Page last updated: 2024-12-10

am 281

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

Description

AM 281: radioligand for cannabinoid CB1 receptors; structure in first source [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Cross-References

ID SourceID
PubMed CID4302962
CHEMBL ID476833
CHEBI ID93039
SCHEMBL ID1517458
MeSH IDM0285161

Synonyms (50)

Synonym
HMS3267K18
BRD-K59419204-001-01-9
am 281
n-(morpholin-4-yl)-5-(4-iodophenyl)-1-(2,4-dichlorphenyl)-4-methyl-1h-pyrazole-3-carboxamide
am281 cpd
am281
1-(2,4-dichlorophenyl)-5-(4-iodophenyl)-4-methyl-n-morpholin-4-ylpyrazole-3-carboxamide
gtpl741
am281, >=98% (hplc)
tocris-1115
NCGC00025009-01
NCGC00025009-02
L023967
bdbm50267372
1-(2,4-dichlorophenyl)-5-(4-iodophenyl)-4-methyl-n-morpholino-1h-pyrazole-3-carboxamide
am-281
CHEMBL476833 ,
202463-68-1
1-(2,4-dichlorophenyl)-5-(4-iodophenyl)-4-methyl-n-4-morpholinyl-1h-pyrazole-3-carboxamide
SCHEMBL1517458
1-(2,4-dichloro-phenyl)-5-(4-iodo-phenyl)-4-methyl-1h-pyrazole-3-carboxylic acid morpholin-4-ylamide
AJFFBPZYXRNAIC-UHFFFAOYSA-N
AKOS024456391
1h-pyrazole-3-carboxamide,1-(2,4-dichlorophenyl)-5-(4-iodophenyl)-4-methyl-n-4-morpholinyl-
SR-01000597389-1
sr-01000597389
1-(2,4-dichlorophenyl)-5-(4-iodophenyl)-4-methyl-n-(morpholin-4-yl)-1h-pyrazole-3-carboxamide
CHEBI:93039
CS-0007129
HY-13505
1h-pyrazole-3-carboxamide, 1-(2,4-dichlorophenyl)-5-(4-iodophenyl)-4-methyl-n-4-morpholinyl-
J-013143
SBP4A4DYH2 ,
n-(morpholin-4-yl)-1-(2,4-dichlorophenyl)-5-(4-iodophenyl)-4-methyl-1h-pyrazole-3-carboxamide
FT-0752198
BCP07951
c21h19cl2in4o2
1-(2,4-dichlorophenyl)-5-(4-iodophe nyl)-4-methyl-n-4-morpholinyl-1h-pyrazole-3-carbox amide
HB2312
EX-A1546
HMS3676I17
unii-sbp4a4dyh2
HMS3412I17
Q27074423
AC-35904
discontinued see m314985
AS-75898
CIA46368
DTXSID601122269
E98706

Research Excerpts

Toxicity

ExcerptReferenceRelevance
" Cisplatin produces a cumulative toxic effect on peripheral nerves, and 30-40% of cancer patients receiving this agent experience pain."( Cannabinoid type-1 receptor reduces pain and neurotoxicity produced by chemotherapy.
Harding-Rose, C; Khasabov, S; Khasabova, IA; Paz, J; Seybold, VS; Simone, DA, 2012
)
0.38
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Drug Classes (2)

ClassDescription
pyrazoles
ring assemblyTwo or more cyclic systems (single rings or fused systems) which are directly joined to each other by double or single bonds are named ring assemblies when the number of such direct ring junctions is one less than the number of cyclic systems involved.
[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 (15)

Potency Measurements

ProteinTaxonomyMeasurementAverage (µ)Min (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Chain A, MAJOR APURINIC/APYRIMIDINIC ENDONUCLEASEHomo sapiens (human)Potency22.38720.003245.467312,589.2998AID2517
Chain A, TYROSYL-DNA PHOSPHODIESTERASEHomo sapiens (human)Potency70.79460.004023.8416100.0000AID485290
Chain A, 2-oxoglutarate OxygenaseHomo sapiens (human)Potency39.81070.177814.390939.8107AID2147
15-lipoxygenase, partialHomo sapiens (human)Potency19.95260.012610.691788.5700AID887
USP1 protein, partialHomo sapiens (human)Potency39.81070.031637.5844354.8130AID504865
Microtubule-associated protein tauHomo sapiens (human)Potency35.48130.180013.557439.8107AID1460
regulator of G-protein signaling 4Homo sapiens (human)Potency8.43680.531815.435837.6858AID504845
cytochrome P450 2D6 isoform 1Homo sapiens (human)Potency12.58930.00207.533739.8107AID891
cytochrome P450 2C19 precursorHomo sapiens (human)Potency7.94330.00255.840031.6228AID899
cytochrome P450 2C9 precursorHomo sapiens (human)Potency6.30960.00636.904339.8107AID883
lethal factor (plasmid)Bacillus anthracis str. A2012Potency31.62280.020010.786931.6228AID912
Histamine H2 receptorCavia porcellus (domestic guinea pig)Potency6.30960.00638.235039.8107AID883
[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)
Cannabinoid receptor 1Rattus norvegicus (Norway rat)Ki0.00450.00020.566510.0000AID49497
Cannabinoid receptor 1Homo sapiens (human)Ki0.42200.00010.50779.6000AID416057
Cannabinoid receptor 2 Homo sapiens (human)Ki4.20000.00000.415610.0000AID417016
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Biological Processes (39)

Processvia Protein(s)Taxonomy
positive regulation of acute inflammatory response to antigenic stimulusCannabinoid receptor 1Homo sapiens (human)
G protein-coupled receptor signaling pathway, coupled to cyclic nucleotide second messengerCannabinoid receptor 1Homo sapiens (human)
adenylate cyclase-modulating G protein-coupled receptor signaling pathwayCannabinoid receptor 1Homo sapiens (human)
spermatogenesisCannabinoid receptor 1Homo sapiens (human)
axonal fasciculationCannabinoid receptor 1Homo sapiens (human)
response to nutrientCannabinoid receptor 1Homo sapiens (human)
memoryCannabinoid receptor 1Homo sapiens (human)
positive regulation of neuron projection developmentCannabinoid receptor 1Homo sapiens (human)
negative regulation of serotonin secretionCannabinoid receptor 1Homo sapiens (human)
positive regulation of fever generationCannabinoid receptor 1Homo sapiens (human)
negative regulation of fatty acid beta-oxidationCannabinoid receptor 1Homo sapiens (human)
regulation of synaptic transmission, GABAergicCannabinoid receptor 1Homo sapiens (human)
response to lipopolysaccharideCannabinoid receptor 1Homo sapiens (human)
negative regulation of mast cell activationCannabinoid receptor 1Homo sapiens (human)
negative regulation of dopamine secretionCannabinoid receptor 1Homo sapiens (human)
response to nicotineCannabinoid receptor 1Homo sapiens (human)
cannabinoid signaling pathwayCannabinoid receptor 1Homo sapiens (human)
response to cocaineCannabinoid receptor 1Homo sapiens (human)
glucose homeostasisCannabinoid receptor 1Homo sapiens (human)
positive regulation of apoptotic processCannabinoid receptor 1Homo sapiens (human)
response to ethanolCannabinoid receptor 1Homo sapiens (human)
negative regulation of action potentialCannabinoid receptor 1Homo sapiens (human)
negative regulation of blood pressureCannabinoid receptor 1Homo sapiens (human)
positive regulation of blood pressureCannabinoid receptor 1Homo sapiens (human)
regulation of insulin secretionCannabinoid receptor 1Homo sapiens (human)
regulation of synaptic transmission, glutamatergicCannabinoid receptor 1Homo sapiens (human)
maternal process involved in female pregnancyCannabinoid receptor 1Homo sapiens (human)
regulation of feeding behaviorCannabinoid receptor 1Homo sapiens (human)
regulation of penile erectionCannabinoid receptor 1Homo sapiens (human)
retrograde trans-synaptic signaling by endocannabinoidCannabinoid receptor 1Homo sapiens (human)
regulation of presynaptic cytosolic calcium ion concentrationCannabinoid receptor 1Homo sapiens (human)
trans-synaptic signaling by endocannabinoid, modulating synaptic transmissionCannabinoid receptor 1Homo sapiens (human)
adenylate cyclase-activating G protein-coupled receptor signaling pathwayCannabinoid receptor 1Homo sapiens (human)
regulation of metabolic processCannabinoid receptor 1Homo sapiens (human)
response to amphetamineCannabinoid receptor 2 Homo sapiens (human)
inflammatory responseCannabinoid receptor 2 Homo sapiens (human)
immune responseCannabinoid receptor 2 Homo sapiens (human)
G protein-coupled receptor signaling pathway, coupled to cyclic nucleotide second messengerCannabinoid receptor 2 Homo sapiens (human)
leukocyte chemotaxisCannabinoid receptor 2 Homo sapiens (human)
negative regulation of synaptic transmission, GABAergicCannabinoid receptor 2 Homo sapiens (human)
response to lipopolysaccharideCannabinoid receptor 2 Homo sapiens (human)
negative regulation of mast cell activationCannabinoid receptor 2 Homo sapiens (human)
cannabinoid signaling pathwayCannabinoid receptor 2 Homo sapiens (human)
negative regulation of action potentialCannabinoid receptor 2 Homo sapiens (human)
regulation of metabolic processCannabinoid receptor 2 Homo sapiens (human)
adenylate cyclase-activating G protein-coupled receptor signaling pathwayCannabinoid receptor 2 Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Molecular Functions (4)

Processvia Protein(s)Taxonomy
cannabinoid receptor activityCannabinoid receptor 1Homo sapiens (human)
protein bindingCannabinoid receptor 1Homo sapiens (human)
identical protein bindingCannabinoid receptor 1Homo sapiens (human)
G protein-coupled receptor activityCannabinoid receptor 1Homo sapiens (human)
protein bindingCannabinoid receptor 2 Homo sapiens (human)
cannabinoid receptor activityCannabinoid receptor 2 Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Ceullar Components (13)

Processvia Protein(s)Taxonomy
mitochondrial outer membraneCannabinoid receptor 1Homo sapiens (human)
plasma membraneCannabinoid receptor 1Homo sapiens (human)
actin cytoskeletonCannabinoid receptor 1Homo sapiens (human)
growth coneCannabinoid receptor 1Homo sapiens (human)
presynaptic membraneCannabinoid receptor 1Homo sapiens (human)
membrane raftCannabinoid receptor 1Homo sapiens (human)
glutamatergic synapseCannabinoid receptor 1Homo sapiens (human)
GABA-ergic synapseCannabinoid receptor 1Homo sapiens (human)
plasma membraneCannabinoid receptor 1Homo sapiens (human)
cytoplasmCannabinoid receptor 1Homo sapiens (human)
plasma membraneCannabinoid receptor 2 Homo sapiens (human)
dendriteCannabinoid receptor 2 Homo sapiens (human)
extrinsic component of cytoplasmic side of plasma membraneCannabinoid receptor 2 Homo sapiens (human)
perikaryonCannabinoid receptor 2 Homo sapiens (human)
endoplasmic reticulumCannabinoid receptor 2 Homo sapiens (human)
plasma membraneCannabinoid receptor 2 Homo sapiens (human)
cytoplasmCannabinoid receptor 2 Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (15)

Assay IDTitleYearJournalArticle
AID1347154Primary screen GU AMC 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.
AID1508630Primary qHTS for small molecule stabilizers of the endoplasmic reticulum resident proteome: Secreted ER Calcium Modulated Protein (SERCaMP) assay2021Cell reports, 04-27, Volume: 35, Issue:4
A target-agnostic screen identifies approved drugs to stabilize the endoplasmic reticulum-resident proteome.
AID417375Antagonist activity at cannabinoid CB1 receptor in rat brain cortical membrane assessed as effect on GTPgammaS binding at 30 uM by liquid scintillation counting relative to CP-559402009Bioorganic & medicinal chemistry, Apr-01, Volume: 17, Issue:7
Synthesis and pharmacological evaluation of coumarin derivatives as cannabinoid receptor antagonists and inverse agonists.
AID19936Partition coefficient (logD7.4)2003Journal of medicinal chemistry, Feb-13, Volume: 46, Issue:4
Synthesis, structure-activity relationship, and evaluation of SR141716 analogues: development of central cannabinoid receptor ligands with lower lipophilicity.
AID417018Binding affinity to rat spleen cannabinoid CB2 receptor2009Bioorganic & medicinal chemistry, Apr-01, Volume: 17, Issue:7
Synthesis and pharmacological evaluation of coumarin derivatives as cannabinoid receptor antagonists and inverse agonists.
AID417377Inverse agonist activity at human recombinant cannabinoid CB1 receptor expressed in HEK293 cells assessed as decrease in GTPgammaS binding at 30 uM by liquid scintillation counting relative to CP-559402009Bioorganic & medicinal chemistry, Apr-01, Volume: 17, Issue:7
Synthesis and pharmacological evaluation of coumarin derivatives as cannabinoid receptor antagonists and inverse agonists.
AID416057Displacement of [3H]CP-55940 form human recombinant CB1 receptor expressed in HEK293 cells by liquid scintillation counting2009European journal of medicinal chemistry, Feb, Volume: 44, Issue:2
Analogs of JHU75528, a PET ligand for imaging of cerebral cannabinoid receptors (CB1): development of ligands with optimized lipophilicity and binding affinity.
AID21880Distribution coefficient was determined2003Journal of medicinal chemistry, Feb-13, Volume: 46, Issue:4
Synthesis, structure-activity relationship, and evaluation of SR141716 analogues: development of central cannabinoid receptor ligands with lower lipophilicity.
AID417016Displacement of [3H]CP-55940 from human recombinant cannabinoid CB2 receptor expressed in HEK293 cells2009Bioorganic & medicinal chemistry, Apr-01, Volume: 17, Issue:7
Synthesis and pharmacological evaluation of coumarin derivatives as cannabinoid receptor antagonists and inverse agonists.
AID49497Binding affinity was determined by using a competition assay with [125 I]- AM251 against rat cannabinoid receptor 12003Journal of medicinal chemistry, Feb-13, Volume: 46, Issue:4
Synthesis, structure-activity relationship, and evaluation of SR141716 analogues: development of central cannabinoid receptor ligands with lower lipophilicity.
AID417014Displacement of [3H]CP-55940 from cannabinoid CB1 receptor in rat brain cortical membrane2009Bioorganic & medicinal chemistry, Apr-01, Volume: 17, Issue:7
Synthesis and pharmacological evaluation of coumarin derivatives as cannabinoid receptor antagonists and inverse agonists.
AID417379Inverse agonist activity at cannabinoid CB1 receptor in rat brain cortical membrane assessed as decrease in GTPgammaS binding at 30 uM by liquid scintillation counting relative to basal level2009Bioorganic & medicinal chemistry, Apr-01, Volume: 17, Issue:7
Synthesis and pharmacological evaluation of coumarin derivatives as cannabinoid receptor antagonists and inverse agonists.
AID1346753Rat CB1 receptor (Cannabinoid receptors)1999AAPS pharmSci, , Volume: 1, Issue:2
Design and synthesis of the CB1 selective cannabinoid antagonist AM281: a potential human SPECT ligand.
AID1345070Human GPR55 (GPR18, GPR55 and GPR119)2010British journal of pharmacology, Jun, Volume: 160, Issue:3
GPR55 ligands promote receptor coupling to multiple signalling pathways.
AID1345070Human GPR55 (GPR18, GPR55 and GPR119)2007British journal of pharmacology, Dec, Volume: 152, Issue:7
The orphan receptor GPR55 is a novel cannabinoid receptor.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (103)

TimeframeStudies, This Drug (%)All Drugs %
pre-19900 (0.00)18.7374
1990's4 (3.88)18.2507
2000's53 (51.46)29.6817
2010's42 (40.78)24.3611
2020's4 (3.88)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 26.41

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 Index26.41 (24.57)
Research Supply Index4.65 (2.92)
Research Growth Index5.27 (4.65)
Search Engine Demand Index25.99 (26.88)
Search Engine Supply Index2.00 (0.95)

This Compound (26.41)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Reviews1 (0.96%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other103 (99.04%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]