TRIPELENNAMINE HYDROCHLORIDE

US Previously Marketed

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

Structure Search

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

Description
Sources: https://www.drugs.com/mtm/tripelennamine.html

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.

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Histamine H1 receptor 315 Target ID: CHEMBL231 Sources: https://www.ncbi.nlm.nih.gov/pubmed/7513381	Antagonist 2778

Conditions

Condition	Modality	Highest Phase	Product
Hives 5 Sources: https://www.drugs.com/mtm/tripelennamine.html	Palliative	Approved 8429	PBZ Approved Use Unknown Launch Date -6.9007678E11
Rashes 5 Sources: https://www.drugs.com/mtm/tripelennamine.html	Palliative	Approved 8429	PBZ Approved Use Unknown Launch Date -6.9007678E11
Sneezing 7 Sources: https://www.drugs.com/mtm/tripelennamine.html	Palliative	Approved 8429	PBZ Approved Use Unknown Launch Date -6.9007678E11

C_max

Value	Dose	Co-administered	Analyte	Population
82 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/3709032	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 EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/3709032	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

Value	Dose	Co-administered	Analyte	Population
398 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/3709032	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 EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/3709032	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

T_1/2

Value	Dose	Co-administered	Analyte	Population
2.9 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/3709032	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 EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/3709032	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

Dose	Population	Adverse 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: https://pubmed.ncbi.nlm.nih.gov/13039563/	healthy, 2 years n = 1 Health Status: healthy Age Group: 2 years Sex: F Population Size: 1 Sources: https://pubmed.ncbi.nlm.nih.gov/13039563/	Other AEs: Weakness, Common cold... Other AEs: Weakness Common cold (grade 1) Cough Rhinorrhea Vomiting Sleepiness Sources: https://pubmed.ncbi.nlm.nih.gov/13039563/
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: https://pubmed.ncbi.nlm.nih.gov/13526305/	unhealthy, 49 years n = 1 Health Status: unhealthy Condition: chronic allergic rhinitis Age Group: 49 years Sex: F Population Size: 1 Sources: https://pubmed.ncbi.nlm.nih.gov/13526305/	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: https://pubmed.ncbi.nlm.nih.gov/13526305/
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: https://pubmed.ncbi.nlm.nih.gov/13640851/	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: https://pubmed.ncbi.nlm.nih.gov/13640851/	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: https://pubmed.ncbi.nlm.nih.gov/13640851/

AEs

Overview

CYP3A4	CYP2C9	CYP2D6	hERG
		inhibitor 1852

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
	UGT enzymes 27

Drug as perpetrator

Target	Modality	Activity	Metabolite	Clinical evidence
CYP2D6 1891	inhibitor 3277 Sources: https://pubmed.ncbi.nlm.nih.gov/9616188/	yes [Ki 4 uM]

Drug as victim

Target	Modality	Activity	Metabolite	Clinical evidence
UGT enzymes 27	substrate 3367 Sources: https://pubmed.ncbi.nlm.nih.gov/1362943/	yes

Sourcing

Vendor/Aggregator	ID	URL
001 Chemical	DY579204	https://www.001chemical.com/chem/91-81-6
1PlusChem LLC	1P00AOZL
A2B Chem	AE98145
ABI Chem	AC1L1KOH
ABI Chem	AC1Q3WSI
ABI Chem	AC1Q3WSJ
AK Scientific	Y1482
AKOS	AKOS025116925
AbovChem LLC	HY-17428
Alfa Chemistry	91-81-6	https://www.alfa-chemistry.com/cas_91-81-6.htm
Ambeed	A147384
Angene	AGN-PC-0Q6RIZ
ApexBio Technology	B1553
Aurora Fine Chemicals LLC	K02.874.628	http://online.aurorafinechemicals.com/info?ID=K02.874.628
BLD Pharm	BD16460
BOC Sciences	154-69-8
BOC Sciences	6138-56-3
BioSynth	W-108029
BlocksMatrix Scientific	147893
Chem Scene	CS-1395
ChemExper Chemical Directory	jlep@@@XleLl{rkMA^RDEEAAP@@@
ChemMol	99173756	http://www.chemmol.com/chemmol/99173756.html
ChemShuttle	113827
Chemieliva Pharmaceutical Co., Ltd	PBCM1043527
Chemspace	CSC020643506
Combi-Blocks	QP-2860
Compound Cloud	197066
Compound Cloud	5587
Compound Cloud	9066
Enamine	BBV-78228896
Enamine	EN300-123046
Enamine	EN300-708778
Frontier Scientific Services	100082092
Frontier Scientific Services	500028055
Hairui	HR141876	http://www.hairuichem.com/en/product/91-81-6.html
HongKong Chemhere	SCE20729
KeyOrganics	AS-59347
Lab Network	LN00337400
Lab Seeker	SC-94044
MedChem Express	HY-17428
MolPort	MolPort-003-894-746
Molcore	MC579204	https://www.molcore.com/product/91-81-6
Molnova	M12195
MuseChem	I009889
NCI Plated 2007	118946
NCI Plated 2007	409943
Norris Pharm	NSZB-A260011
NovoSeek	5587
PI Chemicals	PI-27214
Ryan Scientific	Estriol
Selleck Chemicals	S3146
Sigma Aldrich	1695004
Sigma Aldrich	1695004\|USP
Sigma Aldrich	R288918\|ALDRICH
Sigma Aldrich	T7511
Sigma Aldrich	T7511\|SIAL
Sinfoo Biotech	S017589	http://www.sinfoobiotech.com/product/1020987
Smolecule	S702025	https://www.smolecule.com/products/s702025
StruChem	SC-94044
Syntharise	SRISEC022
TargetMol	T1269
Tetrahedron	TS35445
TimTec	SBB056873
TimTec	ST50411553
Toronto Research Chemicals	T808325
Yick-Vic Chemicals & Pharmaceuticals (HK) Ltd.	PH-1221A
ZINC	ZINC000019117728	http://zinc15.docking.org/substances/ZINC000019117728
eMolecules	300002447
eMolecules	595075
eMolecules	979261
eNovation Chemicals	D763057
mcule	MCULE-1679949518	https://mcule.com/MCULE-1679949518/

PubMed

Title	Date	PubMed
An unusual case of antihistamine intoxication.	1967 Oct	4227701
Pulmonary angiothrombosis caused by "blue velvet" addiction.	1970 Nov	5476210
Central nervous system complications of addiction to "T's and Blues".	1982 Jun	7201092
Pentazocine/tripelennamine (T's and blues) abuse: a five year survey of St. Louis, Missouri.	1982 Oct-Nov	7166138
Fatal intracranial hemorrhage associated with phenylpropanolamine, pentazocine, and tripelennamine overdose.	1985	4093565
Behavioral and developmental effects of prenatal exposure to pentazocine and tripelennamine combinations.	1986 Nov-Dec	3808175
Nitric oxide, superoxide radicals and mast cells in pathogenesis of indomethacin-induced small intestinal lesions in rats.	1999 Mar	10210152
Antinociceptive and antiedematogenic properties and acute toxicity of Tabebuia avellanedae Lor. ex Griseb. inner bark aqueous extract.	2001	11574048
Histamine H1 and H2 receptor antagonists accelerate skin barrier repair and prevent epidermal hyperplasia induced by barrier disruption in a dry environment.	2001 Feb	11180002
Quantitation of antihistamines in pharmaceutical preparations by liquid chromatography with a micellar mobile phase of sodium dodecyl sulfate and pentanol.	2001 Nov-Dec	11767132
H1-receptor antagonist, tripelennamine, does not affect arterial hypoxemia in exercising Thoroughbreds.	2002 Apr	11896018
Managing patients with local anesthetic complications using alternative methods.	2002 May-Jun	12174527
Synthesis and pharmacological identification of neutral histamine H1-receptor antagonists.	2003 Dec 18	14667234
Prostaglandin E2 aggravates gastric mucosal injury induced by histamine in rats through EP1 receptors.	2003 Dec 19	14623033
Mast cell--pituitary interaction: modulation by serine phospholipids.	2004 Dec	15638084
Treatment of allergic rhinitis during pregnancy.	2004 Jan-Feb	15035567
Medicinal plants in Suriname: hypotensive effect of Gossypium barbadense.	2004 Mar	15025864
Involvement of histamine H1 and H2 receptors in the regulation of STAT-1 phosphorylation: inverse agonism exhibited by the receptor antagonists.	2005 Jul	15914334
Analysis of pharmaceutical preparations containing antihistamine drugs by micellar liquid chromatography.	2006 Feb 13	16182504
Myasthenia gravis-like syndrome in a Hereford heifer.	2008 Jan-Feb	18289316
Medullary pain facilitating neurons mediate allodynia in headache-related pain.	2009 Feb	19259966
Ruthenium-catalyzed N-alkylation of amines and sulfonamides using borrowing hydrogen methodology.	2009 Feb 11	19191700
Development of a list of potentially inappropriate drugs for the korean elderly using the delphi method.	2010 Dec	21818443
The use of in vitro technologies coupled with high resolution accurate mass LC-MS for studying drug metabolism in equine drug surveillance.	2010 Jan	20878880
Profiling of a prescription drug library for potential renal drug-drug interactions mediated by the organic cation transporter 2.	2011 Jul 14	21599003

Patents

Sample Use Guides

In Vivo Use Guide

Unknown

Route of Administration: Oral

In Vitro Use Guide

Unknown

Name

Type

Language

TRIPELENNAMINE HYDROCHLORIDE

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