CAS 147-20-6|Neargal|Dayfen|Diphenylpyraline Hydrochloride|Hystryl|Belfene|Diphenylpyralamine|Lyssipoll|Hispril|4-(diphenylmethoxy)-1-methylpiperidine|Diphenylpyrilene|Diafen|Diphenylpyraline|diphen...

General Information

Structure

Molecular Formula

C₁₉H₂₃NO

Molecular Mass

281.39202

Exact Mass

281.17796436

Charge

InChI

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

InChIKey

OWQUZNMMYNAXSL-UHFFFAOYSA-N

Canonic Smiles

CN1CCC(CC1)OC(c1ccccc1)c1ccccc1

Isomeric Smiles

O(C1CCN(CC1)C)C(c1ccccc1)c1ccccc1

Calculated Properties

JChem

LogD (pH = 7.4)

2.18

LogD (pH = 5.5)

0.53

Log P

3.66

Rotatable Bonds

H Donor

H Acceptors

Lipinski's Rule of Five

true

Acid pKa

8.87

Polar Surface Area

12.47

Polarizability

32.73

Molar Refractivity

87.36

LOG S

-3.14

Data Source

Academic Data

Data Source

Names and Identifiers

Brand Name

NeargalHystrylBelfeneDayfenHisprilDiafenLyssipollAllergenMepibenHistrylHistynDafen

Synonyms

DiphenylpyralamineDiphenylpyraline HydrochlorideDiphenylpyrileneDiphenylpyraline4-(diphenylmethoxy)-1-methyl-piperidine4-(benzhydryloxy)-1-methylpiperidinediphenylpyraline1-methyl-4-hydroxypiperidine benzhydryl ether1-methyl-4-piperidyl benzhydryl etherdiphenylpyralamine4-(benzhydryloxy)-N-methylpiperidine

IUPAC name

4-(diphenylmethoxy)-1-methylpiperidine

IUPAC Traditional name

diphenylpyraline

International Nonproprietary Name (INN)

diphenylpyralinedifenilpiralinadiphenylpyralinum

Names and Identifiers

Registration numbers

CAS Number

147-20-6

PubChem CID

3103

PubChem SID

4650493616096448099319623

DrugBank ID

DB01146

Unique Ingredient Identifier

CHEMBL

Wikipedia Title

Chemspider ID

ATC CODE

KEGG ID

CHEBI ID

CompTox Database

PubMed Citation Links

156274331403922445882

LINCS Database

ACToR Database

Reaxys Registry

Patent number

HMDB Database

MetaboLights Database

MTBLS2145MTBLS2878MTBLS804

Drug Central Database

KEGG DRUG Database

BindingDB Database

Beilstein Number

SureChEMBL Database

Registration numbers

Properties

Physical Property

Hydrophobicity(logP)

3.7

Pharmacology Properties

Admin Routes

Oral, Topical

Legal Status

Rx-only

Half Life

24-40 hours

Properties

Related Proteins

No Data Available

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Molecular Spectra

No Data Available

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Molecule Details

DrugBank

DB01146

Drug Groups

approved

Description

Diphenylpyraline is an antihistamine. Antihistamines used in the treatment of allergy act by competing with histamine for H 1-receptor sites on effector cells. Antihistamines prevent, but do not reverse, responses mediated by histamine alone. Antihistamines antagonize, in varying degrees, most of the pharmacological effects of histamine, including urticaria and pruritus.

Indication

For use in the treatment of allergic rhinitis, hay fever, and allergic skin disorders.

Pharmacology

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.

Affected Organisms

Humans and other mammals

Biotransformation

Hepatic

Absorption

Well absorbed after oral administration.

Protein Binding

> 99% in human serum albumin

References

• Lapa GB, Mathews TA, Harp J, Budygin EA, Jones SR: Diphenylpyraline, a histamine H1 receptor antagonist, has psychostimulant properties. Eur J Pharmacol. 2005 Jan 4;506(3):237-40. Epub 2004 Dec 8. [Pubmed]

• Ohno T, Kobayashi S, Hayashi M, Sakurai M, Kanazawa I: Diphenylpyraline-responsive parkinsonism in cerebrotendinous xanthomatosis: long-term follow up of three patients. J Neurol Sci. 2001 Jan 1;182(2):95-7. [Pubmed]

• Puhakka H, Rantanen T, Virolainen E: Diphenylpyraline (Lergobine) in the treatment of patients suffering from allergic and vasomotor rhinitis. J Int Med Res. 1977;5(1):37-41. [Pubmed]

External Links

• [Wikipedia]

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.

Molecule Details

References

PubChem Literature

From Data Sources

• Puhakka H, Rantanen T, Virolainen E: Diphenylpyraline (Lergobine) in the treatment of patients suffering from allergic and vasomotor rhinitis. J Int Med Res. 1977;5(1):37-41. Pubmed

References

Bioactivity

PubChem BioAssay

Bioactivity

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General Information

Calculated Properties

• RDKit

• JChem

Data Source

• Academic Data

Names and Identifiers