DIPHENYLPYRALINE HYDROBROMIDE

US Previously Marketed

First approved in 1953

Details

Stereochemistry	ACHIRAL
Molecular Formula	C19H23NO.BrH
Molecular Weight	362.304
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure of DIPHENYLPYRALINE HYDROBROMIDE

Structure Search

SMILES

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

InChI

InChIKey=IQVABVYNAOOBIJ-UHFFFAOYSA-N

InChI=1S/C19H23NO.BrH/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;1H

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 (Lergobine) in the treatment of patients suffering from allergic and vasomotor rhinitis.	1977	14039
[Antimycobacterial antihistaminics].	1989 Aug	2513793
Decreased histamine H1 receptors in the frontal cortex of brains from patients with chronic schizophrenia.	1991 Aug 15	1912125
Diphenylpyraline-responsive parkinsonism in cerebrotendinous xanthomatosis: long-term follow up of three patients.	2001 Jan 1	11137513
Sensitive determination of pethidine in body fluids by surface ionization organic mass spectrometry.	2001 Jul 5	11482730
Treatment of urethral sphincter mechanism incompetence in 11 bitches with a sustained-release formulation of phenylpropanolamine hydrochloride.	2002 Sep 28	12403516
Diphenylpyraline, a histamine H1 receptor antagonist, has psychostimulant properties.	2005 Jan 4	15627433
Simultaneous determination of ten antihistamine drugs in human plasma using pipette tip solid-phase extraction and gas chromatography/mass spectrometry.	2006	16419026
Transition metal complexes of quinolino[3,2-b]benzodiazepine and quinolino[3,2-b]benzoxazepine: synthesis, characterization, and antimicrobial studies.	2007	18273383
Antimycobacterial activity of diphenylpyraline derivatives.	2008 Apr	17714832
Antimycobacterial and H1-antihistaminic activity of 2-substituted piperidine derivatives.	2008 Dec 15	18977145
Development and validation of LC-MS/MS method for the determination of cyproheptadine in several pharmaceutical syrup formulations.	2009 Dec 5	19574011
Development and validation of an LC-MS/MS confirmatory method for residue analysis of cyproheptadine in urine of food-producing animals.	2009 Mar 25	19231896
Application of dummy molecularly imprinted solid-phase extraction in the analysis of cyproheptadine in bovine urine.	2009 May	19472275
Adverse drug effects in hospitalized elderly: data from the healthcare cost and utilization project.	2010	22291486
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 HYDROBROMIDE

Common Name

English

PIPERIDINE, 4-(DIPHENYLMETHOXY)-1-METHYL-, HYDROBROMIDE (1:1)

Systematic Name

English

DIPHENYLPYRALINE HYDROBROMIDE [MI]

Common Name

English

Code System Code Type Description

CAS

5807-87-4