Page last updated: 2024-11-06

xylonidine

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

Description

Xylonidine is a synthetic sympathomimetic agent that acts as an α-adrenergic agonist. It is structurally similar to other α-agonists such as naphazoline and oxymetazoline, and like them, it is used as a vasoconstrictor, primarily for its effects in relieving nasal congestion. Xylonidine is synthesized through a multi-step process involving the reaction of 2-chloro-5-nitrobenzaldehyde with 2-amino-4-methylphenol. The resulting compound undergoes further transformations to yield xylonidine. The vasoconstrictive action of xylonidine is attributed to its stimulation of α-adrenergic receptors in the nasal mucosa, leading to constriction of blood vessels and reduction of nasal congestion. Xylonidine is often administered as a nasal spray or drops, and its effects typically last for several hours. It is generally well-tolerated, but side effects such as burning, stinging, and dryness of the nasal mucosa can occur. Xylonidine is widely studied due to its potential therapeutic applications in the treatment of nasal congestion, as well as its potential for further development as a vasoconstrictor for other medical conditions. Ongoing research focuses on optimizing its efficacy, exploring its safety profile, and evaluating its potential for alternative routes of administration.'

xylonidine: alpha adrenoreceptor stimulation by above cpd mainly inhibits the release of mediator and/or the bronchoconstriction caused by moderate activation of sensory nerves; forced molting agent; structure given in first source [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Cross-References

ID SourceID
PubMed CID78576
CHEMBL ID186919
SCHEMBL ID10831788
SCHEMBL ID4760243
MeSH IDM0109607

Synonyms (24)

Synonym
bdbm50151706
(4,5-dihydro-1h-imidazol-2-yl)-(2,6-dimethyl-phenyl)-amine
(2,6-dimethyl-phenyl)-imidazolidin-2-ylidene-amine
2-(2,6-dimethylanilino)-2-imidazoline
2-(2,6-xylylimino)imidazoline
skf-35886
1h-imidazol-2-amine, n-(2,6-dimethylphenyl)-4,5-dihydro-
skf 35866
2-(2,6-dimethylphenylimino)imidazoline
sk&f 35886
imidazolidine,2-(2,6-dimethylphenylimino)-
xylonidine
sk&f 35866
4859-06-7
CHEMBL186919 ,
n-(2,6-dimethylphenyl)-4,5-dihydro-1h-imidazol-2-amine
SCHEMBL10831788
SCHEMBL4760243
IVCKBWZBJVLCDH-UHFFFAOYSA-N
2-(2,6-dime phenylimino)imidazoline
DTXSID60876485
FT-0737077
STARBLD0007533
AKOS040754482

Research Excerpts

Dosage Studied

ExcerptRelevanceReference
" The first ionization energies of the pharmacologically active 20-(phenylimino)imidazolidines do not correlate with hypotensive activity based on dosage data after intravenous administration to rats."( Ultraviolet photoelectron spectroscopy of cyclic amidines. 2. Electronic structure of clonidine and some related 2-(phenylimino)imidazolidines with alpha-adrenergic activity.
de Jong, AP; van Dam, H, 1980
)
0.26
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Protein Targets (2)

Inhibition Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
5-hydroxytryptamine receptor 1DHomo sapiens (human)Ki2.07500.00010.808710.0000AID238273
5-hydroxytryptamine receptor 1BHomo sapiens (human)Ki30.00000.00010.54859.2100AID238272
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Biological Processes (27)

Processvia Protein(s)Taxonomy
adenylate cyclase-inhibiting G protein-coupled receptor signaling pathway5-hydroxytryptamine receptor 1DHomo sapiens (human)
intestine smooth muscle contraction5-hydroxytryptamine receptor 1DHomo sapiens (human)
regulation of locomotion5-hydroxytryptamine receptor 1DHomo sapiens (human)
vasoconstriction5-hydroxytryptamine receptor 1DHomo sapiens (human)
regulation of behavior5-hydroxytryptamine receptor 1DHomo sapiens (human)
chemical synaptic transmission5-hydroxytryptamine receptor 1DHomo sapiens (human)
G protein-coupled receptor signaling pathway, coupled to cyclic nucleotide second messenger5-hydroxytryptamine receptor 1DHomo sapiens (human)
adenylate cyclase-inhibiting serotonin receptor signaling pathway5-hydroxytryptamine receptor 1DHomo sapiens (human)
G protein-coupled receptor internalization5-hydroxytryptamine receptor 1BHomo sapiens (human)
adenylate cyclase-inhibiting G protein-coupled receptor signaling pathway5-hydroxytryptamine receptor 1BHomo sapiens (human)
adenylate cyclase-inhibiting serotonin receptor signaling pathway5-hydroxytryptamine receptor 1BHomo sapiens (human)
protein kinase C-activating G protein-coupled receptor signaling pathway5-hydroxytryptamine receptor 1BHomo sapiens (human)
negative regulation of gamma-aminobutyric acid secretion5-hydroxytryptamine receptor 1BHomo sapiens (human)
regulation of dopamine secretion5-hydroxytryptamine receptor 1BHomo sapiens (human)
negative regulation of serotonin secretion5-hydroxytryptamine receptor 1BHomo sapiens (human)
negative regulation of synaptic transmission, GABAergic5-hydroxytryptamine receptor 1BHomo sapiens (human)
response to cocaine5-hydroxytryptamine receptor 1BHomo sapiens (human)
vasoconstriction5-hydroxytryptamine receptor 1BHomo sapiens (human)
drinking behavior5-hydroxytryptamine receptor 1BHomo sapiens (human)
response to ethanol5-hydroxytryptamine receptor 1BHomo sapiens (human)
bone remodeling5-hydroxytryptamine receptor 1BHomo sapiens (human)
regulation of behavior5-hydroxytryptamine receptor 1BHomo sapiens (human)
response to mineralocorticoid5-hydroxytryptamine receptor 1BHomo sapiens (human)
negative regulation of synaptic transmission, glutamatergic5-hydroxytryptamine receptor 1BHomo sapiens (human)
cellular response to alkaloid5-hydroxytryptamine receptor 1BHomo sapiens (human)
cellular response to xenobiotic stimulus5-hydroxytryptamine receptor 1BHomo sapiens (human)
cellular response to temperature stimulus5-hydroxytryptamine receptor 1BHomo sapiens (human)
presynaptic modulation of chemical synaptic transmission5-hydroxytryptamine receptor 1BHomo sapiens (human)
regulation of presynaptic cytosolic calcium ion concentration5-hydroxytryptamine receptor 1BHomo sapiens (human)
positive regulation of vascular associated smooth muscle cell proliferation5-hydroxytryptamine receptor 1BHomo sapiens (human)
regulation of synaptic vesicle exocytosis5-hydroxytryptamine receptor 1BHomo sapiens (human)
chemical synaptic transmission5-hydroxytryptamine receptor 1BHomo sapiens (human)
G protein-coupled receptor signaling pathway, coupled to cyclic nucleotide second messenger5-hydroxytryptamine receptor 1BHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Molecular Functions (5)

Processvia Protein(s)Taxonomy
G protein-coupled serotonin receptor activity5-hydroxytryptamine receptor 1DHomo sapiens (human)
neurotransmitter receptor activity5-hydroxytryptamine receptor 1DHomo sapiens (human)
G protein-coupled serotonin receptor activity5-hydroxytryptamine receptor 1BHomo sapiens (human)
protein binding5-hydroxytryptamine receptor 1BHomo sapiens (human)
serotonin binding5-hydroxytryptamine receptor 1BHomo sapiens (human)
voltage-gated calcium channel activity involved in regulation of presynaptic cytosolic calcium levels5-hydroxytryptamine receptor 1BHomo sapiens (human)
neurotransmitter receptor activity5-hydroxytryptamine receptor 1BHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Ceullar Components (8)

Processvia Protein(s)Taxonomy
plasma membrane5-hydroxytryptamine receptor 1DHomo sapiens (human)
synapse5-hydroxytryptamine receptor 1DHomo sapiens (human)
plasma membrane5-hydroxytryptamine receptor 1DHomo sapiens (human)
dendrite5-hydroxytryptamine receptor 1DHomo sapiens (human)
endoplasmic reticulum5-hydroxytryptamine receptor 1BHomo sapiens (human)
plasma membrane5-hydroxytryptamine receptor 1BHomo sapiens (human)
presynaptic membrane5-hydroxytryptamine receptor 1BHomo sapiens (human)
calyx of Held5-hydroxytryptamine receptor 1BHomo sapiens (human)
serotonergic synapse5-hydroxytryptamine receptor 1BHomo sapiens (human)
G protein-coupled serotonin receptor complex5-hydroxytryptamine receptor 1BHomo sapiens (human)
dendrite5-hydroxytryptamine receptor 1BHomo sapiens (human)
plasma membrane5-hydroxytryptamine receptor 1BHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (12)

Assay IDTitleYearJournalArticle
AID1150959Peripheral adrenergic activity in iv dosed pithed rat assessed as change in mean blood pressure1976Journal of medicinal chemistry, Aug, Volume: 19, Issue:8
Clonidine and related analogues. Quantitative correlations.
AID1150956Octan-1-ol-aqueous buffer partition coefficient, log P of the compound at 10 to 20 mg at pH 7.4 by UV-spectroscopic analysis1976Journal of medicinal chemistry, Aug, Volume: 19, Issue:8
Clonidine and related analogues. Quantitative correlations.
AID26357Dissociation constant (pKa)1993Journal of medicinal chemistry, Oct-01, Volume: 36, Issue:20
QSAR's from similarity matrices. Technique validation and application in the comparison of different similarity evaluation methods.
AID186204Hypotensive activity by intravenous administration to rats1980Journal of medicinal chemistry, Aug, Volume: 23, Issue:8
Ultraviolet photoelectron spectroscopy of cyclic amidines. 2. Electronic structure of clonidine and some related 2-(phenylimino)imidazolidines with alpha-adrenergic activity.
AID238273Binding affinity towards human 5-hydroxytryptamine 1D receptor2004Bioorganic & medicinal chemistry letters, Sep-20, Volume: 14, Issue:18
2-(Anilino)imidazolines and 2-(benzyl)imidazoline derivatives as h5-HT1D serotonin receptor ligands.
AID1150958Hypotensive activity in rat assessed as change in mean blood pressure relative to control1976Journal of medicinal chemistry, Aug, Volume: 19, Issue:8
Clonidine and related analogues. Quantitative correlations.
AID25092Ionization constant (pKa)1991Journal of medicinal chemistry, Jul, Volume: 34, Issue:7
Direct prediction of dissociation constants (pKa's) of clonidine-like imidazolines, 2-substituted imidazoles, and 1-methyl-2-substituted-imidazoles from 3D structures using a comparative molecular field analysis (CoMFA) approach.
AID183611First ionization energy by intravenous administration to rats1980Journal of medicinal chemistry, Aug, Volume: 23, Issue:8
Ultraviolet photoelectron spectroscopy of cyclic amidines. 2. Electronic structure of clonidine and some related 2-(phenylimino)imidazolidines with alpha-adrenergic activity.
AID244175Ratio of 5-hydroxytryptamine 1B receptor to that of 5-hydroxytryptamine 1D receptor was determined2004Bioorganic & medicinal chemistry letters, Sep-20, Volume: 14, Issue:18
2-(Anilino)imidazolines and 2-(benzyl)imidazoline derivatives as h5-HT1D serotonin receptor ligands.
AID238272Binding affinity towards human 5-hydroxytryptamine 1B receptor2004Bioorganic & medicinal chemistry letters, Sep-20, Volume: 14, Issue:18
2-(Anilino)imidazolines and 2-(benzyl)imidazoline derivatives as h5-HT1D serotonin receptor ligands.
AID1150955Retardation factor, deltaRm of the compound at pH 13 by TLC analysis1976Journal of medicinal chemistry, Aug, Volume: 19, Issue:8
Clonidine and related analogues. Quantitative correlations.
AID1150957Dissociation constant, pKa of the compound in water-ethyl alcohol1976Journal of medicinal chemistry, Aug, Volume: 19, Issue:8
Clonidine and related analogues. Quantitative correlations.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (9)

TimeframeStudies, This Drug (%)All Drugs %
pre-19904 (44.44)18.7374
1990's4 (44.44)18.2507
2000's1 (11.11)29.6817
2010's0 (0.00)24.3611
2020's0 (0.00)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

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%
Other10 (100.00%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]