STAVUDINE

/static/temp/default.svg Search structure
Trade Names
Synonyms
D4T
d4T
Status
Molecule Category Free-form
ATC J05AF04
UNII BO9LE4QFZF
EPA CompTox DTXSID1023819

Structure

InChI Key XNKLLVCARDGLGL-JGVFFNPUSA-N
Smiles Cc1cn([C@H]2C=C[C@@H](CO)O2)c(=O)[nH]c1=O
InChI
InChI=1S/C10H12N2O4/c1-6-4-12(10(15)11-9(6)14)8-3-2-7(5-13)16-8/h2-4,7-8,13H,5H2,1H3,(H,11,14,15)/t7-,8+/m0/s1

Physicochemical Descriptors

Property Name Value
Molecular Formula C10H12N2O4
Molecular Weight 224.22
AlogP -0.71
Hydrogen Bond Acceptor 5.0
Hydrogen Bond Donor 2.0
Number of Rotational Bond 2.0
Polar Surface Area 84.32
Molecular species NEUTRAL
Aromatic Rings 1.0
Heavy Atoms 16.0

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
50-500 60-9600 - - -
Secreted protein
- - 44000 - -
Assay Description Organism Bioactivity Reference
Ability to inhibit the replication of HIV-1 IIIB infected C8166 cells Homo sapiens 80.0 nM
Tested in vitro for the antiviral activity in CEM-SS cells infected with HIV-1 Homo sapiens 59.0 nM
Compound was evaluated for the inhibition of HIV replication using HIV-1 infected CEM cells. Homo sapiens 160.0 nM
Compound was evaluated for the inhibition of HIV replication using HIV-2 infected CEM cells. Homo sapiens 270.0 nM
Effective concentration of compound achieving 50% protection in CEM cell lines against the cytopathic effect of HIV-1 Homo sapiens 90.0 nM
Activity against HIV-1 in CEM cells (in vitro) Homo sapiens 800.0 nM
Activity against HIV-2 in CEM cells (in vitro) Homo sapiens 775.0 nM
Compound was tested for anti-HIV-1 activity in CEM/0 cell line Homo sapiens 250.0 nM
Concentration required to protect CEM/0 cells against the cytopathicity of HIV-1 by 50% Human immunodeficiency virus 1 651.0 nM
Concentration required to protect CEM/0 cells against the cytopathicity of HIV-2 by 50% Human immunodeficiency virus 770.0 nM
Effective concentration that causes 50 % inhibition of HIV-1 in CEM/0 cells, was determined. Homo sapiens 0.4 ug.mL-1
Effective concentration that causes 50 % inhibition of HIV-2 in CEM/0 cells, was determined. Homo sapiens 1.45 ug.mL-1
Antiviral activity was measured on HIV-1 in wild-type CEM/O cells Homo sapiens 180.0 nM Antiviral activity was measured on HIV-1 in wild-type CEM/O cells Homo sapiens 180.0 nM
Antiviral activity was measured on HIV-2 in wild-type CEM/O cells Homo sapiens 260.0 nM Antiviral activity was measured on HIV-2 in wild-type CEM/O cells Homo sapiens 260.0 nM
In vitro effective compound concentration required to protect CEM/O cells against the cytopathogenicity of HIV-1 Homo sapiens 651.0 nM
In vitro effective compound concentration required to protect CEM/O cells against the cytopathogenicity of HIV-2 Homo sapiens 770.0 nM
Effective concentration that causes 50 % inhibition of HIV-2 in CEM/TK- cells, was determined. Homo sapiens 45.0 ug.mL-1
In vitro inhibition of HIV-1 replication in human T-lymphocytic cells (CEM). Human immunodeficiency virus 1 180.0 nM
Antiviral activity evaluated as the ability to inhibit the replication of HIV-1 in human T-lymphocytic cells (CEM) Homo sapiens 180.0 nM
In vitro inhibition of HIV-2 replication in human T-lymphocytic cells (CEM). Human immunodeficiency virus 2 260.0 nM
Antiviral activity evaluated as the ability to inhibit the replication of HIV-2 in human T-lymphocytic cells (CEM) Homo sapiens 260.0 nM
Concentration required to protect CEM cells against cytopathicity of HIV-1 by 50% Homo sapiens 651.0 nM
Concentration required to protect CEM cells against cytopathicity of HIV-2 by 50% Homo sapiens 770.0 nM
Effective concentration required to protect Human T-Lymphocyte (CEM) cells against cytopathogenicity of HIV-1 (IIIB) Homo sapiens 210.0 nM
Effective concentration required to protect Human T-Lymphocyte (CEM) cells against cytopathogenicity of HIV-2 (ROD) Homo sapiens 400.0 nM
Compound was tested for anti-HIV activity in TK-deficient CEM cells by p24 production assay Homo sapiens 600.0 nM
Concentration of the drug resulting in 50% reduction of the viral cytopathic effect against HIV-1 replication in CEM cells. Homo sapiens 800.0 nM
Effective concentration that reduces HIV-induced cytopathic effect by 50% was determined by MTT assay. Homo sapiens 80.0 nM
Concentration required to inhibit 50% of HIV-IIIB virus replication Human immunodeficiency virus 1 600.0 nM
Activity against HIV-1 in MT-4 cells (in vitro) Homo sapiens 651.0 nM
Activity against HIV-2 in MT-4 cells (in vitro) Homo sapiens 770.0 nM
Tested in vitro for the antiviral activity in MT-4 cells infected with HIV-1 Homo sapiens 280.0 nM
Antiviral activity was measured on HIV-1 in MT-4 cells Homo sapiens 18.0 nM
Antiviral activity was measured on HIV-2 in MT-4 cells Homo sapiens 22.0 nM
Effective concentration required to protect MT-4 cells against cytopathogenicity of HIV-1 LAI Homo sapiens 710.0 nM
Antimycobacterial activity against Mycobacterium tuberculosis strain H37Rv Mycobacterium tuberculosis 0.0 %
Tested in vitro for the antiviral activity in PBM cells infected with HIV-1 Homo sapiens 50.0 nM
Antiviral activity against HIV I strain (LAV) in human peripheral blood mononuclear (PBM) cells; Range is 0.009 - 0.04 Homo sapiens 9.0 nM
Effective concentration required to inhibit P24 antigen production in PHA-PBM cells exposed to HIV-1 LAI Homo sapiens 40.0 nM
Effective concentration that reduces HIV-induced cytopathic effect by 50% was determined by reverse transcriptase (RT) assay. None 50.0 nM
In vitro antiviral activity against HIV-1 Reverse transcriptase M184V mutant None 500.0 nM
In vitro antiviral activity against HIV-1 Reverse transcriptase wild type None 450.0 nM
Compound was tested for anti-HIV activity in normal peripheral blood mononuclear cells by inhibition of reverse transcriptase activity Homo sapiens 40.0 nM
Compound was tested for anti-HIV activity in normal peripheral blood mononuclear cells by p24 production assay Homo sapiens 20.0 nM
Effective concentration of compound to inhibit human immunodeficiency virus HIV-2 multiplication in CEM wild type cells Human immunodeficiency virus 2 100.0 nM
Effective concentration of compound to inhibit human immunodeficiency virus HIV-2 multiplication in MT-4 infected cells Human immunodeficiency virus 2 500.0 nM
Effective concentration of compound to inhibit human immunodeficiency virus HIV-1 strain N119 multiplication in CEM wild type cells Human immunodeficiency virus 1 800.0 nM
Effective concentration of compound to inhibit human immunodeficiency virus HIV-1 wild type strain IIIB multiplication in CEM wild type cells Human immunodeficiency virus 1 300.0 nM
Effective concentration of compound to inhibit human immunodeficiency virus HIV-1 wild type strain IIIB multiplication in MT-4 infected cells Human immunodeficiency virus 1 500.0 nM
Antiviral activity against HIV1 3B in MT4 cells by MTT assay Human immunodeficiency virus 1 510.0 nM
Antiviral activity against HIV1 in MAGI-CCR5 cells Human immunodeficiency virus 1 62.0 nM
Antiviral activity against HIV1 in CEM/0 cells Human immunodeficiency virus 1 250.0 nM
Antiviral activity against H1V2 in CEM/0 cells Human immunodeficiency virus 2 190.0 nM
Antiviral activity against HIV1 in CEM/0 cells Human immunodeficiency virus 1 480.0 nM
Antiviral activity against HIV2 ROD in CEM/0 cells Human immunodeficiency virus 2 630.0 nM
Inhibition of HIV1 reverse transcriptase Human immunodeficiency virus 1 60.0 nM
Inhibition of HIV1-induced cytopathogenicity in CEM/0 cells Human immunodeficiency virus 1 650.0 nM
Inhibition of HIV2-induced cytopathogenicity in CEM/0 cells Human immunodeficiency virus 2 770.0 nM
Antiviral activity against HIV1 in wild type human CEM cells assessed as virus-induced cytopathic effect after 4 to 5 days by microscopy Human immunodeficiency virus 1 560.0 nM
Antiviral activity against HIV2 in wild type human CEM cells assessed as virus-induced cytopathic effect after 4 to 5 days by microscopy Human immunodeficiency virus 2 790.0 nM
Antiviral activity against 0.1 MOI HIV1 3B infected in human TZM-b1 cells assessed as inhibition of viral replication at 6 uM after 24 hrs by luciferase assay Human immunodeficiency virus 1 50.0 %
Antiviral activity against 0.1 MOI HIV1 3B infected in human TZM-b1 cells assessed as inhibition of viral replication at 2 uM after 24 hrs by luciferase assay Human immunodeficiency virus 1 50.0 %
Antiviral activity against HIV1 in human wild type CEM/0 cellss Human immunodeficiency virus 1 860.0 nM
Antiviral activity against HIV1 in human CEM cells Human immunodeficiency virus 1 480.0 nM
Antiviral activity against HIV2 ROD in human CEM cells Human immunodeficiency virus 2 630.0 nM
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 60.0 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 60.0 nM
Antiviral activity against HIV1 replication in human wild type CEM/0 cells assessed as virus-induced cytopathic effect Human immunodeficiency virus 1 850.0 nM
Antiviral activity against HIV1 reverse transcriptase Y181C mutant infected in human MT2 cells assessed as inhibition of viral replication by MTT assay Human immunodeficiency virus 1 700.0 nM
Antiviral activity against HIV1 reverse transcriptase K103N/Y181C double mutant infected in human MT2 cells assessed as inhibition of viral replication by MTT assay Human immunodeficiency virus 1 500.0 nM
Antiviral activity against HIV1 3B infected in human CEM/0 cells assessed as inhibition of virus-induced cytopathicity after 4 to 5 days Human immunodeficiency virus 1 840.0 nM
Antiviral activity against HIV2 ROD infected in human CEM/0 cells assessed as inhibition of virus-induced cytopathicity after 4 to 5 days Human immunodeficiency virus type 2 (ISOLATE ROD) 750.0 nM
Antiviral activity against HIV1 isolate 056 expressing wild type reverse transcriptase gene by phenosense assay Human immunodeficiency virus 1 510.0 nM
Antiviral activity against HIV1 isolate 057 expressing wild type reverse transcriptase gene by phenosense assay Human immunodeficiency virus 1 480.0 nM
Antiviral activity against HIV1 isolate 066 harboring reverse transcriptase 184V mutant gene by phenosense assay Human immunodeficiency virus 1 460.0 nM
Antiviral activity against HIV1 isolate 070 harboring reverse transcriptase 65R/S68G mutant gene by phenosense assay Human immunodeficiency virus 1 770.0 nM
Antiviral activity against HIV1 isolate 071 harboring reverse transcriptase 65R/S68N/184V mutant gene by phenosense assay Human immunodeficiency virus 1 590.0 nM
Antiviral activity against HIV1 isolate 153 harboring reverse transcriptase L74V mutant gene by phenosense assay Human immunodeficiency virus 1 600.0 nM
Antiviral activity against HIV1 isolate 157 harboring reverse transcriptase L74V/M184V mutant gene by phenosense assay Human immunodeficiency virus 1 420.0 nM
Antiviral activity against HIV1 isolate 166 harboring reverse transcriptase L74V mutant gene obtained as site-directed mutant of NL4-3 by phenosense assay Human immunodeficiency virus 1 630.0 nM
Antiviral activity against HIV1 isolate 174 harboring reverse transcriptase M184V mutant gene obtained as site-directed mutant of NL4-3 by phenosense assay Human immunodeficiency virus 1 400.0 nM
Antiviral activity against HIV1 isolate 180 harboring reverse transcriptase K65R mutant gene obtained as site-directed mutant of NL4-3 by phenosense assay Human immunodeficiency virus 1 830.0 nM
Antiviral activity against HIV1 isolate 185 harboring reverse transcriptase T215Y mutant gene by phenosense assay Human immunodeficiency virus 1 830.0 nM
Antiviral activity against HIV1 isolate 188 harboring reverse transcriptase T215Y/M184V mutant gene by phenosense assay Human immunodeficiency virus 1 650.0 nM
Antiviral activity against HIV1 isolate 192 harboring reverse transcriptase M41L/T215Y mutant gene by phenosense assay Human immunodeficiency virus 1 840.0 nM
Antiviral activity against HIV1 isolate 194 harboring reverse transcriptase M41L/T215Y/M184V mutant gene by phenosense assay Human immunodeficiency virus 1 860.0 nM
Antiviral activity against HIV1 isolate 203 harboring reverse transcriptase M41L/L210W/T215Y/M184V mutant gene by phenosense assay Human immunodeficiency virus 1 880.0 nM
Antiviral activity against HIV1 isolate 206 harboring reverse transcriptase D67N/K70R mutant gene by phenosense assay Human immunodeficiency virus 1 780.0 nM
Antiviral activity against HIV1 isolate 211 harboring reverse transcriptase D67N/K70R/T215F/K219E/M184V mutant gene by phenosense assay Human immunodeficiency virus 1 790.0 nM
Antiviral activity against HIV1 isolate 212 harboring reverse transcriptase L210W/T215Y mutant gene by phenosense assay Human immunodeficiency virus 1 940.0 nM
Antiviral activity against HIV1 isolate 215 harboring reverse transcriptase D67N/K70E mutant gene by phenosense assay Human immunodeficiency virus 1 560.0 nM
Antiviral activity against HIV1 isolate 217 harboring reverse transcriptase D67N/K70E/M184V mutant gene by phenosense assay Human immunodeficiency virus 1 420.0 nM
Antiviral activity against HIV1 isolate 220 harboring reverse transcriptase K70E/M184V mutant gene by phenosense assay Human immunodeficiency virus 1 390.0 nM
Antiviral activity against HIV1 infected in human PBMC assessed as inhibition of viral replication Human immunodeficiency virus 1 100.0 nM
Antiviral activity against HIV-1 infected in wild type CEM cells assessed as inhibition of virus-induced cytopathicity after 4 days Human immunodeficiency virus 1 780.0 nM
Antiviral activity against HIV2 ROD infected in human CEM cells assessed as virus-induced giant cell formation after 4 days by microscopic analysis Human immunodeficiency virus type 2 (ISOLATE ROD) 580.0 nM
Antiviral activity against HIV1 3B infected in human CEM cells assessed as virus-induced giant cell formation after 4 days by microscopic analysis Human immunodeficiency virus 1 390.0 nM
Antiviral activity against HIV-2 ROD infected in human MT4 cells Human immunodeficiency virus type 2 (ISOLATE ROD) 400.0 nM
Antiviral activity against HIV-1 3B infected in human MT4 cells Human immunodeficiency virus 1 260.0 nM
Antiviral activity against HIV1 3B infected in human CEM/0 cells assessed as reduction in virus-induced giant cell formation incubated for 4 to 5 days Human immunodeficiency virus 1 520.0 nM
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 17.22 %
Antibacterial activity against Escherichia coli ATCC 25922 (CO-ADD:GN_001); MIC in CAMBH media using NBS plates, by OD(600) Escherichia coli 4.38 %
Antibacterial activity against Klebsiella pneumoniae MDR ATCC 70063 (CO-ADD:GN_003); MIC in CAMBH media using NBS plates, by OD(600) Klebsiella pneumoniae 14.08 %
Antibacterial activity against Pseudomonas aeruginosa ATCC 27853 (CO-ADD:GN_042); MIC in CAMBH media using NBS plates, by OD(600) Pseudomonas aeruginosa 16.08 %
Antibacterial activity against Acinetobacter baumannii ATCC 19606 (CO-ADD:GN_034); MIC in CAMBH media using NBS plates, by OD600 Acinetobacter baumannii 24.61 %
Antifungal activity against Candida albicans ATCC 90028 (CO-ADD:FG_001); MIC in YNB media using NBS plates, by OD630 Candida albicans 2.99 %
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 0.51 %
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 6.09 %
Antiviral activity against wild type HIV-1 3B infected in human MT4 cells Human immunodeficiency virus 1 400.0 nM
Antiviral activity against HIV-2 ROD infected in human MT4 cells Human immunodeficiency virus type 1 450.0 nM
SARS-CoV-2 3CL-Pro protease inhibition percentage at 20µM by FRET kind of response from peptide substrate Severe acute respiratory syndrome coronavirus 2 9.34 % SARS-CoV-2 3CL-Pro protease inhibition percentage at 20µM by FRET kind of response from peptide substrate Severe acute respiratory syndrome coronavirus 2 0.8086 %
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 -0.1 % 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 -0.07 % 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 -0.07 % 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 -0.1 %
Antiviral activity against HIV1 3B infected in human CEM/0 cells assessed as inhibition of viral-induced giant cell formation incubated for 4 to 5 days by microscopy Human immunodeficiency virus 1 430.0 nM
Antiviral activity against HIV2 ROD infected in human CEM/0 cells assessed as inhibition of viral-induced giant cell formation incubated for 4 to 5 days by microscopy Human immunodeficiency virus type 1 310.0 nM
Antiviral activity against HIV1 3B infected in human CEM/0 cells assessed as inhibition of virus-induced giant cell formation measured after 4 to 5 days by microscopic analysis Human immunodeficiency virus 1 430.0 nM
Antiviral activity against HIV2 ROD infected in human CEM/0 cells assessed as inhibition of virus-induced giant cell formation measured after 4 to 5 days by microscopic analysis Human immunodeficiency virus type 1 310.0 nM
Antiviral activity against HIV1 3B infected in human CEM/0 cells assessed as inhibition of virus-induced syncytia cell formation measured after 4 to 5 days by microscopic analysis Human immunodeficiency virus 1 430.0 nM
Antiviral activity against HIV2 ROD infected in human CEM/0 cells assessed as inhibition of virus-induced syncytia cell formation measured after 4 to 5 days by microscopic analysis Human immunodeficiency virus type 1 220.0 nM
Antiviral activity against HIV1 3B infected in human CEM/0 CD4+ T cells assessed as reduction in virus-induced cytopathogenicity by measuring syncytia cell formation incubated for 4 to 5 days by microscopy Human immunodeficiency virus 1 430.0 nM
Antiviral activity against HIV2 ROD infected in human CEM/0 CD4+ T cells assessed as reduction in virus-induced cytopathogenicity by measuring syncytia cell formation incubated for 4 to 5 days by microscopy Human immunodeficiency virus type 1 310.0 nM

Related Entries

Environmental Exposure

Environmental Exposure Map
Countries
South Africa

Cross References

Resources Reference
ChEBI 63581
ChEMBL CHEMBL991
DrugBank DB00649
DrugCentral 2478
FDA SRS BO9LE4QFZF
Human Metabolome Database HMDB0014787
KEGG C07312
PharmGKB PA451494
PubChem 18283
SureChEMBL SCHEMBL38661
ZINC ZINC000000137884
CONTENTS