Identification

Name
Tripelennamine
Accession Number
DB00792  (APRD00689)
Type
Small Molecule
Groups
Approved, Vet Approved
Description

A histamine H1 antagonist with low sedative action but frequent gastrointestinal irritation. It is used to treat asthma; HAY fever; urticaria; and rhinitis; and also in veterinary applications. Tripelennamine is administered by various routes, including topically. [PubChem]

Structure
Thumb
Synonyms
  • Tripelennamin
  • Tripelennamina
  • Tripélennamine
  • Tripelennaminum
External IDs
RP 2750
Product Ingredients
IngredientUNIICASInChI Key
Tripelennamine citrate30OC46A3J96138-56-3GGRBYIUPUOYRLQ-UHFFFAOYSA-N
Tripelennamine HydrochlorideFWV8GJ56ZN154-69-8FSSICIQKZGUEAE-UHFFFAOYSA-N
Over the Counter Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Bug Bite BalmCream1.00 %TopicalMagically Gone IncNot applicableNot applicableCanada
Pyribenzamine Tab 50mgTablet50 mgOralNovartis1947-12-311999-07-21Canada
Vagin-XCream2 %TopicalAssociated National Brokerage Inc.2001-08-01Not applicableCanada
Vaginex W Tripelennamine Crm 2%Cream2 %VaginalJulius Schmid Canada Ltd.1984-12-311997-08-07Canada
International/Other Brands
Azaron (Chefaro) / PBZ / PBZ-sr / Pyribenzamine (Novartis) / Tripel (Corsa Industries)
Categories
UNII
3C5ORO99TY
CAS number
91-81-6
Weight
Average: 255.358
Monoisotopic: 255.173547687
Chemical Formula
C16H21N3
InChI Key
UFLGIAIHIAPJJC-UHFFFAOYSA-N
InChI
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
IUPAC Name
N-benzyl-N-[2-(dimethylamino)ethyl]pyridin-2-amine
SMILES
CN(C)CCN(CC1=CC=CC=C1)C1=CC=CC=N1

Pharmacology

Indication

Used for the symptomatic relief of hypersensitivity reactions, coughs, and the common cold.

Structured Indications
Not Available
Pharmacodynamics

Used to treat the effects of colds and allergies. Tripelennamine is an antihistamine. Histamine, acting on H1-receptors, produces pruritis, vasodilatation, hypotension, flushing, headache, tachycardia, and bronchoconstriction. Histamine also increases vascular permeability and potentiates pain. Tripelennamine is a histamine H1 antagonist. It competes with histamine for the normal H1-receptor sites on effector cells of the gastrointestinal tract, blood vessels and respiratory tract. It provides effective, temporary relief of sneezing, watery and itchy eyes, and runny nose due to hay fever and other upper respiratory allergies.

Mechanism of action

Tripelennamine binds to the histamine H1 receptor. This blocks the action of endogenous histamine, which subsequently leads to temporary relief of the negative symptoms brought on by histamine.

TargetActionsOrganism
AHistamine H1 receptor
antagonist
Human
Absorption

Well absorbed in the digestive tract.

Volume of distribution
Not Available
Protein binding
Not Available
Metabolism

Hepatic

Route of elimination
Not Available
Half life
Not Available
Clearance
Not Available
Toxicity

Symptoms of overdose include clumsiness or unsteadiness, convulsions, drowsiness, dryness of mouth, nose, or throat, feeling faint, flushing or redness of face, hallucinations, muscle spasms (especially of neck and back), restlessness, shortness of breath or troubled breathing, shuffling walk, tic-like movements of head and face, trembling and shaking of hands and trouble in sleeping.

Affected organisms
  • Humans and other mammals
Pathways
PathwayCategory
Tripelennamine H1-Antihistamine ActionDrug action
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
DrugInteractionDrug group
2,5-Dimethoxy-4-ethylamphetamine2,5-Dimethoxy-4-ethylamphetamine may decrease the sedative activities of Tripelennamine.Experimental, Illicit
3,4-Methylenedioxyamphetamine3,4-Methylenedioxyamphetamine may decrease the sedative activities of Tripelennamine.Experimental, Illicit
4-Bromo-2,5-dimethoxyamphetamine4-Bromo-2,5-dimethoxyamphetamine may decrease the sedative activities of Tripelennamine.Experimental, Illicit
AmphetamineAmphetamine may decrease the sedative activities of Tripelennamine.Approved, Illicit
BenzphetamineBenzphetamine may decrease the sedative activities of Tripelennamine.Approved, Illicit
Benzylpenicilloyl PolylysineTripelennamine may decrease effectiveness of Benzylpenicilloyl Polylysine as a diagnostic agent.Approved
BetahistineThe therapeutic efficacy of Betahistine can be decreased when used in combination with Tripelennamine.Approved
ChlorphentermineChlorphentermine may decrease the sedative activities of Tripelennamine.Illicit, Withdrawn
DextroamphetamineDextroamphetamine may decrease the sedative activities of Tripelennamine.Approved, Illicit
DiethylpropionDiethylpropion may decrease the sedative activities of Tripelennamine.Approved, Illicit
FesoterodineThe serum concentration of the active metabolites of Fesoterodine can be increased when Fesoterodine is used in combination with Tripelennamine.Approved
GepefrineGepefrine may decrease the sedative activities of Tripelennamine.Experimental
HyaluronidaseThe therapeutic efficacy of Hyaluronidase can be decreased when used in combination with Tripelennamine.Approved, Investigational
HydroxyamphetamineHydroxyamphetamine may decrease the sedative activities of Tripelennamine.Approved
Iofetamine I-123Iofetamine I-123 may decrease the sedative activities of Tripelennamine.Approved
LisdexamfetamineLisdexamfetamine may decrease the sedative activities of Tripelennamine.Approved, Investigational
MephedroneMephedrone may decrease the sedative activities of Tripelennamine.Investigational
MephentermineMephentermine may decrease the sedative activities of Tripelennamine.Approved
MethamphetamineMethamphetamine may decrease the sedative activities of Tripelennamine.Approved, Illicit
MethoxyphenamineMethoxyphenamine may decrease the sedative activities of Tripelennamine.Experimental
MetoprololThe serum concentration of Metoprolol can be increased when it is combined with Tripelennamine.Approved, Investigational
MidomafetamineMidomafetamine may decrease the sedative activities of Tripelennamine.Experimental, Illicit, Investigational
MMDAMMDA may decrease the sedative activities of Tripelennamine.Experimental, Illicit
PhenterminePhentermine may decrease the sedative activities of Tripelennamine.Approved, Illicit
PseudoephedrinePseudoephedrine may decrease the sedative activities of Tripelennamine.Approved
RitobegronRitobegron may decrease the sedative activities of Tripelennamine.Investigational
ThioridazineThe serum concentration of Thioridazine can be increased when it is combined with Tripelennamine.Approved, Withdrawn
Food Interactions
Not Available

References

General References
Not Available
External Links
Human Metabolome Database
HMDB14930
KEGG Compound
C07180
PubChem Compound
5587
PubChem Substance
46506125
ChemSpider
5385
BindingDB
81471
ChEBI
9741
ChEMBL
CHEMBL1241
Therapeutic Targets Database
DAP000328
PharmGKB
PA164764429
Drugs.com
Drugs.com Drug Page
Wikipedia
Tripelennamine
ATC Codes
D04AA04 — TripelennamineR06AC04 — Tripelennamine
AHFS Codes
  • 04:04.08 — Ethylenediamine Derivatives
MSDS
Download (74 KB)

Clinical Trials

Clinical Trials
Not Available

Pharmacoeconomics

Manufacturers
  • Novartis pharmaceuticals corp
  • Anabolic inc
  • Barr laboratories inc
  • Heather drug co inc
  • Impax laboratories inc
  • Lannett co inc
  • Nylos trading co inc
  • Parke davis div warner lambert co
  • Watson laboratories inc
Packagers
Dosage forms
FormRouteStrength
CreamTopical1.00 %
TabletOral50 mg
CreamTopical2 %
CreamVaginal2 %
Prices
Unit descriptionCostUnit
Tripelennamine powder9.94USD g
Tripelennamine hcl powder7.35USD g
Dehistine syrup0.03USD ml
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents
Not Available

Properties

State
Solid
Experimental Properties
PropertyValueSource
water solubility587 mg/L (at 30 °C)YALKOWSKY,SH & DANNENFELSER,RM (1992)
logP3.3Not Available
logS-2.64ADME Research, USCD
Predicted Properties
PropertyValueSource
Water Solubility2.84 mg/mLALOGPS
logP3.05ALOGPS
logP3.2ChemAxon
logS-2ALOGPS
pKa (Strongest Basic)8.76ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area19.37 Å2ChemAxon
Rotatable Bond Count6ChemAxon
Refractivity81.27 m3·mol-1ChemAxon
Polarizability29.86 Å3ChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.9325
Blood Brain Barrier+0.9134
Caco-2 permeable+0.7269
P-glycoprotein substrateSubstrate0.7902
P-glycoprotein inhibitor INon-inhibitor0.9577
P-glycoprotein inhibitor IINon-inhibitor0.9639
Renal organic cation transporterInhibitor0.7383
CYP450 2C9 substrateNon-substrate0.8052
CYP450 2D6 substrateNon-substrate0.9116
CYP450 3A4 substrateNon-substrate0.5332
CYP450 1A2 substrateNon-inhibitor0.5861
CYP450 2C9 inhibitorNon-inhibitor0.8713
CYP450 2D6 inhibitorInhibitor0.8663
CYP450 2C19 inhibitorInhibitor0.5878
CYP450 3A4 inhibitorNon-inhibitor0.9792
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.8473
Ames testNon AMES toxic0.9483
CarcinogenicityNon-carcinogens0.9032
BiodegradationNot ready biodegradable0.9961
Rat acute toxicity2.3139 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.7151
hERG inhibition (predictor II)Inhibitor0.6518
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
GC-MS Spectrum - CI-BGC-MSsplash10-0a4i-0090000000-c34cc7c068c800fe56be
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-0bt9-0090000000-334f534255262b94521e
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-03di-0090000000-11e8826e02efb97b98c9
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-00kf-8930000000-1b7607b1d6869ef01c34
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-00kf-9500000000-e76eabb3bb757d44acfa
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-00kf-9400000000-e99107bbb2260bd80b26
MS/MS Spectrum - , positiveLC-MS/MSsplash10-03di-0290000000-1cb8a1736406d2586266

Taxonomy

Description
This compound belongs to the class of organic compounds known as 2-benzylaminopyridines. These are aromatic compounds containing pyridine ring substituted at the 2-position by a benzylamine group.
Kingdom
Organic compounds
Super Class
Benzenoids
Class
Benzene and substituted derivatives
Sub Class
Benzylamines
Direct Parent
2-benzylaminopyridines
Alternative Parents
Dialkylarylamines / Aminopyridines and derivatives / Imidolactams / Heteroaromatic compounds / Trialkylamines / Azacyclic compounds / Organopnictogen compounds / Hydrocarbon derivatives
Substituents
2-benzylaminopyridine / Dialkylarylamine / Aminopyridine / Pyridine / Imidolactam / Heteroaromatic compound / Tertiary amine / Tertiary aliphatic amine / Azacycle / Organoheterocyclic compound
Molecular Framework
Aromatic heteromonocyclic compounds
External Descriptors
aromatic amine (CHEBI:9741)

Targets

Details
1. Histamine H1 receptor
Kind
Protein
Organism
Human
Pharmacological action
Yes
Actions
Antagonist
General Function
Histamine receptor activity
Specific Function
In peripheral tissues, the H1 subclass of histamine receptors mediates the contraction of smooth muscles, increase in capillary permeability due to contraction of terminal venules, and catecholamin...
Gene Name
HRH1
Uniprot ID
P35367
Uniprot Name
Histamine H1 receptor
Molecular Weight
55783.61 Da
References
  1. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352]
  2. Shimizu K, Nakajyo S, Urakawa N: [Drug sensitivity of the isolated stomach and ileal preparation from a vole]. Nihon Heikatsukin Gakkai Zasshi. 1982 May;18(2):93-103. [PubMed:6759742]
  3. Chiba S: Blocking effect of tripelennamine on histamine--induced positive chronotropic and inotropic responses of the dog atrium. Tohoku J Exp Med. 1976 Nov;120(3):299-300. [PubMed:996853]
  4. Sansone M: Antihistaminic-opioid combination: effect on locomotor activity in mice. Pol J Pharmacol Pharm. 1988 Sep-Oct;40(5):515-23. [PubMed:3253717]
  5. Ohta Y, Kobayashi T, Ishiguro I: Role of endogenous serotonin and histamine in the pathogenesis of gastric mucosal lesions in unanaesthetised rats with a single treatment of compound 48/80, a mast cell degranulator. Pharmacol Res. 1999 Apr;39(4):261-7. [PubMed:10208755]
  6. Suzuki T, Mori T, Tsuji M, Misawa M, Onodera K: Interactions between H1-antagonists and opioids: a drug discrimination study. Psychopharmacology (Berl). 1997 Jun;131(4):346-53. [PubMed:9226736]

Enzymes

Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Steroid hydroxylase activity
Specific Function
Responsible for the metabolism of many drugs and environmental chemicals that it oxidizes. It is involved in the metabolism of drugs such as antiarrhythmics, adrenoceptor antagonists, and tricyclic...
Gene Name
CYP2D6
Uniprot ID
P10635
Uniprot Name
Cytochrome P450 2D6
Molecular Weight
55768.94 Da
References
  1. Hamelin BA, Bouayad A, Drolet B, Gravel A, Turgeon J: In vitro characterization of cytochrome P450 2D6 inhibition by classic histamine H1 receptor antagonists. Drug Metab Dispos. 1998 Jun;26(6):536-9. [PubMed:9616188]
  2. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256]
  3. Drug Interactions: Cytochrome P450 Drug Interaction Table [Link]

Drug created on June 13, 2005 07:24 / Updated on November 19, 2017 20:33