Page last updated: 2024-12-09

n-(1,3-benzodioxol-5-ylmethyl)-2,6-dichlorobenzamide

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

Description

N-(1,3-benzodioxol-5-ylmethyl)-2,6-dichlorobenzamide: Cardioprotective Agent; a small-molecule activator of aldehyde dehydrogenase-2 that reduces ischemic damage to the heart [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Cross-References

ID SourceID
PubMed CID831629
CHEMBL ID465952
CHEBI ID94988
SCHEMBL ID503808
MeSH IDM0524997

Synonyms (34)

Synonym
OPREA1_166989
n-benzo[1,3]dioxol-5-ylmethyl-2,6-dichloro-benzamide
MLS001206840
smr000518092
n-(1,3-benzodioxol-5-ylmethyl)-2,6-dichlorobenzamide
STK417030
CHEMBL465952 ,
AKOS000648901
bxb ,
HMS2847P05
S5800
CS-4995
SCHEMBL503808
alda 1
349438-38-6
AC-35356
benzamide, n-(1,3-benzodioxol-5-ylmethyl)-2,6-dichloro-
alda-1
HY-18936
n-(benzo[d][1,3]dioxol-5-ylmethyl)-2,6-dichlorobenzamide
n-[(2h-1,3-benzodioxol-5-yl)methyl]-2,6-dichlorobenzamide
CHEBI:94988
alda-1, >=98% (hplc)
alda1
EX-A3557
BCP17146
Q27166749
BS-16611
BB 0300764
C74792
aldh2 agonist, alda-1
ZNA43838
bdbm50557071
DTXSID801324445

Research Excerpts

Toxicity

ExcerptReferenceRelevance
"Cyclophosphamide (CY)-induced acute cardiotoxicity is a common side effect which is dose dependent."( Aldehyde dehydrogenase 2 activation ameliorates cyclophosphamide-induced acute cardiotoxicity via detoxification of toxic aldehydes and suppression of cardiac cell death.
Chen, Y; Fan, X; Liu, W; Wang, J; Wang, W; Zhai, X; Zhang, Z; Zheng, B, 2018
)
0.48
" About 45% of Han Chinese (East Asians), accounting for 8% of humans, carry a single point mutation in ALDH2*2 (E504K) that leads to accumulation of toxic reactive aldehydes."( Novel and prevalent non-East Asian ALDH2 variants; Implications for global susceptibility to aldehydes' toxicity.
Barrientos, FL; Cervantes, PR; Chen, CH; Ferreira, JCB; Ferreira, ND; Hsu, JH; Joshi, AU; Li, SJ; Maclean, R; Martinez, DD; Mochly-Rosen, D; Quintanares, GHR; Stevens, MC, 2020
)
0.56
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Drug Classes (2)

ClassDescription
carbonyl compoundAny compound containing the carbonyl group, C=O. The term is commonly used in the restricted sense of aldehydes and ketones, although it actually includes carboxylic acids and derivatives.
organohalogen compoundA compound containing at least one carbon-halogen bond (where X is a halogen atom).
[compound class information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Protein Targets (4)

Potency Measurements

ProteinTaxonomyMeasurementAverage (µ)Min (ref.)Avg (ref.)Max (ref.)Bioassay(s)
thioredoxin glutathione reductaseSchistosoma mansoniPotency0.19950.100022.9075100.0000AID485364
DNA polymerase iota isoform a (long)Homo sapiens (human)Potency89.12510.050127.073689.1251AID588590
Guanine nucleotide-binding protein GHomo sapiens (human)Potency2.51191.995325.532750.1187AID624288
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Activation Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Aldehyde dehydrogenase, mitochondrialHomo sapiens (human)EC50 (µMol)4.30004.30004.30004.3000AID1707630
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Biological Processes (11)

Processvia Protein(s)Taxonomy
carbohydrate metabolic processAldehyde dehydrogenase, mitochondrialHomo sapiens (human)
alcohol metabolic processAldehyde dehydrogenase, mitochondrialHomo sapiens (human)
ethanol catabolic processAldehyde dehydrogenase, mitochondrialHomo sapiens (human)
aldehyde catabolic processAldehyde dehydrogenase, mitochondrialHomo sapiens (human)
regulation of dopamine biosynthetic processAldehyde dehydrogenase, mitochondrialHomo sapiens (human)
regulation of serotonin biosynthetic processAldehyde dehydrogenase, mitochondrialHomo sapiens (human)
negative regulation of inflammatory response to antigenic stimulusGuanine nucleotide-binding protein GHomo sapiens (human)
renal water homeostasisGuanine nucleotide-binding protein GHomo sapiens (human)
G protein-coupled receptor signaling pathwayGuanine nucleotide-binding protein GHomo sapiens (human)
regulation of insulin secretionGuanine nucleotide-binding protein GHomo sapiens (human)
cellular response to glucagon stimulusGuanine nucleotide-binding protein GHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Molecular Functions (10)

Processvia Protein(s)Taxonomy
aldehyde dehydrogenase (NAD+) activityAldehyde dehydrogenase, mitochondrialHomo sapiens (human)
aldehyde dehydrogenase [NAD(P)+] activityAldehyde dehydrogenase, mitochondrialHomo sapiens (human)
phenylacetaldehyde dehydrogenase activityAldehyde dehydrogenase, mitochondrialHomo sapiens (human)
electron transfer activityAldehyde dehydrogenase, mitochondrialHomo sapiens (human)
nitroglycerin reductase activityAldehyde dehydrogenase, mitochondrialHomo sapiens (human)
glyceraldehyde-3-phosphate dehydrogenase (NAD+) (non-phosphorylating) activityAldehyde dehydrogenase, mitochondrialHomo sapiens (human)
NAD bindingAldehyde dehydrogenase, mitochondrialHomo sapiens (human)
carboxylesterase activityAldehyde dehydrogenase, mitochondrialHomo sapiens (human)
G protein activityGuanine nucleotide-binding protein GHomo sapiens (human)
adenylate cyclase activator activityGuanine nucleotide-binding protein GHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Ceullar Components (4)

Processvia Protein(s)Taxonomy
mitochondrionAldehyde dehydrogenase, mitochondrialHomo sapiens (human)
mitochondrial matrixAldehyde dehydrogenase, mitochondrialHomo sapiens (human)
extracellular exosomeAldehyde dehydrogenase, mitochondrialHomo sapiens (human)
plasma membraneGuanine nucleotide-binding protein GHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (39)

Assay IDTitleYearJournalArticle
AID588501High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Lethal Factor Protease, MLPCN compound set2010Current protocols in cytometry, Oct, Volume: Chapter 13Microsphere-based flow cytometry protease assays for use in protease activity detection and high-throughput screening.
AID588501High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Lethal Factor Protease, MLPCN compound set2006Cytometry. Part A : the journal of the International Society for Analytical Cytology, May, Volume: 69, Issue:5
Microsphere-based protease assays and screening application for lethal factor and factor Xa.
AID588501High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Lethal Factor Protease, MLPCN compound set2010Assay and drug development technologies, Feb, Volume: 8, Issue:1
High-throughput multiplex flow cytometry screening for botulinum neurotoxin type a light chain protease inhibitors.
AID504810Antagonists of the Thyroid Stimulating Hormone Receptor: HTS campaign2010Endocrinology, Jul, Volume: 151, Issue:7
A small molecule inverse agonist for the human thyroid-stimulating hormone receptor.
AID588499High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain A protease, MLPCN compound set2010Current protocols in cytometry, Oct, Volume: Chapter 13Microsphere-based flow cytometry protease assays for use in protease activity detection and high-throughput screening.
AID588499High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain A protease, MLPCN compound set2006Cytometry. Part A : the journal of the International Society for Analytical Cytology, May, Volume: 69, Issue:5
Microsphere-based protease assays and screening application for lethal factor and factor Xa.
AID588499High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain A protease, MLPCN compound set2010Assay and drug development technologies, Feb, Volume: 8, Issue:1
High-throughput multiplex flow cytometry screening for botulinum neurotoxin type a light chain protease inhibitors.
AID1745845Primary qHTS for Inhibitors of ATXN expression
AID588497High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain F protease, MLPCN compound set2010Current protocols in cytometry, Oct, Volume: Chapter 13Microsphere-based flow cytometry protease assays for use in protease activity detection and high-throughput screening.
AID588497High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain F protease, MLPCN compound set2006Cytometry. Part A : the journal of the International Society for Analytical Cytology, May, Volume: 69, Issue:5
Microsphere-based protease assays and screening application for lethal factor and factor Xa.
AID588497High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain F protease, MLPCN compound set2010Assay and drug development technologies, Feb, Volume: 8, Issue:1
High-throughput multiplex flow cytometry screening for botulinum neurotoxin type a light chain protease inhibitors.
AID651635Viability Counterscreen for Primary qHTS for Inhibitors of ATXN expression
AID504812Inverse Agonists of the Thyroid Stimulating Hormone Receptor: HTS campaign2010Endocrinology, Jul, Volume: 151, Issue:7
A small molecule inverse agonist for the human thyroid-stimulating hormone receptor.
AID395251Increase in human recombinant ALDH2*2 E487K mutant activity expressed in Escherichia coli BL21 cells2008Science (New York, N.Y.), Sep-12, Volume: 321, Issue:5895
Activation of aldehyde dehydrogenase-2 reduces ischemic damage to the heart.
AID395243Activation of human ALDH2 assessed as phosphorylated enzyme at 20 uM in absence of rat PKCepsilon by spectrophotometry2008Science (New York, N.Y.), Sep-12, Volume: 321, Issue:5895
Activation of aldehyde dehydrogenase-2 reduces ischemic damage to the heart.
AID395253Increase in wild type human recombinant ALDH2*1/*1 homotetramer activity expressed in Escherichia coli BL21 cells using wild type allele relative to basal activity2008Science (New York, N.Y.), Sep-12, Volume: 321, Issue:5895
Activation of aldehyde dehydrogenase-2 reduces ischemic damage to the heart.
AID395256Ex vivo cardiac protection in Langendorff perfused Wistar rat heart assessed decrease in myocardial infarct size at 20 uM treated 35 mins before ischemia followed by 60 mins reperfusion by TTC staining2008Science (New York, N.Y.), Sep-12, Volume: 321, Issue:5895
Activation of aldehyde dehydrogenase-2 reduces ischemic damage to the heart.
AID394516Induction of cell-stress in Wistar rat heart assessed as JNK activation at 8.5 mg/kg after 5 mind by Western blot analysis2008Science (New York, N.Y.), Sep-12, Volume: 321, Issue:5895
Activation of aldehyde dehydrogenase-2 reduces ischemic damage to the heart.
AID1762970Anti-myocardial fibrosis activity against cardiac fibroblasts (unknown origin) assessed as reduction in collagen synthesis by measuring reduction in type3 collagen protein expression at 30 uM measured after 24 hrs by western blot analysis2021Bioorganic & medicinal chemistry letters, 07-01, Volume: 43Magnolol, a natural aldehyde dehydrogenase-2 agonist, inhibits the proliferation and collagen synthesis of cardiac fibroblasts.
AID395250Effect on human recombinant his-tagged mitochondrial ALDH5 activity expressed in Escherichia coli BL21 cells at 100 uM2008Science (New York, N.Y.), Sep-12, Volume: 321, Issue:5895
Activation of aldehyde dehydrogenase-2 reduces ischemic damage to the heart.
AID1707630Allosteric activation of recombinant human full-length ALDH2 (18 to 517 residues) expressed in Escherichia coli using acetaldehyde as substrate measured after 3 hrs in presence of NAD+ by fluorescence assay2021European journal of medicinal chemistry, Feb-15, Volume: 212The discovery of novel small molecule allosteric activators of aldehyde dehydrogenase 2.
AID1762965Anti-myocardial fibrosis activity against cardiac fibroblasts (unknown origin) assessed as inhibition of cell viability at 30 uM measured after 24 hrs by MTT assay2021Bioorganic & medicinal chemistry letters, 07-01, Volume: 43Magnolol, a natural aldehyde dehydrogenase-2 agonist, inhibits the proliferation and collagen synthesis of cardiac fibroblasts.
AID1762969Anti-myocardial fibrosis activity against cardiac fibroblasts (unknown origin) assessed as reduction in collagen synthesis by measuring reduction in type1 collagen protein expression at 30 uM measured after 24 hrs by western blot analysis2021Bioorganic & medicinal chemistry letters, 07-01, Volume: 43Magnolol, a natural aldehyde dehydrogenase-2 agonist, inhibits the proliferation and collagen synthesis of cardiac fibroblasts.
AID1762966Anti-myocardial fibrosis activity against cardiac fibroblasts (unknown origin) assessed as inhibition of cell proliferation at 30 uM measured after 24 hrs by EdU incorporation based assay2021Bioorganic & medicinal chemistry letters, 07-01, Volume: 43Magnolol, a natural aldehyde dehydrogenase-2 agonist, inhibits the proliferation and collagen synthesis of cardiac fibroblasts.
AID394517Induction of cell-stress in Wistar rat heart assessed as JNK activation at 8.5 mg/kg after ischemia followed by reperfusion by occluding left anterior descending coronary artery ligation for 35 mins by Western blot analysis2008Science (New York, N.Y.), Sep-12, Volume: 321, Issue:5895
Activation of aldehyde dehydrogenase-2 reduces ischemic damage to the heart.
AID394515Toxicity in Wistar rat assessed as blood parameters at 6 mg/kg/day for 1 week2008Science (New York, N.Y.), Sep-12, Volume: 321, Issue:5895
Activation of aldehyde dehydrogenase-2 reduces ischemic damage to the heart.
AID1707632Protection against middle cerebral artery occlusion-induced Sprague-Dawley rat model of ischemic stroke-like event assessed as reduction in brain infarct size at 50 ug, icv pretreated for 5 mins followed by MCAO surgery for 2 hrs and subsequent reperfusio2021European journal of medicinal chemistry, Feb-15, Volume: 212The discovery of novel small molecule allosteric activators of aldehyde dehydrogenase 2.
AID1762968Anti-myocardial fibrosis activity against cardiac fibroblasts (unknown origin) assessed as reduction in cyclinD1 protein expression at 30 uM measured after 24 hrs by western blot analysis2021Bioorganic & medicinal chemistry letters, 07-01, Volume: 43Magnolol, a natural aldehyde dehydrogenase-2 agonist, inhibits the proliferation and collagen synthesis of cardiac fibroblasts.
AID395244Activation of human ALDH2 assessed as phosphorylated enzyme at 20 uM in presence of rat PKCepsilon by spectrophotometry2008Science (New York, N.Y.), Sep-12, Volume: 321, Issue:5895
Activation of aldehyde dehydrogenase-2 reduces ischemic damage to the heart.
AID1762967Anti-myocardial fibrosis activity against cardiac fibroblasts (unknown origin) assessed as reduction in CDK4 protein expression at 30 uM measured after 24 hrs by western blot analysis2021Bioorganic & medicinal chemistry letters, 07-01, Volume: 43Magnolol, a natural aldehyde dehydrogenase-2 agonist, inhibits the proliferation and collagen synthesis of cardiac fibroblasts.
AID395257Ex vivo cardiac protection in Langendorff perfused Wistar rat heart assessed decrease of CPK release at 20 uM treated 35 mins before ischemia followed by 60 mins reperfusion2008Science (New York, N.Y.), Sep-12, Volume: 321, Issue:5895
Activation of aldehyde dehydrogenase-2 reduces ischemic damage to the heart.
AID395248Effect on alcohol dehydrogenase 1 activity at 100 uM2008Science (New York, N.Y.), Sep-12, Volume: 321, Issue:5895
Activation of aldehyde dehydrogenase-2 reduces ischemic damage to the heart.
AID394514Toxicity in Wistar rat assessed as histopathology at 6 mg/kg/day for 1 week2008Science (New York, N.Y.), Sep-12, Volume: 321, Issue:5895
Activation of aldehyde dehydrogenase-2 reduces ischemic damage to the heart.
AID395252Increase in human recombinant ALDH2*1/*2 E487K mutant heterotetramer activity expressed in Escherichia coli BL21 cells using wild type and mutant allele2008Science (New York, N.Y.), Sep-12, Volume: 321, Issue:5895
Activation of aldehyde dehydrogenase-2 reduces ischemic damage to the heart.
AID395255Activation of wild type human recombinant ALDH2*1 expressed Escherichia coli BL21 cells at 10 uM relative to control2008Science (New York, N.Y.), Sep-12, Volume: 321, Issue:5895
Activation of aldehyde dehydrogenase-2 reduces ischemic damage to the heart.
AID395249Effect on human recombinant his-tagged cytosolic ALDH1A1 activity expressed in Escherichia coli BL21 cells at 100 uM2008Science (New York, N.Y.), Sep-12, Volume: 321, Issue:5895
Activation of aldehyde dehydrogenase-2 reduces ischemic damage to the heart.
AID395254Activation of human recombinant ALDH2*2 E487K mutant expressed Escherichia coli BL21 cells at 10 uM relative to control2008Science (New York, N.Y.), Sep-12, Volume: 321, Issue:5895
Activation of aldehyde dehydrogenase-2 reduces ischemic damage to the heart.
AID394513Reduction of cardiac damage in acute myocardial infarction Wistar rat model assessed as decrease in myocardial infarction at 8.5 mg/kg treated 5 mins before ischemia by TTC staining2008Science (New York, N.Y.), Sep-12, Volume: 321, Issue:5895
Activation of aldehyde dehydrogenase-2 reduces ischemic damage to the heart.
AID395258Reduction of cardiac damage in acute myocardial infarction Wistar rat model assessed as decrease in infarct size at 8.5 mg/kg treated before left anterior descending coronary artery ligation measured after 35 mins of ischemia followed by 60 mins reperfusi2008Science (New York, N.Y.), Sep-12, Volume: 321, Issue:5895
Activation of aldehyde dehydrogenase-2 reduces ischemic damage to the heart.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (68)

TimeframeStudies, This Drug (%)All Drugs %
pre-19900 (0.00)18.7374
1990's0 (0.00)18.2507
2000's2 (2.94)29.6817
2010's53 (77.94)24.3611
2020's13 (19.12)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 11.20

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 Index11.20 (24.57)
Research Supply Index4.23 (2.92)
Research Growth Index5.43 (4.65)
Search Engine Demand Index0.00 (26.88)
Search Engine Supply Index0.00 (0.95)

This Compound (11.20)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Reviews1 (1.47%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other67 (98.53%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]