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Details

Stereochemistry ACHIRAL
Molecular Formula C19H23NO
Molecular Weight 281.392
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of DIPHENYLPYRALINE

SMILES

CN1CCC(CC1)OC(C2=CC=CC=C2)C3=CC=CC=C3

InChI

InChIKey=OWQUZNMMYNAXSL-UHFFFAOYSA-N
InChI=1S/C19H23NO/c1-20-14-12-18(13-15-20)21-19(16-8-4-2-5-9-16)17-10-6-3-7-11-17/h2-11,18-19H,12-15H2,1H3

HIDE SMILES / InChI
Molecular Formula C19H23NO
Molecular Weight 281.392
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Description
Curator's Comment: description was created based on several sources, including https://www.drugbank.ca/drugs/DB01146 | https://www.ncbi.nlm.nih.gov/pubmed/42012 | https://www.ncbi.nlm.nih.gov/pubmed/1912125

Diphenylpyraline is an antihistamine that prevents but does not reverse, responses mediated by histamine alone. Diphenylpyraline antagonizes most of the pharmacological effects of histamine, including urticaria and pruritus. Also, diphenylpyraline may exhibit anticholinergic actions (as do most of the antihistamines) and may thus provide a drying effect on the nasal mucosa. Antihistamines such as diphenylpyraline used in the treatment of allergy act by competing with histamine for H1-receptor sites on effector cells. This reduces the effects of histamine, leading to a temporary reduction of allergy symptoms.

CNS Activity

Originator

Carson, L.E.|Campbell, C.C.
3
Sources: Science (Washington) 1950 Vol.3 No.2895 pp.689-691 pp.

Approval Year

1953
193
Targets

Targets

Primary TargetPharmacologyConditionPotency
Antagonist
2849
 4.1 nM [Ki]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Approved
8583
Belfene

Approved Use

Unknown
Primary
Approved
8583
Belfene

Approved Use

Unknown
Primary
Approved
8583
Belfene

Approved Use

Unknown
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
32 h
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/4156058/
5 mg single, oral
dose: 5 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
DIPHENYLPYRALINE urine
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FED
Sourcing

Sourcing

Vendor/AggregatorIDURL
ChEBI
CHEBI:59788
https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:59788
ZINC
ZINC000000056643
http://zinc15.docking.org/substances/ZINC000000056643
PubMed

PubMed

TitleDatePubMed
Development of a list of potentially inappropriate drugs for the korean elderly using the delphi method.
2010-12
Adverse drug effects in hospitalized elderly: data from the healthcare cost and utilization project.
2010
Development and validation of LC-MS/MS method for the determination of cyproheptadine in several pharmaceutical syrup formulations.
2009-12-05
Application of dummy molecularly imprinted solid-phase extraction in the analysis of cyproheptadine in bovine urine.
2009-05
Development and validation of an LC-MS/MS confirmatory method for residue analysis of cyproheptadine in urine of food-producing animals.
2009-03-25
Antimycobacterial and H1-antihistaminic activity of 2-substituted piperidine derivatives.
2008-12-15
Antimycobacterial activity of diphenylpyraline derivatives.
2008-04
Transition metal complexes of quinolino[3,2-b]benzodiazepine and quinolino[3,2-b]benzoxazepine: synthesis, characterization, and antimicrobial studies.
2007
Simultaneous determination of ten antihistamine drugs in human plasma using pipette tip solid-phase extraction and gas chromatography/mass spectrometry.
2006
Diphenylpyraline, a histamine H1 receptor antagonist, has psychostimulant properties.
2005-01-04
Treatment of urethral sphincter mechanism incompetence in 11 bitches with a sustained-release formulation of phenylpropanolamine hydrochloride.
2002-09-28
Sensitive determination of pethidine in body fluids by surface ionization organic mass spectrometry.
2001-07-05
Diphenylpyraline-responsive parkinsonism in cerebrotendinous xanthomatosis: long-term follow up of three patients.
2001-01-01
Decreased histamine H1 receptors in the frontal cortex of brains from patients with chronic schizophrenia.
1991-08-15
[Antimycobacterial antihistaminics].
1989-08
Diphenylpyraline (Lergobine) in the treatment of patients suffering from allergic and vasomotor rhinitis.
1977
Patents

Patents

07355042
3

Sample Use Guides

In Vivo Use Guide
Up to 6 mg daily in 3-4 divided doses.
Route of Administration: Oral
In Vitro Use Guide
Brain tissue was obtained at autopsy on 18 Japanese patients with chronic schizophrenia. The brain tissues were weighed, homogenized and centrifuged. The specific 3H-mepyramine binding to the brain tissues reached equilibrium values within 20 min after incubation at 25°C. Inhibition of the specific component of the 3H-mepyramine binding by Diphenylpyraline was then studied. The H1 antagonist diphenylpyraline (Ki=4.1nM) was potent competitors for the specific binding of 3H-mepyramine.
Substance Class Chemical
Created
by admin
on Mon Mar 31 17:45:11 GMT 2025
Edited
by admin
on Mon Mar 31 17:45:11 GMT 2025
Record UNII
33361OE3AV
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
DIPHENYLPYRALINE
INN   MI   VANDF   WHO-DD  
INN  
Official Name English
DIPHENYLPYRALINE [MI]
Preferred Name English
DIPHENYLPYRALINE [VANDF]
Common Name English
PIPERIDINE, 4-(DIPHENYLMETHOXY)-1-METHYL
Common Name English
4-(DIPHENYLMETHOXY)-1-METHYLPIPERIDINE
Systematic Name English
diphenylpyraline [INN]
Common Name English
Diphenylpyraline [WHO-DD]
Common Name English
Classification Tree Code System Code
WHO-ATC R06AA57
Created by admin on Mon Mar 31 17:45:11 GMT 2025 , Edited by admin on Mon Mar 31 17:45:11 GMT 2025
WHO-ATC R06AA07
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WHO-VATC QR06AA07
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NCI_THESAURUS C29578
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WHO-VATC QR06AA57
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Code System Code Type Description
EVMPD
SUB07213MIG
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PRIMARY
NCI_THESAURUS
C65423
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PRIMARY
WIKIPEDIA
DIPHENYLPYRALINE
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PRIMARY
MESH
C009871
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PRIMARY
DRUG BANK
DB01146
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PRIMARY
ECHA (EC/EINECS)
205-686-7
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PRIMARY
MERCK INDEX
m4640
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PRIMARY Merck Index
PUBCHEM
3103
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PRIMARY
CHEBI
59788
Created by admin on Mon Mar 31 17:45:11 GMT 2025 , Edited by admin on Mon Mar 31 17:45:11 GMT 2025
PRIMARY
FDA UNII
33361OE3AV
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PRIMARY
IUPHAR
7165
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PRIMARY
DRUG CENTRAL
920
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PRIMARY
SMS_ID
100000082348
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PRIMARY
RXCUI
23386
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PRIMARY RxNorm
EPA CompTox
DTXSID3022952
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PRIMARY
INN
695
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PRIMARY
ChEMBL
CHEMBL1492
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PRIMARY
CAS
147-20-6
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PRIMARY
Related Record Type Details
Structure of PIPRINHYDRINATE
SALT/SOLVATE -> PARENT
Structure of DIPHENYLPYRALINE HYDROCHLORIDE
SALT/SOLVATE -> PARENT
Related Record Type Details
Structure of DIPHENYLPYRALINE
ACTIVE MOIETY
NIH
NCATS
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