Page last updated: 2024-12-06

3-deazaneplanocin

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

Description

3-Deazaneplanocin is a potent inhibitor of adenosine deaminase (ADA) and a nucleoside analog with antiviral and antineoplastic activity. It is a synthetic derivative of the naturally occurring nucleoside neplanocin A, which is produced by the bacterium Streptomyces violaceus. 3-Deazaneplanocin exhibits a similar mechanism of action to neplanocin A, acting as a substrate analog that binds to the active site of ADA and blocks the enzyme's activity.

This compound is being investigated as a potential therapeutic agent for a variety of diseases, including cancer, viral infections, and autoimmune diseases. Research has shown that 3-Deazaneplanocin can inhibit the growth of cancer cells in vitro and in vivo and has demonstrated antiviral activity against a number of viruses, including HIV, hepatitis C virus, and influenza virus.

Due to its potential therapeutic applications, 3-Deazaneplanocin is the subject of ongoing research to further explore its pharmacological properties, optimize its efficacy, and develop safer and more effective treatment regimens.'

3-deazaneplanocin: S-adenosylhomocysteine hydrolase antagonist [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Cross-References

ID SourceID
PubMed CID73087
CHEMBL ID154745
SCHEMBL ID863851
SCHEMBL ID12280736
MeSH IDM0139402

Synonyms (30)

Synonym
HY-10442
3-deazaneplanocin
avs-4275
(-)-1-[(1r,4r,5s)-3-(hydroxymethyl)-4,5-dihydroxy-2-cyclopenten-1-yl]4-aminoimidazo[4,5-c]pyridine
102052-95-9
3-deazaneplanocin-a
c^neplanocin a
(1s,2r,5r)-5-(4-aminoimidazo[4,5-c]pyridin-1-yl)-3-(hydroxymethyl)cyclopent-3-ene-1,2-diol
AKOS005146283
(1s,2r,5r)-5-(4-amino-1h-imidazo[4,5-c]pyridin-1-yl)-3-(hydroxymethyl)cyclopent-3-ene-1,2-diol
CHEMBL154745 ,
3-deazaneplanocin a
3-deaza-neplanocin
unii-544sh4020s
3-cyclopentene-1,2-diol, 5-(4-amino-1h-imidazo(4,5-c)pyridiny-1-yl)-3-(hydroxymethyl)-, (1s-(alpha,2alpha,5beta))-
544sh4020s ,
3-deazaneplanocin,dznep
CS-0357
SCHEMBL863851
(1s,2r,5r)-5-(4-aminoimidazo(4,5-c)pyridin-1-yl)-3-(hydroxymethyl)cyclopent-3-ene-1,2-diol
SCHEMBL12280736
AC-27393
DTXSID30144562
bdbm50096906
3-deazaneplanocin a (dznep
Q15410156
BRD-K77791657-001-01-1
CEA05295
3-deazaneplanocina
3-cyclopentene-1,2-diol, 5-(4-amino-1h-imidazo[4,5-c]pyridin-1-yl)-3-(hydroxymethyl)-, (1s,2r,5r)-

Research Excerpts

Pharmacokinetics

ExcerptReferenceRelevance
" The purpose of this study was to improve the pharmacokinetic characteristics of DZNep in vivo through developing a unilamellar pegylated liposomal formulation encapsulating DZNep (L-DZNep)."( Loading 3-deazaneplanocin A into pegylated unilamellar liposomes by forming transient phenylboronic acid-drug complex and its pharmacokinetic features in Sprague-Dawley rats.
Chan, E; Li, J; Sun, F; Yu, Q, 2012
)
0.81
"3-Deazaneplanocin A (DZNep) has been shown to have anti-cancer activity in numerous cancer types and its continued preclinical, and eventual clinical, drug development will require rapid and sensitive bioanalytical methods in order to quantitate this drug for pharmacokinetic analyses."( A rapid ultra HPLC-MS/MS method for the quantitation and pharmacokinetic analysis of 3-deazaneplanocin A in mice.
Figg, WD; Peer, CJ; Rao, M; Schrump, DS; Shahbazi, S; Spencer, SD; Steeg, PS, 2013
)
2.06
" Antitumor studies on DZNep have been stuck in the preclinical phase because of the lack of information about its integral pharmacokinetic (PK) properties."( Preclinical pharmacokinetic studies of 3-deazaneplanocin A, a potent epigenetic anticancer agent, and its human pharmacokinetic prediction using GastroPlus™.
Chan, E; Duan, X; Lee, L; Sun, F; Wang, X; Yu, Q; Zhang, Z, 2015
)
0.69

Compound-Compound Interactions

ExcerptReferenceRelevance
" The aim of the study presented here was to analyze the effects of a pharmacological inhibition of EZH2 alone and in combination with other anticancer drugs on RTs cells in vitro."( Analysis of the antiproliferative effects of 3-deazaneoplanocin A in combination with standard anticancer agents in rhabdoid tumor cell lines.
Borchardt, C; Clemens, D; Dirksen, U; Frühwald, MC; Kool, M; Unland, R, 2015
)
0.42

Bioavailability

ExcerptReferenceRelevance
"Cell membrane permeability is an important determinant for oral absorption and bioavailability of a drug molecule."( Highly predictive and interpretable models for PAMPA permeability.
Jadhav, A; Kerns, E; Nguyen, K; Shah, P; Sun, H; Xu, X; Yan, Z; Yu, KR, 2017
)
0.46

Dosage Studied

ExcerptRelevanceReference
" The simulated human PBPK model successfully identified that intravenous administration of DZNep at appropriate dosing regimen could be further developed for human non-small cell lung carcinoma treatments."( Preclinical pharmacokinetic studies of 3-deazaneplanocin A, a potent epigenetic anticancer agent, and its human pharmacokinetic prediction using GastroPlus™.
Chan, E; Duan, X; Lee, L; Sun, F; Wang, X; Yu, Q; Zhang, Z, 2015
)
0.69
" DZNep inhibited JH synthesis in a dose-response fashion."( Inhibition of juvenile hormone synthesis in mosquitoes by the methylation inhibitor 3-deazaneplanocin A (DZNep).
Fernandez-Lima, F; Michalkova, V; Noriega, FG; Nouzova, M; Ramirez, CE, 2019
)
0.74
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Protein Targets (2)

Inhibition Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
AdenosylhomocysteinaseHomo sapiens (human)IC50 (µMol)0.44000.00152.11118.7000AID1229551
AdenosylhomocysteinaseHomo sapiens (human)Ki0.00000.00000.18991.9300AID1868663
Histone-lysine N-methyltransferase EZH2Homo sapiens (human)IC50 (µMol)0.08000.00030.50478.9000AID1868615
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Biological Processes (49)

Processvia Protein(s)Taxonomy
one-carbon metabolic processAdenosylhomocysteinaseHomo sapiens (human)
S-adenosylmethionine cycleAdenosylhomocysteinaseHomo sapiens (human)
G1/S transition of mitotic cell cycleHistone-lysine N-methyltransferase EZH2Homo sapiens (human)
negative regulation of transcription by RNA polymerase IIHistone-lysine N-methyltransferase EZH2Homo sapiens (human)
chromatin organizationHistone-lysine N-methyltransferase EZH2Homo sapiens (human)
regulation of DNA-templated transcriptionHistone-lysine N-methyltransferase EZH2Homo sapiens (human)
positive regulation of cell population proliferationHistone-lysine N-methyltransferase EZH2Homo sapiens (human)
positive regulation of epithelial to mesenchymal transitionHistone-lysine N-methyltransferase EZH2Homo sapiens (human)
regulation of gliogenesisHistone-lysine N-methyltransferase EZH2Homo sapiens (human)
skeletal muscle satellite cell maintenance involved in skeletal muscle regenerationHistone-lysine N-methyltransferase EZH2Homo sapiens (human)
cardiac muscle hypertrophy in response to stressHistone-lysine N-methyltransferase EZH2Homo sapiens (human)
cerebellar cortex developmentHistone-lysine N-methyltransferase EZH2Homo sapiens (human)
hippocampus developmentHistone-lysine N-methyltransferase EZH2Homo sapiens (human)
B cell differentiationHistone-lysine N-methyltransferase EZH2Homo sapiens (human)
keratinocyte differentiationHistone-lysine N-methyltransferase EZH2Homo sapiens (human)
positive regulation of cell migrationHistone-lysine N-methyltransferase EZH2Homo sapiens (human)
regulatory ncRNA-mediated heterochromatin formationHistone-lysine N-methyltransferase EZH2Homo sapiens (human)
subtelomeric heterochromatin formationHistone-lysine N-methyltransferase EZH2Homo sapiens (human)
methylationHistone-lysine N-methyltransferase EZH2Homo sapiens (human)
response to estradiolHistone-lysine N-methyltransferase EZH2Homo sapiens (human)
negative regulation of transcription elongation by RNA polymerase IIHistone-lysine N-methyltransferase EZH2Homo sapiens (human)
cellular response to trichostatin AHistone-lysine N-methyltransferase EZH2Homo sapiens (human)
protein modification processHistone-lysine N-methyltransferase EZH2Homo sapiens (human)
hepatocyte homeostasisHistone-lysine N-methyltransferase EZH2Homo sapiens (human)
regulation of circadian rhythmHistone-lysine N-methyltransferase EZH2Homo sapiens (human)
positive regulation of MAP kinase activityHistone-lysine N-methyltransferase EZH2Homo sapiens (human)
positive regulation of GTPase activityHistone-lysine N-methyltransferase EZH2Homo sapiens (human)
negative regulation of keratinocyte differentiationHistone-lysine N-methyltransferase EZH2Homo sapiens (human)
negative regulation of gene expression, epigeneticHistone-lysine N-methyltransferase EZH2Homo sapiens (human)
negative regulation of DNA-templated transcriptionHistone-lysine N-methyltransferase EZH2Homo sapiens (human)
negative regulation of retinoic acid receptor signaling pathwayHistone-lysine N-methyltransferase EZH2Homo sapiens (human)
rhythmic processHistone-lysine N-methyltransferase EZH2Homo sapiens (human)
stem cell differentiationHistone-lysine N-methyltransferase EZH2Homo sapiens (human)
negative regulation of striated muscle cell differentiationHistone-lysine N-methyltransferase EZH2Homo sapiens (human)
synaptic transmission, GABAergicHistone-lysine N-methyltransferase EZH2Homo sapiens (human)
cellular response to hydrogen peroxideHistone-lysine N-methyltransferase EZH2Homo sapiens (human)
G1 to G0 transitionHistone-lysine N-methyltransferase EZH2Homo sapiens (human)
protein localization to chromatinHistone-lysine N-methyltransferase EZH2Homo sapiens (human)
positive regulation of protein serine/threonine kinase activityHistone-lysine N-methyltransferase EZH2Homo sapiens (human)
regulation of kidney developmentHistone-lysine N-methyltransferase EZH2Homo sapiens (human)
liver regenerationHistone-lysine N-methyltransferase EZH2Homo sapiens (human)
facultative heterochromatin formationHistone-lysine N-methyltransferase EZH2Homo sapiens (human)
positive regulation of dendrite developmentHistone-lysine N-methyltransferase EZH2Homo sapiens (human)
negative regulation of cytokine production involved in inflammatory responseHistone-lysine N-methyltransferase EZH2Homo sapiens (human)
positive regulation of cell cycle G1/S phase transitionHistone-lysine N-methyltransferase EZH2Homo sapiens (human)
response to tetrachloromethaneHistone-lysine N-methyltransferase EZH2Homo sapiens (human)
negative regulation of G1/S transition of mitotic cell cycleHistone-lysine N-methyltransferase EZH2Homo sapiens (human)
negative regulation of stem cell differentiationHistone-lysine N-methyltransferase EZH2Homo sapiens (human)
heterochromatin formationHistone-lysine N-methyltransferase EZH2Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Molecular Functions (17)

Processvia Protein(s)Taxonomy
adenosylhomocysteinase activityAdenosylhomocysteinaseHomo sapiens (human)
protein bindingAdenosylhomocysteinaseHomo sapiens (human)
RNA polymerase II cis-regulatory region sequence-specific DNA bindingHistone-lysine N-methyltransferase EZH2Homo sapiens (human)
RNA polymerase II core promoter sequence-specific DNA bindingHistone-lysine N-methyltransferase EZH2Homo sapiens (human)
transcription corepressor bindingHistone-lysine N-methyltransferase EZH2Homo sapiens (human)
chromatin bindingHistone-lysine N-methyltransferase EZH2Homo sapiens (human)
transcription corepressor activityHistone-lysine N-methyltransferase EZH2Homo sapiens (human)
protein bindingHistone-lysine N-methyltransferase EZH2Homo sapiens (human)
protein-lysine N-methyltransferase activityHistone-lysine N-methyltransferase EZH2Homo sapiens (human)
chromatin DNA bindingHistone-lysine N-methyltransferase EZH2Homo sapiens (human)
histone methyltransferase activityHistone-lysine N-methyltransferase EZH2Homo sapiens (human)
ribonucleoprotein complex bindingHistone-lysine N-methyltransferase EZH2Homo sapiens (human)
histone H3K27 methyltransferase activityHistone-lysine N-methyltransferase EZH2Homo sapiens (human)
primary miRNA bindingHistone-lysine N-methyltransferase EZH2Homo sapiens (human)
lncRNA bindingHistone-lysine N-methyltransferase EZH2Homo sapiens (human)
histone H3 methyltransferase activityHistone-lysine N-methyltransferase EZH2Homo sapiens (human)
histone H3K27 trimethyltransferase activityHistone-lysine N-methyltransferase EZH2Homo sapiens (human)
promoter-specific chromatin bindingHistone-lysine N-methyltransferase EZH2Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Ceullar Components (14)

Processvia Protein(s)Taxonomy
nucleusAdenosylhomocysteinaseHomo sapiens (human)
endoplasmic reticulumAdenosylhomocysteinaseHomo sapiens (human)
cytosolAdenosylhomocysteinaseHomo sapiens (human)
melanosomeAdenosylhomocysteinaseHomo sapiens (human)
extracellular exosomeAdenosylhomocysteinaseHomo sapiens (human)
cytosolAdenosylhomocysteinaseHomo sapiens (human)
chromosomeHistone-lysine N-methyltransferase EZH2Homo sapiens (human)
chromosome, telomeric regionHistone-lysine N-methyltransferase EZH2Homo sapiens (human)
nucleusHistone-lysine N-methyltransferase EZH2Homo sapiens (human)
nucleoplasmHistone-lysine N-methyltransferase EZH2Homo sapiens (human)
pronucleusHistone-lysine N-methyltransferase EZH2Homo sapiens (human)
synapseHistone-lysine N-methyltransferase EZH2Homo sapiens (human)
chromatinHistone-lysine N-methyltransferase EZH2Homo sapiens (human)
chromatin silencing complexHistone-lysine N-methyltransferase EZH2Homo sapiens (human)
pericentric heterochromatinHistone-lysine N-methyltransferase EZH2Homo sapiens (human)
ESC/E(Z) complexHistone-lysine N-methyltransferase EZH2Homo sapiens (human)
nucleusHistone-lysine N-methyltransferase EZH2Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (19)

Assay IDTitleYearJournalArticle
AID1347411qHTS to identify inhibitors of the type 1 interferon - major histocompatibility complex class I in skeletal muscle: primary screen against the NCATS Mechanism Interrogation Plate v5.0 (MIPE) Libary2020ACS chemical biology, 07-17, Volume: 15, Issue:7
High-Throughput Screening to Identify Inhibitors of the Type I Interferon-Major Histocompatibility Complex Class I Pathway in Skeletal Muscle.
AID1508591NCATS Rat Liver Microsome Stability Profiling2020Scientific reports, 11-26, Volume: 10, Issue:1
Retrospective assessment of rat liver microsomal stability at NCATS: data and QSAR models.
AID1508612NCATS Parallel Artificial Membrane Permeability Assay (PAMPA) Profiling2017Bioorganic & medicinal chemistry, 02-01, Volume: 25, Issue:3
Highly predictive and interpretable models for PAMPA permeability.
AID1645848NCATS Kinetic Aqueous Solubility Profiling2019Bioorganic & medicinal chemistry, 07-15, Volume: 27, Issue:14
Predictive models of aqueous solubility of organic compounds built on A large dataset of high integrity.
AID1868666Antiproliferative activity against human NCI-H1975 cells2022Journal of medicinal chemistry, 05-26, Volume: 65, Issue:10
Targeting Enhancer of Zeste Homolog 2 for the Treatment of Hematological Malignancies and Solid Tumors: Candidate Structure-Activity Relationships Insights and Evolution Prospects.
AID1868667Antiproliferative activity against human PC-3 cells2022Journal of medicinal chemistry, 05-26, Volume: 65, Issue:10
Targeting Enhancer of Zeste Homolog 2 for the Treatment of Hematological Malignancies and Solid Tumors: Candidate Structure-Activity Relationships Insights and Evolution Prospects.
AID1229558Cytotoxicity against human PC3 cells assessed as inhibition of cell proliferation after 72 hrs by sulforhodamine B assay2015Journal of medicinal chemistry, Jun-25, Volume: 58, Issue:12
Structure-Activity Relationships of Neplanocin A Analogues as S-Adenosylhomocysteine Hydrolase Inhibitors and Their Antiviral and Antitumor Activities.
AID1229557Cytotoxicity against human MDA-MB-231 cells assessed as inhibition of cell proliferation after 72 hrs by sulforhodamine B assay2015Journal of medicinal chemistry, Jun-25, Volume: 58, Issue:12
Structure-Activity Relationships of Neplanocin A Analogues as S-Adenosylhomocysteine Hydrolase Inhibitors and Their Antiviral and Antitumor Activities.
AID1868668Antiproliferative activity against human A549 cells2022Journal of medicinal chemistry, 05-26, Volume: 65, Issue:10
Targeting Enhancer of Zeste Homolog 2 for the Treatment of Hematological Malignancies and Solid Tumors: Candidate Structure-Activity Relationships Insights and Evolution Prospects.
AID1229556Cytotoxicity against human HCT116 cells assessed as inhibition of cell proliferation after 72 hrs by sulforhodamine B assay2015Journal of medicinal chemistry, Jun-25, Volume: 58, Issue:12
Structure-Activity Relationships of Neplanocin A Analogues as S-Adenosylhomocysteine Hydrolase Inhibitors and Their Antiviral and Antitumor Activities.
AID1868665Antiproliferative activity against human NCI-H1299 cells2022Journal of medicinal chemistry, 05-26, Volume: 65, Issue:10
Targeting Enhancer of Zeste Homolog 2 for the Treatment of Hematological Malignancies and Solid Tumors: Candidate Structure-Activity Relationships Insights and Evolution Prospects.
AID1868664Half life in rat2022Journal of medicinal chemistry, 05-26, Volume: 65, Issue:10
Targeting Enhancer of Zeste Homolog 2 for the Treatment of Hematological Malignancies and Solid Tumors: Candidate Structure-Activity Relationships Insights and Evolution Prospects.
AID1173984Inhibition of rabbit erythrocyte SAHase using S-adenosyl-L-homocysteine as substrate assessed as L-homocysteine formation incubated for 5 mins prior to substrate addition measured after 1 hr2014Bioorganic & medicinal chemistry, Dec-15, Volume: 22, Issue:24
Synthesis and antiviral activities of 3-deaza-3-fluoroaristeromycin and its 5' analogues.
AID1229560Cytotoxicity against human SNU638 cells assessed as inhibition of cell proliferation after 72 hrs by sulforhodamine B assay2015Journal of medicinal chemistry, Jun-25, Volume: 58, Issue:12
Structure-Activity Relationships of Neplanocin A Analogues as S-Adenosylhomocysteine Hydrolase Inhibitors and Their Antiviral and Antitumor Activities.
AID1229551Inhibition of recombinant human placental AdoHcy hydrolase expressed in Escherichia coli BL21 using AdoHcy as substrate preincubated for 10 mins followed by substrate addition measured after 20 mins by DTNB coupled assay2015Journal of medicinal chemistry, Jun-25, Volume: 58, Issue:12
Structure-Activity Relationships of Neplanocin A Analogues as S-Adenosylhomocysteine Hydrolase Inhibitors and Their Antiviral and Antitumor Activities.
AID1868615Inhibition of EZH2 (unknown origin)2022Journal of medicinal chemistry, 05-26, Volume: 65, Issue:10
Targeting Enhancer of Zeste Homolog 2 for the Treatment of Hematological Malignancies and Solid Tumors: Candidate Structure-Activity Relationships Insights and Evolution Prospects.
AID1229555Cytotoxicity against human A549 cells assessed as inhibition of cell proliferation after 72 hrs by sulforhodamine B assay2015Journal of medicinal chemistry, Jun-25, Volume: 58, Issue:12
Structure-Activity Relationships of Neplanocin A Analogues as S-Adenosylhomocysteine Hydrolase Inhibitors and Their Antiviral and Antitumor Activities.
AID1229559Cytotoxicity against human SKHEP1 cells assessed as inhibition of cell proliferation after 72 hrs by sulforhodamine B assay2015Journal of medicinal chemistry, Jun-25, Volume: 58, Issue:12
Structure-Activity Relationships of Neplanocin A Analogues as S-Adenosylhomocysteine Hydrolase Inhibitors and Their Antiviral and Antitumor Activities.
AID1868663Inhibition of SAH hydrolase (unknown origin) assessed as inhibition constant2022Journal of medicinal chemistry, 05-26, Volume: 65, Issue:10
Targeting Enhancer of Zeste Homolog 2 for the Treatment of Hematological Malignancies and Solid Tumors: Candidate Structure-Activity Relationships Insights and Evolution Prospects.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (159)

TimeframeStudies, This Drug (%)All Drugs %
pre-19905 (3.14)18.7374
1990's6 (3.77)18.2507
2000's11 (6.92)29.6817
2010's108 (67.92)24.3611
2020's29 (18.24)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 34.81

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 Index34.81 (24.57)
Research Supply Index5.09 (2.92)
Research Growth Index5.82 (4.65)
Search Engine Demand Index45.80 (26.88)
Search Engine Supply Index2.00 (0.95)

This Compound (34.81)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Reviews7 (4.35%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other154 (95.65%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]