Page last updated: 2024-12-06

4'-thiothymidine

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Description

4'-thiothymidine is a nucleoside analog that has been studied as a potential antiviral agent. It is a synthetic analog of thymidine, a naturally occurring nucleoside found in DNA. The sulfur atom in the 4'-position of the sugar moiety is thought to be responsible for its antiviral activity. 4'-thiothymidine has been shown to inhibit the replication of a variety of viruses, including herpes simplex virus, cytomegalovirus, and human immunodeficiency virus. The mechanism of its antiviral action is thought to involve the inhibition of viral DNA polymerase, which is an enzyme essential for viral replication. 4'-thiothymidine has also been investigated for its potential anticancer activity. Studies have shown that it can inhibit the growth of various cancer cell lines. It is currently under investigation for its potential therapeutic use in treating viral infections and cancer.'

4'-thiothymidine: RN & structure given in first source [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Cross-References

ID SourceID
PubMed CID10923208
CHEMBL ID463660
SCHEMBL ID6266871
MeSH IDM0191853
PubMed CID72371
CHEMBL ID445596
SCHEMBL ID1942500
MeSH IDM0191853

Synonyms (17)

Synonym
1-[(2s,4s,5r)-4-hydroxy-5-(hydroxymethyl)tetrahydrothiophen-2-yl]-5-methyl-pyrimidine-2,4-dione
134111-35-6
4'-thiothymidine
CHEMBL463660
SCHEMBL6266871
1-[(2s,4s,5r)-4-hydroxy-5-(hydroxymethyl)thiolan-2-yl]-5-methylpyrimidine-2,4-dione
134111-33-4
1-[(2r,4s,5r)-4-hydroxy-5-(hydroxymethyl)tetrahydrothiophen-2-yl]-5-methyl-pyrimidine-2,4-dione
brn 4322066
thymidine, 4'-thio-
1-[(2r,4s,5r)-4-hydroxy-5-(hydroxymethyl)thiolan-2-yl]-5-methylpyrimidine-2,4-dione
CHEMBL445596
SCHEMBL1942500
IVUDHNYLTWOARV-XLPZGREQSA-N
4/'-thiothymidine
DTXSID20928454
1-(2-deoxy-4-thiopentofuranosyl)-4-hydroxy-5-methylpyrimidin-2(1h)-one
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Bioassays (36)

Assay IDTitleYearJournalArticle
AID104471Inhibitory dose required to reduce the viability of MT-4 cells by 50%1991Journal of medicinal chemistry, Sep, Volume: 34, Issue:9
The synthesis and antiviral activity of some 4'-thio-2'-deoxy nucleoside analogues.
AID104817Minimum inhibitory concentration required to reduce cytopathogenicity of human immunodeficiency virus-1 (HIV-1) in MT-4 cells by 50%; No activity below ID50 observed1991Journal of medicinal chemistry, Sep, Volume: 34, Issue:9
The synthesis and antiviral activity of some 4'-thio-2'-deoxy nucleoside analogues.
AID105823Minimum inhibitory concentration required to reduce cytopathogenicity of Herpes Virus-1 (HSV-1) in MRC -5 cells by 50%. 1991Journal of medicinal chemistry, Sep, Volume: 34, Issue:9
The synthesis and antiviral activity of some 4'-thio-2'-deoxy nucleoside analogues.
AID105824Minimum inhibitory concentration required to reduce cytopathogenicity of Varicella Zoster Virus (VZV) in MRC-5 cells by 50%. 1991Journal of medicinal chemistry, Sep, Volume: 34, Issue:9
The synthesis and antiviral activity of some 4'-thio-2'-deoxy nucleoside analogues.
AID218050Minimum inhibitory concentration required to reduce cytopathogenicity of Herpes Virus-2 (HSV-2) in vero cells by 50%. 1991Journal of medicinal chemistry, Sep, Volume: 34, Issue:9
The synthesis and antiviral activity of some 4'-thio-2'-deoxy nucleoside analogues.
AID79241The concentration required to produce a 50% inhibition of clone formation in human epidermoid carcinoma H-Ep-2 cells1991Journal of medicinal chemistry, Aug, Volume: 34, Issue:8
Synthesis and biological activity of 2'-deoxy-4'-thio pyrimidine nucleosides.
AID217769Inhibitory dose required to reduce the viability of vero cells by 50%1991Journal of medicinal chemistry, Sep, Volume: 34, Issue:9
The synthesis and antiviral activity of some 4'-thio-2'-deoxy nucleoside analogues.
AID381856Activity of 10 U/mL Escherichia coli thymidine phosphorylase assessed as drug phosphorylation after 24 hrs2008Bioorganic & medicinal chemistry, Apr-01, Volume: 16, Issue:7
Kinetic parameters and recognition of thymidine analogues with varying functional groups by thymidine phosphorylase.
AID105827Minimum inhibitory concentration required to reduce cytopathogenicity of cytomegalovirus (CMV) in MRC-5 cells by 50%; ND=Not determined1991Journal of medicinal chemistry, Sep, Volume: 34, Issue:9
The synthesis and antiviral activity of some 4'-thio-2'-deoxy nucleoside analogues.
AID98517The concentration required to produce a 50% reduction in the rate of cell proliferation in murine leukemia L1210 cells1991Journal of medicinal chemistry, Aug, Volume: 34, Issue:8
Synthesis and biological activity of 2'-deoxy-4'-thio pyrimidine nucleosides.
AID542166Antiviral activity against Vaccinia virus WR infected in HFF assessed as reduction of plaque formation after 3 days2009Antimicrobial agents and chemotherapy, Feb, Volume: 53, Issue:2
Activities of certain 5-substituted 4'-thiopyrimidine nucleosides against orthopoxvirus infections.
AID543526Ratio of compound EC50 to cidofovir EC50 for Vaccinia virus Copenhagen2009Antimicrobial agents and chemotherapy, Feb, Volume: 53, Issue:2
Activities of certain 5-substituted 4'-thiopyrimidine nucleosides against orthopoxvirus infections.
AID29739Toxicity of compound was measured after ip administration to mice.1991Journal of medicinal chemistry, Sep, Volume: 34, Issue:9
The synthesis and antiviral activity of some 4'-thio-2'-deoxy nucleoside analogues.
AID542163Antiproliferative activity against HFF after 3 days by coulter counter assay2009Antimicrobial agents and chemotherapy, Feb, Volume: 53, Issue:2
Activities of certain 5-substituted 4'-thiopyrimidine nucleosides against orthopoxvirus infections.
AID542165Antiviral activity against Vaccinia virus Copenhagen infected in HFF assessed as reduction of plaque formation after 3 days2009Antimicrobial agents and chemotherapy, Feb, Volume: 53, Issue:2
Activities of certain 5-substituted 4'-thiopyrimidine nucleosides against orthopoxvirus infections.
AID79241The concentration required to produce a 50% inhibition of clone formation in human epidermoid carcinoma H-Ep-2 cells1991Journal of medicinal chemistry, Aug, Volume: 34, Issue:8
Synthesis and biological activity of 2'-deoxy-4'-thio pyrimidine nucleosides.
AID98517The concentration required to produce a 50% reduction in the rate of cell proliferation in murine leukemia L1210 cells1991Journal of medicinal chemistry, Aug, Volume: 34, Issue:8
Synthesis and biological activity of 2'-deoxy-4'-thio pyrimidine nucleosides.
AID105826Minimum inhibitory concentration required to reduce cytopathogenicity of cytomegalovirus (CMV) in MRC-5 cells by 50%. 1991Journal of medicinal chemistry, Sep, Volume: 34, Issue:9
The synthesis and antiviral activity of some 4'-thio-2'-deoxy nucleoside analogues.
AID44034The concentration required to inhibit cell growth to 50% of untreated controls in human T-cell leukemia CCRF-CEM cells1991Journal of medicinal chemistry, Aug, Volume: 34, Issue:8
Synthesis and biological activity of 2'-deoxy-4'-thio pyrimidine nucleosides.
AID563744Antiviral activity against HSV2 MS infected in HFF after 3 days by plaque reduction assay2009Antimicrobial agents and chemotherapy, Dec, Volume: 53, Issue:12
Inhibition of herpesvirus replication by 5-substituted 4'-thiopyrimidine nucleosides.
AID218050Minimum inhibitory concentration required to reduce cytopathogenicity of Herpes Virus-2 (HSV-2) in vero cells by 50%. 1991Journal of medicinal chemistry, Sep, Volume: 34, Issue:9
The synthesis and antiviral activity of some 4'-thio-2'-deoxy nucleoside analogues.
AID105824Minimum inhibitory concentration required to reduce cytopathogenicity of Varicella Zoster Virus (VZV) in MRC-5 cells by 50%. 1991Journal of medicinal chemistry, Sep, Volume: 34, Issue:9
The synthesis and antiviral activity of some 4'-thio-2'-deoxy nucleoside analogues.
AID563745Antiproliferative activity against HFF after 3 days by Coulter counting analysis2009Antimicrobial agents and chemotherapy, Dec, Volume: 53, Issue:12
Inhibition of herpesvirus replication by 5-substituted 4'-thiopyrimidine nucleosides.
AID542421Antiviral activity against Cowpox virus Brighton infected in HFF assessed as reduction of plaque formation after 3 days2009Antimicrobial agents and chemotherapy, Feb, Volume: 53, Issue:2
Activities of certain 5-substituted 4'-thiopyrimidine nucleosides against orthopoxvirus infections.
AID217769Inhibitory dose required to reduce the viability of vero cells by 50%1991Journal of medicinal chemistry, Sep, Volume: 34, Issue:9
The synthesis and antiviral activity of some 4'-thio-2'-deoxy nucleoside analogues.
AID22167Half life was measured in mice.1991Journal of medicinal chemistry, Sep, Volume: 34, Issue:9
The synthesis and antiviral activity of some 4'-thio-2'-deoxy nucleoside analogues.
AID563743Cytotoxicity against HFF after 3 days by MTS assay2009Antimicrobial agents and chemotherapy, Dec, Volume: 53, Issue:12
Inhibition of herpesvirus replication by 5-substituted 4'-thiopyrimidine nucleosides.
AID542164Cytotoxicity against HFF after 7 days by neutral red uptake assay2009Antimicrobial agents and chemotherapy, Feb, Volume: 53, Issue:2
Activities of certain 5-substituted 4'-thiopyrimidine nucleosides against orthopoxvirus infections.
AID543528Ratio of compound EC50 to cidofovir EC50 for Cowpox virus Brighton2009Antimicrobial agents and chemotherapy, Feb, Volume: 53, Issue:2
Activities of certain 5-substituted 4'-thiopyrimidine nucleosides against orthopoxvirus infections.
AID563742Selectivity index, ratio of CC50 for HFF to EC50 for HSV2 MS infected in HFF2009Antimicrobial agents and chemotherapy, Dec, Volume: 53, Issue:12
Inhibition of herpesvirus replication by 5-substituted 4'-thiopyrimidine nucleosides.
AID381856Activity of 10 U/mL Escherichia coli thymidine phosphorylase assessed as drug phosphorylation after 24 hrs2008Bioorganic & medicinal chemistry, Apr-01, Volume: 16, Issue:7
Kinetic parameters and recognition of thymidine analogues with varying functional groups by thymidine phosphorylase.
AID543527Ratio of compound EC50 to cidofovir EC50 for Vaccinia virus WR2009Antimicrobial agents and chemotherapy, Feb, Volume: 53, Issue:2
Activities of certain 5-substituted 4'-thiopyrimidine nucleosides against orthopoxvirus infections.
AID105823Minimum inhibitory concentration required to reduce cytopathogenicity of Herpes Virus-1 (HSV-1) in MRC -5 cells by 50%. 1991Journal of medicinal chemistry, Sep, Volume: 34, Issue:9
The synthesis and antiviral activity of some 4'-thio-2'-deoxy nucleoside analogues.
AID104817Minimum inhibitory concentration required to reduce cytopathogenicity of human immunodeficiency virus-1 (HIV-1) in MT-4 cells by 50%; No activity below ID50 observed1991Journal of medicinal chemistry, Sep, Volume: 34, Issue:9
The synthesis and antiviral activity of some 4'-thio-2'-deoxy nucleoside analogues.
AID104471Inhibitory dose required to reduce the viability of MT-4 cells by 50%1991Journal of medicinal chemistry, Sep, Volume: 34, Issue:9
The synthesis and antiviral activity of some 4'-thio-2'-deoxy nucleoside analogues.
AID19860Maximum plasma level was measured in mice.1991Journal of medicinal chemistry, Sep, Volume: 34, Issue:9
The synthesis and antiviral activity of some 4'-thio-2'-deoxy nucleoside analogues.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (27)

TimeframeStudies, This Drug (%)All Drugs %
pre-19900 (0.00)18.7374
1990's9 (33.33)18.2507
2000's8 (29.63)29.6817
2010's7 (25.93)24.3611
2020's3 (11.11)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 12.66

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 weak demand-to-supply ratio for research on this compound.

MetricThis Compound (vs All)
Research Demand Index12.66 (24.57)
Research Supply Index1.79 (2.92)
Research Growth Index4.45 (4.65)
Search Engine Demand Index0.00 (26.88)
Search Engine Supply Index0.00 (0.95)

This Compound (12.66)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Trials0 (0.00%)5.53%
Reviews0 (0.00%)6.00%
Reviews0 (0.00%)6.00%
Case Studies3 (12.00%)4.05%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Observational0 (0.00%)0.25%
Other22 (88.00%)84.16%
Other5 (100.00%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]