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
Structure for Tripelennamine (DB00792)
- 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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Indication Type Indication Combined Product Details Approval Level Age Group Patient Characteristics Dose Form Symptomatic treatment of Itching caused by insect bites ••• ••• ••••• Symptomatic treatment of Itching caused by jellyfish stings ••• ••• ••••• Symptomatic treatment of Itching caused by nettles ••• ••• ••••• - Contraindications & Blackbox Warnings
Prevent Adverse Drug Events TodayTap into our Clinical API for life-saving information on contraindications & blackbox warnings, population restrictions, harmful risks, & more.Avoid life-threatening adverse drug events with our Clinical API- 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.
Target Actions Organism AHistamine H1 receptor antagonistHumans - 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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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
Pathway Category Tripelennamine H1-Antihistamine Action Drug action - Pharmacogenomic Effects/ADRs Browse all" title="About SNP Mediated Effects/ADRs" id="snp-actions-info" class="drug-info-popup" href="javascript:void(0);">
- Not Available
Interactions
- Drug Interactions Learn More" title="About Drug Interactions" id="structured-interactions-info" class="drug-info-popup" href="javascript:void(0);">
- 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.
Drug Interaction Integrate drug-drug
interactions in your softwareAcebutolol The metabolism of Acebutolol can be decreased when combined with Tripelennamine. Acetaminophen The metabolism of Acetaminophen can be decreased when combined with Tripelennamine. Almotriptan The metabolism of Almotriptan can be decreased when combined with Tripelennamine. Alogliptin The metabolism of Alogliptin can be decreased when combined with Tripelennamine. Aminophenazone The metabolism of Aminophenazone can be decreased when combined with Tripelennamine. - Food Interactions
- No interactions found.
Products
Drug product information from 10+ global regionsOur datasets provide approved product information including:dosage, form, labeller, route of administration, and marketing period.Access drug product information from over 10 global regions.- Product Ingredients
Ingredient UNII CAS InChI Key Tripelennamine citrate 30OC46A3J9 6138-56-3 GGRBYIUPUOYRLQ-UHFFFAOYSA-N Tripelennamine hydrochloride FWV8GJ56ZN 154-69-8 FSSICIQKZGUEAE-UHFFFAOYSA-N - International/Other Brands
- Azaron (Chefaro) / Pyribenzamine (Novartis) / Tripel (Corsa Industries)
- Over the Counter Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Bug Bite Balm Cream 1.00 % Topical Magically Gone Inc Not applicable Not applicable Canada 
Pyribenzamine Tab 50mg Tablet 50 mg / tab Oral Novartis 1947-12-31 1999-07-21 Canada Vagin-X Cream 2 % Topical Associated National Brokerage Inc. 2001-08-01 2018-03-12 Canada Vaginex W Tripelennamine Crm 2% Cream 2 % Vaginal Julius Schmid Canada Ltd. 1984-12-31 1997-08-07 Canada
Categories
- ATC Codes
- R06AC04 — Tripelennamine
- R06AC — Substituted ethylene diamines
- R06A — ANTIHISTAMINES FOR SYSTEMIC USE
- R06 — ANTIHISTAMINES FOR SYSTEMIC USE
- R — RESPIRATORY SYSTEM
- Drug Categories
- Amines
- Aminopyridines
- Anti-Allergic Agents
- Antihistamines for Systemic Use
- Antihistamines for Topical Use
- Antipruritics, Incl. Antihistamines, Anesthetics, Etc.
- Cytochrome P-450 CYP2D6 Inhibitors
- Cytochrome P-450 CYP2D6 Inhibitors (strength unknown)
- Cytochrome P-450 Enzyme Inhibitors
- Dermatologicals
- Diamines
- Ethylenediamine Derivatives
- Ethylenediamines
- Histamine Agents
- Histamine Antagonists
- Histamine H1 Antagonists
- Neurotransmitter Agents
- Polyamines
- Pyridines
- Substituted Ethylene Diamines
- 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
- External Links
- Human Metabolome Database
- HMDB0014930
- KEGG Compound
- C07180
- PubChem Compound
- 5587
- PubChem Substance
- 46506125
- ChemSpider
- 5385
- BindingDB
- 81471
- 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 Learn More" title="About Clinical Trials" id="clinical-trials-info" class="drug-info-popup" href="javascript:void(0);">
Phase Status Purpose Conditions Count
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
Form Route Strength Stick Topical 20 mg/g Cream Topical 1.00 % Tablet Oral 50 mg / tab Cream Topical 2 % Cream Vaginal 2 % - Prices
Unit description Cost Unit Tripelennamine powder 9.94USD g Tripelennamine hcl powder 7.35USD g Dehistine syrup 0.03USD ml DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.- Patents
- Not Available
Properties
- State
- Solid
- Experimental Properties
Property Value Source water solubility 587 mg/L (at 30 °C) YALKOWSKY,SH & DANNENFELSER,RM (1992) logP 3.3 Not Available logS -2.64 ADME Research, USCD - Predicted Properties
Property Value Source Water Solubility 2.84 mg/mL ALOGPS logP 3.05 ALOGPS logP 3.2 Chemaxon logS -2 ALOGPS pKa (Strongest Basic) 8.76 Chemaxon Physiological Charge 1 Chemaxon Hydrogen Acceptor Count 3 Chemaxon Hydrogen Donor Count 0 Chemaxon Polar Surface Area 19.37 Å2 Chemaxon Rotatable Bond Count 6 Chemaxon Refractivity 81.27 m3·mol-1 Chemaxon Polarizability 29.86 Å3 Chemaxon Number of Rings 2 Chemaxon Bioavailability 1 Chemaxon Rule of Five Yes Chemaxon Ghose Filter Yes Chemaxon Veber's Rule Yes Chemaxon MDDR-like Rule No Chemaxon - Predicted ADMET Features
Property Value Probability Human Intestinal Absorption + 0.9325 Blood Brain Barrier + 0.9134 Caco-2 permeable + 0.7269 P-glycoprotein substrate Substrate 0.7902 P-glycoprotein inhibitor I Non-inhibitor 0.9577 P-glycoprotein inhibitor II Non-inhibitor 0.9639 Renal organic cation transporter Inhibitor 0.7383 CYP450 2C9 substrate Non-substrate 0.8052 CYP450 2D6 substrate Non-substrate 0.9116 CYP450 3A4 substrate Non-substrate 0.5332 CYP450 1A2 substrate Non-inhibitor 0.5861 CYP450 2C9 inhibitor Non-inhibitor 0.8713 CYP450 2D6 inhibitor Inhibitor 0.8663 CYP450 2C19 inhibitor Inhibitor 0.5878 CYP450 3A4 inhibitor Non-inhibitor 0.9792 CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.8473 Ames test Non AMES toxic 0.9483 Carcinogenicity Non-carcinogens 0.9032 Biodegradation Not ready biodegradable 0.9961 Rat acute toxicity 2.3139 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.7151 hERG inhibition (predictor II) Inhibitor 0.6518
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
- Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 170.7734601 predictedDarkChem Lite v0.1.0 [M-H]- 153.41164 predictedDeepCCS 1.0 (2019) [M+H]+ 170.9737601 predictedDarkChem Lite v0.1.0 [M+H]+ 155.76964 predictedDeepCCS 1.0 (2019) [M+Na]+ 171.0601601 predictedDarkChem Lite v0.1.0 [M+Na]+ 161.86284 predictedDeepCCS 1.0 (2019)
Targets
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Use our structured and evidence-based datasets to unlock newinsights and accelerate drug research.
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- 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
- Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [Article]
- 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]
- 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]
- Sansone M: Antihistaminic-opioid combination: effect on locomotor activity in mice. Pol J Pharmacol Pharm. 1988 Sep-Oct;40(5):515-23. [Article]
- 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]
- 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
- 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]
- 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]
- Flockhart Table of Drug Interactions [Link]
Carriers
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- BinderRegulator
- 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
- 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 February 20, 2024 23:54