Page last updated: 2024-11-07

amthamine

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

Description

amthamine: histamine H2 receptor agonist; structure & RN given in first source; RN given refers to parent cpd [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Cross-References

ID SourceID
PubMed CID126688
CHEMBL ID293762
CHEBI ID92694
SCHEMBL ID400272
MeSH IDM0205037

Synonyms (27)

Synonym
BRD-K39670393-303-01-3
5-(2-aminoethyl)-4-methyl-1,3-thiazol-2-amine
bdbm22881
NCGC00024719-01
tocris-0668
amthamine
NCGC00024719-02
CHEMBL293762
142437-67-0
2-amino-5-(2-aminoethyl)-4-methylthiazole
L000107
FT-0694778
AKOS006271424
A-4730 ,
unii-n4zj2d98hm
n4zj2d98hm ,
5-thiazoleethanamine, 2-amino-4-methyl-
gtpl4025
SCHEMBL400272
DTXSID80162039
CHEBI:92694
J-007652
2-amino-4-methylthiazole-5-ethanamine
5-(2-aminoethyl)-4-methylthiazol-2-amine
Q4748889
2-amino-4-methyl-5-thiazoleethanamine
EN300-1074385

Research Excerpts

Actions

Amthamine-evoked increase in ACTH and corticosterone secretion was not markedly influenced by any cyclooxygenase blocker applied. Amthamine caused an increase in the sinus rate of spontaneously beating guinea-pig atria.

ExcerptReferenceRelevance
"The amthamine-evoked increase in ACTH and corticosterone secretion was not markedly influenced by any cyclooxygenase blocker applied in the present experiment."( Influence of cyclooxygenase inhibitors on the central histaminergic stimulations of hypothalamic - pituitary - adrenal axis.
Bugajski, AJ; Bugajski, J; Gadek-Michalska, A; Głód, R; Thor, P, 2003
)
0.8
"Amthamine caused an increase in the sinus rate of spontaneously beating guinea-pig atria (pD2 = 6.72) and in the contractility of the electrically driven guinea-pig papillary muscle (pD2 = 6.17) and of the human atrium (pD2 = 5.38)."( In vitro cardiac pharmacology of the new histamine H2-receptor agonist amthamine: comparisons with histamine and dimaprit.
Bertaccini, G; Coruzzi, G; Poli, E; Pozzoli, C; Timmerman, H, 1993
)
1.24

Bioavailability

ExcerptReferenceRelevance
"The bioisosteric replacement of the guanidino group in arpromidine-like histamine H(2) receptor (H(2)R) agonists by an acylguanidine moiety is a useful approach to obtain potent H(2)R agonists with improved oral bioavailability and blood-brain barrier penetration."( N(G)-acylated aminothiazolylpropylguanidines as potent and selective histamine H(2) receptor agonists.
Bernhardt, G; Birnkammer, T; Buschauer, A; Dove, S; Elz, S; Ghorai, P; Kraus, A; Schnell, D; Seifert, R, 2009
)
0.35

Dosage Studied

ExcerptRelevanceReference
" All three agents denoted similar cAMP maximal responses in dose-response experiments."( The time-course of cyclic AMP signaling is critical for leukemia U-937 cell differentiation.
Baldi, A; Davio, C; Fernández, N; Legnazzi, BL; Monczor, F; Riveiro, ME; Shayo, C, 2004
)
0.32
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Drug Classes (1)

ClassDescription
thiazolesAn azole in which the five-membered heterocyclic aromatic skeleton contains a N atom and one S 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 (6)

Potency Measurements

ProteinTaxonomyMeasurementAverage (µ)Min (ref.)Avg (ref.)Max (ref.)Bioassay(s)
TDP1 proteinHomo sapiens (human)Potency29.09290.000811.382244.6684AID686979
vitamin D3 receptor isoform VDRAHomo sapiens (human)Potency35.48130.354828.065989.1251AID504847
[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)
Histamine H2 receptorHomo sapiens (human)Ki6.30960.00062.197310.0000AID548984
Histamine H4 receptorHomo sapiens (human)Ki5.01190.00060.478710.0000AID1798265; AID548981
[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)
Histamine H2 receptorHomo sapiens (human)EC50 (µMol)0.19050.11481.77695.4954AID697893
Histamine H1 receptorHomo sapiens (human)EC50 (µMol)15.84890.00040.18810.7943AID548979
Histamine H2 receptorCavia porcellus (domestic guinea pig)EC50 (µMol)0.19050.00030.57191.2023AID697896
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Biological Processes (18)

Processvia Protein(s)Taxonomy
gastric acid secretionHistamine H2 receptorHomo sapiens (human)
immune responseHistamine H2 receptorHomo sapiens (human)
positive regulation of vasoconstrictionHistamine H2 receptorHomo sapiens (human)
G protein-coupled serotonin receptor signaling pathwayHistamine H2 receptorHomo sapiens (human)
chemical synaptic transmissionHistamine H2 receptorHomo sapiens (human)
G protein-coupled receptor signaling pathway, coupled to cyclic nucleotide second messengerHistamine H2 receptorHomo sapiens (human)
inflammatory responseHistamine H1 receptorHomo sapiens (human)
G protein-coupled receptor signaling pathwayHistamine H1 receptorHomo sapiens (human)
phospholipase C-activating G protein-coupled receptor signaling pathwayHistamine H1 receptorHomo sapiens (human)
memoryHistamine H1 receptorHomo sapiens (human)
visual learningHistamine H1 receptorHomo sapiens (human)
regulation of vascular permeabilityHistamine H1 receptorHomo sapiens (human)
positive regulation of vasoconstrictionHistamine H1 receptorHomo sapiens (human)
regulation of synaptic plasticityHistamine H1 receptorHomo sapiens (human)
cellular response to histamineHistamine H1 receptorHomo sapiens (human)
G protein-coupled serotonin receptor signaling pathwayHistamine H1 receptorHomo sapiens (human)
G protein-coupled receptor signaling pathway, coupled to cyclic nucleotide second messengerHistamine H1 receptorHomo sapiens (human)
chemical synaptic transmissionHistamine H1 receptorHomo sapiens (human)
inflammatory responseHistamine H4 receptorHomo sapiens (human)
positive regulation of cytosolic calcium ion concentrationHistamine H4 receptorHomo sapiens (human)
biological_processHistamine H4 receptorHomo sapiens (human)
regulation of MAPK cascadeHistamine H4 receptorHomo sapiens (human)
G protein-coupled serotonin receptor signaling pathwayHistamine H4 receptorHomo sapiens (human)
adenylate cyclase-inhibiting G protein-coupled acetylcholine receptor signaling pathwayHistamine H4 receptorHomo sapiens (human)
G protein-coupled receptor signaling pathway, coupled to cyclic nucleotide second messengerHistamine H4 receptorHomo sapiens (human)
chemical synaptic transmissionHistamine H4 receptorHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Molecular Functions (4)

Processvia Protein(s)Taxonomy
histamine receptor activityHistamine H2 receptorHomo sapiens (human)
G protein-coupled serotonin receptor activityHistamine H2 receptorHomo sapiens (human)
neurotransmitter receptor activityHistamine H2 receptorHomo sapiens (human)
histamine receptor activityHistamine H1 receptorHomo sapiens (human)
G protein-coupled serotonin receptor activityHistamine H1 receptorHomo sapiens (human)
neurotransmitter receptor activityHistamine H1 receptorHomo sapiens (human)
histamine receptor activityHistamine H4 receptorHomo sapiens (human)
G protein-coupled serotonin receptor activityHistamine H4 receptorHomo sapiens (human)
G protein-coupled acetylcholine receptor activityHistamine H4 receptorHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Ceullar Components (4)

Processvia Protein(s)Taxonomy
plasma membraneHistamine H2 receptorHomo sapiens (human)
synapseHistamine H2 receptorHomo sapiens (human)
plasma membraneHistamine H2 receptorHomo sapiens (human)
dendriteHistamine H2 receptorHomo sapiens (human)
cytosolHistamine H1 receptorHomo sapiens (human)
plasma membraneHistamine H1 receptorHomo sapiens (human)
synapseHistamine H1 receptorHomo sapiens (human)
dendriteHistamine H1 receptorHomo sapiens (human)
plasma membraneHistamine H1 receptorHomo sapiens (human)
plasma membraneHistamine H4 receptorHomo sapiens (human)
plasma membraneHistamine H4 receptorHomo sapiens (human)
dendriteHistamine H4 receptorHomo sapiens (human)
synapseHistamine H4 receptorHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (18)

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.
AID548979Agonist activity at human recombinant histamine H1 receptor expressed in Sf9 cells coexpressing RGS4 by steady-state GTPase activity assay2010Bioorganic & medicinal chemistry letters, Dec-15, Volume: 20, Issue:24
Histamine H4 receptor agonists.
AID548984Displacement of [125I]iodoaminopotentidine from human histamine H2 receptor expressed in CHO cells2010Bioorganic & medicinal chemistry letters, Dec-15, Volume: 20, Issue:24
Histamine H4 receptor agonists.
AID697899Selectivity index, ratio of EC50 for human H2R-Gsalphas to EC50 for guinea pig H2R-Gsalphas by by steady state GTPase activity assay2012Journal of medicinal chemistry, Feb-09, Volume: 55, Issue:3
The bivalent ligand approach leads to highly potent and selective acylguanidine-type histamine H₂ receptor agonists.
AID697894Potency index, ratio of pEC50 for compound to pEC50 for histamine at human H2R-Gsalphas expressed in Sf9 cells at 0.1 nM to 10 uM by steady state GTPase activity assay2012Journal of medicinal chemistry, Feb-09, Volume: 55, Issue:3
The bivalent ligand approach leads to highly potent and selective acylguanidine-type histamine H₂ receptor agonists.
AID697897Potency index, ratio of pEC50 for compound to pEC50 for histamine at guinea pig H2R-Gsalphas expressed in Sf9 cells at 0.1 nM to 10 uM by steady state GTPase activity assay2012Journal of medicinal chemistry, Feb-09, Volume: 55, Issue:3
The bivalent ligand approach leads to highly potent and selective acylguanidine-type histamine H₂ receptor agonists.
AID697895Intrinsic agonist activity at guinea pig H2R-Gsalphas expressed in Sf9 cells by steady state GTPase activity assay relative to histamine2012Journal of medicinal chemistry, Feb-09, Volume: 55, Issue:3
The bivalent ligand approach leads to highly potent and selective acylguanidine-type histamine H₂ receptor agonists.
AID697900Agonist activity at H2R in spontaneously beating guinea pig right atrium assessed as increase in heart rate2012Journal of medicinal chemistry, Feb-09, Volume: 55, Issue:3
The bivalent ligand approach leads to highly potent and selective acylguanidine-type histamine H₂ receptor agonists.
AID697901Potency index, ratio of pEC50 for compound to pEC50 for H2R in spontaneously beating guinea pig right atrium2012Journal of medicinal chemistry, Feb-09, Volume: 55, Issue:3
The bivalent ligand approach leads to highly potent and selective acylguanidine-type histamine H₂ receptor agonists.
AID697892Intrinsic agonist activity at human H2R-Gsalphas expressed in Sf9 cells by steady state GTPase activity assay relative to histamine2012Journal of medicinal chemistry, Feb-09, Volume: 55, Issue:3
The bivalent ligand approach leads to highly potent and selective acylguanidine-type histamine H₂ receptor agonists.
AID697893Agonist activity at human H2R-Gsalphas expressed in Sf9 cells at 0.1 nM to 10 uM by steady state GTPase activity assay2012Journal of medicinal chemistry, Feb-09, Volume: 55, Issue:3
The bivalent ligand approach leads to highly potent and selective acylguanidine-type histamine H₂ receptor agonists.
AID697896Agonist activity at guinea pig H2R-Gsalphas expressed in Sf9 cells at 0.1 nM to 10 uM by steady state GTPase activity assay2012Journal of medicinal chemistry, Feb-09, Volume: 55, Issue:3
The bivalent ligand approach leads to highly potent and selective acylguanidine-type histamine H₂ receptor agonists.
AID548994Agonist activity at human histamine H4 receptor expressed in human SK-N-MC cells by CRE-beta galactosidase reporter gene assay relative to histamine2010Bioorganic & medicinal chemistry letters, Dec-15, Volume: 20, Issue:24
Histamine H4 receptor agonists.
AID548981Displacement of [3H]-histamine from human histamine H4 receptor expressed in Sf9 cells coexpressing RGS19, Galphai2, Gbeta1gamma22010Bioorganic & medicinal chemistry letters, Dec-15, Volume: 20, Issue:24
Histamine H4 receptor agonists.
AID697902Intrinsic agonist activity at H2R in spontaneously beating guinea pig right atrium assessed as increase in heart rate relative to histamine2012Journal of medicinal chemistry, Feb-09, Volume: 55, Issue:3
The bivalent ligand approach leads to highly potent and selective acylguanidine-type histamine H₂ receptor agonists.
AID1798265H4R Radioligand Binding Assay from Article 10.1124/jpet.105.087965: \\Evaluation of histamine H1-, H2-, and H3-receptor ligands at the human histamine H4 receptor: identification of 4-methylhistamine as the first potent and selective H4 receptor agonist.\\2005The Journal of pharmacology and experimental therapeutics, Sep, Volume: 314, Issue:3
Evaluation of histamine H1-, H2-, and H3-receptor ligands at the human histamine H4 receptor: identification of 4-methylhistamine as the first potent and selective H4 receptor agonist.
AID1346095Human H2 receptor (Histamine receptors)2009ChemMedChem, Feb, Volume: 4, Issue:2
N(G)-acylated aminothiazolylpropylguanidines as potent and selective histamine H(2) receptor agonists.
[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's10 (31.25)18.2507
2000's10 (31.25)29.6817
2010's8 (25.00)24.3611
2020's4 (12.50)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 25.69

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 Index25.69 (24.57)
Research Supply Index3.53 (2.92)
Research Growth Index4.54 (4.65)
Search Engine Demand Index29.35 (26.88)
Search Engine Supply Index2.00 (0.95)

This Compound (25.69)

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%
Other33 (100.00%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]