Triprolidine
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Basic information
- CAS
486-12-4- Standard SMILES
Cc1ccc(/C(=C\CN2CCCC2)c2ccccn2)cc1- InChIKey
CBEQULMOCCWAQT-WOJGMQOQSA-N- Molecular formula
- C19H22N2
- Average molar mass
- 278.4 g/mol
- Monoisotopic mass
- 278.1782987
Overview
Triprolidine is an N-alkylpyrrolidine that is acrivastine in which the pyridine ring is lacking the propenoic acid substituent. It is a sedating antihistamine that is used (generally as the monohydrochloride monohydrate) for the relief of the symptoms of uticaria, rhinitis, and various pruritic skin disorders. It has a role as a H1-receptor antagonist. It is a member of pyridines, a N-alkylpyrrolidine and an olefinic compound. It is a conjugate base of a triprolidine(1+).
Names & identifiers
- Preferred name
- Triprolidine
- IUPAC
- 2-[(E)-1-(4-methylphenyl)-3-pyrrolidin-1-ylprop-1-enyl]pyridine
- English name
- Triprolidine
- Molecular formula
- C19H22N2
- Molecular weight
- 278.39
Names & synonyms
triprolidine486-12-4TriprolidinActidilTripolidinaTriprolidinumTriprolidinaDTXSID3023718trans-1-(2-Pyridyl)-3-pyrrolidino-1-p-tolylprop-1-eneNCI-C614502-[(E)-1-(4-methylphenyl)-3-pyrrolidin-1-ylprop-1-enyl]pyridinetrans-1-(4-Methylphenyl)-1-(2-pyridyl)-3-pyrrolidinoprop-1-ene
Show more names
(e)-pyridinTripyrolidineTriprolidine USP/EP/BPTriprolidine (Standard)(E)-1-(2-pyridyl)-3-pyrrolidin-1-yl-1-p-tolylpropene
trans-2-(3-(1-Pyrrolidinyl)-1-p-tolylpropenyl)pyridine2L8T9S52QM2-[(1E)-1-(4-methylphenyl)-3-(pyrrolidin-1-yl)prop-1-en-1-yl]pyridineDTXCID203718CHEBI:84116Pyridine, 2-(3-(1-pyrrolidinyl)-1-p-tolylpropenyl)-, (E)-(E)-2-[3-(1-Pyrrolidinyl)-1-p-toluenepropenyl]pyridine(E)-2-(3-(1-pyrrolidinyl)-1-p-toluenepropenyl)pyridine
Database identifiers
- CAS
486-12-4
Properties
Computed structural propertiesFilling in
- XLogP
- 3.9
- Topological polar surface area
- 16.1 Ų
- Hydrogen bond donors
- 0
- Hydrogen bond acceptors
- 2
- Rotatable bonds
- 4
- Heavy atoms
- 21
- Formal charge
- 0
- Complexity
- 335
Experimental & physicochemical properties
Drugs
Pharmaceuticals -> Listed in ZINC15
Pharmaceuticals
LogP
4
3.87
Color/FormCrystals from light petroleum
Solubility5.37e-02 g/L
Human Drugs
Breast Feeding; Lactation; Milk, Human; Antihistamines
Pharmaceuticals
Melting Point
59-61 °C
60 °C
Physical DescriptionSolid
Dissociation Constants
9.69
9.25
Collision Cross Section167.67 Ų [M+H]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
Hazard information
Other Safety InformationIMAP assessments - Pyridine, 2-[1-(4-methylphenyl)-3-(1-pyrrolidinyl)-1-propenyl]-, (E)-: Environment tier I assessment
FDA Requirements
Manufacturers, packers, and distributors of drug and drug products for human use are responsible for complying with the labeling, certification, and usage requirements as prescribed by the Federal Food, Drug, and Cosmetic Act, as amended (secs 201-902, 52 Stat. 1040 et seq., as amended; 21 U.S.C. 321-392).
Safety & protection
Disposal Methods
SRP: At the time of review, criteria for land treatment or burial (sanitary landfill) disposal practices are subject to significant revision. Prior to implementing land disposal of waste residue (including waste sludge), consult with environmental regulatory agencies for guidance on acceptable disposal practices.
Toxicology
Interactions
Concurrent use /of ototoxic medications/ with antihistamines may mask the symptoms of ototoxicity such as tinnitus, dizziness, or vertigo. /Antihistamines/
Concurrent use of monoamine oxidase (MAO) inhibitors with antihistamines may prolong and intensify the anticholinergic and CNS depressant effects of antihistamines; concurrent use is not recommended. /Antihistamines/
Concurrent use /with alcohol or other CNS depression-producing medications/ may potentiate the CNS depressant effects of either these medications or antihistamines; also, concurrent use of maprotiline or tricyclic antidepressants may potentiate the anticholinergic effects of either antihistamines or these medications. /Antihistamines/
Anticholinergic effects may be potentiated when /anticholinergics or other medications with anticholinergic activity/ are used concurrently with antihistamines; patients should be advised to report occurrence of gastrointestinal problems promptly since paralytic ileus may occur with concurrent therapy. /Antihistamines/
Chemistry & industry
Pharmacology
ATC Code
R - Respiratory system
QR - Respiratory system
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.
Antihistamines used in the treatment of allergy act by competing with histamine for H1-receptor sites on effector cells. They thereby prevent, but do not reverse, responses mediated by histamine alone. Antihistamines antagonize, in varying degrees, most of the pharmacological effects of histamine, including urticaria and pruritus. Also, the anticholinergic actions of most antihistamines provide a drying effect on the nasal mucosa. /Antihistamines/
Antihistamines used in the treatment of allergy act by competing with histamine for H1-receptor sites on effector cells. They thereby prevent, but do not reverse, responses mediated by histamine alone. Antihistamines antagonize, in varying degrees, most of the pharmacological effects of histamine, including urticaria and pruritus. Also, the anticholinergic actions of most antihistamines provide a drying effect on the nasal mucosa. /Antihistamines/
H1 antagonists inhibit most responses of smooth muscle to histamine. Antagonism of the constrictor action of histamine on respiratory smooth muscle is easily shown in vivo and in vitro. /Histamine Antagonists: H1 Antagonists/
Related reactions
7 records
Compound notes
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