U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

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
2778
 4.1 nM [Ki]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Approved
8429
Belfene

Approved Use

Unknown
Primary
Approved
8429
Belfene

Approved Use

Unknown
Primary
Approved
8429
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 unknown
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
Diphenylpyraline (Lergobine) in the treatment of patients suffering from allergic and vasomotor rhinitis.
1977
[Antimycobacterial antihistaminics].
1989 Aug
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
Antimycobacterial activity of diphenylpyraline derivatives.
2008 Apr
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

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 Fri Dec 15 15:04:00 UTC 2023
Edited
by admin
on Fri Dec 15 15:04:00 UTC 2023
Record UNII
33361OE3AV
Record Status Validated (UNII)
Record Version
  • Download
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
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
Created by admin on Fri Dec 15 15:04:00 UTC 2023 , Edited by admin on Fri Dec 15 15:04:00 UTC 2023
WHO-ATC R06AA07
Created by admin on Fri Dec 15 15:04:00 UTC 2023 , Edited by admin on Fri Dec 15 15:04:00 UTC 2023
WHO-VATC QR06AA07
Created by admin on Fri Dec 15 15:04:00 UTC 2023 , Edited by admin on Fri Dec 15 15:04:00 UTC 2023
NCI_THESAURUS C29578
Created by admin on Fri Dec 15 15:04:00 UTC 2023 , Edited by admin on Fri Dec 15 15:04:00 UTC 2023
WHO-VATC QR06AA57
Created by admin on Fri Dec 15 15:04:00 UTC 2023 , Edited by admin on Fri Dec 15 15:04:00 UTC 2023
Code System Code Type Description
EVMPD
SUB07213MIG
Created by admin on Fri Dec 15 15:04:00 UTC 2023 , Edited by admin on Fri Dec 15 15:04:00 UTC 2023
PRIMARY
NCI_THESAURUS
C65423
Created by admin on Fri Dec 15 15:04:00 UTC 2023 , Edited by admin on Fri Dec 15 15:04:00 UTC 2023
PRIMARY
WIKIPEDIA
DIPHENYLPYRALINE
Created by admin on Fri Dec 15 15:04:00 UTC 2023 , Edited by admin on Fri Dec 15 15:04:00 UTC 2023
PRIMARY
MESH
C009871
Created by admin on Fri Dec 15 15:04:00 UTC 2023 , Edited by admin on Fri Dec 15 15:04:00 UTC 2023
PRIMARY
DRUG BANK
DB01146
Created by admin on Fri Dec 15 15:04:00 UTC 2023 , Edited by admin on Fri Dec 15 15:04:00 UTC 2023
PRIMARY
ECHA (EC/EINECS)
205-686-7
Created by admin on Fri Dec 15 15:04:00 UTC 2023 , Edited by admin on Fri Dec 15 15:04:00 UTC 2023
PRIMARY
MERCK INDEX
m4640
Created by admin on Fri Dec 15 15:04:00 UTC 2023 , Edited by admin on Fri Dec 15 15:04:00 UTC 2023
PRIMARY Merck Index
PUBCHEM
3103
Created by admin on Fri Dec 15 15:04:00 UTC 2023 , Edited by admin on Fri Dec 15 15:04:00 UTC 2023
PRIMARY
CHEBI
59788
Created by admin on Fri Dec 15 15:04:00 UTC 2023 , Edited by admin on Fri Dec 15 15:04:00 UTC 2023
PRIMARY
FDA UNII
33361OE3AV
Created by admin on Fri Dec 15 15:04:00 UTC 2023 , Edited by admin on Fri Dec 15 15:04:00 UTC 2023
PRIMARY
IUPHAR
7165
Created by admin on Fri Dec 15 15:04:00 UTC 2023 , Edited by admin on Fri Dec 15 15:04:00 UTC 2023
PRIMARY
DRUG CENTRAL
920
Created by admin on Fri Dec 15 15:04:00 UTC 2023 , Edited by admin on Fri Dec 15 15:04:00 UTC 2023
PRIMARY
SMS_ID
100000082348
Created by admin on Fri Dec 15 15:04:00 UTC 2023 , Edited by admin on Fri Dec 15 15:04:00 UTC 2023
PRIMARY
RXCUI
23386
Created by admin on Fri Dec 15 15:04:00 UTC 2023 , Edited by admin on Fri Dec 15 15:04:00 UTC 2023
PRIMARY RxNorm
EPA CompTox
DTXSID3022952
Created by admin on Fri Dec 15 15:04:00 UTC 2023 , Edited by admin on Fri Dec 15 15:04:00 UTC 2023
PRIMARY
INN
695
Created by admin on Fri Dec 15 15:04:00 UTC 2023 , Edited by admin on Fri Dec 15 15:04:00 UTC 2023
PRIMARY
ChEMBL
CHEMBL1492
Created by admin on Fri Dec 15 15:04:00 UTC 2023 , Edited by admin on Fri Dec 15 15:04:00 UTC 2023
PRIMARY
CAS
147-20-6
Created by admin on Fri Dec 15 15:04:00 UTC 2023 , Edited by admin on Fri Dec 15 15:04:00 UTC 2023
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
PRIVACY ACT
ACCESSIBILITY
DISCLAIMER
HHS VULNERABILITY DISCLOSURE
For language access assistance, contact the NCATS Public Information Officer
National Center for Advancing Translational Sciences (NCATS),
6701 Democracy Boulevard, Bethesda MD 20892-4874 • 301-594-8966