Triprolidine

Triprolidine is an over-the-counter first-generation antihistamine with strong anticholinergic properties.^[1] 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.^[2] As with many antihistamines, the most common side effect is drowsiness.^[1]

Trade namesFlonase Nighttime Allergy Relief, Actidil, others

AHFS/Drugs.comMonograph

Pregnancy
category

• C (US)

Routes of
administrationBy mouth

Quick facts Clinical data, Trade names ...

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 Y
PubChem CID	5282443
IUPHAR/BPS	1228
DrugBank	DB00427 Y
ChemSpider	4445597 Y
UNII	2L8T9S52QM
KEGG	D01782 N
ChEBI	CHEBI:84116 N
ChEMBL	ChEMBL855 Y
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+ Y Key:CBEQULMOCCWAQT-WOJGMQOQSA-N Y
NY (what is this?)  (verify)

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Triprolidine was patented in 1948 and came into medical use in 1953,^[3] and has mostly been replaced in popular cold and flu medications by other drugs such as diphenhydramine, promethazine, chlorpheniramine, loratadine and fexofenadine.