Tripelennamine

Identification

Summary

Tripelennamine is a histamine H1 antagonist used to treat hypersensitivity reactions, coughs, and the common cold.

Generic Name
Tripelennamine
DrugBank Accession Number
DB00792
Background

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.

Type
Small Molecule
Groups
Approved, Vet approved
Structure
Weight
Average: 255.358
Monoisotopic: 255.173547687
Chemical Formula
C16H21N3
Synonyms
  • Tripelennamin
  • Tripelennamina
  • Tripélennamine
  • Tripelennamine
  • Tripelennaminum
External IDs
  • RP 2750

Pharmacology

Indication

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

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Associated Conditions
Indication TypeIndicationCombined Product DetailsApproval LevelAge GroupPatient CharacteristicsDose Form
Symptomatic treatment ofItching caused by insect bites••• ••••••••
Symptomatic treatment ofItching caused by jellyfish stings••• ••••••••
Symptomatic treatment ofItching caused by nettles••• ••••••••
Contraindications & Blackbox Warnings
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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
Humans
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

Adverse Effects
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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.

Pathways
PathwayCategory
Tripelennamine H1-Antihistamine ActionDrug action
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
DrugInteraction
AcebutololThe metabolism of Acebutolol can be decreased when combined with Tripelennamine.
AcetaminophenThe metabolism of Acetaminophen can be decreased when combined with Tripelennamine.
AlmotriptanThe metabolism of Almotriptan can be decreased when combined with Tripelennamine.
AlogliptinThe metabolism of Alogliptin can be decreased when combined with Tripelennamine.
AminophenazoneThe metabolism of Aminophenazone can be decreased when combined with Tripelennamine.
Food Interactions
No interactions found.

Products

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Product Ingredients
IngredientUNIICASInChI Key
Tripelennamine citrate30OC46A3J96138-56-3GGRBYIUPUOYRLQ-UHFFFAOYSA-N
Tripelennamine hydrochlorideFWV8GJ56ZN154-69-8FSSICIQKZGUEAE-UHFFFAOYSA-N
International/Other Brands
Azaron (Chefaro) / Pyribenzamine (Novartis) / Tripel (Corsa Industries)
Over the Counter Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
Bug Bite BalmCream1.00 %TopicalMagically Gone IncNot applicableNot applicableCanada flag
Pyribenzamine Tab 50mgTablet50 mg / tabOralNovartis1947-12-311999-07-21Canada flag
Vagin-XCream2 %TopicalAssociated National Brokerage Inc.2001-08-012018-03-12Canada flag
Vaginex W Tripelennamine Crm 2%Cream2 %VaginalJulius Schmid Canada Ltd.1984-12-311997-08-07Canada flag

Categories

ATC Codes
R06AC04 — TripelennamineD04AA04 — Tripelennamine
Drug Categories
Chemical TaxonomyProvided by Classyfire
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 / Amine / Aminopyridine / Aromatic heteromonocyclic compound / Azacycle / Dialkylarylamine / Heteroaromatic compound / Hydrocarbon derivative / Imidolactam / Organic nitrogen compound
Molecular Framework
Aromatic heteromonocyclic compounds
External Descriptors
aromatic amine (CHEBI:9741)
Affected organisms
  • Humans and other mammals

Chemical Identifiers

UNII
3C5ORO99TY
CAS number
91-81-6
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

References

General References
Not Available
Human Metabolome Database
HMDB0014930
KEGG Compound
C07180
PubChem Compound
5587
PubChem Substance
46506125
ChemSpider
5385
BindingDB
81471
RxNav
10847
ChEBI
9741
ChEMBL
CHEMBL1241
ZINC
ZINC000019117728
Therapeutic Targets Database
DAP000328
PharmGKB
PA164764429
Drugs.com
Drugs.com Drug Page
Wikipedia
Tripelennamine
MSDS
Download (74 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount

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
  • C.O. Truxton Inc.
  • Cypress Pharmaceutical Inc.
  • Gallipot
  • Spectrum Pharmaceuticals
Dosage Forms
FormRouteStrength
StickTopical20 mg/g
CreamTopical1.00 %
TabletOral50 mg / tab
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-MSsplash10-0a4l-9200000000-0d2486042b7353578cae
GC-MS Spectrum - CI-BGC-MSsplash10-0a4i-0090000000-c34cc7c068c800fe56be
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
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-0a4i-0090000000-c4824625a8e618d94678
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-0udi-2190000000-9644653791ac11899d1f
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-08fr-2190000000-a2db4f7da8aabef20430
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-001i-3900000000-db8ea930b932bbb7d44e
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-014l-9700000000-19a1ba8ca172ae819063
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-0ue9-0900000000-2bb44c32c86d9d0ba503
Predicted 1H NMR Spectrum1D NMRNot Applicable
Predicted 13C NMR Spectrum1D NMRNot Applicable
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-170.7734601
predicted
DarkChem Lite v0.1.0
[M-H]-153.41164
predicted
DeepCCS 1.0 (2019)
[M+H]+170.9737601
predicted
DarkChem Lite v0.1.0
[M+H]+155.76964
predicted
DeepCCS 1.0 (2019)
[M+Na]+171.0601601
predicted
DarkChem Lite v0.1.0
[M+Na]+161.86284
predicted
DeepCCS 1.0 (2019)

Targets

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insights and accelerate drug research.
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Details
1. Histamine H1 receptor
Kind
Protein
Organism
Humans
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. [Article]
  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. [Article]
  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. [Article]
  4. Sansone M: Antihistaminic-opioid combination: effect on locomotor activity in mice. Pol J Pharmacol Pharm. 1988 Sep-Oct;40(5):515-23. [Article]
  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. [Article]
  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. [Article]

Enzymes

Kind
Protein
Organism
Humans
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. [Article]
  2. He N, Zhang WQ, Shockley D, Edeki T: Inhibitory effects of H1-antihistamines on CYP2D6- and CYP2C9-mediated drug metabolic reactions in human liver microsomes. Eur J Clin Pharmacol. 2002 Feb;57(12):847-51. [Article]
  3. Flockhart Table of Drug Interactions [Link]

Carriers

Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Binder
Regulator
General Function
Toxic substance binding
Specific Function
Serum albumin, the main protein of plasma, has a good binding capacity for water, Ca(2+), Na(+), K(+), fatty acids, hormones, bilirubin and drugs. Its main function is the regulation of the colloid...
Gene Name
ALB
Uniprot ID
P02768
Uniprot Name
Serum albumin
Molecular Weight
69365.94 Da
References
  1. Martinez-Gomez MA, Carril-Aviles MM, Sagrado S, Villanueva-Camanas RM, Medina-Hernandez MJ: Characterization of antihistamine-human serum protein interactions by capillary electrophoresis. J Chromatogr A. 2007 Apr 20;1147(2):261-9. doi: 10.1016/j.chroma.2007.02.054. Epub 2007 Feb 22. [Article]

Drug created at June 13, 2005 13:24 / Updated at March 28, 2024 03:23