Page last updated: 2024-12-10

mk 0608

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

Description

7-deaza-2'-C-methyladenosine: an antiviral agent [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Cross-References

ID SourceID
PubMed CID3011893
CHEMBL ID236207
SCHEMBL ID733423
MeSH IDM0535762

Synonyms (40)

Synonym
AKOS015840274
7-deaza-2'-c-methyl-adenosine
(2r,3r,4r,5r)-2-(4-aminopyrrolo[2,3-d]pyrimidin-7-yl)-5-(hydroxymethyl)-3-methyl-tetrahydrofuran-3,4-diol
7h-pyrrolo[2,3-d]pyrimidin-4-amine, 7-(2-c-methyl-b-d-ribofuranosyl)-
beta-2'-c-methyl-7-deaza-adenosine
CHEMBL236207
7-deaza-2'-c-methyladenosine
443642-29-3
(2r,3r,4r,5r)-2-(4-aminopyrrolo[2,3-d]pyrimidin-7-yl)-5-(hydroxymethyl)-3-methyloxolane-3,4-diol
A7035
(2r,3r,4r,5r)-2-(4-amino-7h-pyrrolo[2,3-d]pyrimidin-7-yl)-5-(hydroxymethyl)-3-methyl-tetrahydrofuran-3,4-diol
(2r,3r,4r,5r)-2-(4-amino-7h-pyrrolo[2,3-d]pyrimidin-7-yl)-5-(hydroxymethyl)-3-methyltetrahydrofuran-3,4-diol
7h-pyrrolo(2,3-d)pyrimidin-4-amine, 7-(2-c-methyl-beta-d-ribofuranosyl)-
mk 0608
mk-0608
unii-qrr62j6wef
qrr62j6wef ,
AKOS015901326
7h-pyrrolo(2,3-d)pyrimidin-4-amine, 7-(2-c-methyl-.beta.-d-ribofuranosyl)-
1001913-41-2
SCHEMBL733423
IRZRJANZDIOOIF-GAJNKVMBSA-N
4-amino-7-(2-c-methyl-beta-d-ribofuranosyl)-7h-pyrrolo[2,3-d]pyrimidine
4-amino-7-(2'-methyl-beta-d-ribofuranosyl)-7h-pyrrolo[2,3-d]pyrimidine
7-(2'-c-methyl-beta-d-ribofuranosyl)-4-amino-pyrrolo[2,3-d]pyrimidine
mk-608
mfcd14584964
BBL103031
STL556840
7-(2-c-methyl-beta-d-ribofuranosyl)-7h-pyrrolo[2,3-d]pyrimidin-4-amine
CS-0002510
(2r,3r,4r,5r)-2-(4-amino-7h-pyrrolo[2,3-d]pyrimidin-7-yl)-5-(hydroxymethyl)-3-methyl tetrahydrofuran-3,4-diol
F12808
lamevudine
Q23309937
DTXSID60963208
HY-10244
h5v ,
AS-82894
7-deaza-2'-c-methyl-d-adenosine

Research Excerpts

Bioavailability

ExcerptReferenceRelevance
" 2'-C-Methyladenosine was found to be susceptible to enzymatic conversions by adenosine deaminase and purine nucleoside phosphorylase, and it displayed limited oral bioavailability in the rat."( Structure-activity relationship of heterobase-modified 2'-C-methyl ribonucleosides as inhibitors of hepatitis C virus RNA replication.
Ball, RG; Bennett, CF; Bera, S; Bhat, B; Bhat, N; Bosserman, M; Brooks, J; Burlein, C; Carroll, SS; Colwell, LF; Cook, PD; Dande, P; Eldrup, AB; Fay, JF; Flores, OA; Getty, K; LaFemina, RL; Leone, J; MacCoss, M; McMasters, DR; Olsen, DB; Prakash, TP; Prhavc, M; Song, Q; Tomassini, JE; Von Langen, D; Wolanski, B, 2004
)
0.32
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Bioassays (36)

Assay IDTitleYearJournalArticle
AID438027Antiviral activity against Dengue virus by cell based assay2009Journal of medicinal chemistry, Dec-24, Volume: 52, Issue:24
The medicinal chemistry of dengue fever.
AID662447Cytotoxicity against human HuH7 cells after 24 hrs by MTS assay2012Bioorganic & medicinal chemistry letters, Jun-15, Volume: 22, Issue:12
Synthesis and characterization of 2'-C-Me branched C-nucleosides as HCV polymerase inhibitors.
AID1156121Cytotoxicity against human HuH7 cells by MTT assay2014ACS medicinal chemistry letters, Jun-12, Volume: 5, Issue:6
Discovery and Synthesis of C-Nucleosides as Potential New Anti-HCV Agents.
AID1542953Antiviral activity against Zika virus MR766 infected in African green monkey Vero E6 cells assessed as reduction in virus yield2019ACS medicinal chemistry letters, Apr-11, Volume: 10, Issue:4
Scaffold Morphing Approach To Expand the Toolbox of Broad-Spectrum Antivirals Blocking Dengue/Zika Replication.
AID740798Cytotoxicity against human HuH7 cells2013Bioorganic & medicinal chemistry letters, Apr-01, Volume: 23, Issue:7
Synthesis and evaluation against hepatitis C virus of 7-deaza analogues of 2'-C-methyl-6-O-methyl guanosine nucleoside and L-Alanine ester phosphoramidates.
AID662448Inhibition of HCV genotype 1b NS5B after 90 mins2012Bioorganic & medicinal chemistry letters, Jun-15, Volume: 22, Issue:12
Synthesis and characterization of 2'-C-Me branched C-nucleosides as HCV polymerase inhibitors.
AID1636906Inhibition of DOT1L (unknown origin) at 200 uM using chicken nucleosome as substrate in presence of [3H]SAM incubated for 1 hr by TopCount method2016Bioorganic & medicinal chemistry letters, 09-15, Volume: 26, Issue:18
New small molecule inhibitors of histone methyl transferase DOT1L with a nitrile as a non-traditional replacement for heavy halogen atoms.
AID1206545Antiviral activity in HCV 2a JFH1 infected in HUH 7-lunet cells after 3 days by Dual-Glo luciferase assay2015Journal of medicinal chemistry, May-14, Volume: 58, Issue:9
Highly Selective Phosphatidylinositol 4-Kinase IIIβ Inhibitors and Structural Insight into Their Mode of Action.
AID662521Prodrug activation in Golden Syrian hamster liver assessed as compound triphosphate form at 20 mg/kg, po after 4 to 24 hrs2012Bioorganic & medicinal chemistry letters, Jun-15, Volume: 22, Issue:12
Synthesis and characterization of 2'-C-Me branched C-nucleosides as HCV polymerase inhibitors.
AID1542955Selectivity index, ratio of CC50 for African green monkey Vero B cells to EC50 for Dengue virus type 2 NGC infected in African green monkey Vero B cells2019ACS medicinal chemistry letters, Apr-11, Volume: 10, Issue:4
Scaffold Morphing Approach To Expand the Toolbox of Broad-Spectrum Antivirals Blocking Dengue/Zika Replication.
AID1638600Antiviral activity against West Nile virus2019Journal of medicinal chemistry, 03-14, Volume: 62, Issue:5
DDX3X Helicase Inhibitors as a New Strategy To Fight the West Nile Virus Infection.
AID1156120Antiviral activity against Hepatitis C virus assessed as inhibition of subgenomic replicon RNA replication2014ACS medicinal chemistry letters, Jun-12, Volume: 5, Issue:6
Discovery and Synthesis of C-Nucleosides as Potential New Anti-HCV Agents.
AID672003Antiviral activity against Hepatitis C virus genotype 1b infected in human HBI10A cells assessed as inhibition of viral replication in presence of 10% FBS2012Bioorganic & medicinal chemistry, Aug-01, Volume: 20, Issue:15
Synthesis and antiviral properties of novel 7-heterocyclic substituted 7-deaza-adenine nucleoside inhibitors of Hepatitis C NS5B polymerase.
AID1542950Antiviral activity against Zika virus2019ACS medicinal chemistry letters, Apr-11, Volume: 10, Issue:4
Scaffold Morphing Approach To Expand the Toolbox of Broad-Spectrum Antivirals Blocking Dengue/Zika Replication.
AID1206546Cytotoxicity against human HeLa cells2015Journal of medicinal chemistry, May-14, Volume: 58, Issue:9
Highly Selective Phosphatidylinositol 4-Kinase IIIβ Inhibitors and Structural Insight into Their Mode of Action.
AID1206542Anticoxsackie activity in CVB3 strain Nancy infected in human HeLa cells assessed as inhibition of virus-induced cytopathic effect after 4 hrs by XTT assay2015Journal of medicinal chemistry, May-14, Volume: 58, Issue:9
Highly Selective Phosphatidylinositol 4-Kinase IIIβ Inhibitors and Structural Insight into Their Mode of Action.
AID299923Antiviral activity against HCV genotype 1b in Huh7 cells assessed as inhibition of viral RNA replication after 72 hrs by ribonuclease protection assay2007Bioorganic & medicinal chemistry, Aug-01, Volume: 15, Issue:15
Synthesis and HCV inhibitory properties of 9-deaza- and 7,9-dideaza-7-oxa-2'-C-methyladenosine.
AID1206544Antiviral activity in HCV 1b infected in HUH 7-lunet cells after 3 days by Dual-Glo luciferase assay2015Journal of medicinal chemistry, May-14, Volume: 58, Issue:9
Highly Selective Phosphatidylinositol 4-Kinase IIIβ Inhibitors and Structural Insight into Their Mode of Action.
AID740799Antiviral activity against Hepatitis C virus assessed as inhibition of viral replication2013Bioorganic & medicinal chemistry letters, Apr-01, Volume: 23, Issue:7
Synthesis and evaluation against hepatitis C virus of 7-deaza analogues of 2'-C-methyl-6-O-methyl guanosine nucleoside and L-Alanine ester phosphoramidates.
AID245909Cytotoxicity against HB-1 cells in an MTS-based assay2004Journal of medicinal chemistry, Oct-07, Volume: 47, Issue:21
Structure-activity relationship of heterobase-modified 2'-C-methyl ribonucleosides as inhibitors of hepatitis C virus RNA replication.
AID246173Inhibition of HCV RNA replication in a subgenomic bicistronic replicon assay in HB-1 cells2004Journal of medicinal chemistry, Oct-07, Volume: 47, Issue:21
Structure-activity relationship of heterobase-modified 2'-C-methyl ribonucleosides as inhibitors of hepatitis C virus RNA replication.
AID299922Antiviral activity against HCV genotype 1b in Huh7 cells assessed as inhibition of viral RNA replication after 24 hrs by ribonuclease protection assay2007Bioorganic & medicinal chemistry, Aug-01, Volume: 15, Issue:15
Synthesis and HCV inhibitory properties of 9-deaza- and 7,9-dideaza-7-oxa-2'-C-methyladenosine.
AID1542949Antiviral activity against Dengue virus2019ACS medicinal chemistry letters, Apr-11, Volume: 10, Issue:4
Scaffold Morphing Approach To Expand the Toolbox of Broad-Spectrum Antivirals Blocking Dengue/Zika Replication.
AID1156129Inhibition of N-terminal His6-tagged Hepatitis C virus genotype 1b isolate Con1 NS5B RNA-dependent RNA polymerase activity by plate reader analysis2014ACS medicinal chemistry letters, Jun-12, Volume: 5, Issue:6
Discovery and Synthesis of C-Nucleosides as Potential New Anti-HCV Agents.
AID1542952Cytotoxicity in African green monkey Vero B cells assessed as reduction in cell viability by MTS assay2019ACS medicinal chemistry letters, Apr-11, Volume: 10, Issue:4
Scaffold Morphing Approach To Expand the Toolbox of Broad-Spectrum Antivirals Blocking Dengue/Zika Replication.
AID1070548Selectivity ratio of EC50 for HCV harboring NS5B RNA dependent RNA polymerase S282T mutant to EC50 for wild-type HCV2014Journal of medicinal chemistry, Mar-13, Volume: 57, Issue:5
Discovery of the first C-nucleoside HCV polymerase inhibitor (GS-6620) with demonstrated antiviral response in HCV infected patients.
AID1542956Selectivity index, ratio of CC50 for African green monkey Vero E6 cells to EC50 for Zika virus MR766 infected in African green monkey Vero E6 cells2019ACS medicinal chemistry letters, Apr-11, Volume: 10, Issue:4
Scaffold Morphing Approach To Expand the Toolbox of Broad-Spectrum Antivirals Blocking Dengue/Zika Replication.
AID299924Cytotoxicity against Huh7 cells after 24 hrs by MTS assay2007Bioorganic & medicinal chemistry, Aug-01, Volume: 15, Issue:15
Synthesis and HCV inhibitory properties of 9-deaza- and 7,9-dideaza-7-oxa-2'-C-methyladenosine.
AID662523Prodrug activation in Sprague-Dawley rat liver assessed as compound triphosphate form at 2 mg/kg, po after 4 to 24 hrs2012Bioorganic & medicinal chemistry letters, Jun-15, Volume: 22, Issue:12
Synthesis and characterization of 2'-C-Me branched C-nucleosides as HCV polymerase inhibitors.
AID1156119Antiviral activity against Hepatitis C virus genotype 1b infected in human HuH7 cells assessed as inhibition of subgenomic replicon RNA replication after 72 hrs by luciferase reporter assay2014ACS medicinal chemistry letters, Jun-12, Volume: 5, Issue:6
Discovery and Synthesis of C-Nucleosides as Potential New Anti-HCV Agents.
AID1206543Antirhinovirus activity in HRVM infected in H1-HeLa cells assessed as inhibition of virus-induced cytopathic effect after 3 days by Cell-Titer Glo viability assay2015Journal of medicinal chemistry, May-14, Volume: 58, Issue:9
Highly Selective Phosphatidylinositol 4-Kinase IIIβ Inhibitors and Structural Insight into Their Mode of Action.
AID1156128Inhibition of Hepatitis C virus NS5B RNA-dependent RNA polymerase activity2014ACS medicinal chemistry letters, Jun-12, Volume: 5, Issue:6
Discovery and Synthesis of C-Nucleosides as Potential New Anti-HCV Agents.
AID662449Stability of the compound assessed as compound remaining at 10 uM after 60 mins in presence of bovine adenosine deaminase2012Bioorganic & medicinal chemistry letters, Jun-15, Volume: 22, Issue:12
Synthesis and characterization of 2'-C-Me branched C-nucleosides as HCV polymerase inhibitors.
AID1542951Antiviral activity against Dengue virus type 2 NGC infected in African green monkey Vero B cells assessed as reduction in virus yield2019ACS medicinal chemistry letters, Apr-11, Volume: 10, Issue:4
Scaffold Morphing Approach To Expand the Toolbox of Broad-Spectrum Antivirals Blocking Dengue/Zika Replication.
AID1542954Cytotoxicity in African green monkey Vero E6 cells assessed as reduction in cell viability by MTS assay2019ACS medicinal chemistry letters, Apr-11, Volume: 10, Issue:4
Scaffold Morphing Approach To Expand the Toolbox of Broad-Spectrum Antivirals Blocking Dengue/Zika Replication.
AID662446Antiviral activity against HCV genotype 1b infected in human HuH7 cells assessed as cytoprotection after 24 hrs2012Bioorganic & medicinal chemistry letters, Jun-15, Volume: 22, Issue:12
Synthesis and characterization of 2'-C-Me branched C-nucleosides as HCV polymerase inhibitors.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (22)

TimeframeStudies, This Drug (%)All Drugs %
pre-19900 (0.00)18.7374
1990's0 (0.00)18.2507
2000's5 (22.73)29.6817
2010's16 (72.73)24.3611
2020's1 (4.55)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 17.03

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 Index17.03 (24.57)
Research Supply Index3.14 (2.92)
Research Growth Index4.98 (4.65)
Search Engine Demand Index10.37 (26.88)
Search Engine Supply Index2.00 (0.95)

This Compound (17.03)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Reviews1 (4.55%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other21 (95.45%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]