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

Details

Stereochemistry ACHIRAL
Molecular Formula C16H21N3
Molecular Weight 255.358
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of TRIPELENNAMINE

SMILES

CN(C)CCN(CC1=CC=CC=C1)C2=CC=CC=N2

InChI

InChIKey=UFLGIAIHIAPJJC-UHFFFAOYSA-N
InChI=1S/C16H21N3/c1-18(2)12-13-19(16-10-6-7-11-17-16)14-15-8-4-3-5-9-15/h3-11H,12-14H2,1-2H3

HIDE SMILES / InChI

Molecular Formula C16H21N3
Molecular Weight 255.358
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Tripelennamine (sold as Pyribenzamine by Novartis) is a drug that is used as an antipruritic and first-generation antihistamine. Histamine acting on H1-receptors produces vasodilatation, hypotension, flushing, headache, tachycardia, and bronchoconstriction. Histamine also increases vascular permeability and potentiates pain. Tripelennamine can be used in the treatment of asthma, hay fever, rhinitis, and urticaria, but is now less common as newer antihistamines have replaced it.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Palliative
PBZ

Approved Use

Unknown

Launch Date

1948
Palliative
PBZ

Approved Use

Unknown

Launch Date

1948
Palliative
PBZ

Approved Use

Unknown

Launch Date

1948
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
82 ng/mL
50 mg single, intramuscular
dose: 50 mg
route of administration: Intramuscular
experiment type: SINGLE
co-administered:
TRIPELENNAMINE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
199 ng/mL
100 mg single, intramuscular
dose: 100 mg
route of administration: Intramuscular
experiment type: SINGLE
co-administered:
TRIPELENNAMINE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
398 ng × h/mL
50 mg single, intramuscular
dose: 50 mg
route of administration: Intramuscular
experiment type: SINGLE
co-administered:
TRIPELENNAMINE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
804 ng × h/mL
100 mg single, intramuscular
dose: 100 mg
route of administration: Intramuscular
experiment type: SINGLE
co-administered:
TRIPELENNAMINE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
2.9 h
50 mg single, intramuscular
dose: 50 mg
route of administration: Intramuscular
experiment type: SINGLE
co-administered:
TRIPELENNAMINE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
4.4 h
100 mg single, intramuscular
dose: 100 mg
route of administration: Intramuscular
experiment type: SINGLE
co-administered:
TRIPELENNAMINE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
Doses

Doses

DosePopulationAdverse events​
100 mg 1 times / day single, oral
Studied dose
Dose: 100 mg, 1 times / day
Route: oral
Route: single
Dose: 100 mg, 1 times / day
Sources:
healthy, 2 years
n = 1
Health Status: healthy
Age Group: 2 years
Sex: F
Population Size: 1
Sources:
Other AEs: Weakness, Common cold...
Other AEs:
Weakness
Common cold (grade 1)
Cough
Rhinorrhea
Vomiting
Sleepiness
Sources:
25 mg 3 times / day multiple, oral
Studied dose
Dose: 25 mg, 3 times / day
Route: oral
Route: multiple
Dose: 25 mg, 3 times / day
Co-administed with::
antistin(50 mg; 11 days)
Sources:
unhealthy, 49 years
n = 1
Health Status: unhealthy
Condition: chronic allergic rhinitis
Age Group: 49 years
Sex: F
Population Size: 1
Sources:
Other AEs: Coma, Common cold...
Other AEs:
Coma
Common cold
Nausea
Diarrhoea
Back pain
Headache (grade 3)
Appetite lost
Dry cough
Pyrexia
Abdominal pain (grade 3)
Vomiting
Disorientation
Sources:
50 mg 3 times / day multiple, oral
Recommended
Dose: 50 mg, 3 times / day
Route: oral
Route: multiple
Dose: 50 mg, 3 times / day
Sources:
unhealthy, median age 36 years
n = 90
Health Status: unhealthy
Condition: chronic allergic rhinitis
Age Group: median age 36 years
Sex: M+F
Population Size: 90
Sources:
Other AEs: Sedation, Sedation...
Other AEs:
Sedation (grade 1, 8.9%)
Sedation (grade 2, 6.7%)
Dizziness (5.5%)
Nausea (4.4%)
Nose dryness (2.2%)
Sources:
AEs

AEs

AESignificanceDosePopulation
Cough
100 mg 1 times / day single, oral
Studied dose
Dose: 100 mg, 1 times / day
Route: oral
Route: single
Dose: 100 mg, 1 times / day
Sources:
healthy, 2 years
n = 1
Health Status: healthy
Age Group: 2 years
Sex: F
Population Size: 1
Sources:
Rhinorrhea
100 mg 1 times / day single, oral
Studied dose
Dose: 100 mg, 1 times / day
Route: oral
Route: single
Dose: 100 mg, 1 times / day
Sources:
healthy, 2 years
n = 1
Health Status: healthy
Age Group: 2 years
Sex: F
Population Size: 1
Sources:
Sleepiness
100 mg 1 times / day single, oral
Studied dose
Dose: 100 mg, 1 times / day
Route: oral
Route: single
Dose: 100 mg, 1 times / day
Sources:
healthy, 2 years
n = 1
Health Status: healthy
Age Group: 2 years
Sex: F
Population Size: 1
Sources:
Vomiting
100 mg 1 times / day single, oral
Studied dose
Dose: 100 mg, 1 times / day
Route: oral
Route: single
Dose: 100 mg, 1 times / day
Sources:
healthy, 2 years
n = 1
Health Status: healthy
Age Group: 2 years
Sex: F
Population Size: 1
Sources:
Weakness
100 mg 1 times / day single, oral
Studied dose
Dose: 100 mg, 1 times / day
Route: oral
Route: single
Dose: 100 mg, 1 times / day
Sources:
healthy, 2 years
n = 1
Health Status: healthy
Age Group: 2 years
Sex: F
Population Size: 1
Sources:
Common cold grade 1
100 mg 1 times / day single, oral
Studied dose
Dose: 100 mg, 1 times / day
Route: oral
Route: single
Dose: 100 mg, 1 times / day
Sources:
healthy, 2 years
n = 1
Health Status: healthy
Age Group: 2 years
Sex: F
Population Size: 1
Sources:
Appetite lost
25 mg 3 times / day multiple, oral
Studied dose
Dose: 25 mg, 3 times / day
Route: oral
Route: multiple
Dose: 25 mg, 3 times / day
Co-administed with::
antistin(50 mg; 11 days)
Sources:
unhealthy, 49 years
n = 1
Health Status: unhealthy
Condition: chronic allergic rhinitis
Age Group: 49 years
Sex: F
Population Size: 1
Sources:
Back pain
25 mg 3 times / day multiple, oral
Studied dose
Dose: 25 mg, 3 times / day
Route: oral
Route: multiple
Dose: 25 mg, 3 times / day
Co-administed with::
antistin(50 mg; 11 days)
Sources:
unhealthy, 49 years
n = 1
Health Status: unhealthy
Condition: chronic allergic rhinitis
Age Group: 49 years
Sex: F
Population Size: 1
Sources:
Coma
25 mg 3 times / day multiple, oral
Studied dose
Dose: 25 mg, 3 times / day
Route: oral
Route: multiple
Dose: 25 mg, 3 times / day
Co-administed with::
antistin(50 mg; 11 days)
Sources:
unhealthy, 49 years
n = 1
Health Status: unhealthy
Condition: chronic allergic rhinitis
Age Group: 49 years
Sex: F
Population Size: 1
Sources:
Common cold
25 mg 3 times / day multiple, oral
Studied dose
Dose: 25 mg, 3 times / day
Route: oral
Route: multiple
Dose: 25 mg, 3 times / day
Co-administed with::
antistin(50 mg; 11 days)
Sources:
unhealthy, 49 years
n = 1
Health Status: unhealthy
Condition: chronic allergic rhinitis
Age Group: 49 years
Sex: F
Population Size: 1
Sources:
Diarrhoea
25 mg 3 times / day multiple, oral
Studied dose
Dose: 25 mg, 3 times / day
Route: oral
Route: multiple
Dose: 25 mg, 3 times / day
Co-administed with::
antistin(50 mg; 11 days)
Sources:
unhealthy, 49 years
n = 1
Health Status: unhealthy
Condition: chronic allergic rhinitis
Age Group: 49 years
Sex: F
Population Size: 1
Sources:
Disorientation
25 mg 3 times / day multiple, oral
Studied dose
Dose: 25 mg, 3 times / day
Route: oral
Route: multiple
Dose: 25 mg, 3 times / day
Co-administed with::
antistin(50 mg; 11 days)
Sources:
unhealthy, 49 years
n = 1
Health Status: unhealthy
Condition: chronic allergic rhinitis
Age Group: 49 years
Sex: F
Population Size: 1
Sources:
Dry cough
25 mg 3 times / day multiple, oral
Studied dose
Dose: 25 mg, 3 times / day
Route: oral
Route: multiple
Dose: 25 mg, 3 times / day
Co-administed with::
antistin(50 mg; 11 days)
Sources:
unhealthy, 49 years
n = 1
Health Status: unhealthy
Condition: chronic allergic rhinitis
Age Group: 49 years
Sex: F
Population Size: 1
Sources:
Nausea
25 mg 3 times / day multiple, oral
Studied dose
Dose: 25 mg, 3 times / day
Route: oral
Route: multiple
Dose: 25 mg, 3 times / day
Co-administed with::
antistin(50 mg; 11 days)
Sources:
unhealthy, 49 years
n = 1
Health Status: unhealthy
Condition: chronic allergic rhinitis
Age Group: 49 years
Sex: F
Population Size: 1
Sources:
Pyrexia
25 mg 3 times / day multiple, oral
Studied dose
Dose: 25 mg, 3 times / day
Route: oral
Route: multiple
Dose: 25 mg, 3 times / day
Co-administed with::
antistin(50 mg; 11 days)
Sources:
unhealthy, 49 years
n = 1
Health Status: unhealthy
Condition: chronic allergic rhinitis
Age Group: 49 years
Sex: F
Population Size: 1
Sources:
Vomiting
25 mg 3 times / day multiple, oral
Studied dose
Dose: 25 mg, 3 times / day
Route: oral
Route: multiple
Dose: 25 mg, 3 times / day
Co-administed with::
antistin(50 mg; 11 days)
Sources:
unhealthy, 49 years
n = 1
Health Status: unhealthy
Condition: chronic allergic rhinitis
Age Group: 49 years
Sex: F
Population Size: 1
Sources:
Abdominal pain grade 3
25 mg 3 times / day multiple, oral
Studied dose
Dose: 25 mg, 3 times / day
Route: oral
Route: multiple
Dose: 25 mg, 3 times / day
Co-administed with::
antistin(50 mg; 11 days)
Sources:
unhealthy, 49 years
n = 1
Health Status: unhealthy
Condition: chronic allergic rhinitis
Age Group: 49 years
Sex: F
Population Size: 1
Sources:
Headache grade 3
25 mg 3 times / day multiple, oral
Studied dose
Dose: 25 mg, 3 times / day
Route: oral
Route: multiple
Dose: 25 mg, 3 times / day
Co-administed with::
antistin(50 mg; 11 days)
Sources:
unhealthy, 49 years
n = 1
Health Status: unhealthy
Condition: chronic allergic rhinitis
Age Group: 49 years
Sex: F
Population Size: 1
Sources:
Nose dryness 2.2%
50 mg 3 times / day multiple, oral
Recommended
Dose: 50 mg, 3 times / day
Route: oral
Route: multiple
Dose: 50 mg, 3 times / day
Sources:
unhealthy, median age 36 years
n = 90
Health Status: unhealthy
Condition: chronic allergic rhinitis
Age Group: median age 36 years
Sex: M+F
Population Size: 90
Sources:
Nausea 4.4%
50 mg 3 times / day multiple, oral
Recommended
Dose: 50 mg, 3 times / day
Route: oral
Route: multiple
Dose: 50 mg, 3 times / day
Sources:
unhealthy, median age 36 years
n = 90
Health Status: unhealthy
Condition: chronic allergic rhinitis
Age Group: median age 36 years
Sex: M+F
Population Size: 90
Sources:
Dizziness 5.5%
50 mg 3 times / day multiple, oral
Recommended
Dose: 50 mg, 3 times / day
Route: oral
Route: multiple
Dose: 50 mg, 3 times / day
Sources:
unhealthy, median age 36 years
n = 90
Health Status: unhealthy
Condition: chronic allergic rhinitis
Age Group: median age 36 years
Sex: M+F
Population Size: 90
Sources:
Sedation grade 1, 8.9%
50 mg 3 times / day multiple, oral
Recommended
Dose: 50 mg, 3 times / day
Route: oral
Route: multiple
Dose: 50 mg, 3 times / day
Sources:
unhealthy, median age 36 years
n = 90
Health Status: unhealthy
Condition: chronic allergic rhinitis
Age Group: median age 36 years
Sex: M+F
Population Size: 90
Sources:
Sedation grade 2, 6.7%
50 mg 3 times / day multiple, oral
Recommended
Dose: 50 mg, 3 times / day
Route: oral
Route: multiple
Dose: 50 mg, 3 times / day
Sources:
unhealthy, median age 36 years
n = 90
Health Status: unhealthy
Condition: chronic allergic rhinitis
Age Group: median age 36 years
Sex: M+F
Population Size: 90
Sources:
Overview

Overview

CYP3A4CYP2C9CYP2D6hERG

OverviewOther

Other InhibitorOther SubstrateOther Inducer

Drug as perpetrator​

Drug as perpetrator​

TargetModalityActivityMetaboliteClinical evidence
yes [Ki 4 uM]
Drug as victim

Drug as victim

TargetModalityActivityMetaboliteClinical evidence
yes
Sourcing

Sourcing

Vendor/AggregatorIDURL
PubMed

PubMed

TitleDatePubMed
Pulmonary angiothrombosis caused by "blue velvet" addiction.
1970 Nov
Antihistaminic-opioid combination: effect on locomotor activity in mice.
1988 Sep-Oct
Nitric oxide, superoxide radicals and mast cells in pathogenesis of indomethacin-induced small intestinal lesions in rats.
1999 Mar
Inhibitory effects of H1-antihistamines on CYP2D6- and CYP2C9-mediated drug metabolic reactions in human liver microsomes.
2002 Feb
Managing patients with local anesthetic complications using alternative methods.
2002 May-Jun
Prostaglandin E2 aggravates gastric mucosal injury induced by histamine in rats through EP1 receptors.
2003 Dec 19
Myasthenia gravis-like syndrome in a Hereford heifer.
2008 Jan-Feb
Chest swelling and Fever in an intravenous drug user.
2008 May
Anomalous photophysics of H1 antihistamines in aqueous solution.
2009 May 14
Profiling of a prescription drug library for potential renal drug-drug interactions mediated by the organic cation transporter 2.
2011 Jul 14
Patents

Patents

Sample Use Guides

Unknown
Route of Administration: Oral
Unknown
Substance Class Chemical
Created
by admin
on Sat Dec 16 16:29:16 GMT 2023
Edited
by admin
on Sat Dec 16 16:29:16 GMT 2023
Record UNII
3C5ORO99TY
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
TRIPELENNAMINE
HSDB   INN   MI   VANDF   WHO-DD  
INN  
Official Name English
tripelennamine [INN]
Common Name English
TRIPELENNAMINE [VANDF]
Common Name English
Tripelennamine [WHO-DD]
Common Name English
.BETA.-DIMETHYLAMINOETHYL-2-PYRIDYLAMINOTOLUENE
Systematic Name English
N,N-DIMETHYL-N'-BENZYL-N'-(.ALPHA.-PYRIDYL)ETHYLENEDIAMINE
Common Name English
TRIPELENNAMINE [MI]
Common Name English
TRIPELENNAMINE [HSDB]
Common Name English
1,2-ETHANEDIAMINE, N,N-DIMETHYL-N'-(PHENYLMETHYL)-N'-2-PYRIDINYL-
Systematic Name English
N-BENZYL-N',N'-DIMETHYL-N-PYRIDIN-2-YLETHANE-1,2-DIAMINE
Systematic Name English
N-BENZYL-N',N'-DIMETHYL-N-(2-PYRIDYL)ETHYLENEDIAMINE
Systematic Name English
2-(BENZYL(2-DIMETHYLAMINOETHYL)AMINO)PYRIDINE
Systematic Name English
N,N-DIMETHYL-N'-(PHENYLMETHYL)-N'-2-PYRIDINYL-1,2-ETHANEDIAMINE
Systematic Name English
NSC-118946
Code English
Classification Tree Code System Code
WHO-ATC R06AC04
Created by admin on Sat Dec 16 16:29:17 GMT 2023 , Edited by admin on Sat Dec 16 16:29:17 GMT 2023
WHO-VATC QR06AC04
Created by admin on Sat Dec 16 16:29:17 GMT 2023 , Edited by admin on Sat Dec 16 16:29:17 GMT 2023
NCI_THESAURUS C29578
Created by admin on Sat Dec 16 16:29:17 GMT 2023 , Edited by admin on Sat Dec 16 16:29:17 GMT 2023
WHO-VATC QD04AA04
Created by admin on Sat Dec 16 16:29:17 GMT 2023 , Edited by admin on Sat Dec 16 16:29:17 GMT 2023
WHO-ATC D04AA04
Created by admin on Sat Dec 16 16:29:17 GMT 2023 , Edited by admin on Sat Dec 16 16:29:17 GMT 2023
CFR 21 CFR 556.741
Created by admin on Sat Dec 16 16:29:17 GMT 2023 , Edited by admin on Sat Dec 16 16:29:17 GMT 2023
Code System Code Type Description
FDA UNII
3C5ORO99TY
Created by admin on Sat Dec 16 16:29:17 GMT 2023 , Edited by admin on Sat Dec 16 16:29:17 GMT 2023
PRIMARY
WIKIPEDIA
TRIPELENNAMINE
Created by admin on Sat Dec 16 16:29:17 GMT 2023 , Edited by admin on Sat Dec 16 16:29:17 GMT 2023
PRIMARY
EPA CompTox
DTXSID8023717
Created by admin on Sat Dec 16 16:29:17 GMT 2023 , Edited by admin on Sat Dec 16 16:29:17 GMT 2023
PRIMARY
NSC
118946
Created by admin on Sat Dec 16 16:29:17 GMT 2023 , Edited by admin on Sat Dec 16 16:29:17 GMT 2023
PRIMARY
INN
1548
Created by admin on Sat Dec 16 16:29:17 GMT 2023 , Edited by admin on Sat Dec 16 16:29:17 GMT 2023
PRIMARY
CAS
91-81-6
Created by admin on Sat Dec 16 16:29:17 GMT 2023 , Edited by admin on Sat Dec 16 16:29:17 GMT 2023
PRIMARY
PUBCHEM
5587
Created by admin on Sat Dec 16 16:29:17 GMT 2023 , Edited by admin on Sat Dec 16 16:29:17 GMT 2023
PRIMARY
EVMPD
SUB11322MIG
Created by admin on Sat Dec 16 16:29:17 GMT 2023 , Edited by admin on Sat Dec 16 16:29:17 GMT 2023
PRIMARY
RXCUI
10847
Created by admin on Sat Dec 16 16:29:17 GMT 2023 , Edited by admin on Sat Dec 16 16:29:17 GMT 2023
PRIMARY RxNorm
DRUG CENTRAL
2762
Created by admin on Sat Dec 16 16:29:17 GMT 2023 , Edited by admin on Sat Dec 16 16:29:17 GMT 2023
PRIMARY
ChEMBL
CHEMBL1241
Created by admin on Sat Dec 16 16:29:17 GMT 2023 , Edited by admin on Sat Dec 16 16:29:17 GMT 2023
PRIMARY
LACTMED
Tripelennamine
Created by admin on Sat Dec 16 16:29:17 GMT 2023 , Edited by admin on Sat Dec 16 16:29:17 GMT 2023
PRIMARY
DAILYMED
3C5ORO99TY
Created by admin on Sat Dec 16 16:29:17 GMT 2023 , Edited by admin on Sat Dec 16 16:29:17 GMT 2023
PRIMARY
MERCK INDEX
m11180
Created by admin on Sat Dec 16 16:29:17 GMT 2023 , Edited by admin on Sat Dec 16 16:29:17 GMT 2023
PRIMARY Merck Index
MESH
D014309
Created by admin on Sat Dec 16 16:29:17 GMT 2023 , Edited by admin on Sat Dec 16 16:29:17 GMT 2023
PRIMARY
NCI_THESAURUS
C61991
Created by admin on Sat Dec 16 16:29:17 GMT 2023 , Edited by admin on Sat Dec 16 16:29:17 GMT 2023
PRIMARY
ECHA (EC/EINECS)
202-100-1
Created by admin on Sat Dec 16 16:29:17 GMT 2023 , Edited by admin on Sat Dec 16 16:29:17 GMT 2023
PRIMARY
DRUG BANK
DB00792
Created by admin on Sat Dec 16 16:29:17 GMT 2023 , Edited by admin on Sat Dec 16 16:29:17 GMT 2023
PRIMARY
SMS_ID
100000076931
Created by admin on Sat Dec 16 16:29:17 GMT 2023 , Edited by admin on Sat Dec 16 16:29:17 GMT 2023
PRIMARY
HSDB
5191
Created by admin on Sat Dec 16 16:29:17 GMT 2023 , Edited by admin on Sat Dec 16 16:29:17 GMT 2023
PRIMARY
IUPHAR
7318
Created by admin on Sat Dec 16 16:29:17 GMT 2023 , Edited by admin on Sat Dec 16 16:29:17 GMT 2023
PRIMARY
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