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

Details

Stereochemistry ACHIRAL
Molecular Formula C16H21N3.ClH
Molecular Weight 291.819
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of TRIPELENNAMINE HYDROCHLORIDE

SMILES

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

InChI

InChIKey=FSSICIQKZGUEAE-UHFFFAOYSA-N
InChI=1S/C16H21N3.ClH/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;1H

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

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

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
Cholinesterase inhibition by phenothiazine and nonphenothiazine antihistaminics: analysis of its postulated role in synergizing organophosphate toxicity.
1975 Feb
Central nervous system complications of addiction to "T's and Blues".
1982 Jun
Fatal intracranial hemorrhage associated with phenylpropanolamine, pentazocine, and tripelennamine overdose.
1985
Behavioral and developmental effects of prenatal exposure to pentazocine and tripelennamine combinations.
1986 Nov-Dec
Antihistaminics enhance morphine-, but not amphetamine- and scopolamine-induced hyperactivity in mice.
1987
Nitric oxide, superoxide radicals and mast cells in pathogenesis of indomethacin-induced small intestinal lesions in rats.
1999 Mar
Antinociceptive and antiedematogenic properties and acute toxicity of Tabebuia avellanedae Lor. ex Griseb. inner bark aqueous extract.
2001
Histamine H1 and H2 receptor antagonists accelerate skin barrier repair and prevent epidermal hyperplasia induced by barrier disruption in a dry environment.
2001 Feb
Quantitation of antihistamines in pharmaceutical preparations by liquid chromatography with a micellar mobile phase of sodium dodecyl sulfate and pentanol.
2001 Nov-Dec
H1-receptor antagonist, tripelennamine, does not affect arterial hypoxemia in exercising Thoroughbreds.
2002 Apr
Prostaglandin E2 aggravates gastric mucosal injury induced by histamine in rats through EP1 receptors.
2003 Dec 19
Management of rhinitis and asthma in pregnancy.
2003 Jun
On the mechanisms underlying histamine induction of gastric mucosal lesions in rats with partial gastric vascular occlusion.
2003 Jun
Treatment of allergic rhinitis during pregnancy.
2004 Jan-Feb
Medicinal plants in Suriname: hypotensive effect of Gossypium barbadense.
2004 Mar
Role of N-methyl-D-aspartate receptors in gastric mucosal blood flow induced by histamine.
2004 Sep 1
Involvement of histamine H1 and H2 receptors in the regulation of STAT-1 phosphorylation: inverse agonism exhibited by the receptor antagonists.
2005 Jul
Analysis of pharmaceutical preparations containing antihistamine drugs by micellar liquid chromatography.
2006 Feb 13
Characterization of antihistamine-human serum protein interactions by capillary electrophoresis.
2007 Apr 20
Myasthenia gravis-like syndrome in a Hereford heifer.
2008 Jan-Feb
Medullary pain facilitating neurons mediate allodynia in headache-related pain.
2009 Feb
Ruthenium-catalyzed N-alkylation of amines and sulfonamides using borrowing hydrogen methodology.
2009 Feb 11
Anomalous photophysics of H1 antihistamines in aqueous solution.
2009 May 14
Development of a list of potentially inappropriate drugs for the korean elderly using the delphi method.
2010 Dec
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 Fri Dec 15 15:02:17 GMT 2023
Edited
by admin
on Fri Dec 15 15:02:17 GMT 2023
Record UNII
FWV8GJ56ZN
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
TRIPELENNAMINE HYDROCHLORIDE
GREEN BOOK   MART.   MI   ORANGE BOOK   USP   USP-RS   VANDF   WHO-DD  
Common Name English
TRIPELENNAMINE HYDROCHLORIDE [ORANGE BOOK]
Common Name English
AZARON
Brand Name English
Tripelennamine hydrochloride [WHO-DD]
Common Name English
VETIBENZAMINA
Brand Name English
PYRIBENZAMINE
Brand Name English
2-[Benzyl[2-(dimethylamino)ethyl]amino]pyridine monohydrochloride
Systematic Name English
1,2-ETHANEDIAMINE, N,N-DIMETHYL-N'-(PHENYLMETHYL)-N'-2-PYRIDINYL-, MONOHYDROCHLORIDE
Common Name English
TRIPELENNAMINE HYDROCHLORIDE [GREEN BOOK]
Common Name English
TRIPELENNAMINE HYDROCHLORIDE [MART.]
Common Name English
TRIPELENNAMINE HCL
Common Name English
TRIPELENNAMINE HYDROCHLORIDE [VANDF]
Common Name English
TRIPELENNAMINE HYDROCHLORIDE [MI]
Common Name English
TRIPELENNAMINE HYDROCHLORIDE [USP-RS]
Common Name English
DEHISTIN
Brand Name English
NSC-409943
Code English
TRIPELENNAMINE HYDROCHLORIDE [USP MONOGRAPH]
Common Name English
Classification Tree Code System Code
CFR 21 CFR 522.2615
Created by admin on Fri Dec 15 15:02:17 GMT 2023 , Edited by admin on Fri Dec 15 15:02:17 GMT 2023
NCI_THESAURUS C29578
Created by admin on Fri Dec 15 15:02:17 GMT 2023 , Edited by admin on Fri Dec 15 15:02:17 GMT 2023
Code System Code Type Description
EVMPD
SUB04981MIG
Created by admin on Fri Dec 15 15:02:17 GMT 2023 , Edited by admin on Fri Dec 15 15:02:17 GMT 2023
PRIMARY
FDA UNII
FWV8GJ56ZN
Created by admin on Fri Dec 15 15:02:17 GMT 2023 , Edited by admin on Fri Dec 15 15:02:17 GMT 2023
PRIMARY
RXCUI
91063
Created by admin on Fri Dec 15 15:02:17 GMT 2023 , Edited by admin on Fri Dec 15 15:02:17 GMT 2023
PRIMARY RxNorm
NSC
409943
Created by admin on Fri Dec 15 15:02:17 GMT 2023 , Edited by admin on Fri Dec 15 15:02:17 GMT 2023
PRIMARY
ChEMBL
CHEMBL1241
Created by admin on Fri Dec 15 15:02:17 GMT 2023 , Edited by admin on Fri Dec 15 15:02:17 GMT 2023
PRIMARY
CAS
154-69-8
Created by admin on Fri Dec 15 15:02:17 GMT 2023 , Edited by admin on Fri Dec 15 15:02:17 GMT 2023
PRIMARY
PUBCHEM
9066
Created by admin on Fri Dec 15 15:02:17 GMT 2023 , Edited by admin on Fri Dec 15 15:02:17 GMT 2023
PRIMARY
RS_ITEM_NUM
1695004
Created by admin on Fri Dec 15 15:02:17 GMT 2023 , Edited by admin on Fri Dec 15 15:02:17 GMT 2023
PRIMARY
SMS_ID
100000084668
Created by admin on Fri Dec 15 15:02:17 GMT 2023 , Edited by admin on Fri Dec 15 15:02:17 GMT 2023
PRIMARY
DAILYMED
FWV8GJ56ZN
Created by admin on Fri Dec 15 15:02:17 GMT 2023 , Edited by admin on Fri Dec 15 15:02:17 GMT 2023
PRIMARY
NCI_THESAURUS
C47774
Created by admin on Fri Dec 15 15:02:17 GMT 2023 , Edited by admin on Fri Dec 15 15:02:17 GMT 2023
PRIMARY
ECHA (EC/EINECS)
205-833-5
Created by admin on Fri Dec 15 15:02:17 GMT 2023 , Edited by admin on Fri Dec 15 15:02:17 GMT 2023
PRIMARY
DRUG BANK
DBSALT000689
Created by admin on Fri Dec 15 15:02:17 GMT 2023 , Edited by admin on Fri Dec 15 15:02:17 GMT 2023
PRIMARY
EPA CompTox
DTXSID6026248
Created by admin on Fri Dec 15 15:02:17 GMT 2023 , Edited by admin on Fri Dec 15 15:02:17 GMT 2023
PRIMARY
MERCK INDEX
m11180
Created by admin on Fri Dec 15 15:02:17 GMT 2023 , Edited by admin on Fri Dec 15 15:02:17 GMT 2023
PRIMARY Merck Index
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ACTIVE MOIETY