Page last updated: 2024-12-11

diacetyldiphenylurea bisguanylhydrazone

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

Description

diacetyldiphenylurea bisguanylhydrazone: antineoplastic agent particularly effective as an antileukemic agent; has been shown to be active against leukemia L1210 in mice; minor descriptor (75-86); on-line & INDEX MEDICUS search CARBANILIDES (75-86); RN given refers to parent cpd [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Cross-References

ID SourceID
PubMed CID6328182
CHEMBL ID142485
SCHEMBL ID13431057
MeSH IDM0263235

Synonyms (20)

Synonym
ddug
brn 2793715
urea, 1,3-bis(p-acetylphenyl)-, bisamidinohydrazone
1,3-bis(p-acetylphenyl)urea bisamidinohydrazone
4,4'-diacetylcarbanilide 4,4'-bis(amidinohydrazone)
diacetyldiphenylurea bisguanylhydrazone
carbanilide, 4,4'-diacetyl-, 4,4'-bis(aminohydrazone)
4,4'-diacetyldiphenylurea-bis-(guanylhydrazone)
hydrazinecarboximidamide, 2,2'-(carbonylbis(imino-4,1-phenyleneethylidyne)bis-
CHEMBL142485
bdbm34063
1,3-bis[4-[(e)-n-(diaminomethylideneamino)-c-methylcarbonimidoyl]phenyl]urea
13284-07-6
hydrazinecarboximidamide, 2,2'-(carbonylbis(imino-4,1-phenyleneethylidyne))bis-
SCHEMBL13431057
4,4'-diacetyldiphenylurea-bis(guanylhydrazone)
(2e)-2-(1-{4-[({4-[(1e)-n-carbamimidoylethanehydrazonoyl]phenyl}carbamoyl)amino]phenyl}ethylidene)hydrazinecarboximidamide (non-preferred name)
1048364-29-9
NCGC00487389-01
(2e,2'e)-2,2'-(((carbonylbis(azanediyl))bis(4,1-phenylene))bis(ethan-1-yl-1-ylidene))bis(hydrazinecarboximidamide)

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 (1)

Inhibition Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Serine/threonine-protein kinase Chk2Homo sapiens (human)IC50 (µMol)0.22000.00300.34823.5000AID1799260; AID1799261
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Biological Processes (25)

Processvia Protein(s)Taxonomy
DNA damage responseSerine/threonine-protein kinase Chk2Homo sapiens (human)
signal transduction in response to DNA damageSerine/threonine-protein kinase Chk2Homo sapiens (human)
DNA damage checkpoint signalingSerine/threonine-protein kinase Chk2Homo sapiens (human)
G2/M transition of mitotic cell cycleSerine/threonine-protein kinase Chk2Homo sapiens (human)
double-strand break repairSerine/threonine-protein kinase Chk2Homo sapiens (human)
regulation of DNA-templated transcriptionSerine/threonine-protein kinase Chk2Homo sapiens (human)
protein phosphorylationSerine/threonine-protein kinase Chk2Homo sapiens (human)
DNA damage responseSerine/threonine-protein kinase Chk2Homo sapiens (human)
DNA damage response, signal transduction by p53 class mediator resulting in cell cycle arrestSerine/threonine-protein kinase Chk2Homo sapiens (human)
DNA damage response, signal transduction by p53 class mediator resulting in transcription of p21 class mediatorSerine/threonine-protein kinase Chk2Homo sapiens (human)
intrinsic apoptotic signaling pathway in response to DNA damageSerine/threonine-protein kinase Chk2Homo sapiens (human)
protein catabolic processSerine/threonine-protein kinase Chk2Homo sapiens (human)
mitotic intra-S DNA damage checkpoint signalingSerine/threonine-protein kinase Chk2Homo sapiens (human)
regulation of protein catabolic processSerine/threonine-protein kinase Chk2Homo sapiens (human)
signal transduction in response to DNA damageSerine/threonine-protein kinase Chk2Homo sapiens (human)
intrinsic apoptotic signaling pathway in response to DNA damage by p53 class mediatorSerine/threonine-protein kinase Chk2Homo sapiens (human)
positive regulation of DNA-templated transcriptionSerine/threonine-protein kinase Chk2Homo sapiens (human)
protein autophosphorylationSerine/threonine-protein kinase Chk2Homo sapiens (human)
protein stabilizationSerine/threonine-protein kinase Chk2Homo sapiens (human)
cell divisionSerine/threonine-protein kinase Chk2Homo sapiens (human)
thymocyte apoptotic processSerine/threonine-protein kinase Chk2Homo sapiens (human)
cellular response to gamma radiationSerine/threonine-protein kinase Chk2Homo sapiens (human)
mitotic spindle assemblySerine/threonine-protein kinase Chk2Homo sapiens (human)
replicative senescenceSerine/threonine-protein kinase Chk2Homo sapiens (human)
regulation of signal transduction by p53 class mediatorSerine/threonine-protein kinase Chk2Homo sapiens (human)
regulation of autophagosome assemblySerine/threonine-protein kinase Chk2Homo sapiens (human)
mitotic DNA damage checkpoint signalingSerine/threonine-protein kinase Chk2Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Molecular Functions (9)

Processvia Protein(s)Taxonomy
protein serine/threonine kinase activitySerine/threonine-protein kinase Chk2Homo sapiens (human)
protein bindingSerine/threonine-protein kinase Chk2Homo sapiens (human)
ATP bindingSerine/threonine-protein kinase Chk2Homo sapiens (human)
protein kinase bindingSerine/threonine-protein kinase Chk2Homo sapiens (human)
ubiquitin protein ligase bindingSerine/threonine-protein kinase Chk2Homo sapiens (human)
identical protein bindingSerine/threonine-protein kinase Chk2Homo sapiens (human)
protein homodimerization activitySerine/threonine-protein kinase Chk2Homo sapiens (human)
metal ion bindingSerine/threonine-protein kinase Chk2Homo sapiens (human)
protein serine kinase activitySerine/threonine-protein kinase Chk2Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Ceullar Components (6)

Processvia Protein(s)Taxonomy
chromosome, telomeric regionSerine/threonine-protein kinase Chk2Homo sapiens (human)
nucleoplasmSerine/threonine-protein kinase Chk2Homo sapiens (human)
Golgi apparatusSerine/threonine-protein kinase Chk2Homo sapiens (human)
PML bodySerine/threonine-protein kinase Chk2Homo sapiens (human)
cytoplasmSerine/threonine-protein kinase Chk2Homo sapiens (human)
nucleusSerine/threonine-protein kinase Chk2Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (13)

Assay IDTitleYearJournalArticle
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.
AID1130855Displacement of ethidium from poly[d(A-T)]-poly[d(A-T)] DNA (unknown origin) by fluorimetric assay1979Journal of medicinal chemistry, Oct, Volume: 22, Issue:10
Potential antitumor agents. 31. Quantitative structure-activity relationships for the antileukemic bis(guanylhydrazones).
AID1130856Displacement of ethidium from poly[d(G-C)]-poly[d(G-C)] DNA (unknown origin) by fluorimetric assay1979Journal of medicinal chemistry, Oct, Volume: 22, Issue:10
Potential antitumor agents. 31. Quantitative structure-activity relationships for the antileukemic bis(guanylhydrazones).
AID1130853Anti-leukemic activity against mouse L1210 cells allografted in ip dosed DBA2 mouse assessed as optimum drug dose required for the effect administered qd for 1 to 4 days1979Journal of medicinal chemistry, Oct, Volume: 22, Issue:10
Potential antitumor agents. 31. Quantitative structure-activity relationships for the antileukemic bis(guanylhydrazones).
AID1130854Binding affinity to DNA (unknown origin) assessed as decrease in velocity of L1210 DNA-dependent DNA polymerase reaction1979Journal of medicinal chemistry, Oct, Volume: 22, Issue:10
Potential antitumor agents. 31. Quantitative structure-activity relationships for the antileukemic bis(guanylhydrazones).
AID341692Therapeutic index, ratio of CC50 for BHK15 cells to EC50 IRES-luciferase tagged Yellow fever virus2008Journal of medicinal chemistry, Aug-14, Volume: 51, Issue:15
Design, synthesis, and biological evaluation of antiviral agents targeting flavivirus envelope proteins.
AID1130852Anti-leukemic activity against mouse L1210 cells allografted in ip dosed DBA2 mouse assessed as increase in host lifespan administered qd for 1 to 4 days1979Journal of medicinal chemistry, Oct, Volume: 22, Issue:10
Potential antitumor agents. 31. Quantitative structure-activity relationships for the antileukemic bis(guanylhydrazones).
AID341691Cytotoxicity against BHK15 cells assessed as cell viability after 36 hrs by MTT assay2008Journal of medicinal chemistry, Aug-14, Volume: 51, Issue:15
Design, synthesis, and biological evaluation of antiviral agents targeting flavivirus envelope proteins.
AID341690Antiviral activity against IRES-luciferase tagged Yellow fever virus in BHK15 cells assessed as reduction of luciferase activity after 36 hrs2008Journal of medicinal chemistry, Aug-14, Volume: 51, Issue:15
Design, synthesis, and biological evaluation of antiviral agents targeting flavivirus envelope proteins.
AID26757DNA binding dissociation constant as KD; No data1984Journal of medicinal chemistry, Apr, Volume: 27, Issue:4
Interactions of antitumor drugs with natural DNA: 1H NMR study of binding mode and kinetics.
AID1799260In Vitro Protein Kinase Assay from Article 10.1124/mol.107.035832: \\Identification of a Bis-guanylhydrazone [4,4'-Diacetyldiphenylurea-bis(guanylhydrazone); NSC 109555] as a novel chemotype for inhibition of Chk2 kinase.\\2007Molecular pharmacology, Oct, Volume: 72, Issue:4
Identification of a Bis-guanylhydrazone [4,4'-Diacetyldiphenylurea-bis(guanylhydrazone); NSC 109555] as a novel chemotype for inhibition of Chk2 kinase.
AID1799261IMAP High-Throughput Screening from Article 10.1124/mol.107.035832: \\Identification of a Bis-guanylhydrazone [4,4'-Diacetyldiphenylurea-bis(guanylhydrazone); NSC 109555] as a novel chemotype for inhibition of Chk2 kinase.\\2007Molecular pharmacology, Oct, Volume: 72, Issue:4
Identification of a Bis-guanylhydrazone [4,4'-Diacetyldiphenylurea-bis(guanylhydrazone); NSC 109555] as a novel chemotype for inhibition of Chk2 kinase.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (12)

TimeframeStudies, This Drug (%)All Drugs %
pre-19907 (58.33)18.7374
1990's0 (0.00)18.2507
2000's3 (25.00)29.6817
2010's2 (16.67)24.3611
2020's0 (0.00)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 11.65

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 Index11.65 (24.57)
Research Supply Index2.56 (2.92)
Research Growth Index4.21 (4.65)
Search Engine Demand Index0.00 (26.88)
Search Engine Supply Index0.00 (0.95)

This Compound (11.65)

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%
Other12 (100.00%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]