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Details

Stereochemistry ACHIRAL
Molecular Formula C19H23NO.ClH
Molecular Weight 317.853
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of DIPHENYLPYRALINE HYDROCHLORIDE

SMILES

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

InChI

InChIKey=LPRLDRXGWKXRMQ-UHFFFAOYSA-N
InChI=1S/C19H23NO.ClH/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
Molecular Formula ClH
Molecular Weight 36.461
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE
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
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
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

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 15:13:37 UTC 2023
Edited
by admin
on Fri Dec 15 15:13:37 UTC 2023
Record UNII
G9FU7F1E87
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
DIPHENYLPYRALINE HYDROCHLORIDE
JAN   MART.   MI   ORANGE BOOK   VANDF   WHO-DD  
Common Name English
DIPHENYLPYRALINE HCL
Common Name English
Diphenylpyraline hydrochloride [WHO-DD]
Common Name English
HISPRIL
Brand Name English
DIPHENYLPYRALINE HYDROCHLORIDE [VANDF]
Common Name English
4-(Diphenylmethoxy)-1-methylpiperidine hydrochloride
Systematic Name English
PIPERIDINE, 4-(DIPHENYLMETHOXY)-1-METHYL-, HYDROCHLORIDE
Systematic Name English
NSC-61825
Code English
DIPHENYLPYRALINE HYDROCHLORIDE [ORANGE BOOK]
Common Name English
DIPHENYLPYRALINE HYDROCHLORIDE [JAN]
Common Name English
DIPHENYLPYRALINE HYDROCHLORIDE [MI]
Common Name English
DIPHENYLPYRALINE HYDROCHLORIDE [MART.]
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C29578
Created by admin on Fri Dec 15 15:13:37 UTC 2023 , Edited by admin on Fri Dec 15 15:13:37 UTC 2023
Code System Code Type Description
NSC
61825
Created by admin on Fri Dec 15 15:13:37 UTC 2023 , Edited by admin on Fri Dec 15 15:13:37 UTC 2023
PRIMARY
CHEBI
31508
Created by admin on Fri Dec 15 15:13:37 UTC 2023 , Edited by admin on Fri Dec 15 15:13:37 UTC 2023
PRIMARY
EVMPD
SUB01778MIG
Created by admin on Fri Dec 15 15:13:37 UTC 2023 , Edited by admin on Fri Dec 15 15:13:37 UTC 2023
PRIMARY
PUBCHEM
66063
Created by admin on Fri Dec 15 15:13:37 UTC 2023 , Edited by admin on Fri Dec 15 15:13:37 UTC 2023
PRIMARY
EPA CompTox
DTXSID7047772
Created by admin on Fri Dec 15 15:13:37 UTC 2023 , Edited by admin on Fri Dec 15 15:13:37 UTC 2023
PRIMARY
NCI_THESAURUS
C65424
Created by admin on Fri Dec 15 15:13:37 UTC 2023 , Edited by admin on Fri Dec 15 15:13:37 UTC 2023
PRIMARY
FDA UNII
G9FU7F1E87
Created by admin on Fri Dec 15 15:13:37 UTC 2023 , Edited by admin on Fri Dec 15 15:13:37 UTC 2023
PRIMARY
MERCK INDEX
m4640
Created by admin on Fri Dec 15 15:13:37 UTC 2023 , Edited by admin on Fri Dec 15 15:13:37 UTC 2023
PRIMARY Merck Index
RXCUI
203155
Created by admin on Fri Dec 15 15:13:37 UTC 2023 , Edited by admin on Fri Dec 15 15:13:37 UTC 2023
PRIMARY RxNorm
ChEMBL
CHEMBL1492
Created by admin on Fri Dec 15 15:13:37 UTC 2023 , Edited by admin on Fri Dec 15 15:13:37 UTC 2023
PRIMARY
DRUG BANK
DBSALT000807
Created by admin on Fri Dec 15 15:13:37 UTC 2023 , Edited by admin on Fri Dec 15 15:13:37 UTC 2023
PRIMARY
ECHA (EC/EINECS)
205-049-3
Created by admin on Fri Dec 15 15:13:37 UTC 2023 , Edited by admin on Fri Dec 15 15:13:37 UTC 2023
PRIMARY
SMS_ID
100000087536
Created by admin on Fri Dec 15 15:13:37 UTC 2023 , Edited by admin on Fri Dec 15 15:13:37 UTC 2023
PRIMARY
CAS
132-18-3
Created by admin on Fri Dec 15 15:13:37 UTC 2023 , Edited by admin on Fri Dec 15 15:13:37 UTC 2023
PRIMARY
MESH
C009871
Created by admin on Fri Dec 15 15:13:37 UTC 2023 , Edited by admin on Fri Dec 15 15:13:37 UTC 2023
PRIMARY
Related Record Type Details
Structure of DIPHENYLPYRALINE
PARENT -> SALT/SOLVATE
Related Record Type Details
Structure of DIPHENYLPYRALINE
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