Triprolidine

Triprolidine
Clinical data
Trade names	Flonase Nighttime Allergy Relief, Actidil, others
AHFS/Drugs.com	Monograph
Pregnancy; category	C (US);
Routes of; administration	By mouth
ATC code	R06AX07 (WHO) ;
Legal status
Legal status	US: OTC;
Pharmacokinetic data
Bioavailability	Oral: 4%
Protein binding	90%
Metabolism	Hepatic (CYP2D6)
Elimination half-life	4–6 hours
Excretion	Renal
Identifiers
	IUPAC name 2-[(E)-1-(4-methylphenyl)-3-pyrrolidin-1-yl-; prop-1-enyl]pyridine;
CAS Number	486-12-4 ;
PubChem CID	5282443;
IUPHAR/BPS	1228;
DrugBank	DB00427 ;
ChemSpider	4445597 ;
UNII	2L8T9S52QM;
KEGG	D01782 ;
ChEBI	CHEBI:84116 ;
ChEMBL	ChEMBL855 ;
CompTox Dashboard (EPA)	DTXSID3023718 ;
ECHA InfoCard	100.006.934
Chemical and physical data
Formula	C19H22N2
Molar mass	278.399 g·mol−1
3D model (JSmol)	Interactive image;
Melting point	60 °C (140 °F)
Solubility in water	500 mg/mL (20 °C)
	SMILES n3c(\C(=C\CN1CCCC1)c2ccc(cc2)C)cccc3;
	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+ ; Key:CBEQULMOCCWAQT-WOJGMQOQSA-N ;
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Triprolidine is an over-the-counter first-generation antihistamine with strong anticholinergic properties. It is used to combat the symptoms associated with allergies and is sometimes combined with other medications in preparations designed to provide general relief for flu-like symptoms. As with many antihistamines, the most common side effect is drowsiness.

Triprolidine was patented in 1948 and came into medical use in 1953, and has mostly been replaced in popular cold and flu medications by other drugs such as diphenhydramine, promethazine, chlorpheniramine, loratadine and fexofenadine.

References

1 2 Goldsmith P, Dowd PM (January 1993). "The new H1 antihistamines. Treatment of urticaria and other clinical problems". Dermatologic Clinics. 11 (1): 87–95. doi:10.1016/S0733-8635(18)30285-7. PMID 8094649.
↑ Williams BO, Liao SH, Lai AA, Arnold JD, Perkins JG, Blum MR, Findlay JW (1984). "Bioavailability of pseudoephedrine and triprolidine from combination and single-ingredient products". Clinical Pharmacy. 3 (6): 638–43. PMID 6509877.
↑ Fischer J, Ganellin CR (2006). Analogue-based Drug Discovery. John Wiley & Sons. p. 546. ISBN 9783527607495.

[Goldsmith-1] 1 2 Goldsmith P, Dowd PM (January 1993). "The new H1 antihistamines. Treatment of urticaria and other clinical problems". Dermatologic Clinics. 11 (1): 87–95. doi:10.1016/S0733-8635(18)30285-7. PMID 8094649.

[2] Williams BO, Liao SH, Lai AA, Arnold JD, Perkins JG, Blum MR, Findlay JW (1984). "Bioavailability of pseudoephedrine and triprolidine from combination and single-ingredient products". Clinical Pharmacy. 3 (6): 638–43. PMID 6509877.

[Fis2006-3] Fischer J, Ganellin CR (2006). Analogue-based Drug Discovery. John Wiley & Sons. p. 546. ISBN 9783527607495.

v t e Antihistamines (R06)
Benzimidazoles (*)	Astemizole Azelastine Bilastine Emedastine Mizolastine Talastine
Diarylmethanes	Diarylmethoxyalkylamines: Bromazine (bromodiphenhydramine) Carbinoxamine Chlorphenoxamine Clemastine Diphenhydramine (+naproxen) Diphenylpyraline Doxylamine Ebastine Orphenadrine Diphenylmethanolpiperidines: Fexofenadine Terfenadine Diphenylmethylpiperazines: Buclizine Cetirizine Levocetirizine Chlorcyclizine Cinnarizine Cyclizine Etodroxizine Hydroxyzine Meclizine Oxatomide Phenylpyridinylpropanamines: Brompheniramine Chlorphenamine Dexbrompheniramine (+pseudoephedrine) Dexchlorpheniramine (+betamethasone) Pheniramine Others: Acrivastine Bamipine Dimetindene Phenyltoloxamine Pyrrobutamine Quifenadine Triprolidine
Ethylenediamines	Antazoline Chloropyramine Histapyrrodine Mepyramine (pyrilamine) Methapyrilene Phenbenzamine Thenalidine Tripelennamine (pyribenzamine)
Tricyclics	Dibenzocycloheptenes: Antidepressants (e.g., amitriptyline) Azatadine Cyproheptadine Deptropine Desloratadine Ketotifen Loratadine Rupatadine Phenothiazines: Alimemazine Fenethazine Hydroxyethylpromethazine Isothipendyl Mequitazine Methdilazine Oxomemazine Promethazine Others: Antidepressants (e.g., doxepin, mirtazapine, trimipramine) Epinastine Latrepirdine Mebhydrolin Olopatadine Perlapine Phenindamine Pimethixene
Others	Phenylpiperazines: Antidepressants (e.g., trazodone) Phenbenzamine
For topical use	Bamipine Chloropyramine Chlorphenoxamine Clemastine Dimetindene Diphenhydramine Doxepin Isothipendyl Mepyramine (pyrilamine) Promethazine

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See also: Psychedelics Dissociatives Entactogens Stimulants Depressants List of hallucinogens

Triprolidine

See also

References