Triprolidine

Structural formula
General
Non-proprietary name	Triprolidine ( INN )
other names	2 - [( E ) -1- (4-methylphenyl) -3-pyrrolidin-1-ylprop-1-enyl] pyridine ( IUPAC ); Triprolidinum ( Latin );
Molecular formula	C 19 H 22 N 2 (triprolidine) ; C 19 H 22 N 2 · HCl · H 2 O (triprolidine · hydrochloride · mono hydrate ) ;
Brief description	Solid
External identifiers / databases
EC number	207-627-0
ECHA InfoCard	100.006.934
PubChem	5282443
ChemSpider	4445597
DrugBank	DB00427
Wikidata	Q417654
Drug information
ATC code	R06 AX07
Drug class	Antihistamine
properties
Molar mass	278.39 g mol −1 (triprolidine) ; 332.87 g mol −1 (triprolidine hydrochloride monohydrate) ;
Melting point	59-61 ° C (triprolidine) ; 116–118 ° C (triprolidine hydrochloride monohydrate) ;
solubility	moderate solubility in water, methanol and ethanol (triprolidine · hydrochloride · mono hydrate )
safety instructions
	Please note the exemption from the labeling requirement for drugs, medical devices, cosmetics, food and animal feed
GHS labeling of hazardous substances Hydrochloride; Caution
H and P phrases	H: 302-315-319-335
	P: 261-305 + 351 + 338
	As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Triprolidine (in combination with pseudoephedrine hydrochloride under the trade name: Rhinopront ^® Kombi) is a first generation antihistamine . It acts as an antagonist at the H ₁ receptor and inhibits the neurotransmitter acetylcholine (→ anticholinergic effect). Triprolidine is also a weak inhibitor of the CYP 2D6 enzyme system. Its average half-life is relatively short at 4 hours compared to other antihistamines.

Triprolidine is used as a monopreparation or combined preparation (mostly with pseudoephedrine ) for the treatment of allergies or colds. In one study, however, no noticeable benefit of a combination preparation with pseudoephedrine could be proven.

Side effects

The most common side effects are skin rashes (with or without irritation), racing heart, xerostomia , urinary retention (especially if the prostate is enlarged ) and vertigo .

Like most first generation antihistamines, triprolidine has an impact on the nervous system. In a study, a few minutes after ingestion and for 7 hours, a slight influence on the ability to coordinate was found.

Another study examined whether triprolidine has analgesic properties; When administered alone, no analgesic properties could be observed, but a combination with dipipanone led to an intensification of the analgesia.

In another study, after taking triprolidine and pseudoephedrine once , a higher concentration of both active substances in breast milk than in serum was found in the test persons, whereby the concentration of triprolidine in breast milk was more variable than that of pseudoephedrine.

Individual evidence

↑ Entry on Triprolidine in the DrugBank of the University of Alberta , accessed August 16, 2008.
↑ ^a ^b ^c The Merck Index. An Encyclopaedia of Chemicals, Drugs and Biologicals. 14th edition, 2006, p. 1674, ISBN 978-0-911910-00-1 .
↑ ^a ^b Data sheet Triprolidine hydrochloride from Sigma-Aldrich , accessed on April 25, 2011 ( PDF ).
↑ DW Empey, MF Frosolono, DT Hughes, JG Perkins: Comparison of pseudoephedrine and triprolidine, alone and in combination in preventing nasal congestion in subjects with allergic rhinitis using nasal histamine challenge. In: British Journal of Clinical Pharmacology . Volume 18, Number 1, July 1984, pp. 86-89, PMID 6204666 , PMC 1463593 (free full text).
↑ AN Nicholson: Effect of the antihistamines, brompheniramine maleate and triprolidine hydrochloride, on performance in man. In: British Journal of Clinical Pharmacology . Volume 8, Number 4, October 1979, pp. 321-324, PMID 508506 , PMC 1429839 (free full text).
^ A. Telekes, RL Holland, DA Withington, AW Peck: Effects of triprolidine and dipipanone in the cold induced pain test, and the central nervous system of healthy volunteers. In: British Journal of Clinical Pharmacology . Volume 24, Number 1, July 1987, pp. 43-50, PMID 3620284 , PMC 1386278 (free full text).
↑ JW Findlay, RF Butz, JM Sailstad, JT Warren, RM Welch: Pseudoephedrine and triprolidine in plasma and breast milk of nursing mothers. In: British Journal of Clinical Pharmacology . Volume 18, Number 6, December 1984, pp. 901-906, PMID 6529531 , PMC 1463694 (free full text).

[DrugBank-1] Entry on Triprolidine in the DrugBank of the University of Alberta , accessed August 16, 2008.

[MerckIndex-2] The Merck Index. An Encyclopaedia of Chemicals, Drugs and Biologicals. 14th edition, 2006, p. 1674, ISBN 978-0-911910-00-1 .

[Sigma-3] Data sheet Triprolidine hydrochloride from Sigma-Aldrich , accessed on April 25, 2011 ( PDF ).

[4] DW Empey, MF Frosolono, DT Hughes, JG Perkins: Comparison of pseudoephedrine and triprolidine, alone and in combination in preventing nasal congestion in subjects with allergic rhinitis using nasal histamine challenge. In: British Journal of Clinical Pharmacology . Volume 18, Number 1, July 1984, pp. 86-89, PMID 6204666 , PMC 1463593 (free full text).

[5] AN Nicholson: Effect of the antihistamines, brompheniramine maleate and triprolidine hydrochloride, on performance in man. In: British Journal of Clinical Pharmacology . Volume 8, Number 4, October 1979, pp. 321-324, PMID 508506 , PMC 1429839 (free full text).

[6] A. Telekes, RL Holland, DA Withington, AW Peck: Effects of triprolidine and dipipanone in the cold induced pain test, and the central nervous system of healthy volunteers. In: British Journal of Clinical Pharmacology . Volume 24, Number 1, July 1987, pp. 43-50, PMID 3620284 , PMC 1386278 (free full text).

[7] JW Findlay, RF Butz, JM Sailstad, JT Warren, RM Welch: Pseudoephedrine and triprolidine in plasma and breast milk of nursing mothers. In: British Journal of Clinical Pharmacology . Volume 18, Number 6, December 1984, pp. 901-906, PMID 6529531 , PMC 1463694 (free full text).