Page last updated: 2024-12-08

sk&f 91486

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Description

3-(4(5)-imidazolyl)propylguanidine: partial agonist at histamine H(2)-receptor; structure [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Cross-References

ID Source	ID
PubMed CID	182527
CHEMBL ID	325327
SCHEMBL ID	2791864
MeSH ID	M0058077

Synonyms (13)

Synonym
skf 91486
sk&f-91486
sk-91486
CHEMBL325327 ,
46129-28-6
skf-91486
guanidine, (3-(1h-imidazol-4-yl)propyl)-
3-(4(5)-imidazolyl)propylguanidine
sk&f 91486
bdbm50413501
SCHEMBL2791864
3-(1h-imidazol-4-yl)propylguanidine
DTXSID40196739

[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Protein Targets (3)

Activation Measurements

Protein	Taxonomy	Measurement	Average	Min (ref.)	Avg (ref.)	Max (ref.)	Bioassay(s)
Histamine H2 receptor	Homo sapiens (human)	EC50 (µMol)	2.5704	0.1148	1.7769	5.4954	AID414924
Histamine H4 receptor	Homo sapiens (human)	EC50 (µMol)	0.0081	0.0074	0.6016	10.0000	AID414926
Histamine H3 receptor	Homo sapiens (human)	EC50 (µMol)	0.0076	0.0000	0.0947	3.1623	AID414925
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Biological Processes (12)

Process	via Protein(s)	Taxonomy
gastric acid secretion	Histamine H2 receptor	Homo sapiens (human)
immune response	Histamine H2 receptor	Homo sapiens (human)
positive regulation of vasoconstriction	Histamine H2 receptor	Homo sapiens (human)
G protein-coupled serotonin receptor signaling pathway	Histamine H2 receptor	Homo sapiens (human)
chemical synaptic transmission	Histamine H2 receptor	Homo sapiens (human)
G protein-coupled receptor signaling pathway, coupled to cyclic nucleotide second messenger	Histamine H2 receptor	Homo sapiens (human)
inflammatory response	Histamine H4 receptor	Homo sapiens (human)
positive regulation of cytosolic calcium ion concentration	Histamine H4 receptor	Homo sapiens (human)
biological_process	Histamine H4 receptor	Homo sapiens (human)
regulation of MAPK cascade	Histamine H4 receptor	Homo sapiens (human)
G protein-coupled serotonin receptor signaling pathway	Histamine H4 receptor	Homo sapiens (human)
adenylate cyclase-inhibiting G protein-coupled acetylcholine receptor signaling pathway	Histamine H4 receptor	Homo sapiens (human)
G protein-coupled receptor signaling pathway, coupled to cyclic nucleotide second messenger	Histamine H4 receptor	Homo sapiens (human)
chemical synaptic transmission	Histamine H4 receptor	Homo sapiens (human)
neurotransmitter secretion	Histamine H3 receptor	Homo sapiens (human)
G protein-coupled serotonin receptor signaling pathway	Histamine H3 receptor	Homo sapiens (human)
G protein-coupled receptor signaling pathway, coupled to cyclic nucleotide second messenger	Histamine H3 receptor	Homo sapiens (human)
chemical synaptic transmission	Histamine H3 receptor	Homo sapiens (human)
adenylate cyclase-inhibiting G protein-coupled acetylcholine receptor signaling pathway	Histamine H3 receptor	Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Molecular Functions (4)

Process	via Protein(s)	Taxonomy
histamine receptor activity	Histamine H2 receptor	Homo sapiens (human)
G protein-coupled serotonin receptor activity	Histamine H2 receptor	Homo sapiens (human)
neurotransmitter receptor activity	Histamine H2 receptor	Homo sapiens (human)
histamine receptor activity	Histamine H4 receptor	Homo sapiens (human)
G protein-coupled serotonin receptor activity	Histamine H4 receptor	Homo sapiens (human)
G protein-coupled acetylcholine receptor activity	Histamine H4 receptor	Homo sapiens (human)
histamine receptor activity	Histamine H3 receptor	Homo sapiens (human)
G protein-coupled acetylcholine receptor activity	Histamine H3 receptor	Homo sapiens (human)
G protein-coupled serotonin receptor activity	Histamine H3 receptor	Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Ceullar Components (4)

Process	via Protein(s)	Taxonomy
plasma membrane	Histamine H2 receptor	Homo sapiens (human)
synapse	Histamine H2 receptor	Homo sapiens (human)
plasma membrane	Histamine H2 receptor	Homo sapiens (human)
dendrite	Histamine H2 receptor	Homo sapiens (human)
plasma membrane	Histamine H4 receptor	Homo sapiens (human)
plasma membrane	Histamine H4 receptor	Homo sapiens (human)
dendrite	Histamine H4 receptor	Homo sapiens (human)
synapse	Histamine H4 receptor	Homo sapiens (human)
plasma membrane	Histamine H3 receptor	Homo sapiens (human)
presynapse	Histamine H3 receptor	Homo sapiens (human)
plasma membrane	Histamine H3 receptor	Homo sapiens (human)
synapse	Histamine H3 receptor	Homo sapiens (human)
dendrite	Histamine H3 receptor	Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (10)

Assay ID	Title	Year	Journal	Article
AID414924	Agonist activity at human H2 receptor expressed in insect Sf9 cells co-expressing GsalphaS fusion protein assessed as gamma[32P]GTP binding by liquid scintillation counting	2009	Journal of medicinal chemistry, Apr-23, Volume: 52, Issue:8	N(G)-acylated imidazolylpropylguanidines as potent histamine H4 receptor agonists: selectivity by variation of the N(G)-substituent.
AID414931	Intrinsic activity at human H2 receptor expressed in insect Sf9 cells co-expressing GsalphaS fusion protein assessed as gamma[32P]GTP binding at 10 uM by liquid scintillation counting relative to histamine	2009	Journal of medicinal chemistry, Apr-23, Volume: 52, Issue:8	N(G)-acylated imidazolylpropylguanidines as potent histamine H4 receptor agonists: selectivity by variation of the N(G)-substituent.
AID414932	Intrinsic activity at human H3 receptor expressed in insect Sf9 cells co-expressing Gialpha2, Gbeta1gamma2 and RGS4 assessed as gamma[32P]GTP binding at 10 uM by liquid scintillation counting relative to histamine	2009	Journal of medicinal chemistry, Apr-23, Volume: 52, Issue:8	N(G)-acylated imidazolylpropylguanidines as potent histamine H4 receptor agonists: selectivity by variation of the N(G)-substituent.
AID183458	Tested for inhibition of histamine-stimulated gastric acid secretion in the lumen-perfused anesthetized rat expressed as intravenous dose which reduces a near maximal secretion to 50%	1981	Journal of medicinal chemistry, Aug, Volume: 24, Issue:8	1980 Award in Medicinal Chemistry: Medicinal chemistry and dynamic structure-activity analysis in the discovery of drugs acting at histamine H2 receptors.
AID414925	Agonist activity at human H3 receptor expressed in insect Sf9 cells co-expressing Gialpha2, Gbeta1gamma2 and RGS4 assessed as gamma[32P]GTP binding by liquid scintillation counting	2009	Journal of medicinal chemistry, Apr-23, Volume: 52, Issue:8	N(G)-acylated imidazolylpropylguanidines as potent histamine H4 receptor agonists: selectivity by variation of the N(G)-substituent.
AID414933	Intrinsic activity at human H4 receptor expressed in insect Sf9 cells co-expressing RGS19 fusion protein and Gialpha2, Gbeta1gamma2 assessed as gamma[32P]GTP binding at 10 uM by liquid scintillation counting relative to histamine	2009	Journal of medicinal chemistry, Apr-23, Volume: 52, Issue:8	N(G)-acylated imidazolylpropylguanidines as potent histamine H4 receptor agonists: selectivity by variation of the N(G)-substituent.
AID88166	Histamine H2 receptor agonistic activity in guinea pig right atrium	1992	Journal of medicinal chemistry, Aug-21, Volume: 35, Issue:17	Histamine H2-receptor agonists. Synthesis, in vitro pharmacology, and qualitative structure-activity relationships of substituted 4- and 5-(2-aminoethyl)thiazoles.
AID414930	Intrinsic activity at human H1 receptor expressed in insect Sf9 cells co-expressing RGS4 assessed as gamma[32P]GTP binding at 10 uM by liquid scintillation counting relative to histamine	2009	Journal of medicinal chemistry, Apr-23, Volume: 52, Issue:8	N(G)-acylated imidazolylpropylguanidines as potent histamine H4 receptor agonists: selectivity by variation of the N(G)-substituent.
AID414927	Antagonist activity at human H1 receptor expressed in insect Sf9 cells co-expressing RGS4 assessed as inhibition of histamine-induced gamma[32P]GTP binding by liquid scintillation counting	2009	Journal of medicinal chemistry, Apr-23, Volume: 52, Issue:8	N(G)-acylated imidazolylpropylguanidines as potent histamine H4 receptor agonists: selectivity by variation of the N(G)-substituent.
AID414926	Agonist activity at human H4 receptor expressed in insect Sf9 cells co-expressing RGS19 fusion protein and Gialpha2, Gbeta1gamma2 assessed as gamma[32P]GTP binding by liquid scintillation counting	2009	Journal of medicinal chemistry, Apr-23, Volume: 52, Issue:8	N(G)-acylated imidazolylpropylguanidines as potent histamine H4 receptor agonists: selectivity by variation of the N(G)-substituent.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (6)

Timeframe	Studies, This Drug (%)	All Drugs %
pre-1990	2 (33.33)	18.7374
1990's	2 (33.33)	18.2507
2000's	2 (33.33)	29.6817
2010's	0 (0.00)	24.3611
2020's	0 (0.00)	2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 12.41

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 weak demand-to-supply ratio for research on this compound.

Metric	This Compound (vs All)
Research Demand Index	12.41 (24.57)
Research Supply Index	1.95 (2.92)
Research Growth Index	4.36 (4.65)
Search Engine Demand Index	0.00 (26.88)
Search Engine Supply Index	0.00 (0.95)

This Compound (12.41)

All Compounds (24.57)

Study Types

Publication Type	This drug (%)	All Drugs (%)
Trials	0 (0.00%)	5.53%
Reviews	0 (0.00%)	6.00%
Case Studies	0 (0.00%)	4.05%
Observational	0 (0.00%)	0.25%
Other	6 (100.00%)	84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Substance	Relationship Strength	Studies	Classes	Roles
histamine [no description available]	8.08	5	aralkylamino compound; imidazoles	human metabolite; mouse metabolite; neurotransmitter
pimagedine pimagedine: diamine oxidase & nitric oxide synthase inhibitor; an advanced glycosylation end product inhibitor; used in the treatment of diabetic complications; structure. aminoguanidine : A one-carbon compound whose unique structure renders it capable of acting as a derivative of hydrazine, guanidine or formamide.	2.02	1	guanidines; one-carbon compound	EC 1.14.13.39 (nitric oxide synthase) inhibitor; EC 1.4.3.4 (monoamine oxidase) inhibitor
dimaprit Dimaprit: A histamine H2 receptor agonist that is often used to study the activity of histamine and its receptors.	1.98	1	imidothiocarbamic ester
imetit imetit: structure given in first source. imetit : An imidothiocarbamic ester that consists of isothiourea in which the thiol hydrogen is substituted by a 2-(imidazol-4-yl)ethyl group. An extremely potent, high affinity agonist at H3 and H4 receptors (Ki values are 0.3 and 2.7 nM respectively). Induces shape change in eosinophils with an EC50 of 25 nM. Centrally active following systemic administration.	1.96	1	imidazoles; imidothiocarbamic ester	H3-receptor agonist; H4-receptor agonist
impromidine Impromidine: A highly potent and specific histamine H2 receptor agonist. It has been used diagnostically as a gastric secretion indicator.	1.98	1
1-hexadecyl-2-acetyl-glycero-3-phosphocholine Platelet Activating Factor: A phospholipid derivative formed by PLATELETS; BASOPHILS; NEUTROPHILS; MONOCYTES; and MACROPHAGES. It is a potent platelet aggregating agent and inducer of systemic anaphylactic symptoms, including HYPOTENSION; THROMBOCYTOPENIA; NEUTROPENIA; and BRONCHOCONSTRICTION.. 2-O-acetyl-1-O-hexadecyl-sn-glycero-3-phosphocholine : A 2-acetyl-1-alkyl-sn-glycero-3-phosphocholine betaine which has hexadecyl as the alkyl group. PAF is a potent phospholipid activator and mediator of many leukocyte functions, including platelet aggregation, inflammation, and anaphylaxis.	2.02	1	2-acetyl-1-alkyl-sn-glycero-3-phosphocholine	antihypertensive agent; beta-adrenergic antagonist; bronchoconstrictor agent; hematologic agent; vasodilator agent
metiamide Metiamide: A histamine H2 receptor antagonist that is used as an anti-ulcer agent.	1.97	1	imidazoles
burimamide Burimamide: An antagonist of histamine that appears to block both H2 and H3 histamine receptors. It has been used in the treatment of ulcers.	1.97	1	imidazoles
thioperamide thioperamide: structure given in first source; histamine H3 receptor antagonist	2.05	1	primary aliphatic amine

Condition	Relationship Strength	Studies
Muscle Contraction A process leading to shortening and/or development of tension in muscle tissue. Muscle contraction occurs by a sliding filament mechanism whereby actin filaments slide inward among the myosin filaments.	1.98	1
Asthma, Bronchial [description not available]	2.02	1
Disease Models, Animal Naturally-occurring or experimentally-induced animal diseases with pathological processes analogous to human diseases.	2.02	1
Asthma A form of bronchial disorder with three distinct components: airway hyper-responsiveness (RESPIRATORY HYPERSENSITIVITY), airway INFLAMMATION, and intermittent AIRWAY OBSTRUCTION. It is characterized by spasmodic contraction of airway smooth muscle, WHEEZING, and dyspnea (DYSPNEA, PAROXYSMAL).	2.02	1
Bronchial Hyperreactivity Tendency of the smooth muscle of the tracheobronchial tree to contract more intensely in response to a given stimulus than it does in the response seen in normal individuals. This condition is present in virtually all symptomatic patients with asthma. The most prominent manifestation of this smooth muscle contraction is a decrease in airway caliber that can be readily measured in the pulmonary function laboratory.	2.02	1

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