Page last updated: 2024-11-12

dimethylenastron

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

Description

dimethylenastron: a kinesin Eg5 inhibitor and antiproliferative agent; structure in first source [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Cross-References

ID SourceID
PubMed CID11609157
SCHEMBL ID5178439
MeSH IDM0508952

Synonyms (24)

Synonym
7,7-dimethyl-4-(3-hydroxyphenyl)-5-oxo-3,4,5,6,7,8-hexahydroquinazolin-2(1h)-thione
eg5 inhibitor iii, dimethylenastron
4-(3-hydroxyphenyl)-7,7-dimethyl-2-sulfanylidene-3,4,6,8-tetrahydro-1h-quinazolin-5-one
dimethylenastron
863774-58-7
SCHEMBL5178439
eg5 inhibitor iii
AKOS025142068
2,3,4,6,7,8-hexahydro-4-(3-hydroxyphenyl)-7,7-dimethyl-2-thioxo-5(1h)-quinazolinone
AC-35426
CS-5480
HY-19944
DTXSID40469410
NCGC00387255-02
eg5 inhibitor iiidimethylenastron
BCP17179
AS-16431
dimethyl enastron
C76804
A917740
NCGC00387255-04
mfcd09264157
eg5 inhibitor iii,dimethylenastron
D5812

Research Excerpts

Bioavailability

ExcerptReferenceRelevance
"The ATP-binding cassette transporter P-glycoprotein (P-gp) is known to limit both brain penetration and oral bioavailability of many chemotherapy drugs."( A High-Throughput Screen of a Library of Therapeutics Identifies Cytotoxic Substrates of P-glycoprotein.
Ambudkar, SV; Brimacombe, KR; Chen, L; Gottesman, MM; Guha, R; Hall, MD; Klumpp-Thomas, C; Lee, OW; Lee, TD; Lusvarghi, S; Robey, RW; Shen, M; Tebase, BG, 2019
)
0.51
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Protein Targets (8)

Potency Measurements

ProteinTaxonomyMeasurementAverage (µ)Min (ref.)Avg (ref.)Max (ref.)Bioassay(s)
cytochrome P450 family 3 subfamily A polypeptide 4Homo sapiens (human)Potency2.68370.01237.983543.2770AID1645841
GVesicular stomatitis virusPotency2.13170.01238.964839.8107AID1645842
cytochrome P450 2D6Homo sapiens (human)Potency8.48660.00108.379861.1304AID1645840
Interferon betaHomo sapiens (human)Potency2.13170.00339.158239.8107AID1645842
HLA class I histocompatibility antigen, B alpha chain Homo sapiens (human)Potency2.13170.01238.964839.8107AID1645842
Inositol hexakisphosphate kinase 1Homo sapiens (human)Potency2.13170.01238.964839.8107AID1645842
cytochrome P450 2C9, partialHomo sapiens (human)Potency2.13170.01238.964839.8107AID1645842
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Inhibition Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Kinesin-like protein KIF11Homo sapiens (human)IC50 (µMol)0.20000.00011.405710.0000AID1405697; AID1610651; AID300454
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Biological Processes (54)

Processvia Protein(s)Taxonomy
cell surface receptor signaling pathway via JAK-STATInterferon betaHomo sapiens (human)
response to exogenous dsRNAInterferon betaHomo sapiens (human)
B cell activation involved in immune responseInterferon betaHomo sapiens (human)
cell surface receptor signaling pathwayInterferon betaHomo sapiens (human)
cell surface receptor signaling pathway via JAK-STATInterferon betaHomo sapiens (human)
response to virusInterferon betaHomo sapiens (human)
positive regulation of autophagyInterferon betaHomo sapiens (human)
cytokine-mediated signaling pathwayInterferon betaHomo sapiens (human)
natural killer cell activationInterferon betaHomo sapiens (human)
positive regulation of peptidyl-serine phosphorylation of STAT proteinInterferon betaHomo sapiens (human)
cellular response to interferon-betaInterferon betaHomo sapiens (human)
B cell proliferationInterferon betaHomo sapiens (human)
negative regulation of viral genome replicationInterferon betaHomo sapiens (human)
innate immune responseInterferon betaHomo sapiens (human)
positive regulation of innate immune responseInterferon betaHomo sapiens (human)
regulation of MHC class I biosynthetic processInterferon betaHomo sapiens (human)
negative regulation of T cell differentiationInterferon betaHomo sapiens (human)
positive regulation of transcription by RNA polymerase IIInterferon betaHomo sapiens (human)
defense response to virusInterferon betaHomo sapiens (human)
type I interferon-mediated signaling pathwayInterferon betaHomo sapiens (human)
neuron cellular homeostasisInterferon betaHomo sapiens (human)
cellular response to exogenous dsRNAInterferon betaHomo sapiens (human)
cellular response to virusInterferon betaHomo sapiens (human)
negative regulation of Lewy body formationInterferon betaHomo sapiens (human)
negative regulation of T-helper 2 cell cytokine productionInterferon betaHomo sapiens (human)
positive regulation of apoptotic signaling pathwayInterferon betaHomo sapiens (human)
response to exogenous dsRNAInterferon betaHomo sapiens (human)
B cell differentiationInterferon betaHomo sapiens (human)
natural killer cell activation involved in immune responseInterferon betaHomo sapiens (human)
adaptive immune responseInterferon betaHomo sapiens (human)
T cell activation involved in immune responseInterferon betaHomo sapiens (human)
humoral immune responseInterferon betaHomo sapiens (human)
positive regulation of T cell mediated cytotoxicityHLA class I histocompatibility antigen, B alpha chain Homo sapiens (human)
adaptive immune responseHLA class I histocompatibility antigen, B alpha chain Homo sapiens (human)
antigen processing and presentation of endogenous peptide antigen via MHC class I via ER pathway, TAP-independentHLA class I histocompatibility antigen, B alpha chain Homo sapiens (human)
regulation of T cell anergyHLA class I histocompatibility antigen, B alpha chain Homo sapiens (human)
defense responseHLA class I histocompatibility antigen, B alpha chain Homo sapiens (human)
immune responseHLA class I histocompatibility antigen, B alpha chain Homo sapiens (human)
detection of bacteriumHLA class I histocompatibility antigen, B alpha chain Homo sapiens (human)
regulation of interleukin-12 productionHLA class I histocompatibility antigen, B alpha chain Homo sapiens (human)
regulation of interleukin-6 productionHLA class I histocompatibility antigen, B alpha chain Homo sapiens (human)
protection from natural killer cell mediated cytotoxicityHLA class I histocompatibility antigen, B alpha chain Homo sapiens (human)
innate immune responseHLA class I histocompatibility antigen, B alpha chain Homo sapiens (human)
regulation of dendritic cell differentiationHLA class I histocompatibility antigen, B alpha chain Homo sapiens (human)
antigen processing and presentation of endogenous peptide antigen via MHC class IbHLA class I histocompatibility antigen, B alpha chain Homo sapiens (human)
mitotic cell cycleKinesin-like protein KIF11Homo sapiens (human)
microtubule-based movementKinesin-like protein KIF11Homo sapiens (human)
spindle organizationKinesin-like protein KIF11Homo sapiens (human)
mitotic spindle organizationKinesin-like protein KIF11Homo sapiens (human)
mitotic centrosome separationKinesin-like protein KIF11Homo sapiens (human)
regulation of mitotic centrosome separationKinesin-like protein KIF11Homo sapiens (human)
cell divisionKinesin-like protein KIF11Homo sapiens (human)
mitotic spindle assemblyKinesin-like protein KIF11Homo sapiens (human)
spindle elongationKinesin-like protein KIF11Homo sapiens (human)
inositol phosphate metabolic processInositol hexakisphosphate kinase 1Homo sapiens (human)
phosphatidylinositol phosphate biosynthetic processInositol hexakisphosphate kinase 1Homo sapiens (human)
negative regulation of cold-induced thermogenesisInositol hexakisphosphate kinase 1Homo sapiens (human)
inositol phosphate biosynthetic processInositol hexakisphosphate kinase 1Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Molecular Functions (22)

Processvia Protein(s)Taxonomy
cytokine activityInterferon betaHomo sapiens (human)
cytokine receptor bindingInterferon betaHomo sapiens (human)
type I interferon receptor bindingInterferon betaHomo sapiens (human)
protein bindingInterferon betaHomo sapiens (human)
chloramphenicol O-acetyltransferase activityInterferon betaHomo sapiens (human)
TAP bindingHLA class I histocompatibility antigen, B alpha chain Homo sapiens (human)
signaling receptor bindingHLA class I histocompatibility antigen, B alpha chain Homo sapiens (human)
protein bindingHLA class I histocompatibility antigen, B alpha chain Homo sapiens (human)
peptide antigen bindingHLA class I histocompatibility antigen, B alpha chain Homo sapiens (human)
TAP bindingHLA class I histocompatibility antigen, B alpha chain Homo sapiens (human)
protein-folding chaperone bindingHLA class I histocompatibility antigen, B alpha chain Homo sapiens (human)
microtubule motor activityKinesin-like protein KIF11Homo sapiens (human)
protein bindingKinesin-like protein KIF11Homo sapiens (human)
ATP bindingKinesin-like protein KIF11Homo sapiens (human)
microtubule bindingKinesin-like protein KIF11Homo sapiens (human)
protein kinase bindingKinesin-like protein KIF11Homo sapiens (human)
plus-end-directed microtubule motor activityKinesin-like protein KIF11Homo sapiens (human)
inositol-1,3,4,5,6-pentakisphosphate kinase activityInositol hexakisphosphate kinase 1Homo sapiens (human)
inositol hexakisphosphate kinase activityInositol hexakisphosphate kinase 1Homo sapiens (human)
inositol heptakisphosphate kinase activityInositol hexakisphosphate kinase 1Homo sapiens (human)
inositol hexakisphosphate 5-kinase activityInositol hexakisphosphate kinase 1Homo sapiens (human)
protein bindingInositol hexakisphosphate kinase 1Homo sapiens (human)
ATP bindingInositol hexakisphosphate kinase 1Homo sapiens (human)
inositol hexakisphosphate 1-kinase activityInositol hexakisphosphate kinase 1Homo sapiens (human)
inositol hexakisphosphate 3-kinase activityInositol hexakisphosphate kinase 1Homo sapiens (human)
inositol 5-diphosphate pentakisphosphate 5-kinase activityInositol hexakisphosphate kinase 1Homo sapiens (human)
inositol diphosphate tetrakisphosphate kinase activityInositol hexakisphosphate kinase 1Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Ceullar Components (29)

Processvia Protein(s)Taxonomy
extracellular spaceInterferon betaHomo sapiens (human)
extracellular regionInterferon betaHomo sapiens (human)
Golgi membraneHLA class I histocompatibility antigen, B alpha chain Homo sapiens (human)
endoplasmic reticulumHLA class I histocompatibility antigen, B alpha chain Homo sapiens (human)
Golgi apparatusHLA class I histocompatibility antigen, B alpha chain Homo sapiens (human)
plasma membraneHLA class I histocompatibility antigen, B alpha chain Homo sapiens (human)
cell surfaceHLA class I histocompatibility antigen, B alpha chain Homo sapiens (human)
ER to Golgi transport vesicle membraneHLA class I histocompatibility antigen, B alpha chain Homo sapiens (human)
membraneHLA class I histocompatibility antigen, B alpha chain Homo sapiens (human)
secretory granule membraneHLA class I histocompatibility antigen, B alpha chain Homo sapiens (human)
phagocytic vesicle membraneHLA class I histocompatibility antigen, B alpha chain Homo sapiens (human)
early endosome membraneHLA class I histocompatibility antigen, B alpha chain Homo sapiens (human)
recycling endosome membraneHLA class I histocompatibility antigen, B alpha chain Homo sapiens (human)
extracellular exosomeHLA class I histocompatibility antigen, B alpha chain Homo sapiens (human)
lumenal side of endoplasmic reticulum membraneHLA class I histocompatibility antigen, B alpha chain Homo sapiens (human)
MHC class I protein complexHLA class I histocompatibility antigen, B alpha chain Homo sapiens (human)
extracellular spaceHLA class I histocompatibility antigen, B alpha chain Homo sapiens (human)
external side of plasma membraneHLA class I histocompatibility antigen, B alpha chain Homo sapiens (human)
spindle poleKinesin-like protein KIF11Homo sapiens (human)
spindle microtubuleKinesin-like protein KIF11Homo sapiens (human)
spindleKinesin-like protein KIF11Homo sapiens (human)
cytosolKinesin-like protein KIF11Homo sapiens (human)
microtubuleKinesin-like protein KIF11Homo sapiens (human)
membraneKinesin-like protein KIF11Homo sapiens (human)
mitotic spindleKinesin-like protein KIF11Homo sapiens (human)
kinesin complexKinesin-like protein KIF11Homo sapiens (human)
protein-containing complexKinesin-like protein KIF11Homo sapiens (human)
nucleusKinesin-like protein KIF11Homo sapiens (human)
mitotic spindleKinesin-like protein KIF11Homo sapiens (human)
fibrillar centerInositol hexakisphosphate kinase 1Homo sapiens (human)
nucleoplasmInositol hexakisphosphate kinase 1Homo sapiens (human)
cytosolInositol hexakisphosphate kinase 1Homo sapiens (human)
nucleusInositol hexakisphosphate kinase 1Homo sapiens (human)
cytoplasmInositol hexakisphosphate kinase 1Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (19)

Assay IDTitleYearJournalArticle
AID1347160Primary screen NINDS Rhodamine qHTS for Zika virus inhibitors2020Proceedings of the National Academy of Sciences of the United States of America, 12-08, Volume: 117, Issue:49
Therapeutic candidates for the Zika virus identified by a high-throughput screen for Zika protease inhibitors.
AID1296008Cytotoxic Profiling of Annotated Libraries Using Quantitative High-Throughput Screening2020SLAS discovery : advancing life sciences R & D, 01, Volume: 25, Issue:1
Cytotoxic Profiling of Annotated and Diverse Chemical Libraries Using Quantitative High-Throughput Screening.
AID1346987P-glycoprotein substrates identified in KB-8-5-11 adenocarcinoma cell line, qHTS therapeutic library screen2019Molecular pharmacology, 11, Volume: 96, Issue:5
A High-Throughput Screen of a Library of Therapeutics Identifies Cytotoxic Substrates of P-glycoprotein.
AID1346986P-glycoprotein substrates identified in KB-3-1 adenocarcinoma cell line, qHTS therapeutic library screen2019Molecular pharmacology, 11, Volume: 96, Issue:5
A High-Throughput Screen of a Library of Therapeutics Identifies Cytotoxic Substrates of P-glycoprotein.
AID1347159Primary screen GU Rhodamine qHTS for Zika virus inhibitors: Unlinked NS2B-NS3 protease assay2020Proceedings of the National Academy of Sciences of the United States of America, 12-08, Volume: 117, Issue:49
Therapeutic candidates for the Zika virus identified by a high-throughput screen for Zika protease inhibitors.
AID496950Antiproliferative activity against human KBV1 cells overexpressing MDR1 after 72 hrs by Alamar blue assay in presence of zosuquidar2010Journal of medicinal chemistry, Aug-12, Volume: 53, Issue:15
Structural basis for inhibition of Eg5 by dihydropyrimidines: stereoselectivity of antimitotic inhibitors enastron, dimethylenastron and fluorastrol.
AID496943Antiproliferative activity against human BxPC3 cells after 72 hrs by Alamar blue assay2010Journal of medicinal chemistry, Aug-12, Volume: 53, Issue:15
Structural basis for inhibition of Eg5 by dihydropyrimidines: stereoselectivity of antimitotic inhibitors enastron, dimethylenastron and fluorastrol.
AID496948Drug resistant ratio of EC50 for human KBV1 cells overexpressing MDR1 to EC50 for KB3-1 cells2010Journal of medicinal chemistry, Aug-12, Volume: 53, Issue:15
Structural basis for inhibition of Eg5 by dihydropyrimidines: stereoselectivity of antimitotic inhibitors enastron, dimethylenastron and fluorastrol.
AID496947Antiproliferative activity against human KBV1 cells overexpressing MDR1 after 72 hrs by Alamar blue assay2010Journal of medicinal chemistry, Aug-12, Volume: 53, Issue:15
Structural basis for inhibition of Eg5 by dihydropyrimidines: stereoselectivity of antimitotic inhibitors enastron, dimethylenastron and fluorastrol.
AID496949Antiproliferative activity against human KB3-1 cells after 72 hrs by Alamar blue assay in presence of zosuquidar2010Journal of medicinal chemistry, Aug-12, Volume: 53, Issue:15
Structural basis for inhibition of Eg5 by dihydropyrimidines: stereoselectivity of antimitotic inhibitors enastron, dimethylenastron and fluorastrol.
AID496945Antiproliferative activity against human NCI-H1299 cells after 72 hrs by Alamar blue assay2010Journal of medicinal chemistry, Aug-12, Volume: 53, Issue:15
Structural basis for inhibition of Eg5 by dihydropyrimidines: stereoselectivity of antimitotic inhibitors enastron, dimethylenastron and fluorastrol.
AID465253Competitive inhibition of affinity bead (R)-2-Amino-N-{2-[2-(2-amino-ethoxy)-ethoxy]-ethyl}-3-[(4-methoxy-phenyl)-diphenyl-methylsulfanyl]-propionamide binding to KSP in human HCT116 cells at 10 umol/L pretreated for 3 hrs by Western blot analysis2010Bioorganic & medicinal chemistry letters, Mar-01, Volume: 20, Issue:5
Biochemical analysis of cellular target of S-trityl-L-cysteine derivatives using affinity matrix.
AID300454Inhibition of Eg5 ATPase activity expressed in Escherichia coli after 12 hrs2007Bioorganic & medicinal chemistry, Oct-01, Volume: 15, Issue:19
New chemical tools for investigating human mitotic kinesin Eg5.
AID496946Antiproliferative activity against human KB3-1 cells after 72 hrs by Alamar blue assay2010Journal of medicinal chemistry, Aug-12, Volume: 53, Issue:15
Structural basis for inhibition of Eg5 by dihydropyrimidines: stereoselectivity of antimitotic inhibitors enastron, dimethylenastron and fluorastrol.
AID496941Antiproliferative activity against human HCT116 cells after 72 hrs by Alamar blue assay2010Journal of medicinal chemistry, Aug-12, Volume: 53, Issue:15
Structural basis for inhibition of Eg5 by dihydropyrimidines: stereoselectivity of antimitotic inhibitors enastron, dimethylenastron and fluorastrol.
AID496944Antiproliferative activity against human K562 cells after 72 hrs by Alamar blue assay2010Journal of medicinal chemistry, Aug-12, Volume: 53, Issue:15
Structural basis for inhibition of Eg5 by dihydropyrimidines: stereoselectivity of antimitotic inhibitors enastron, dimethylenastron and fluorastrol.
AID1610651Inhibition of recombinant human His-tagged Eg5 (1 to 368 residues) assessed as reduction in ATPase activity by Bradford reagent based assay
AID1405697Inhibition of human Eg52018European journal of medicinal chemistry, Aug-05, Volume: 156Synthesis and anticancer activity of new dihydropyrimidinone derivatives.
AID496942Antiproliferative activity against human hTERT-HME1 cells after 72 hrs by Alamar blue assay2010Journal of medicinal chemistry, Aug-12, Volume: 53, Issue:15
Structural basis for inhibition of Eg5 by dihydropyrimidines: stereoselectivity of antimitotic inhibitors enastron, dimethylenastron and fluorastrol.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (17)

TimeframeStudies, This Drug (%)All Drugs %
pre-19900 (0.00)18.7374
1990's0 (0.00)18.2507
2000's4 (23.53)29.6817
2010's11 (64.71)24.3611
2020's2 (11.76)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 19.32

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 Index19.32 (24.57)
Research Supply Index2.89 (2.92)
Research Growth Index4.58 (4.65)
Search Engine Demand Index15.26 (26.88)
Search Engine Supply Index2.00 (0.95)

This Compound (19.32)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Reviews0 (0.00%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other17 (100.00%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]