Page last updated: 2024-12-10

burimamide

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

Description

Burimamide: An antagonist of histamine that appears to block both H2 and H3 histamine receptors. It has been used in the treatment of ulcers. [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Cross-References

ID SourceID
PubMed CID3032915
CHEMBL ID12160
CHEBI ID3221
SCHEMBL ID7860369
MeSH IDM0003056

Synonyms (26)

Synonym
chembl12160 ,
bdbm22888
1-[4-(1h-imidazol-5-yl)butyl]-3-methylthiourea
PDSP1_001097
C07448 ,
34970-69-9
burimamide
PDSP2_001081
NCGC00167790-01
thiourea, n-(4-(1h-imidazol-4-yl)butyl)-n'-methyl-
chebi:3221 ,
AC1MHUYH ,
unii-tn5a4od2tv
tn5a4od2tv ,
n-(4-imidazol-4-ylbutyl)-n'-methylthiourea
n-methyl-n'-(4(5)-imidazolylbutyl)thiourea
n-methyl-n'-(4-(4(5)-imidazolyl)butyl)thiourea
thiourea, n-(4-(1h-imidazol-5-yl)butyl)-n'-methyl-
n-methyl-n'-[4-(4-imidazolyl)butyl]thiourea
HXRBAVXGYZUSED-UHFFFAOYSA-N
SCHEMBL7860369
1-[4-(1h-imidazol-5-yl)butyl]-3-methyl-thiourea
DTXSID00188519
bdbm50483128
Q3268750
AKOS040745638

Research Excerpts

Treatment

ExcerptReferenceRelevance
"Pretreatment with burimamide inhibited the secretory response to Ba++."( Ba++ as a gastric stimulant: release of histamine.
Rangachari, PK, 1975
)
0.58

Dosage Studied

H2-receptor antagonists burimamide, metiamide and cimetidine were labelled with 35S, 14C or 3H and dosed to rats. Whole body autoradiography showed that the stomach was predominantly labelled in the glandular mucosa from 5 to 120 min after administration.

ExcerptRelevanceReference
" A linear dose-response relationship was obtained for theophylline."( Acid secretion by guinea-pig isolated stomach.
Holton, P; Spencer, J, 1976
)
0.26
" On Cimetidine administered at a usual dosage over a 4--6 week period, serious side-effects must not be expected."( [Treatment of peptic ulcer with histamine H2 receptor antagonists].
Demling, L; Domschke, S; Domschke, W, 1977
)
0.26
" When the H2-receptor antagonists burimamide, metiamide and cimetidine were labelled with 35S, 14C or 3H and dosed to rats, whole body autoradiography showed that the stomach was predominantly labelled in the glandular mucosa from 5 to 120 min after administration."( Localization of histamine and histamine H2-receptor antagonists in the gastric mucosa.
Cross, SA, 1977
)
0.54
"For the definition of histamine receptors the following prerequisites must be fulfilled: (1) Course of dose-response curves according to the mass-action law; (2) parallel displacement of these curves to the right in the presence of antagonists; (3) inhibition only by specific histamine antagonists; (4) slope of a Schild-plot not significantly different from unity."( [Histamine and its role in peptic gastric diseases: the discovery of histamine-H2-receptor antagonists].
Barth, H; Lorenz, W, 1978
)
0.26
" The dose-response curves were shifted to the right in a parallel fashion by promethazine (3 x 10(-6)M)+."( Cardiac histamine receptors: differences between left and right atria and right ventricle.
McNeill, JH; Verma, SC, 1977
)
0.26
" 2 The effect of histamine on both mitogen and antigen dose-response curves suggests a non-competitive, probably physiological antagonism."( Inhibition of guinea-pig lymphocyte activation by histamine and histamine analogues.
Beets, JL; Dale, MM, 1979
)
0.26
" The experiments with burimamide did not permit the calculation of dose-response relationship."( The inhibition of salivary secretion by histamine H2-antagonists--a study on the cat submandibular gland.
Erjavec, F; Stanovnik, L, 1983
)
0.58
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Drug Classes (1)

ClassDescription
imidazolesA five-membered organic heterocycle containing two nitrogen atoms at positions 1 and 3, or any of its derivatives; compounds containing an imidazole skeleton.
[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)
Chain A, Putative fructose-1,6-bisphosphate aldolaseGiardia intestinalisPotency11.19360.140911.194039.8107AID2451
phosphopantetheinyl transferaseBacillus subtilisPotency6.30960.141337.9142100.0000AID1490
[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)Ki3.98110.00062.197310.0000AID548984; AID88474
Histamine H1 receptorCavia porcellus (domestic guinea pig)Ki316.22800.00261.783210.0000AID87068
Histamine H4 receptorHomo sapiens (human)Ki0.08660.00060.478710.0000AID1798265; AID548981; AID89900
Histamine H3 receptorHomo sapiens (human)Ki0.04850.00010.33998.5110AID1798266; AID86459
[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 H4 receptorHomo sapiens (human)EC50 (µMol)0.02000.00740.601610.0000AID548993
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Biological Processes (12)

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 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)
neurotransmitter secretionHistamine H3 receptorHomo sapiens (human)
G protein-coupled serotonin receptor signaling pathwayHistamine H3 receptorHomo sapiens (human)
G protein-coupled receptor signaling pathway, coupled to cyclic nucleotide second messengerHistamine H3 receptorHomo sapiens (human)
chemical synaptic transmissionHistamine H3 receptorHomo sapiens (human)
adenylate cyclase-inhibiting G protein-coupled acetylcholine receptor signaling pathwayHistamine H3 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 H4 receptorHomo sapiens (human)
G protein-coupled serotonin receptor activityHistamine H4 receptorHomo sapiens (human)
G protein-coupled acetylcholine receptor activityHistamine H4 receptorHomo sapiens (human)
histamine receptor activityHistamine H3 receptorHomo sapiens (human)
G protein-coupled acetylcholine receptor activityHistamine H3 receptorHomo sapiens (human)
G protein-coupled serotonin receptor activityHistamine H3 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)
plasma membraneHistamine H4 receptorHomo sapiens (human)
plasma membraneHistamine H4 receptorHomo sapiens (human)
dendriteHistamine H4 receptorHomo sapiens (human)
synapseHistamine H4 receptorHomo sapiens (human)
plasma membraneHistamine H3 receptorHomo sapiens (human)
presynapseHistamine H3 receptorHomo sapiens (human)
plasma membraneHistamine H3 receptorHomo sapiens (human)
synapseHistamine H3 receptorHomo sapiens (human)
dendriteHistamine H3 receptorHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (20)

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.
AID87068Displacement of [3H]mepyramine bound to membranes of CHO cells expressing guinea pig H1 receptors1995Journal of medicinal chemistry, Jun-09, Volume: 38, Issue:12
New analogs of burimamide as potent and selective histamine H3 receptor antagonists: the effect of chain length variation of the alkyl spacer and modifications of the N-thiourea substituent.
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.
AID89723In vitro antagonism of the histamine H3-receptor in the rat cerebral cortex.1995Journal of medicinal chemistry, Aug-18, Volume: 38, Issue:17
Design of potent non-thiourea H3-receptor histamine antagonists.
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.
AID185280The compound was tested for its ability to inhibit histamine-induced gastric acid secretion in the rat at a dose of 90 mg/kg, sc1980Journal of medicinal chemistry, Mar, Volume: 23, Issue:3
Inhibition of histamine-induced gastric secretion by flavone-6-carboxylic acids.
AID549001Agonist activity at histamine H3 receptor in guinea pig ileum2010Bioorganic & medicinal chemistry letters, Dec-15, Volume: 20, Issue:24
Histamine H4 receptor agonists.
AID1135357Antagonist at histamine H2 receptor in guinea pig atrium assessed as inhibition of histamine-induced response1977Journal of medicinal chemistry, Jul, Volume: 20, Issue:7
Cyanoguanidine-thiourea equivalence in the development of the histamine H2-receptor antagonist, cimetidine.
AID548993Agonist activity at human histamine H4 receptor expressed in human SK-N-MC cells by CRE-beta galactosidase reporter gene assay2010Bioorganic & medicinal chemistry letters, Dec-15, Volume: 20, Issue:24
Histamine H4 receptor agonists.
AID86446Evaluated for antagonist activity against Histamine H3 receptor and represented as KB.1990Journal of medicinal chemistry, Jan, Volume: 33, Issue:1
Histamine H3 ligands: just pharmacological tools or potential therapeutic agents?
AID88474Displacement of [125 I]iodoaminopotentidine bound to membranes of CHO cells expressing human H2 receptors1995Journal of medicinal chemistry, Jun-09, Volume: 38, Issue:12
New analogs of burimamide as potent and selective histamine H3 receptor antagonists: the effect of chain length variation of the alkyl spacer and modifications of the N-thiourea substituent.
AID87695Evaluated for antagonist activity against Histamine H2 receptor and represented as KB.1990Journal of medicinal chemistry, Jan, Volume: 33, Issue:1
Histamine H3 ligands: just pharmacological tools or potential therapeutic agents?
AID89900Binding affinity to the human histamine H4 receptor2003Journal of medicinal chemistry, Sep-11, Volume: 46, Issue:19
The first potent and selective non-imidazole human histamine H4 receptor antagonists.
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.
AID86292In vitro inhibitory effect of histamine H3 antagonist on the electrically evoked contractile response of isolated guinea pig jejunum segments.1995Journal of medicinal chemistry, Jun-09, Volume: 38, Issue:12
New analogs of burimamide as potent and selective histamine H3 receptor antagonists: the effect of chain length variation of the alkyl spacer and modifications of the N-thiourea substituent.
AID1135358Antagonist at histamine H2 receptor in rat uterus assessed as inhibition of histamine-induced response1977Journal of medicinal chemistry, Jul, Volume: 20, Issue:7
Cyanoguanidine-thiourea equivalence in the development of the histamine H2-receptor antagonist, cimetidine.
AID86459Binding affinity to the human histamine H3 receptor2003Journal of medicinal chemistry, Sep-11, Volume: 46, Issue:19
The first potent and selective non-imidazole human histamine H4 receptor antagonists.
AID1798266H3R 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.
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.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (164)

TimeframeStudies, This Drug (%)All Drugs %
pre-1990139 (84.76)18.7374
1990's17 (10.37)18.2507
2000's5 (3.05)29.6817
2010's1 (0.61)24.3611
2020's2 (1.22)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 31.59

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 Index31.59 (24.57)
Research Supply Index5.20 (2.92)
Research Growth Index4.37 (4.65)
Search Engine Demand Index44.85 (26.88)
Search Engine Supply Index2.00 (0.95)

This Compound (31.59)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials3 (1.69%)5.53%
Reviews12 (6.74%)6.00%
Case Studies2 (1.12%)4.05%
Observational0 (0.00%)0.25%
Other161 (90.45%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]