Page last updated: 2024-12-05

diphenylpyraline

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

Description

Diphenylpyraline is an antihistamine medication that was first synthesized in the 1950s. It acts as an antagonist of histamine receptors, particularly the H1 receptor, which is involved in allergic reactions. Diphenylpyraline is used to treat a variety of allergic conditions, including hay fever, urticaria, and angioedema. It is also sometimes used to treat motion sickness. Diphenylpyraline is available in oral and nasal spray formulations. The drug has a long history of use and is generally considered safe and effective, although it can cause drowsiness as a side effect. It has been studied extensively for its antihistamine activity, pharmacological properties, and clinical applications. Diphenylpyraline's importance lies in its ability to effectively alleviate symptoms of allergic reactions and provide relief for patients suffering from these conditions.'

diphenylpyraline: RN given refers to parent cpd; structure [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

allergen : A chemical compound, or part thereof, which causes the onset of an allergic reaction by interacting with any of the molecular pathways involved in an allergy. [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]

diphenylpyraline : A member of the class of piperidines that is the benzhydryl ether derivative of 1-methyl-4-hydroxypiperidine. A sedating antihistamine, it is used as the hydrochloride for the symptomatic relief of allergic conditions including rhinitis and hay fever, and in pruritic skin disorders. It is also used as the teoclate salt (piprinhydrinate) as an ingredient in compound preparations for the symptomatic relief of coughs and the common cold. [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]

Cross-References

ID SourceID
PubMed CID3103
CHEMBL ID1492
CHEBI ID59788
SCHEMBL ID119077
MeSH IDM0054943

Synonyms (104)

Synonym
BRD-K22936972-003-05-3
KBIO1_000851
DIVK1C_000851
4-diphenylmethoxy-1-methylpiperidine
147-20-6
4-[(diphenylmethyl)oxy]-1-methylpiperidine
SPECTRUM_001002
PRESTWICK3_000707
PRESTWICK2_000707
an 1041
piperidine, 4-(diphenylmethoxy)-1-methyl-
NCGC00016395-01
cas-132-18-3
SPECTRUM5_000917
BSPBIO_001922
NCGC00178908-02
NCGC00178908-01
BSPBIO_000893
mepiben
diphenylpyrilene
histyn
p 253
brn 0245467
lyssipoll
einecs 205-686-7
histryl
n-methylpiperidyl-(4)-benzhydrylaether salzsauren salze [german]
allergen
hispril
diphenylpyraline [inn:ban]
belfene
neargal
diphenylpyralinum [inn-latin]
difenilpiralina [inn-spanish]
dayfen
AB00053461
4-benzhydryloxy-1-methyl-piperidine
4-(diphenylmethoxy)-1-methylpiperidine
diphenylpyraline
nsc61825
4-(benzhydryloxy)-n-methylpiperidine
diphenylpyralamine
1-methyl-4-piperidyl benzhydryl ether
DB01146
1-methyl-4-hydroxypiperidine benzhydryl ether
4-(benzhydryloxy)-1-methylpiperidine
OPREA1_289175
IDI1_000851
KBIO3_001142
KBIO2_006618
KBIO2_001482
KBIOSS_001482
KBIO2_004050
KBIOGR_001121
NINDS_000851
NCIOPEN2_007716
PRESTWICK1_000707
SPECTRUM2_000982
SPECTRUM3_000401
SPBIO_001043
SPBIO_002814
SPECTRUM4_000521
PRESTWICK0_000707
BPBIO1_000983
bdbm50241333
CHEMBL1492 ,
difenilpiralina
diphenylpyralinum
CHEBI:59788 ,
L001180
diphenylpyraline (inn)
D07862
FT-0657213
4-benzhydryloxy-1-methylpiperidine
A808623
NCGC00016395-03
NCGC00016395-02
hystryl
unii-33361oe3av
33361oe3av ,
5-21-01-00053 (beilstein handbook reference)
n-methylpiperidyl-(4)-benzhydrylaether salzsauren salze
AKOS015889312
diphenylpyraline [vandf]
diphenylpyraline [mi]
diphenylpyraline [who-dd]
piperidine, 4-(diphenylmethoxy)-1-methyl
diphenylpyraline [inn]
gtpl7165
SCHEMBL119077
4-(diphenylmethoxy)-1-(methyl)piperidine
n-methyl-4-(benzhydryloxy)piperidine
diafen (salt/mix)
AB00053461_14
AB00053461_15
DTXSID3022952
AC-9855
SBI-0051354.P003
Q411150
BRD-K22936972-003-15-2
MS-23999
HY-107431
EN300-18530977
CS-0028462

Research Excerpts

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

Roles (2)

RoleDescription
H1-receptor antagonistH1-receptor antagonists are the drugs that selectively bind to but do not activate histamine H1 receptors, thereby blocking the actions of endogenous histamine.
cholinergic antagonistAny drug that binds to but does not activate cholinergic receptors, thereby blocking the actions of acetylcholine or cholinergic agonists.
[role 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]

Drug Classes (2)

ClassDescription
piperidines
tertiary amineA compound formally derived from ammonia by replacing three hydrogen atoms by hydrocarbyl groups.
[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]

Pathways (1)

PathwayProteinsCompounds
Diphenylpyraline H1-Antihistamine Action87

Protein Targets (3)

Potency Measurements

ProteinTaxonomyMeasurementAverage (µ)Min (ref.)Avg (ref.)Max (ref.)Bioassay(s)
phosphopantetheinyl transferaseBacillus subtilisPotency39.81070.141337.9142100.0000AID1490
cytochrome P450 2D6 isoform 1Homo sapiens (human)Potency6.30960.00207.533739.8107AID891
[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)
Bile salt export pumpHomo sapiens (human)IC50 (µMol)508.80000.11007.190310.0000AID1449628
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Biological Processes (22)

Processvia Protein(s)Taxonomy
fatty acid metabolic processBile salt export pumpHomo sapiens (human)
bile acid biosynthetic processBile salt export pumpHomo sapiens (human)
xenobiotic metabolic processBile salt export pumpHomo sapiens (human)
xenobiotic transmembrane transportBile salt export pumpHomo sapiens (human)
response to oxidative stressBile salt export pumpHomo sapiens (human)
bile acid metabolic processBile salt export pumpHomo sapiens (human)
response to organic cyclic compoundBile salt export pumpHomo sapiens (human)
bile acid and bile salt transportBile salt export pumpHomo sapiens (human)
canalicular bile acid transportBile salt export pumpHomo sapiens (human)
protein ubiquitinationBile salt export pumpHomo sapiens (human)
regulation of fatty acid beta-oxidationBile salt export pumpHomo sapiens (human)
carbohydrate transmembrane transportBile salt export pumpHomo sapiens (human)
bile acid signaling pathwayBile salt export pumpHomo sapiens (human)
cholesterol homeostasisBile salt export pumpHomo sapiens (human)
response to estrogenBile salt export pumpHomo sapiens (human)
response to ethanolBile salt export pumpHomo sapiens (human)
xenobiotic export from cellBile salt export pumpHomo sapiens (human)
lipid homeostasisBile salt export pumpHomo sapiens (human)
phospholipid homeostasisBile salt export pumpHomo sapiens (human)
positive regulation of bile acid secretionBile salt export pumpHomo sapiens (human)
regulation of bile acid metabolic processBile salt export pumpHomo sapiens (human)
transmembrane transportBile salt export pumpHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Molecular Functions (8)

Processvia Protein(s)Taxonomy
protein bindingBile salt export pumpHomo sapiens (human)
ATP bindingBile salt export pumpHomo sapiens (human)
ABC-type xenobiotic transporter activityBile salt export pumpHomo sapiens (human)
bile acid transmembrane transporter activityBile salt export pumpHomo sapiens (human)
canalicular bile acid transmembrane transporter activityBile salt export pumpHomo sapiens (human)
carbohydrate transmembrane transporter activityBile salt export pumpHomo sapiens (human)
ABC-type bile acid transporter activityBile salt export pumpHomo sapiens (human)
ATP hydrolysis activityBile salt export pumpHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Ceullar Components (12)

Processvia Protein(s)Taxonomy
basolateral plasma membraneBile salt export pumpHomo sapiens (human)
Golgi membraneBile salt export pumpHomo sapiens (human)
endosomeBile salt export pumpHomo sapiens (human)
plasma membraneBile salt export pumpHomo sapiens (human)
cell surfaceBile salt export pumpHomo sapiens (human)
apical plasma membraneBile salt export pumpHomo sapiens (human)
intercellular canaliculusBile salt export pumpHomo sapiens (human)
intracellular canaliculusBile salt export pumpHomo sapiens (human)
recycling endosomeBile salt export pumpHomo sapiens (human)
recycling endosome membraneBile salt export pumpHomo sapiens (human)
extracellular exosomeBile salt export pumpHomo sapiens (human)
membraneBile salt export pumpHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (11)

Assay IDTitleYearJournalArticle
AID504749qHTS profiling for inhibitors of Plasmodium falciparum proliferation2011Science (New York, N.Y.), Aug-05, Volume: 333, Issue:6043
Chemical genomic profiling for antimalarial therapies, response signatures, and molecular targets.
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.
AID493017Wombat Data for BeliefDocking2005Bioorganic & medicinal chemistry letters, Nov-15, Volume: 15, Issue:22
The synthesis and biological evaluation of dopamine transporter inhibiting activity of substituted diphenylmethoxypiperidines.
AID255050Displacement of [125I]RTI-55 dopamine transporter binding in rat striatal membrane2005Bioorganic & medicinal chemistry letters, Nov-15, Volume: 15, Issue:22
The synthesis and biological evaluation of dopamine transporter inhibiting activity of substituted diphenylmethoxypiperidines.
AID311934Dissociation constant, pKa of the compound2008Journal of medicinal chemistry, Jan-24, Volume: 51, Issue:2
Identification of new functional inhibitors of acid sphingomyelinase using a structure-property-activity relation model.
AID311932Inhibition of ASM in human H4 cells assessed as residual activity at 10 uM2008Journal of medicinal chemistry, Jan-24, Volume: 51, Issue:2
Identification of new functional inhibitors of acid sphingomyelinase using a structure-property-activity relation model.
AID1142753Vascular activity in receptor-dependent rat mesenteric resistance artery assessed as inhibition of noradrenaline-induced contraction at 3 x 10'-6 M after 5 mins2014Bioorganic & medicinal chemistry letters, Jun-01, Volume: 24, Issue:11
Vascular effects of diphenylmethoxypiperidine-derived dopamine uptake inhibitors.
AID256094Locomotor activity in mice after intraperitoneal administration at 17.8 lmol/kg2005Bioorganic & medicinal chemistry letters, Nov-15, Volume: 15, Issue:22
The synthesis and biological evaluation of dopamine transporter inhibiting activity of substituted diphenylmethoxypiperidines.
AID1142754Vascular activity in receptor-dependent rat mesenteric resistance artery assessed as inhibition of noradrenaline-induced contraction at 3 x 10'-6 M after 5 mins relative to maximal response to KCl2014Bioorganic & medicinal chemistry letters, Jun-01, Volume: 24, Issue:11
Vascular effects of diphenylmethoxypiperidine-derived dopamine uptake inhibitors.
AID1142752Vascular activity in receptor-independent rat mesenteric resistance artery assessed as inhibition of KCl-induced contraction at 3 x 10'-6 M after 5 mins2014Bioorganic & medicinal chemistry letters, Jun-01, Volume: 24, Issue:11
Vascular effects of diphenylmethoxypiperidine-derived dopamine uptake inhibitors.
AID1449628Inhibition of human BSEP expressed in baculovirus transfected fall armyworm Sf21 cell membranes vesicles assessed as reduction in ATP-dependent [3H]-taurocholate transport into vesicles incubated for 5 mins by Topcount based rapid filtration method2012Drug metabolism and disposition: the biological fate of chemicals, Dec, Volume: 40, Issue:12
Mitigating the inhibition of human bile salt export pump by drugs: opportunities provided by physicochemical property modulation, in silico modeling, and structural modification.
[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-199015 (46.88)18.7374
1990's4 (12.50)18.2507
2000's6 (18.75)29.6817
2010's6 (18.75)24.3611
2020's1 (3.13)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 43.33

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

MetricThis Compound (vs All)
Research Demand Index43.33 (24.57)
Research Supply Index3.61 (2.92)
Research Growth Index4.50 (4.65)
Search Engine Demand Index53.90 (26.88)
Search Engine Supply Index2.00 (0.95)

This Compound (43.33)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials2 (5.88%)5.53%
Reviews0 (0.00%)6.00%
Case Studies2 (5.88%)4.05%
Observational0 (0.00%)0.25%
Other30 (88.24%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]