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Details

Stereochemistry ACHIRAL
Molecular Formula C19H23NO
Molecular Weight 281.392
Optical Activity UNSPECIFIED
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

Description

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

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
4.1 nM [Ki]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Belfene
Primary
Belfene
Primary
Belfene
PubMed

PubMed

TitleDatePubMed
Diphenylpyraline (Lergobine) in the treatment of patients suffering from allergic and vasomotor rhinitis.
1977
[Antimycobacterial antihistaminics].
1989 Aug
Decreased histamine H1 receptors in the frontal cortex of brains from patients with chronic schizophrenia.
1991 Aug 15
Diphenylpyraline-responsive parkinsonism in cerebrotendinous xanthomatosis: long-term follow up of three patients.
2001 Jan 1
Sensitive determination of pethidine in body fluids by surface ionization organic mass spectrometry.
2001 Jul 5
Treatment of urethral sphincter mechanism incompetence in 11 bitches with a sustained-release formulation of phenylpropanolamine hydrochloride.
2002 Sep 28
Diphenylpyraline, a histamine H1 receptor antagonist, has psychostimulant properties.
2005 Jan 4
Simultaneous determination of ten antihistamine drugs in human plasma using pipette tip solid-phase extraction and gas chromatography/mass spectrometry.
2006
Transition metal complexes of quinolino[3,2-b]benzodiazepine and quinolino[3,2-b]benzoxazepine: synthesis, characterization, and antimicrobial studies.
2007
Antimycobacterial activity of diphenylpyraline derivatives.
2008 Apr
Antimycobacterial and H1-antihistaminic activity of 2-substituted piperidine derivatives.
2008 Dec 15
Development and validation of LC-MS/MS method for the determination of cyproheptadine in several pharmaceutical syrup formulations.
2009 Dec 5
Development and validation of an LC-MS/MS confirmatory method for residue analysis of cyproheptadine in urine of food-producing animals.
2009 Mar 25
Application of dummy molecularly imprinted solid-phase extraction in the analysis of cyproheptadine in bovine urine.
2009 May
Adverse drug effects in hospitalized elderly: data from the healthcare cost and utilization project.
2010
Development of a list of potentially inappropriate drugs for the korean elderly using the delphi method.
2010 Dec
Patents

Patents

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.
Name Type Language
DIPHENYLPYRALINE
INN   MI   VANDF   WHO-DD  
INN  
Official Name English
DIPHENYLPYRALINE [VANDF]
Common Name English
PIPERIDINE, 4-(DIPHENYLMETHOXY)-1-METHYL
Common Name English
DIPHENYLPYRALINE [WHO-DD]
Common Name English
4-(DIPHENYLMETHOXY)-1-METHYLPIPERIDINE
Systematic Name English
DIPHENYLPYRALINE [INN]
Common Name English
DIPHENYLPYRALINE [MI]
Common Name English
Classification Tree Code System Code
WHO-ATC R06AA57
Created by admin on Tue Mar 06 12:00:10 UTC 2018 , Edited by admin on Tue Mar 06 12:00:10 UTC 2018
WHO-ATC R06AA07
Created by admin on Tue Mar 06 12:00:10 UTC 2018 , Edited by admin on Tue Mar 06 12:00:10 UTC 2018
WHO-VATC QR06AA07
Created by admin on Tue Mar 06 12:00:10 UTC 2018 , Edited by admin on Tue Mar 06 12:00:10 UTC 2018
WHO-VATC QR06AA57
Created by admin on Tue Mar 06 12:00:10 UTC 2018 , Edited by admin on Tue Mar 06 12:00:10 UTC 2018
Code System Code Type Description
EVMPD
SUB07213MIG
Created by admin on Tue Mar 06 12:00:10 UTC 2018 , Edited by admin on Tue Mar 06 12:00:10 UTC 2018
PRIMARY
NCI_THESAURUS
C65423
Created by admin on Tue Mar 06 12:00:10 UTC 2018 , Edited by admin on Tue Mar 06 12:00:10 UTC 2018
PRIMARY
WIKIPEDIA
DIPHENYLPYRALINE
Created by admin on Tue Mar 06 12:00:10 UTC 2018 , Edited by admin on Tue Mar 06 12:00:10 UTC 2018
PRIMARY
MESH
C009871
Created by admin on Tue Mar 06 12:00:10 UTC 2018 , Edited by admin on Tue Mar 06 12:00:10 UTC 2018
PRIMARY
DRUG BANK
DB01146
Created by admin on Tue Mar 06 12:00:10 UTC 2018 , Edited by admin on Tue Mar 06 12:00:10 UTC 2018
PRIMARY
ECHA (EC/EINECS)
205-686-7
Created by admin on Tue Mar 06 12:00:10 UTC 2018 , Edited by admin on Tue Mar 06 12:00:10 UTC 2018
PRIMARY
MERCK INDEX
M4640
Created by admin on Tue Mar 06 12:00:10 UTC 2018 , Edited by admin on Tue Mar 06 12:00:10 UTC 2018
PRIMARY Merck Index
PUBCHEM
3103
Created by admin on Tue Mar 06 12:00:10 UTC 2018 , Edited by admin on Tue Mar 06 12:00:10 UTC 2018
PRIMARY SWITZERF
IUPHAR
7165
Created by admin on Tue Mar 06 12:00:10 UTC 2018 , Edited by admin on Tue Mar 06 12:00:10 UTC 2018
PRIMARY
RXCUI
23386
Created by admin on Tue Mar 06 12:00:10 UTC 2018 , Edited by admin on Tue Mar 06 12:00:10 UTC 2018
PRIMARY RxNorm
EPA CompTox
147-20-6
Created by admin on Tue Mar 06 12:00:10 UTC 2018 , Edited by admin on Tue Mar 06 12:00:10 UTC 2018
PRIMARY
INN
695
Created by admin on Tue Mar 06 12:00:10 UTC 2018 , Edited by admin on Tue Mar 06 12:00:10 UTC 2018
PRIMARY
ChEMBL
CHEMBL1492
Created by admin on Tue Mar 06 12:00:10 UTC 2018 , Edited by admin on Tue Mar 06 12:00:10 UTC 2018
PRIMARY
CAS
147-20-6
Created by admin on Tue Mar 06 12:00:10 UTC 2018 , Edited by admin on Tue Mar 06 12:00:10 UTC 2018
PRIMARY