Page last updated: 2024-11-07

l 694247

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Description

L 694247: a 5-HT(1D) receptor agonist; structure in first source [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Cross-References

ID SourceID
PubMed CID132059
CHEMBL ID39317
CHEBI ID92341
SCHEMBL ID1321182
MeSH IDM0227204

Synonyms (42)

Synonym
unii-pz5dp5en56
pz5dp5en56 ,
HMS3266D14
BRD-K18816859-001-01-4
gtpl15
PDSP2_001378
BIOMOL-NT_000112
NCGC00024787-01
tocris-0781
BPBIO1_000001
l694247
l-694,247
NCGC00024787-02
PDSP1_001394
l-694247
137403-12-4
methanesulfonamide, n-(4-((5-(3-(2-aminoethyl)-1h-indol-5-yl)-1,2,4-oxadiazol-3-yl)methyl)phenyl)-
2-(5-(3-(4-(methylsulfonylamino)benzyl)-1,2,4-oxadiazol-5-yl)-1h-indole-3-yl)ethylamine
l 694247
CHEMBL39317
L000336
n-[4-[[5-[3-(2-aminoethyl)-1h-indol-5-yl]-1,2,4-oxadiazol-3-yl]methyl]phenyl]methanesulfonamide
SCHEMBL1321182
n-(4-((5-(3-(2-aminoethyl)-1h-indol-5-yl)-1,2,4-oxadiazol-3-yl)methyl)phenyl)methanesulfonamide
AKOS016003154
bdbm50406771
2-[5-[3-(4-methylsulfonylamino)benzyl-1,2,4-oxadiazol-5-yl]-1h-indol-3-yl]ethanamine
methanesulfonamide,n-[4-[[5-[3-(2-aminoethyl)-1h-indol-5-yl]-1,2,4-oxadiazol-3-yl]methyl]phenyl]-
DTXSID20160175
SR-01000597694-1
sr-01000597694
CHEBI:92341
J-007018
HMS3675J15
HMS3411J15
Q6456076
l-694247;l 694,247; l694,247
BCP29991
EX-A3241
A846232
methanesulfonamide, n-[4-[[5-[3-(2-aminoethyl)-1h-indol-5-yl]-1,2,4-oxadiazol-3-yl]methyl]phenyl]-
n-(4-((5-(3-(2-azanylethyl)-1h-indol-5-yl)-1,2,4-oxadiazol-3-yl)methyl)phenyl)methanesulfonamide

Research Excerpts

Bioavailability

ExcerptReferenceRelevance
" The objective of this work was to identify potent and selective 5-HT1D receptor agonists with high oral bioavailability and low central nervous system penetration."( Synthesis and serotonergic activity of N,N-dimethyl-2-[5-(1,2,4-triazol-1-ylmethyl)-1H-indol-3-yl]ethylamine and analogues: potent agonists for 5-HT1D receptors.
Baker, R; Beer, MS; Davey, WB; Guiblin, AR; Jelley, RA; Reeve, AJ; Routledge, H; Sternfeld, F; Street, LJ; Watt, AP, 1995
)
0.29
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Drug Classes (1)

ClassDescription
tryptaminesTryptamine and its substitution derivatives.
[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 (36)

Potency Measurements

ProteinTaxonomyMeasurementAverage (µ)Min (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Chain A, 2-oxoglutarate OxygenaseHomo sapiens (human)Potency28.18380.177814.390939.8107AID2147
Chain A, CruzipainTrypanosoma cruziPotency31.62280.002014.677939.8107AID1476
TDP1 proteinHomo sapiens (human)Potency20.59620.000811.382244.6684AID686978
regulator of G-protein signaling 4Homo sapiens (human)Potency4.27150.531815.435837.6858AID504845
glucocerebrosidaseHomo sapiens (human)Potency39.81070.01268.156944.6684AID2101
cytochrome P450 2D6 isoform 1Homo sapiens (human)Potency0.12590.00207.533739.8107AID891
cytochrome P450 2C19 precursorHomo sapiens (human)Potency15.84890.00255.840031.6228AID899
cytochrome P450 2C9 precursorHomo sapiens (human)Potency31.62280.00636.904339.8107AID883
15-hydroxyprostaglandin dehydrogenase [NAD(+)] isoform 1Homo sapiens (human)Potency28.18380.001815.663839.8107AID894
cytochrome P450 3A4 isoform 1Homo sapiens (human)Potency15.84890.031610.279239.8107AID884; AID885
lethal factor (plasmid)Bacillus anthracis str. A2012Potency12.58930.020010.786931.6228AID912
Gamma-aminobutyric acid receptor subunit piRattus norvegicus (Norway rat)Potency15.84891.000012.224831.6228AID885
Gamma-aminobutyric acid receptor subunit beta-1Rattus norvegicus (Norway rat)Potency15.84891.000012.224831.6228AID885
Gamma-aminobutyric acid receptor subunit deltaRattus norvegicus (Norway rat)Potency15.84891.000012.224831.6228AID885
Gamma-aminobutyric acid receptor subunit gamma-2Rattus norvegicus (Norway rat)Potency15.84891.000012.224831.6228AID885
Gamma-aminobutyric acid receptor subunit alpha-5Rattus norvegicus (Norway rat)Potency15.84891.000012.224831.6228AID885
Gamma-aminobutyric acid receptor subunit alpha-3Rattus norvegicus (Norway rat)Potency15.84891.000012.224831.6228AID885
Gamma-aminobutyric acid receptor subunit gamma-1Rattus norvegicus (Norway rat)Potency15.84891.000012.224831.6228AID885
Gamma-aminobutyric acid receptor subunit alpha-2Rattus norvegicus (Norway rat)Potency15.84891.000012.224831.6228AID885
Gamma-aminobutyric acid receptor subunit alpha-4Rattus norvegicus (Norway rat)Potency15.84891.000012.224831.6228AID885
Gamma-aminobutyric acid receptor subunit gamma-3Rattus norvegicus (Norway rat)Potency15.84891.000012.224831.6228AID885
Gamma-aminobutyric acid receptor subunit alpha-6Rattus norvegicus (Norway rat)Potency15.84891.000012.224831.6228AID885
Histamine H2 receptorCavia porcellus (domestic guinea pig)Potency31.62280.00638.235039.8107AID883
Gamma-aminobutyric acid receptor subunit alpha-1Rattus norvegicus (Norway rat)Potency15.84891.000012.224831.6228AID885
Gamma-aminobutyric acid receptor subunit beta-3Rattus norvegicus (Norway rat)Potency15.84891.000012.224831.6228AID885
Gamma-aminobutyric acid receptor subunit beta-2Rattus norvegicus (Norway rat)Potency15.84891.000012.224831.6228AID885
GABA theta subunitRattus norvegicus (Norway rat)Potency15.84891.000012.224831.6228AID885
Gamma-aminobutyric acid receptor subunit epsilonRattus norvegicus (Norway rat)Potency15.84891.000012.224831.6228AID885
[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)
5-hydroxytryptamine receptor 1AHomo sapiens (human)IC50 (µMol)0.00320.00010.666410.0000AID3979
5-hydroxytryptamine receptor 2CRattus norvegicus (Norway rat)IC50 (µMol)0.31620.00040.629810.0000AID5077
5-hydroxytryptamine receptor 2ARattus norvegicus (Norway rat)IC50 (µMol)0.31620.00040.908610.0000AID5077
5-hydroxytryptamine receptor 2CHomo sapiens (human)IC50 (µMol)0.31620.00011.03029.0000AID4749
5-hydroxytryptamine receptor 2BRattus norvegicus (Norway rat)IC50 (µMol)0.31620.00040.615610.0000AID5077
5-hydroxytryptamine receptor 3ARattus norvegicus (Norway rat)IC50 (µMol)10.00000.00021.13514.6000AID6282
5-hydroxytryptamine receptor 1DSus scrofa (pig)IC50 (µMol)0.00030.00030.64963.7153AID4857; AID4864
5-hydroxytryptamine receptor 3BRattus norvegicus (Norway rat)IC50 (µMol)10.00000.00041.17424.6000AID6282
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Biological Processes (30)

Processvia Protein(s)Taxonomy
behavioral fear response5-hydroxytryptamine receptor 1AHomo sapiens (human)
G protein-coupled receptor signaling pathway5-hydroxytryptamine receptor 1AHomo sapiens (human)
adenylate cyclase-inhibiting serotonin receptor signaling pathway5-hydroxytryptamine receptor 1AHomo sapiens (human)
serotonin receptor signaling pathway5-hydroxytryptamine receptor 1AHomo sapiens (human)
gamma-aminobutyric acid signaling pathway5-hydroxytryptamine receptor 1AHomo sapiens (human)
positive regulation of cell population proliferation5-hydroxytryptamine receptor 1AHomo sapiens (human)
regulation of serotonin secretion5-hydroxytryptamine receptor 1AHomo sapiens (human)
regulation of vasoconstriction5-hydroxytryptamine receptor 1AHomo sapiens (human)
exploration behavior5-hydroxytryptamine receptor 1AHomo sapiens (human)
regulation of dopamine metabolic process5-hydroxytryptamine receptor 1AHomo sapiens (human)
serotonin metabolic process5-hydroxytryptamine receptor 1AHomo sapiens (human)
regulation of hormone secretion5-hydroxytryptamine receptor 1AHomo sapiens (human)
regulation of behavior5-hydroxytryptamine receptor 1AHomo sapiens (human)
chemical synaptic transmission5-hydroxytryptamine receptor 1AHomo sapiens (human)
G protein-coupled receptor signaling pathway, coupled to cyclic nucleotide second messenger5-hydroxytryptamine receptor 1AHomo sapiens (human)
behavioral fear response5-hydroxytryptamine receptor 2CHomo sapiens (human)
intracellular calcium ion homeostasis5-hydroxytryptamine receptor 2CHomo sapiens (human)
phospholipase C-activating G protein-coupled receptor signaling pathway5-hydroxytryptamine receptor 2CHomo sapiens (human)
phospholipase C-activating serotonin receptor signaling pathway5-hydroxytryptamine receptor 2CHomo sapiens (human)
locomotory behavior5-hydroxytryptamine receptor 2CHomo sapiens (human)
feeding behavior5-hydroxytryptamine receptor 2CHomo sapiens (human)
positive regulation of phosphatidylinositol biosynthetic process5-hydroxytryptamine receptor 2CHomo sapiens (human)
cGMP-mediated signaling5-hydroxytryptamine receptor 2CHomo sapiens (human)
regulation of nervous system process5-hydroxytryptamine receptor 2CHomo sapiens (human)
regulation of appetite5-hydroxytryptamine receptor 2CHomo sapiens (human)
regulation of corticotropin-releasing hormone secretion5-hydroxytryptamine receptor 2CHomo sapiens (human)
positive regulation of fat cell differentiation5-hydroxytryptamine receptor 2CHomo sapiens (human)
positive regulation of calcium-mediated signaling5-hydroxytryptamine receptor 2CHomo sapiens (human)
release of sequestered calcium ion into cytosol5-hydroxytryptamine receptor 2CHomo sapiens (human)
positive regulation of ERK1 and ERK2 cascade5-hydroxytryptamine receptor 2CHomo sapiens (human)
G protein-coupled serotonin receptor signaling pathway5-hydroxytryptamine receptor 2CHomo sapiens (human)
serotonin receptor signaling pathway5-hydroxytryptamine receptor 2CHomo sapiens (human)
G protein-coupled receptor signaling pathway, coupled to cyclic nucleotide second messenger5-hydroxytryptamine receptor 2CHomo sapiens (human)
chemical synaptic transmission5-hydroxytryptamine receptor 2CHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Molecular Functions (8)

Processvia Protein(s)Taxonomy
G protein-coupled serotonin receptor activity5-hydroxytryptamine receptor 1AHomo sapiens (human)
protein binding5-hydroxytryptamine receptor 1AHomo sapiens (human)
receptor-receptor interaction5-hydroxytryptamine receptor 1AHomo sapiens (human)
neurotransmitter receptor activity5-hydroxytryptamine receptor 1AHomo sapiens (human)
serotonin binding5-hydroxytryptamine receptor 1AHomo sapiens (human)
Gq/11-coupled serotonin receptor activity5-hydroxytryptamine receptor 2CHomo sapiens (human)
G protein-coupled serotonin receptor activity5-hydroxytryptamine receptor 2CHomo sapiens (human)
protein binding5-hydroxytryptamine receptor 2CHomo sapiens (human)
identical protein binding5-hydroxytryptamine receptor 2CHomo sapiens (human)
serotonin binding5-hydroxytryptamine receptor 2CHomo sapiens (human)
1-(4-iodo-2,5-dimethoxyphenyl)propan-2-amine binding5-hydroxytryptamine receptor 2CHomo sapiens (human)
neurotransmitter receptor activity5-hydroxytryptamine receptor 2CHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Ceullar Components (4)

Processvia Protein(s)Taxonomy
plasma membrane5-hydroxytryptamine receptor 1AHomo sapiens (human)
synapse5-hydroxytryptamine receptor 1AHomo sapiens (human)
plasma membrane5-hydroxytryptamine receptor 1AHomo sapiens (human)
dendrite5-hydroxytryptamine receptor 1AHomo sapiens (human)
plasma membraneGamma-aminobutyric acid receptor subunit gamma-2Rattus norvegicus (Norway rat)
plasma membrane5-hydroxytryptamine receptor 2CHomo sapiens (human)
synapse5-hydroxytryptamine receptor 2CHomo sapiens (human)
G protein-coupled serotonin receptor complex5-hydroxytryptamine receptor 2CHomo sapiens (human)
plasma membrane5-hydroxytryptamine receptor 2CHomo sapiens (human)
dendrite5-hydroxytryptamine receptor 2CHomo sapiens (human)
plasma membraneGamma-aminobutyric acid receptor subunit alpha-1Rattus norvegicus (Norway rat)
plasma membraneGamma-aminobutyric acid receptor subunit beta-2Rattus norvegicus (Norway rat)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (17)

Assay IDTitleYearJournalArticle
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.
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.
AID4864Displacement of radioligand [3H]5-HT binding to 5-hydroxytryptamine 1D receptor in pig caudate membrane1993Journal of medicinal chemistry, May-28, Volume: 36, Issue:11
Synthesis and serotonergic activity of 5-(oxadiazolyl)tryptamines: potent agonists for 5-HT1D receptors.
AID4749Displacement of [3H]mesulergine from pig cortex 5-hydroxytryptamine 1C receptor1993Journal of medicinal chemistry, May-28, Volume: 36, Issue:11
Synthesis and serotonergic activity of 5-(oxadiazolyl)tryptamines: potent agonists for 5-HT1D receptors.
AID19418Partition coefficient (logD7.4)1995Journal of medicinal chemistry, May-12, Volume: 38, Issue:10
Synthesis and serotonergic activity of N,N-dimethyl-2-[5-(1,2,4-triazol-1-ylmethyl)-1H-indol-3-yl]ethylamine and analogues: potent agonists for 5-HT1D receptors.
AID5077isplacement of [3H]DOB from rat cortex homogenate 5-hydroxytryptamine 2 receptor1993Journal of medicinal chemistry, May-28, Volume: 36, Issue:11
Synthesis and serotonergic activity of 5-(oxadiazolyl)tryptamines: potent agonists for 5-HT1D receptors.
AID167019Relative maximum is the relative efficacy for serotonergic activity on rabbit saphenous vein with respect to 1 uM 5-HT1993Journal of medicinal chemistry, May-28, Volume: 36, Issue:11
Synthesis and serotonergic activity of 5-(oxadiazolyl)tryptamines: potent agonists for 5-HT1D receptors.
AID3979Displacement of [3H]8-OH-DPAT from pig cortex 5-hydroxytryptamine 1A receptor1993Journal of medicinal chemistry, May-28, Volume: 36, Issue:11
Synthesis and serotonergic activity of 5-(oxadiazolyl)tryptamines: potent agonists for 5-HT1D receptors.
AID167003Serotonergic activity was assessed in vitro on the New Zealand white rabbit saphenous vein preparation1993Journal of medicinal chemistry, May-28, Volume: 36, Issue:11
Synthesis and serotonergic activity of 5-(oxadiazolyl)tryptamines: potent agonists for 5-HT1D receptors.
AID6282Displacement of [3H]-Q-ICS 205-930 from rat cortex homogenate 5-hydroxytryptamine 3 receptor1993Journal of medicinal chemistry, May-28, Volume: 36, Issue:11
Synthesis and serotonergic activity of 5-(oxadiazolyl)tryptamines: potent agonists for 5-HT1D receptors.
AID4857Binding activity against 5-hydroxytryptamine 1D receptor from pig caudate membrane using [3H]5-HT as radioligand1995Journal of medicinal chemistry, May-12, Volume: 38, Issue:10
Synthesis and serotonergic activity of N,N-dimethyl-2-[5-(1,2,4-triazol-1-ylmethyl)-1H-indol-3-yl]ethylamine and analogues: potent agonists for 5-HT1D receptors.
AID26301Partition coefficient (logD7.4)1993Journal of medicinal chemistry, May-28, Volume: 36, Issue:11
Synthesis and serotonergic activity of 5-(oxadiazolyl)tryptamines: potent agonists for 5-HT1D receptors.
AID1159607Screen for inhibitors of RMI FANCM (MM2) intereaction2016Journal of biomolecular screening, Jul, Volume: 21, Issue:6
A High-Throughput Screening Strategy to Identify Protein-Protein Interaction Inhibitors That Block the Fanconi Anemia DNA Repair Pathway.
AID1346264Human 5-HT1B receptor (5-Hydroxytryptamine receptors)1999European journal of pharmacology, Sep-10, Volume: 380, Issue:2-3
Identification of an amino acid residue important for binding of methiothepin and sumatriptan to the human 5-HT(1B) receptor.
AID624210Agonists at Human 5-Hydroxytryptamine receptor 5-HT1A1997Naunyn-Schmiedeberg's archives of pharmacology, Jun, Volume: 355, Issue:6
Agonist activity of antimigraine drugs at recombinant human 5-HT1A receptors: potential implications for prophylactic and acute therapy.
AID1345615Human 5-HT1A receptor (5-Hydroxytryptamine receptors)1997Naunyn-Schmiedeberg's archives of pharmacology, Jun, Volume: 355, Issue:6
Agonist activity of antimigraine drugs at recombinant human 5-HT1A receptors: potential implications for prophylactic and acute therapy.
AID1346528Human 5-HT1D receptor (5-Hydroxytryptamine receptors)1998Molecular pharmacology, Dec, Volume: 54, Issue:6
Chimeric receptor analysis of the ketanserin binding site in the human 5-Hydroxytryptamine1D receptor: importance of the second extracellular loop and fifth transmembrane domain in antagonist binding.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (32)

TimeframeStudies, This Drug (%)All Drugs %
pre-19900 (0.00)18.7374
1990's17 (53.13)18.2507
2000's6 (18.75)29.6817
2010's6 (18.75)24.3611
2020's3 (9.38)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 10.99

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 Index10.99 (24.57)
Research Supply Index3.50 (2.92)
Research Growth Index4.48 (4.65)
Search Engine Demand Index0.00 (26.88)
Search Engine Supply Index0.00 (0.95)

This Compound (10.99)

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%
Other32 (100.00%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]