Page last updated: 2024-12-07

2-chloroadenine

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

Description

2-Chloroadenine is a synthetic adenine analog that has shown significant biological activity. It is typically synthesized via chlorination of adenine using a reagent such as N-chlorosuccinimide. 2-chloroadenine has been investigated for its potential antiviral, anti-cancer, and anti-inflammatory effects. It has been shown to inhibit the replication of certain viruses, including herpes simplex virus and cytomegalovirus, by interfering with viral DNA polymerase. Additionally, 2-chloroadenine has demonstrated cytotoxic activity against various cancer cell lines. Its mechanism of action involves inhibiting DNA synthesis and inducing apoptosis. Research on 2-chloroadenine is ongoing to explore its potential therapeutic applications. The compound's unique chemical structure and biological activity make it a promising candidate for the development of new drugs for treating viral infections, cancer, and other diseases.'

6-amino-2-chloropurine: RN & structure given in first source [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Cross-References

ID SourceID
PubMed CID94904
CHEMBL ID134192
SCHEMBL ID29745
MeSH IDM0189627

Synonyms (62)

Synonym
AC-1007
2-chloro-6-aminopurine ,
nsc-7362
purine, 6-amino-2-chloro-
1h-purin-6-amine, 2-chloro-
adenine, 2-chloro-
nsc7362
2-chloroadenine
sq 22,982
sq 22982
6-amino-2-chloropurine
inchi=1/c5h4cln5/c6-5-10-3(7)2-4(11-5)9-1-8-2/h1h,(h3,7,8,9,10,11
9h-purin-6-amine, 2-chloro-
1839-18-5
2-chloro-9h-purin-6-amine
CHEMBL134192 ,
bdbm50056180
2-chloro-9h-purin-6-ylamine
2-chloro-7h-purin-6-amine
AKOS005257637
AKOS006281627
C2575
6-amino-2-chloro-purine
nsc 7362
unii-a05ol9v6om
ai3-52061
a05ol9v6om ,
FT-0601064
PS-4933
AB01672
AM799
SCHEMBL29745
6-amino-2-chloro-7h-purine
clade
2-chloro-1h-purin-6-amine
HBJGQJWNMZDFKL-UHFFFAOYSA-N
2-chloro-1h-purine-6-amine
mfcd00037925
2-chloradenin
Q-200260
DTXSID30171515
AKOS028109325
2-chloro-9h-purin-6-amine, aldrichcpr
2-chloroadenine, 97%
cladribine impurity c, european pharmacopoeia (ep) reference standard
2-chloro-7h-purin-6-amine (2-chloroadenine)
SY035219
STL555064
BCP20072
2-chloro-6-amino purine
2-chloroadenine [usp impurity]
cladribine impurity c [ep impurity]
sq-22982
6-amino-2-chloro-9h-purine
BBL101268
31458-56-7
cladribine impurity c
EN300-194273
PD131302
CS-W017715
Z1741971500
HY-W016999

Research Excerpts

Toxicity

ExcerptReferenceRelevance
" In vitro exposure of leukemia cells to CAde showed that it was eight times less toxic as compared to CdA."( Cytotoxicity and pharmacokinetics of cladribine metabolite, 2-chloroadenine in patients with leukemia.
Albertioni, F; Juliusson, G; Larsson, R; Liliemark, J; Lindemalm, S, 2004
)
0.57

Pharmacokinetics

ExcerptReferenceRelevance
" After iv infusion, the half-life was the same for CdA and CAde, but after oral administration the half-life was doubled for CAde."( Cytotoxicity and pharmacokinetics of cladribine metabolite, 2-chloroadenine in patients with leukemia.
Albertioni, F; Juliusson, G; Larsson, R; Liliemark, J; Lindemalm, S, 2004
)
0.57
[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)
Cyclin-dependent kinase 1Homo sapiens (human)IC50 (µMol)1,000.00000.00041.345210.0000AID51555
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Biological Processes (55)

Processvia Protein(s)Taxonomy
G1/S transition of mitotic cell cycleCyclin-dependent kinase 1Homo sapiens (human)
G2/M transition of mitotic cell cycleCyclin-dependent kinase 1Homo sapiens (human)
microtubule cytoskeleton organizationCyclin-dependent kinase 1Homo sapiens (human)
DNA replicationCyclin-dependent kinase 1Homo sapiens (human)
DNA repairCyclin-dependent kinase 1Homo sapiens (human)
chromatin remodelingCyclin-dependent kinase 1Homo sapiens (human)
regulation of transcription by RNA polymerase IICyclin-dependent kinase 1Homo sapiens (human)
protein phosphorylationCyclin-dependent kinase 1Homo sapiens (human)
apoptotic processCyclin-dependent kinase 1Homo sapiens (human)
DNA damage responseCyclin-dependent kinase 1Homo sapiens (human)
mitotic nuclear membrane disassemblyCyclin-dependent kinase 1Homo sapiens (human)
centrosome cycleCyclin-dependent kinase 1Homo sapiens (human)
pronuclear fusionCyclin-dependent kinase 1Homo sapiens (human)
response to xenobiotic stimulusCyclin-dependent kinase 1Homo sapiens (human)
response to toxic substanceCyclin-dependent kinase 1Homo sapiens (human)
positive regulation of gene expressionCyclin-dependent kinase 1Homo sapiens (human)
negative regulation of gene expressionCyclin-dependent kinase 1Homo sapiens (human)
positive regulation of G2/M transition of mitotic cell cycleCyclin-dependent kinase 1Homo sapiens (human)
regulation of Schwann cell differentiationCyclin-dependent kinase 1Homo sapiens (human)
response to amineCyclin-dependent kinase 1Homo sapiens (human)
response to activityCyclin-dependent kinase 1Homo sapiens (human)
cell migrationCyclin-dependent kinase 1Homo sapiens (human)
peptidyl-serine phosphorylationCyclin-dependent kinase 1Homo sapiens (human)
peptidyl-threonine phosphorylationCyclin-dependent kinase 1Homo sapiens (human)
chromosome condensationCyclin-dependent kinase 1Homo sapiens (human)
epithelial cell differentiationCyclin-dependent kinase 1Homo sapiens (human)
animal organ regenerationCyclin-dependent kinase 1Homo sapiens (human)
protein localization to kinetochoreCyclin-dependent kinase 1Homo sapiens (human)
positive regulation of protein import into nucleusCyclin-dependent kinase 1Homo sapiens (human)
regulation of circadian rhythmCyclin-dependent kinase 1Homo sapiens (human)
negative regulation of apoptotic processCyclin-dependent kinase 1Homo sapiens (human)
response to ethanolCyclin-dependent kinase 1Homo sapiens (human)
positive regulation of DNA replicationCyclin-dependent kinase 1Homo sapiens (human)
regulation of embryonic developmentCyclin-dependent kinase 1Homo sapiens (human)
response to cadmium ionCyclin-dependent kinase 1Homo sapiens (human)
response to copper ionCyclin-dependent kinase 1Homo sapiens (human)
symbiont entry into host cellCyclin-dependent kinase 1Homo sapiens (human)
fibroblast proliferationCyclin-dependent kinase 1Homo sapiens (human)
rhythmic processCyclin-dependent kinase 1Homo sapiens (human)
response to axon injuryCyclin-dependent kinase 1Homo sapiens (human)
cell divisionCyclin-dependent kinase 1Homo sapiens (human)
ventricular cardiac muscle cell developmentCyclin-dependent kinase 1Homo sapiens (human)
positive regulation of cardiac muscle cell proliferationCyclin-dependent kinase 1Homo sapiens (human)
positive regulation of mitotic sister chromatid segregationCyclin-dependent kinase 1Homo sapiens (human)
protein-containing complex assemblyCyclin-dependent kinase 1Homo sapiens (human)
cellular response to hydrogen peroxideCyclin-dependent kinase 1Homo sapiens (human)
ERK1 and ERK2 cascadeCyclin-dependent kinase 1Homo sapiens (human)
cellular response to organic cyclic compoundCyclin-dependent kinase 1Homo sapiens (human)
Golgi disassemblyCyclin-dependent kinase 1Homo sapiens (human)
positive regulation of protein localization to nucleusCyclin-dependent kinase 1Homo sapiens (human)
regulation of attachment of mitotic spindle microtubules to kinetochoreCyclin-dependent kinase 1Homo sapiens (human)
microtubule cytoskeleton organization involved in mitosisCyclin-dependent kinase 1Homo sapiens (human)
positive regulation of mitochondrial ATP synthesis coupled electron transportCyclin-dependent kinase 1Homo sapiens (human)
mitotic G2 DNA damage checkpoint signalingCyclin-dependent kinase 1Homo sapiens (human)
protein deubiquitinationCyclin-dependent kinase 1Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Molecular Functions (14)

Processvia Protein(s)Taxonomy
virus receptor activityCyclin-dependent kinase 1Homo sapiens (human)
chromatin bindingCyclin-dependent kinase 1Homo sapiens (human)
protein kinase activityCyclin-dependent kinase 1Homo sapiens (human)
protein serine/threonine kinase activityCyclin-dependent kinase 1Homo sapiens (human)
cyclin-dependent protein serine/threonine kinase activityCyclin-dependent kinase 1Homo sapiens (human)
protein bindingCyclin-dependent kinase 1Homo sapiens (human)
ATP bindingCyclin-dependent kinase 1Homo sapiens (human)
RNA polymerase II CTD heptapeptide repeat kinase activityCyclin-dependent kinase 1Homo sapiens (human)
kinase activityCyclin-dependent kinase 1Homo sapiens (human)
cyclin bindingCyclin-dependent kinase 1Homo sapiens (human)
Hsp70 protein bindingCyclin-dependent kinase 1Homo sapiens (human)
histone kinase activityCyclin-dependent kinase 1Homo sapiens (human)
cyclin-dependent protein kinase activityCyclin-dependent kinase 1Homo sapiens (human)
protein serine kinase activityCyclin-dependent kinase 1Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Ceullar Components (18)

Processvia Protein(s)Taxonomy
mitochondrial matrixCyclin-dependent kinase 1Homo sapiens (human)
chromosome, telomeric regionCyclin-dependent kinase 1Homo sapiens (human)
nucleusCyclin-dependent kinase 1Homo sapiens (human)
nucleoplasmCyclin-dependent kinase 1Homo sapiens (human)
mitochondrionCyclin-dependent kinase 1Homo sapiens (human)
endoplasmic reticulum membraneCyclin-dependent kinase 1Homo sapiens (human)
centrosomeCyclin-dependent kinase 1Homo sapiens (human)
cytosolCyclin-dependent kinase 1Homo sapiens (human)
spindle microtubuleCyclin-dependent kinase 1Homo sapiens (human)
membraneCyclin-dependent kinase 1Homo sapiens (human)
midbodyCyclin-dependent kinase 1Homo sapiens (human)
extracellular exosomeCyclin-dependent kinase 1Homo sapiens (human)
mitotic spindleCyclin-dependent kinase 1Homo sapiens (human)
cyclin A1-CDK1 complexCyclin-dependent kinase 1Homo sapiens (human)
cyclin A2-CDK1 complexCyclin-dependent kinase 1Homo sapiens (human)
cyclin B1-CDK1 complexCyclin-dependent kinase 1Homo sapiens (human)
cyclin-dependent protein kinase holoenzyme complexCyclin-dependent kinase 1Homo sapiens (human)
cytoplasmCyclin-dependent kinase 1Homo sapiens (human)
nucleusCyclin-dependent kinase 1Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (3)

Assay IDTitleYearJournalArticle
AID1452128Inhibition of ATPgammaS-BODIPY binding to Thermotoga maritima His-tagged HK853 expressed in Escherichia coli BL21(DE3)pLysS Rosetta preincubated for 30 mins prior to ATPgammaS-BODIPY addition measured after 1 hr by coomassie staining-based SDS-PAGE analys2017Journal of medicinal chemistry, 10-12, Volume: 60, Issue:19
Rational Design of Selective Adenine-Based Scaffolds for Inactivation of Bacterial Histidine Kinases.
AID51555Inhibition of purified Cdc2 p34/Cyclin B obtained from M phase oocytes of the starfish Marthasterias glacialis (precipitation at the higher concentration tested)1997Journal of medicinal chemistry, Feb-14, Volume: 40, Issue:4
Cytokinin-derived cyclin-dependent kinase inhibitors: synthesis and cdc2 inhibitory activity of olomoucine and related compounds.
AID1065710Displacement of [2,8-3H]-adenosine from Trypanosoma brucei AT1/P2 expressed in bloodstream stage of Trypanosoma brucei brucei B482013Journal of medicinal chemistry, Dec-27, Volume: 56, Issue:24
Structure-activity relationships of synthetic cordycepin analogues as experimental therapeutics for African trypanosomiasis.
[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's8 (36.36)18.2507
2000's7 (31.82)29.6817
2010's5 (22.73)24.3611
2020's2 (9.09)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 20.50

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 Index20.50 (24.57)
Research Supply Index3.26 (2.92)
Research Growth Index4.46 (4.65)
Search Engine Demand Index18.60 (26.88)
Search Engine Supply Index2.00 (0.95)

This Compound (20.50)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials2 (8.70%)5.53%
Reviews0 (0.00%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other21 (91.30%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]