DIPHENYLPYRALINE

US Previously Marketed

First approved in 1953

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 Search

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
Sources: http://www.tabletwise.com/medicine/diphenylpyraline-hydrochloride
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

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Histamine H1 receptor 315 Target ID: CHEMBL231 Sources: https://www.ncbi.nlm.nih.gov/pubmed/1912125	Antagonist 2778		4.1 nM [Ki]

Conditions

Condition	Modality	Highest Phase	Product
Rhinitis 20 Sources: http://www.tabletwise.com/medicine/diphenylpyraline-hydrochloride/uses-benefits-working	Primary	Approved 8429	Belfene Approved Use Unknown
Pruritus 29 Sources: http://www.tabletwise.com/medicine/diphenylpyraline	Primary	Approved 8429	Belfene Approved Use Unknown
Allergic rhinitis 100 Sources: http://www.tabletwise.com/medicine/diphenylpyraline-hydrochloride/uses-benefits-working	Primary	Approved 8429	Belfene Approved Use Unknown

T_1/2

Value	Dose	Co-administered	Analyte	Population
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 unknown	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FED

Sourcing

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

PubMed

Title	Date	PubMed
Diphenylpyraline, a histamine H1 receptor antagonist, has psychostimulant properties.	2005 Jan 4	15627433
Development of a list of potentially inappropriate drugs for the korean elderly using the delphi method.	2010 Dec	21818443

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

Official 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

DIPHENYLPYRALINE [MI]

Common Name

English

Classification Tree Code System Code

WHO-ATC

R06AA57