytopathic effect by formazan-based conventional colorimetric technique Human immunodeficiency virus 1 1.0 nM
Antiviral activity against HIV1 infected in human MT2 cells assessed as inhibition of viral replication Human immunodeficiency virus 1 130.0 nM
Antiviral activity against HIV1 infected in human PBMC assessed as inhibition of viral replication Human immunodeficiency virus 1 200.0 nM
Mitochondrial toxicity in human HepG2 cells assessed as percent inhibition of mitochondrial DNA at 10 uM after 14 days by real-time PCR Homo sapiens 99.88 %
Mitochondrial toxicity in human HepG2 cells assessed as percent inhibition of beta-actin DNA at 10 uM after 14 days by real-time PCR Homo sapiens 61.39 %
Antiviral activity against HIV1 3B infected in human MT4 cells coinjected with HTLV1 assessed as reduction in virus induced cytopathicity measured 5 days post infection by MTT assay Human immunodeficiency virus 1 0.043 ug.mL-1
Antiviral activity against HIV2 ROD infected in human MT4 cells assessed as reduction in virus induced cytopathicity measured 5 days post infection by MTT assay Human immunodeficiency virus type 2 (ISOLATE ROD) 0.04 ug.mL-1
Antiviral activity against HIV-1 3B infected in human MT4 cells assessed as inhibition of virus-induced syncytium formation after 5 days by MTT assay Human immunodeficiency virus 1 750.0 nM
Antiviral activity against HIV-2 ROD infected in human MT4 cells assessed as inhibition of virus-induced syncytium formation after 5 days by MTT assay Human immunodeficiency virus type 2 (ISOLATE ROD) 880.0 nM
Antiviral activity against HIV2 ROD infected in MT4 cells assessed as inhibition of virus-induced cytopathogenicity by MTT assay Human immunodeficiency virus type 2 (ISOLATE ROD) 0.19 ug.mL-1
Antiviral activity against HIV1 3B infected in MT4 cells assessed as inhibition of virus-induced cytopathogenicity by MTT assay Human immunodeficiency virus 1 0.16 ug.mL-1
Antiviral activity against Human immunodeficiency virus 2 ROD infected in MT4 cells assessed as inhibition of virus-induced cytopathogenicity by MTT assay Human immunodeficiency virus type 2 (ISOLATE ROD) 400.0 nM
Antiviral activity against Human immunodeficiency virus 1 3B infected in MT4 cells assessed as inhibition of virus-induced cytopathogenicity by MTT assay Human immunodeficiency virus 1 400.0 nM
Antiviral activity against wild type HIV-1 3B infected in human MT4 cells assessed as protection against virus-induced cytopathogenicity after 5 days by MTT assay Human immunodeficiency virus 1 460.0 nM
Antiviral activity against HIV-2 ROD infected in human CEM/0 cells Human immunodeficiency virus type 2 (ISOLATE ROD) 500.0 nM
Antiviral activity against wild-type HIV-1 3B infected in human MT4 cells assessed as protection against virus-induced cytopathic effect measured 5 days post-infection by MTT assay Human immunodeficiency virus 1 570.0 nM
Antiviral activity against HIV1 infected in human H9 cells assessed as protection against virus-induced cytopathic effect by tetrazolium reduction based colorimetric technique Human immunodeficiency virus 1 79.0 nM
Antiviral activity against HIV1 3B infected in human MT4 cells assessed as protection against virus-induced cytopathic effect after 5 days MTT assay Human immunodeficiency virus 1 0.16 ug.mL-1
Antiviral activity against HIV2 ROD infected in human MT4 cells assessed as protection against virus-induced cytopathic effect after 5 days MTT assay Human immunodeficiency virus type 2 (ISOLATE ROD) 0.19 ug.mL-1
Mitochondrial toxicity in human HepG2 cells assessed as inhibition of cytochrome c oxidase subunit 2 DNA levels at 10 uM measured on day 14 by RT-PCR method relative to nuclear beta-actin DNA levels Homo sapiens 96.0 %
Cytotoxicity against human HepG2 cells assessed as inhibition of nuclear DNA levels at 10 uM measured on day 14 by RT-PCR method relative to nuclear beta-actin DNA levels Homo sapiens 53.0 %
Antibacterial activity against Staphylococcus aureus MRSA ATCC 43300 (CO-ADD:GP_020); MIC in CAMBH media, using NBS plates, by OD(600) Staphylococcus aureus subsp. aureus 4.24 %
Antibacterial activity against Escherichia coli ATCC 25922 (CO-ADD:GN_001); MIC in CAMBH media using NBS plates, by OD(600) Escherichia coli -9.44 %
Antibacterial activity against Klebsiella pneumoniae MDR ATCC 70063 (CO-ADD:GN_003); MIC in CAMBH media using NBS plates, by OD(600) Klebsiella pneumoniae 8.0 %
Antibacterial activity against Pseudomonas aeruginosa ATCC 27853 (CO-ADD:GN_042); MIC in CAMBH media using NBS plates, by OD(600) Pseudomonas aeruginosa 1.57 %
Antibacterial activity against Acinetobacter baumannii ATCC 19606 (CO-ADD:GN_034); MIC in CAMBH media using NBS plates, by OD600 Acinetobacter baumannii 3.66 %
Antifungal activity against Candida albicans ATCC 90028 (CO-ADD:FG_001); MIC in YNB media using NBS plates, by OD630 Candida albicans 0.46 %
Antifungal activity against Cryptococcus neoformans H99 ATCC 208821 (CO-ADD:FG_002); MIC in YNB media using NBS plates, by Resazurin OD(600-570) Cryptococcus neoformans -0.26 %
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 0.17 %
Mitochondrial toxicity in human HepG2 cells assessed as inhibition of cytochrome c oxidase subunit 2 DNA level at 10 uM followed by medium plus drugs replenishment every 3 to 4 days for 14 days relative to control Homo sapiens 84.0 %
Mitochondrial toxicity in human HepG2 cells assessed as inhibition of nuclear ribosomal-DNA level at 10 uM followed by medium plus drugs replenishment every 3 to 4 days for 14 days relative to control Homo sapiens 50.0 %
SARS-CoV-2 3CL-Pro protease inhibition percentage at 20µM by FRET kind of response from peptide substrate Severe acute respiratory syndrome coronavirus 2 25.63 % SARS-CoV-2 3CL-Pro protease inhibition percentage at 20µM by FRET kind of response from peptide substrate Severe acute respiratory syndrome coronavirus 2 5.14 %
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 0.0 % 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 -0.04 % 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 -0.04 % 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 0.0 %
Antiviral activity against HIV-1 infected in human CEM-SS cells assessed as reduction in viral multiplication by measuring decrease in reverse transcriptase activity incubated for 5 days Human immunodeficiency virus 1 67.0 nM
Antiviral activity against HIV-1 infected in human CEM-SS cells assessed as reduction in viral multiplication by measuring decrease in reverse transcriptase activity incubated for 5 days in presence of AZT Human immunodeficiency virus 1 16.0 nM
Antiviral activity against HIV-1 infected in human CEM-SS cells assessed as reduction in viral multiplication by measuring decrease in reverse transcriptase activity incubated for 5 days in presence of ddA Human immunodeficiency virus 1 10.0 nM
Antiviral activity against HIV-1 infected in human MT4 cells assessed as reduction in virus-indued cytopathogenicity incubated for 5 days in presence of AZT by MTT assay Human immunodeficiency virus 1 83.0 nM
Antiviral activity against HIV-1 infected in human CEM-TK(-) cells assessed as reduction in viral multiplication by measuring decrease in reverse transcriptase activity incubated for 6 days Human immunodeficiency virus 1 15.0 nM
Antiviral activity against HIV-1 infected in human CEM-TK(-) cells assessed as reduction in viral multiplication by measuring decrease in reverse transcriptase activity incubated for 6 days in presence of AZT Human immunodeficiency virus 1 9.0 nM

Related Entries

Environmental Exposure

Environmental Exposure Map
Countries
South Africa

Cross References

Resources Reference
ChEBI 10101
ChEMBL CHEMBL853
DrugBank DB00943
DrugCentral 2856
FDA SRS 6L3XT8CB3I
Human Metabolome Database HMDB0015078
Guide to Pharmacology 4828
KEGG C07207
PharmGKB PA451950
PubChem 24066
SureChEMBL SCHEMBL3598
ZINC ZINC000000039906
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