Triprolidine

Synonyms :
Actahist, Actidil, Actifed, Allerfed, Corphed, Histafed, Myfed, Myidyl, SID144204470, SID26751829, Trilitron, Triphed, Tripolidina, Triprolidin, Triprolidine, Triprolidinum

Status : approved

Therapeutic Classification

ANTIHISTAMINES FOR SYSTEMIC USE

RESPIRATORY SYSTEM
ANTIHISTAMINES FOR SYSTEMIC USE
ANTIHISTAMINES FOR SYSTEMIC USE

Description

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. [PubChem]

Used

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.

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.

Dosage

Form Route Strength
Syrup oral 15 mg
Tablet oral 30 mg
Tablet oral 500 mg
Liquid oral 30 mg
Tablet oral 60 mg
Tablet, coated oral 60; 2.5 mg/1; mg
Syrup oral 2.5 mg/5mL
Syrup oral 10; 10; 2.5 mg/5mL; mg/5mL; mg/5mL
Syrup oral .938 mg/mL
Syrup oral 20; 10; 2.5 mg/5mL; mg/5mL; mg/5mL
Syrup oral 10; 2.5 mg/5mL; mg/5mL
Liquid oral 10; 15; 1.25 mg/mL; mg/mL; mg/mL
Syrup oral 30 mg
Syrup oral 30; 1.25 mg/5mL; mg/5mL
Syrup oral 1.25; 30; 10 mg/5mL; mg/5mL; mg/5mL
Liquid oral .625 mg/mL
Tablet, film coated oral 60; 2.5 mg/1; mg

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.

Toxic Effect

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

Absorption

Rapidly absorbed in the intestinal tract.

Half Life

4 to 6 hours.

Chemical Classification

This compound belongs to the class of organic compounds known as phenylpropenes. These are compounds containing a phenylpropene moiety, which consists of a propene substituent bound to a phenyl group.

Phenylpropenes

Organic compounds

Benzenoids

Benzene and substituted derivatives

Phenylpropenes

Salt : Triprolidine Hydrochloride

Chemical Name

Actahist

Brands

name Dosage form Country
Actifed DM Syrup syrup Canada
Actifed DM Syrup syrup Canada
Actifed DM Tablets tablet Canada
Actifed DM Tablets tablet Canada
Actifed Plus Caplet tablet Canada
Actifed Plus Caplets tablet Canada
Actifed Syrup liquid Canada
Actifed Tablets tablet Canada
Actifed Tablets tablet Canada
Aprodine tablet, film coated US
Aprodine tablet, film coated US
Coactifed tablet Canada
Coactifed syrup Canada
Coactifed syrup Canada
Cotrifed liquid Canada
Covan Syrup syrup Canada
Ed-a-hist Pse tablet, coated US
Histex syrup US
Histex Ac syrup US
Histex Pd Drops syrup US
Histex-dm syrup US
Histex-pe syrup US
Poly Hist Nc liquid US
Ratio-cotridin syrup Canada
Ratio-cotridin Expectorant syrup Canada
Silafed syrup US
Triacin-c syrup US
Triprofed Tab tablet Canada
Vanahist Pd liquid US
Wal-act tablet, film coated US

Drug Drug Interactions

  •  Acebutolol  : May enhance the adverse/toxic effect of other Sympathomimetics.
  •  Acetazolamide  : May increase the serum concentration of Alpha-/Beta-Agonists (Indirect-Acting).
  •  Aclidinium  : May enhance the anticholinergic effect of Anticholinergic Agents.
  •  Amphetamine  : May diminish the sedative effect of Antihistamines.
  •  Aripiprazole  : CYP2D6 Inhibitors (Weak) may increase the serum concentration of Aripiprazole.
  •  Atomoxetine  : May enhance the hypertensive effect of Sympathomimetics. Atomoxetine may enhance the tachycardic effect of Sympathomimetics.
  •  Benzphetamine  : May enhance the adverse/toxic effect of other Sympathomimetics.
  •  Benzylpenicilloyl Polylysine  : Antihistamines may diminish the diagnostic effect of Benzylpenicilloyl Polylysine.
  •  Benzylpenicilloyl Polylysine  : Alpha-/Beta-Agonists may diminish the diagnostic effect of Benzylpenicilloyl Polylysine.
  •  Betahistine  : Antihistamines may diminish the therapeutic effect of Betahistine.
  •  Botulinum Toxin Type A  : Anticholinergic Agents may enhance the anticholinergic effect of AbobotulinumtoxinA.
  •  Botulinum Toxin Type A  : Anticholinergic Agents may enhance the anticholinergic effect of OnabotulinumtoxinA.
  •  Botulinum Toxin Type B  : Anticholinergic Agents may enhance the anticholinergic effect of RimabotulinumtoxinB.
  •  Buprenorphine  : CNS Depressants may enhance the CNS depressant effect of Buprenorphine.
  •  Cathinone  : May diminish the sedative effect of Antihistamines.
  •  Chlorphentermine  : May enhance the adverse/toxic effect of other Sympathomimetics.
  •  Clenbuterol  : May enhance the adverse/toxic effect of other Sympathomimetics.
  •  Diclofenamide  : May increase the serum concentration of Alpha-/Beta-Agonists (Indirect-Acting).
  •  Dobutamine  : May enhance the adverse/toxic effect of other Sympathomimetics.
  •  Dopamine  : May enhance the adverse/toxic effect of other Sympathomimetics.
  •  Doxylamine  : May enhance the CNS depressant effect of CNS Depressants.
  •  Dronabinol  : May enhance the CNS depressant effect of CNS Depressants.
  •  Dronabinol  : May enhance the CNS depressant effect of CNS Depressants.
  •  Droperidol  : May enhance the CNS depressant effect of CNS Depressants.
  •  Epinephrine  : May enhance the adverse/toxic effect of other Sympathomimetics.
  •  Ethoxzolamide  : May increase the serum concentration of Alpha-/Beta-Agonists (Indirect-Acting).
  •  Fenoterol  : May enhance the adverse/toxic effect of other Sympathomimetics.
  •  Fentanyl  : Alpha-/Beta-Agonists (Indirect-Acting) may decrease the serum concentration of Fentanyl. Specifically, Fentanyl nasal spray serum concentrations may decrease and onset of effect may be delayed.
  •  Formoterol  : May enhance the adverse/toxic effect of other Sympathomimetics.
  •  Glucagon recombinant  : Anticholinergic Agents may enhance the adverse/toxic effect of Glucagon. Specifically, the risk of gastrointestinal adverse effects may be increased.
  •  Hyaluronidase  : Antihistamines may diminish the therapeutic effect of Hyaluronidase.
  •  Hydrocodone  : CNS Depressants may enhance the CNS depressant effect of Hydrocodone.
  •  Hydroxyzine  : May enhance the CNS depressant effect of CNS Depressants.
  •  Isoprenaline  : May enhance the adverse/toxic effect of other Sympathomimetics.
  •  Itopride  : Anticholinergic Agents may diminish the therapeutic effect of Itopride.
  •  Labetalol  : May enhance the adverse/toxic effect of other Sympathomimetics.
  •  Linezolid  : May enhance the hypertensive effect of Sympathomimetics.
  •  Magnesium Sulfate  : May enhance the CNS depressant effect of CNS Depressants.
  •  Mephentermine  : May enhance the adverse/toxic effect of other Sympathomimetics.
  •  Metaraminol  : May enhance the adverse/toxic effect of other Sympathomimetics.
  •  Methamphetamine  : May enhance the adverse/toxic effect of other Sympathomimetics.
  •  Methotrimeprazine  : CNS Depressants may enhance the CNS depressant effect of Methotrimeprazine. Methotrimeprazine may enhance the CNS depressant effect of CNS Depressants.
  •  Methoxamine  : May enhance the adverse/toxic effect of other Sympathomimetics.
  •  Metyrosine  : CNS Depressants may enhance the sedative effect of Metyrosine.
  •  Mianserin  : May enhance the anticholinergic effect of Anticholinergic Agents.
  •  Midodrine  : May enhance the adverse/toxic effect of other Sympathomimetics.
  •  Minocycline  : May enhance the CNS depressant effect of CNS Depressants.
  •  Mirabegron  : Anticholinergic Agents may enhance the adverse/toxic effect of Mirabegron.
  •  Mirtazapine  : CNS Depressants may enhance the CNS depressant effect of Mirtazapine.
  •  Nabilone  : May enhance the CNS depressant effect of CNS Depressants.
  •  Naphazoline  : May enhance the adverse/toxic effect of other Sympathomimetics.
  •  Norepinephrine  : May enhance the adverse/toxic effect of other Sympathomimetics.
  •  Orciprenaline  : May enhance the adverse/toxic effect of other Sympathomimetics.
  •  Orphenadrine  : CNS Depressants may enhance the CNS depressant effect of Orphenadrine.
  •  Oxymetazoline  : May enhance the adverse/toxic effect of other Sympathomimetics.
  •  Paraldehyde  : CNS Depressants may enhance the CNS depressant effect of Paraldehyde.
  •  Perampanel  : May enhance the CNS depressant effect of CNS Depressants.
  •  Phenmetrazine  : May enhance the adverse/toxic effect of other Sympathomimetics.
  •  Phentermine  : May enhance the adverse/toxic effect of other Sympathomimetics.
  •  Phenylephrine  : May enhance the adverse/toxic effect of other Sympathomimetics.
  •  Phenylpropanolamine  : May enhance the adverse/toxic effect of other Sympathomimetics.
  •  Potassium Chloride  : Anticholinergic Agents may enhance the ulcerogenic effect of Potassium Chloride.
  •  Pramipexole  : CNS Depressants may enhance the sedative effect of Pramipexole.
  •  Pramlintide  : May enhance the anticholinergic effect of Anticholinergic Agents. These effects are specific to the GI tract.
  •  Ritodrine  : May enhance the adverse/toxic effect of other Sympathomimetics.
  •  Ropinirole  : CNS Depressants may enhance the sedative effect of Ropinirole.
  •  Rotigotine  : CNS Depressants may enhance the sedative effect of Rotigotine.
  •  Rufinamide  : May enhance the adverse/toxic effect of CNS Depressants. Specifically, sleepiness and dizziness may be enhanced.
  •  Salmeterol  : May enhance the adverse/toxic effect of other Sympathomimetics.
  •  Secretin  : Anticholinergic Agents may diminish the therapeutic effect of Secretin.
  •  Sodium oxybate  : May enhance the CNS depressant effect of CNS Depressants.
  •  Spironolactone  : May diminish the vasoconstricting effect of Alpha-/Beta-Agonists.
  •  Sulpiride  : Anticholinergic Agents may diminish the therapeutic effect of LevoSulpiride.
  •  Suvorexant  : CNS Depressants may enhance the CNS depressant effect of Suvorexant.
  •  Tapentadol  : May enhance the CNS depressant effect of CNS Depressants.
  •  Tedizolid Phosphate  : May enhance the hypertensive effect of Sympathomimetics. Tedizolid may enhance the tachycardic effect of Sympathomimetics.
  •  Terbutaline  : May enhance the adverse/toxic effect of other Sympathomimetics.
  •  Thalidomide  : CNS Depressants may enhance the CNS depressant effect of Thalidomide.
  •  Tiotropium  : Anticholinergic Agents may enhance the anticholinergic effect of Tiotropium.
  •  Topiramate  : Anticholinergic Agents may enhance the adverse/toxic effect of Topiramate.
  •  Umeclidinium  : May enhance the anticholinergic effect of Anticholinergic Agents.
  •  Zolpidem  : CNS Depressants may enhance the CNS depressant effect of Zolpidem.

Calculated Property

kind Value Source
logP 4.14 ALOGPS
logS -3.7 ALOGPS
Water Solubility 5.37e-02 g/l ALOGPS
logP 4.05 ChemAxon
IUPAC Name 2-[(1E)-1-(4-methylphenyl)-3-(pyrrolidin-1-yl)prop-1-en-1-yl]pyridine ChemAxon
Traditional IUPAC Name triprolidine ChemAxon
Molecular Weight 278.3914 ChemAxon
Monoisotopic Weight 278.178298714 ChemAxon
SMILES CC1=CC=C(C=C1)C(=C/CN1CCCC1)C1=CC=CC=N1 ChemAxon
Molecular Formula C19H22N2 ChemAxon
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+ ChemAxon
InChIKey InChIKey=CBEQULMOCCWAQT-WOJGMQOQSA-N ChemAxon
Polar Surface Area (PSA) 16.13 ChemAxon
Refractivity 98.53 ChemAxon
Polarizability 33.09 ChemAxon
Rotatable Bond Count 4 ChemAxon
H Bond Acceptor Count 2 ChemAxon
H Bond Donor Count 0 ChemAxon
pKa (strongest basic) 8.64 ChemAxon
Physiological Charge 1 ChemAxon
Number of Rings 3 ChemAxon
Bioavailability 1 ChemAxon
Rule of Five 1 ChemAxon
Ghose Filter 1 ChemAxon
MDDR-Like Rule 0 ChemAxon

Affected organism

Humans and other mammals

Target within organism

  • Histamine H1 receptor : in Human