Triprolidine

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
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.

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Associated Conditions
Indication TypeIndicationCombined Product DetailsApproval LevelAge GroupPatient CharacteristicsDose Form
Treatment ofAllergic conjunctivitis••• •••
Used in combination for symptomatic treatment ofNasal congestionCombination Product in combination with: Pseudoephedrine (DB00852)•••••••••••••••••••• ••••••• ••••••
Used in combination for symptomatic treatment ofNasal congestionCombination Product in combination with: Pseudoephedrine (DB00852)•••••••••••••••••••• ••••••• ••••••
Used in combination for symptomatic treatment ofNasal congestionCombination Product in combination with: Pseudoephedrine (DB00852)•••••••••••••••••••• ••••••• ••••••
Treatment ofPerennial allergic rhinitis••• •••
Contraindications & Blackbox Warnings
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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.

TargetActionsOrganism
AHistamine H1 receptor
antagonist
Humans
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
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Toxicity

Symptoms of overdose include drowsiness, weakness, inco-ordination, difficulty with micturition, respiratory depression, hypotension, agitation, irritability, convulsions, hypertension, palpitation and tachycardia.

Pathways
PathwayCategory
Triprolidine 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
1,2-BenzodiazepineThe risk or severity of CNS depression can be increased when Triprolidine is combined with 1,2-Benzodiazepine.
AcetazolamideThe risk or severity of CNS depression can be increased when Triprolidine is combined with Acetazolamide.
AcetophenazineThe risk or severity of CNS depression can be increased when Triprolidine is combined with Acetophenazine.
AcrivastineThe risk or severity of QTc prolongation can be increased when Triprolidine is combined with Acrivastine.
AdenosineThe 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

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Product Ingredients
IngredientUNIICASInChI Key
Triprolidine hydrochlorideNG7A104R3J550-70-9WYUYEJNGHIOFOC-NWBUNABESA-N
Triprolidine hydrochloride monohydrateYAN7R5L8906138-79-0CUZMOIXUFHOLLN-UMVVUDSKSA-N
Product Images
International/Other Brands
Anmin (AND) / Venen (Sato Seiyaku)
Brand Name Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
TripohistLiquid1.25 mg/5mLOralBreckenridge Pharmaceutical, Inc.2008-01-312011-12-31US flag
Over the Counter Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
AllerdineLiquid0.625 mg/1mLOralWoodward Pharma Services Llc2018-06-092020-03-15US flag
Childrens PediaClear AllergyLiquid0.313 mg/1mLOralGM Pharmaceuticals, INC2019-06-25Not applicableUS flag
Childrens PediaClear PDLiquid1.25 mg/2mLOralGM Pharmaceuticals, INC2019-07-01Not applicableUS flag
Dr Manzanilla InfantSyrup0.938 mg/1mLOralKey Therapeutics2019-08-112020-03-31US flag
Dr Manzanilla PediatricSyrup2.5 mg/5mLOralKey Therapeutics2019-08-112020-03-31US flag
Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing EndRegionImage
A-FERIN DECO ŞURUP, 100 MLTriprolidine hydrochloride (1.25 mg/5mL) + Pseudoephedrine (30 mg/5mL)SyrupOralHÜSNÜ ARSAN İLAÇLARI A.Ş.2020-08-142018-08-17Turkey flag
A-FERIN DECO TABLET, 20 ADETTriprolidine hydrochloride (2.5 mg) + Pseudoephedrine (60 mg)TabletOralHÜSNÜ ARSAN İLAÇLARI A.Ş.2020-08-142018-08-17Turkey flag
A-FERIN SINUS 500/30/1.25 MG FİLM KAPLI TABLET, 20 ADETTriprolidine hydrochloride (1.25 mg) + Acetaminophen (500 mg) + Pseudoephedrine hydrochloride (30 mg)Tablet, coatedOralHÜSNÜ ARSAN İLAÇLARI A.Ş.2002-05-03Not applicableTurkey flag
ACTIDEM OKSURUK SURUBU, 150 MLTriprolidine (1.25 mg/5mL) + Dextromethorphan (10 mg/5mL) + Pseudoephedrine (30 mg/5mL)SyrupOralGLAXOSMİTHKLİNE İLAÇLARI SAN. VE TİC. A.Ş.1995-09-152023-03-20Turkey flag
ACTİFED 30 MG/5 ML + 1,25 MG/5 ML ŞURUPTriprolidine hydrochloride monohydrate (1.25 mg/5mL) + Pseudoephedrine hydrochloride (30 mg/5mL)SyrupOralGLAXOSMITHKLINE TÜKETİCİ SAĞLIĞI A.Ş.2013-01-29Not applicableTurkey flag
Unapproved/Other Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing EndRegionImage
EndalTriprolidine hydrochloride monohydrate (1.25 mg/5mL) + Dextromethorphan hydrobromide monohydrate (10 mg/5mL)LiquidOralPoly Pharmaceuticals, Inc.2023-05-22Not applicableUS flag
TripohistTriprolidine hydrochloride monohydrate (1.25 mg/5mL)LiquidOralBreckenridge Pharmaceutical, Inc.2008-01-312011-12-31US flag
Tripohist DTriprolidine hydrochloride monohydrate (1.25 mg/5mL) + Pseudoephedrine hydrochloride (45 mg/5mL)LiquidOralBreckenridge Pharmaceutical, Inc.2008-01-012011-12-31US flag
Triprolidine HCl PSE HClTriprolidine hydrochloride monohydrate (0.938 mg/1mL) + Pseudoephedrine hydrochloride (10 mg/1mL)LiquidOralRiver's Edge Pharmaceuticals, LLC2010-03-012010-03-31US flag
WhitubenTriprolidine 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)CapsuleOralOASIS TRADING2018-11-22Not applicableUS flag

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
  1. Mann KV, Crowe JP, Tietze KJ: Nonsedating histamine H1-receptor antagonists. Clin Pharm. 1989 May;8(5):331-44. [Article]
  2. Simons FE: H1-receptor antagonists. Comparative tolerability and safety. Drug Saf. 1994 May;10(5):350-80. [Article]
  3. Paton DM, Webster DR: Clinical pharmacokinetics of H1-receptor antagonists (the antihistamines). Clin Pharmacokinet. 1985 Nov-Dec;10(6):477-97. [Article]
  4. 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]
Human Metabolome Database
HMDB0014571
KEGG Drug
D01782
PubChem Compound
5282443
PubChem Substance
46505403
ChemSpider
4445597
BindingDB
50292411
RxNav
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
PhaseStatusPurposeConditionsCount

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
FormRouteStrength
ElixirOral10 mg/5ml
SyrupOral100 mg/5ml
Tablet, film coatedOral
SyrupOral10 mg/5ml
LiquidOral0.313 mg/1mL
LiquidOral1.25 mg/2mL
TabletOral
ElixirOral
Kit; solutionOral
Tablet, coatedOral
TabletOral2.5 mg/1
SyrupOral2.5 mg/5mL
Tablet, chewableOral1.25 mg/1
SyrupOral1.25 mg/1mL
Kit; tablet, coatedOral
Kit; liquidOral
SolutionOral
Kit; tablet, coated; tablet, film coatedOral
KitOral
SyrupOral30 mg/5ml
SyrupOral
LiquidOral1.25 mg/5mL
LiquidOral
LiquidOral0.625 mg/1mL
LiquidOral0.938 mg/1mL
LiquidOral2.5 mg/5mL
SyrupOral0.938 mg/1mL
CapsuleOral
TabletOral2.5 mg
Prices
Unit descriptionCostUnit
Triprolidine hcl crystals40.33USD g
Triprolidine 1.25 mg/5 ml liq0.15USD ml
Tripohist 1.25 mg/5 ml liquid0.14USD ml
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents
Not Available

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)60 °CPhysProp
water solubility74.9 mg/LNot Available
logP3.92HANSCH,C ET AL. (1995)
Predicted Properties
PropertyValueSource
Water Solubility0.0537 mg/mLALOGPS
logP4.14ALOGPS
logP4.05Chemaxon
logS-3.7ALOGPS
pKa (Strongest Basic)8.64Chemaxon
Physiological Charge1Chemaxon
Hydrogen Acceptor Count2Chemaxon
Hydrogen Donor Count0Chemaxon
Polar Surface Area16.13 Å2Chemaxon
Rotatable Bond Count4Chemaxon
Refractivity98.53 m3·mol-1Chemaxon
Polarizability33.06 Å3Chemaxon
Number of Rings3Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterYesChemaxon
Veber's RuleYesChemaxon
MDDR-like RuleNoChemaxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+0.9905
Blood Brain Barrier+0.9664
Caco-2 permeable-0.5814
P-glycoprotein substrateSubstrate0.6644
P-glycoprotein inhibitor IInhibitor0.8311
P-glycoprotein inhibitor IINon-inhibitor0.6624
Renal organic cation transporterInhibitor0.8612
CYP450 2C9 substrateNon-substrate0.8143
CYP450 2D6 substrateNon-substrate0.9116
CYP450 3A4 substrateNon-substrate0.6075
CYP450 1A2 substrateNon-inhibitor0.8613
CYP450 2C9 inhibitorNon-inhibitor0.9071
CYP450 2D6 inhibitorInhibitor0.8932
CYP450 2C19 inhibitorNon-inhibitor0.9025
CYP450 3A4 inhibitorNon-inhibitor0.8309
CYP450 inhibitory promiscuityHigh CYP Inhibitory Promiscuity0.8598
Ames testNon AMES toxic0.9132
CarcinogenicityNon-carcinogens0.9551
BiodegradationNot ready biodegradable0.9833
Rat acute toxicity2.7123 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Strong inhibitor0.7001
hERG inhibition (predictor II)Non-inhibitor0.5557
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-MSsplash10-001i-9550000000-61fa9fbbd86c1d8132d5
GC-MS Spectrum - EI-BGC-MSsplash10-0a4i-2690000000-a4b47440bb135b0a9add
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-0a4i-0090000000-0520fb51257b8f103fbd
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-0a4i-0090000000-32c7edd76d98d863433c
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-004i-0490000000-f86247098495329198bc
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-00lr-3920000000-95768fed8b39c043337b
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-001i-0910000000-bd9cc0ca256e89ba906e
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-014i-0940000000-b7653af7f45da80b8e7c
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]-185.5576783
predicted
DarkChem Lite v0.1.0
[M-H]-167.40639
predicted
DeepCCS 1.0 (2019)
[M+H]+186.2565783
predicted
DarkChem Lite v0.1.0
[M+H]+169.76439
predicted
DeepCCS 1.0 (2019)
[M+Na]+185.4530783
predicted
DarkChem Lite v0.1.0
[M+Na]+175.85754
predicted
DeepCCS 1.0 (2019)

Targets

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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. 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]
  2. 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]
  3. 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]
  4. 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]
  5. 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]
  6. Estelle F, Simons R: H1-receptor antagonists: safety issues. Ann Allergy Asthma Immunol. 1999 Nov;83(5):481-8. [Article]
  7. Mann KV, Crowe JP, Tietze KJ: Nonsedating histamine H1-receptor antagonists. Clin Pharm. 1989 May;8(5):331-44. [Article]
  8. Simons FE: H1-receptor antagonists. Comparative tolerability and safety. Drug Saf. 1994 May;10(5):350-80. [Article]
  9. Paton DM, Webster DR: Clinical pharmacokinetics of H1-receptor antagonists (the antihistamines). Clin Pharmacokinet. 1985 Nov-Dec;10(6):477-97. [Article]
  10. 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
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 18, 2024 16:24