Identification
- Summary
Triprolidine is a sedating antihistamine combined with pseudoephedrine and guaifenesin in various types of cold and allergy medications to relieve allergy symptoms, hay fever and common cold symptoms, and to aid in sleep.
- Brand Names
- Covan, Histex Ac, Histex Pd Reformulated Mar 2014, Histex Syrup, Pseudodine C, Triacin-C, Vanaclear
- Generic Name
- Triprolidine
- DrugBank Accession Number
- DB00427
- Background
First generation histamine H1 antagonist used in allergic rhinitis; asthma; and urticaria. It is a component of cough and cold medicines. It may cause drowsiness.
- Type
- Small Molecule
- Groups
- Approved
- Structure
Structure for Triprolidine (DB00427)
- Weight
- Average: 278.3914
Monoisotopic: 278.178298714 - Chemical Formula
- C19H22N2
- Synonyms
- (E)-2-[3-(1-pyrrolidinyl)-1-p-toluenepropenyl]pyridine
- trans-1-(2-pyridyl)-3-pyrrolidino-1-p-tolylprop-1-ene
- trans-1-(4-methylphenyl)-1-(2-pyridyl)-3-pyrrolidinoprop-1-ene
- Tripolidina
- Triprolidin
- Triprolidina
- Triprolidine
- Triprolidinum
Pharmacology
- Indication
For the symptomatic relief of seasonal or perennial allergic rhinitis or nonallergic rhinitis; allergic conjunctivitis; and mild, uncomplicated allergic skin manifestations of urticaria and angioedema. Also used in combination with other agents for the symptomatic relief of symptoms associated with the common cold.
Reduce drug development failure ratesBuild, train, & validate machine-learning modelswith evidence-based and structured datasets.Build, train, & validate predictive machine-learning models with structured datasets.- Associated Conditions
Indication Type Indication Combined Product Details Approval Level Age Group Patient Characteristics Dose Form Treatment of Allergic conjunctivitis ••• ••• Used in combination for symptomatic treatment of Nasal congestion Combination Product in combination with: Pseudoephedrine (DB00852) •••••••••••• •••••••• ••••••• •••••• Used in combination for symptomatic treatment of Nasal congestion Combination Product in combination with: Pseudoephedrine (DB00852) •••••••••••• •••••••• ••••••• •••••• Used in combination for symptomatic treatment of Nasal congestion Combination Product in combination with: Pseudoephedrine (DB00852) •••••••••••• •••••••• ••••••• •••••• Treatment of Perennial allergic rhinitis ••• ••• - 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
In allergic reactions an allergen interacts with and cross-links surface IgE antibodies on mast cells and basophils. Once the mast cell-antibody-antigen complex is formed, a complex series of events occurs that eventually leads to cell-degranulation and the release of histamine (and other chemical mediators) from the mast cell or basophil. Once released, histamine can react with local or widespread tissues through histamine receptors. Histamine, acting on H1-receptors, produces pruritis, vasodilatation, hypotension, flushing, headache, tachycardia, and bronchoconstriction. Histamine also increases vascular permeability and potentiates pain. Triprolidine, is a histamine H1 antagonist that 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. Triprolidine has anticholinergic and sedative effects.
- Mechanism of action
Triprolidine 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
Rapidly absorbed in the intestinal tract.
- Volume of distribution
Not Available
- Protein binding
Not Available
- Metabolism
- Not Available
- Route of elimination
Not Available
- Half-life
4 to 6 hours.
- Clearance
Not Available
- Adverse Effects
Improve decision support & research outcomesWith structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates. View sample adverse effects data in our new Data Library!Improve decision support & research outcomes with our structured adverse effects data.- Toxicity
Symptoms of overdose include drowsiness, weakness, inco-ordination, difficulty with micturition, respiratory depression, hypotension, agitation, irritability, convulsions, hypertension, palpitation and tachycardia.
- Pathways
Pathway Category Triprolidine 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 software1,2-Benzodiazepine The risk or severity of CNS depression can be increased when Triprolidine is combined with 1,2-Benzodiazepine. Acetazolamide The risk or severity of CNS depression can be increased when Triprolidine is combined with Acetazolamide. Acetophenazine The risk or severity of CNS depression can be increased when Triprolidine is combined with Acetophenazine. Acrivastine The risk or severity of QTc prolongation can be increased when Triprolidine is combined with Acrivastine. Adenosine The risk or severity of QTc prolongation can be increased when Triprolidine is combined with Adenosine. - Food Interactions
- Avoid alcohol. Taking with alcohol may increase drowsiness.
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 Triprolidine hydrochloride NG7A104R3J 550-70-9 WYUYEJNGHIOFOC-NWBUNABESA-N Triprolidine hydrochloride monohydrate YAN7R5L890 6138-79-0 CUZMOIXUFHOLLN-UMVVUDSKSA-N - Product Images
- International/Other Brands
- Anmin (AND) / Venen (Sato Seiyaku)
- Brand Name Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Tripohist Liquid 1.25 mg/5mL Oral Breckenridge Pharmaceutical, Inc. 2008-01-31 2011-12-31 US 
- Over the Counter Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Allerdine Liquid 0.625 mg/1mL Oral Woodward Pharma Services Llc 2018-06-09 2020-03-15 US Childrens PediaClear Allergy Liquid 0.313 mg/1mL Oral GM Pharmaceuticals, INC 2019-06-25 Not applicable US Childrens PediaClear PD Liquid 1.25 mg/2mL Oral GM Pharmaceuticals, INC 2019-07-01 Not applicable US Dr Manzanilla Infant Syrup 0.938 mg/1mL Oral Key Therapeutics 2019-08-11 2020-03-31 US Dr Manzanilla Pediatric Syrup 2.5 mg/5mL Oral Key Therapeutics 2019-08-11 2020-03-31 US - Mixture Products
Name Ingredients Dosage Route Labeller Marketing Start Marketing End Region Image A-FERIN DECO ŞURUP, 100 ML Triprolidine hydrochloride (1.25 mg/5mL) + Pseudoephedrine (30 mg/5mL) Syrup Oral HÜSNÜ ARSAN İLAÇLARI A.Ş. 2020-08-14 2018-08-17 Turkey 
A-FERIN DECO TABLET, 20 ADET Triprolidine hydrochloride (2.5 mg) + Pseudoephedrine (60 mg) Tablet Oral HÜSNÜ ARSAN İLAÇLARI A.Ş. 2020-08-14 2018-08-17 Turkey A-FERIN SINUS 500/30/1.25 MG FİLM KAPLI TABLET, 20 ADET Triprolidine hydrochloride (1.25 mg) + Acetaminophen (500 mg) + Pseudoephedrine hydrochloride (30 mg) Tablet, coated Oral HÜSNÜ ARSAN İLAÇLARI A.Ş. 2002-05-03 Not applicable Turkey ACTIDEM OKSURUK SURUBU, 150 ML Triprolidine (1.25 mg/5mL) + Dextromethorphan (10 mg/5mL) + Pseudoephedrine (30 mg/5mL) Syrup Oral GLAXOSMİTHKLİNE İLAÇLARI SAN. VE TİC. A.Ş. 1995-09-15 2023-03-20 Turkey ACTIFED COMPOUND LINCTUS Triprolidine hydrochloride (1.25 mg/5ml) + Codeine phosphate (10 mg/5ml) + Pseudoephedrine hydrochloride (30 mg/5ml) Elixir Oral GSK CONSUMER HEALTHCARE SINGAPORE PTE. LTD. 1989-05-18 Not applicable Singapore 
- Unapproved/Other Products
Name Ingredients Dosage Route Labeller Marketing Start Marketing End Region Image Endal Triprolidine hydrochloride monohydrate (1.25 mg/5mL) + Dextromethorphan hydrobromide monohydrate (10 mg/5mL) Liquid Oral Poly Pharmaceuticals, Inc. 2023-05-22 Not applicable US Tripohist Triprolidine hydrochloride monohydrate (1.25 mg/5mL) Liquid Oral Breckenridge Pharmaceutical, Inc. 2008-01-31 2011-12-31 US Tripohist D Triprolidine hydrochloride monohydrate (1.25 mg/5mL) + Pseudoephedrine hydrochloride (45 mg/5mL) Liquid Oral Breckenridge Pharmaceutical, Inc. 2008-01-01 2011-12-31 US Triprolidine HCl PSE HCl Triprolidine hydrochloride monohydrate (0.938 mg/1mL) + Pseudoephedrine hydrochloride (10 mg/1mL) Liquid Oral River's Edge Pharmaceuticals, LLC 2010-03-01 2010-03-31 US Whituben Triprolidine hydrochloride monohydrate (0.66 mg/1) + Acetaminophen (180 mg/1) + DL-Methylephedrine hydrochloride (12.5 mg/1) + Dextromethorphan hydrobromide monohydrate (8 mg/1) + Guaifenesin (20.84 mg/1) + Pseudoephedrine hydrochloride (15 mg/1) Capsule Oral OASIS TRADING 2018-11-22 Not applicable US
Categories
- ATC Codes
- R06AX07 — Triprolidine
- Drug Categories
- Chemical TaxonomyProvided by Classyfire
- Description
- This compound belongs to the class of organic compounds known as styrenes. These are organic compounds containing an ethenylbenzene moiety.
- Kingdom
- Organic compounds
- Super Class
- Benzenoids
- Class
- Benzene and substituted derivatives
- Sub Class
- Styrenes
- Direct Parent
- Styrenes
- Alternative Parents
- Toluenes / Pyridines and derivatives / N-alkylpyrrolidines / Heteroaromatic compounds / Trialkylamines / Azacyclic compounds / Organopnictogen compounds / Hydrocarbon derivatives
- Substituents
- Amine / Aromatic heteromonocyclic compound / Azacycle / Heteroaromatic compound / Hydrocarbon derivative / N-alkylpyrrolidine / Organic nitrogen compound / Organoheterocyclic compound / Organonitrogen compound / Organopnictogen compound
- Molecular Framework
- Aromatic heteromonocyclic compounds
- External Descriptors
- pyridines, olefinic compound, N-alkylpyrrolidine (CHEBI:84116)
- Affected organisms
- Humans and other mammals
Chemical Identifiers
- UNII
- 2L8T9S52QM
- CAS number
- 486-12-4
- InChI Key
- CBEQULMOCCWAQT-WOJGMQOQSA-N
- InChI
- InChI=1S/C19H22N2/c1-16-7-9-17(10-8-16)18(19-6-2-3-12-20-19)11-15-21-13-4-5-14-21/h2-3,6-12H,4-5,13-15H2,1H3/b18-11+
- IUPAC Name
- 2-[(1E)-1-(4-methylphenyl)-3-(pyrrolidin-1-yl)prop-1-en-1-yl]pyridine
- SMILES
- CC1=CC=C(C=C1)C(=C/CN1CCCC1)\C1=CC=CC=N1
References
- General References
- Mann KV, Crowe JP, Tietze KJ: Nonsedating histamine H1-receptor antagonists. Clin Pharm. 1989 May;8(5):331-44. [Article]
- Simons FE: H1-receptor antagonists. Comparative tolerability and safety. Drug Saf. 1994 May;10(5):350-80. [Article]
- Paton DM, Webster DR: Clinical pharmacokinetics of H1-receptor antagonists (the antihistamines). Clin Pharmacokinet. 1985 Nov-Dec;10(6):477-97. [Article]
- Telekes A, Holland RL, Withington DA, Peck AW: Effects of triprolidine and dipipanone in the cold induced pain test, and the central nervous system of healthy volunteers. Br J Clin Pharmacol. 1987 Jul;24(1):43-50. [Article]
- External Links
- Human Metabolome Database
- HMDB0014571
- KEGG Drug
- D01782
- PubChem Compound
- 5282443
- PubChem Substance
- 46505403
- ChemSpider
- 4445597
- BindingDB
- 50292411
- 10849
- ChEBI
- 84116
- ChEMBL
- CHEMBL855
- ZINC
- ZINC000012503099
- Therapeutic Targets Database
- DAP001065
- PharmGKB
- PA451797
- Guide to Pharmacology
- GtP Drug Page
- Drugs.com
- Drugs.com Drug Page
- Wikipedia
- Triprolidine
- MSDS
- Download (72.7 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
- Glaxosmithkline
- Usl pharma inc
- Alpharma us pharmaceuticals division
- Halsey drug co inc
- Pharmaceutical assoc inc div beach products
- Vitarine pharmaceuticals inc
- Watson laboratories inc
- Packagers
- Breckenridge Pharmaceuticals
- Centurion Labs
- Corvit Pharmaceuticals
- Dispensing Solutions
- Great Southern Laboratories
- Kaiser Foundation Hospital
- Major Pharmaceuticals
- Qualitest
- Spectrum Pharmaceuticals
- Tri Med Laboratories Inc.
- Vindex Pharmaceuticals Inc.
- Wockhardt Ltd.
- Dosage Forms
Form Route Strength Elixir Oral 10 mg/5ml Syrup Oral 100 mg/5ml Tablet, film coated Oral Syrup Oral 10 mg/5ml Liquid Oral 0.313 mg/1mL Liquid Oral 1.25 mg/2mL Tablet Oral Elixir Oral Kit; solution Oral Tablet, coated Oral Tablet Oral 2.5 mg/1 Syrup Oral 2.5 mg/5mL Tablet, chewable Oral 1.25 mg/1 Syrup Oral 1.25 mg/1mL Kit; tablet, coated Oral Kit; liquid Oral Solution Oral Kit; tablet, coated; tablet, film coated Oral Kit Oral Syrup Oral 30 mg/5ml Syrup Oral Liquid Oral 1.25 mg/5mL Liquid Oral Liquid Oral 0.625 mg/1mL Liquid Oral 0.938 mg/1mL Liquid Oral 2.5 mg/5mL Syrup Oral 0.938 mg/1mL Capsule Oral Tablet Oral 2.5 mg - Prices
Unit description Cost Unit Triprolidine hcl crystals 40.33USD g Triprolidine 1.25 mg/5 ml liq 0.15USD ml Tripohist 1.25 mg/5 ml liquid 0.14USD 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 melting point (°C) 60 °C PhysProp water solubility 74.9 mg/L Not Available logP 3.92 HANSCH,C ET AL. (1995) - Predicted Properties
Property Value Source Water Solubility 0.0537 mg/mL ALOGPS logP 4.14 ALOGPS logP 4.05 Chemaxon logS -3.7 ALOGPS pKa (Strongest Basic) 8.64 Chemaxon Physiological Charge 1 Chemaxon Hydrogen Acceptor Count 2 Chemaxon Hydrogen Donor Count 0 Chemaxon Polar Surface Area 16.13 Å2 Chemaxon Rotatable Bond Count 4 Chemaxon Refractivity 98.53 m3·mol-1 Chemaxon Polarizability 33.06 Å3 Chemaxon Number of Rings 3 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 + 0.9905 Blood Brain Barrier + 0.9664 Caco-2 permeable - 0.5814 P-glycoprotein substrate Substrate 0.6644 P-glycoprotein inhibitor I Inhibitor 0.8311 P-glycoprotein inhibitor II Non-inhibitor 0.6624 Renal organic cation transporter Inhibitor 0.8612 CYP450 2C9 substrate Non-substrate 0.8143 CYP450 2D6 substrate Non-substrate 0.9116 CYP450 3A4 substrate Non-substrate 0.6075 CYP450 1A2 substrate Non-inhibitor 0.8613 CYP450 2C9 inhibitor Non-inhibitor 0.9071 CYP450 2D6 inhibitor Inhibitor 0.8932 CYP450 2C19 inhibitor Non-inhibitor 0.9025 CYP450 3A4 inhibitor Non-inhibitor 0.8309 CYP450 inhibitory promiscuity High CYP Inhibitory Promiscuity 0.8598 Ames test Non AMES toxic 0.9132 Carcinogenicity Non-carcinogens 0.9551 Biodegradation Not ready biodegradable 0.9833 Rat acute toxicity 2.7123 LD50, mol/kg Not applicable hERG inhibition (predictor I) Strong inhibitor 0.7001 hERG inhibition (predictor II) Non-inhibitor 0.5557
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
- Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 185.5576783 predictedDarkChem Lite v0.1.0 [M-H]- 167.40639 predictedDeepCCS 1.0 (2019) [M+H]+ 186.2565783 predictedDarkChem Lite v0.1.0 [M+H]+ 169.76439 predictedDeepCCS 1.0 (2019) [M+Na]+ 185.4530783 predictedDarkChem Lite v0.1.0 [M+Na]+ 175.85754 predictedDeepCCS 1.0 (2019)
Targets
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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
- Peroutka SJ, Snyder SH: Two distinct serotonin receptors: regional variations in receptor binding in mammalian brain. Brain Res. 1981 Mar 16;208(2):339-47. [Article]
- Claro E, Arbones L, Garcia A, Picatoste F: Phosphoinositide hydrolysis mediated by histamine H1-receptors in rat brain cortex. Eur J Pharmacol. 1986 Apr 16;123(2):187-96. [Article]
- Kuzmin AI, Zaretsky DV, Kalenikova EI, Zaretskaja MV, Medvedev OS, Chazov EI: The effect of histamine receptor antagonists on stress-induced catecholamine secretion: an adrenomedullary microdialysis study in the rat. Eur J Pharmacol. 1999 Aug 13;378(3):311-6. [Article]
- Ziganshina LE, Ziganshin AU, Hoyle CH, Burnstock G: Acute paw oedema formation induced by ATP: re-evaluation of the mechanisms involved. Inflamm Res. 1996 Feb;45(2):96-102. [Article]
- Hiroi T, Ohishi N, Imaoka S, Yabusaki Y, Fukui H, Funae Y: Mepyramine, a histamine H1 receptor antagonist, inhibits the metabolic activity of rat and human P450 2D forms. J Pharmacol Exp Ther. 1995 Feb;272(2):939-44. [Article]
- Estelle F, Simons R: H1-receptor antagonists: safety issues. Ann Allergy Asthma Immunol. 1999 Nov;83(5):481-8. [Article]
- Mann KV, Crowe JP, Tietze KJ: Nonsedating histamine H1-receptor antagonists. Clin Pharm. 1989 May;8(5):331-44. [Article]
- Simons FE: H1-receptor antagonists. Comparative tolerability and safety. Drug Saf. 1994 May;10(5):350-80. [Article]
- Paton DM, Webster DR: Clinical pharmacokinetics of H1-receptor antagonists (the antihistamines). Clin Pharmacokinet. 1985 Nov-Dec;10(6):477-97. [Article]
- Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [Article]
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 23:31