Triprolidine

Triprolidine
Clinical data
Trade namesFlonase Nighttime Allergy Relief, Actidil, Myidil, Actifed (in the latter combined with pseudoephedrine and either dextromethorphan or guaifenesin)
AHFS/Drugs.comMonograph
Pregnancy
category
  • C (US)
Routes of
administration		Oral
ATC code
Legal status
Legal status
Pharmacokinetic data
Bioavailability4% oral
Protein binding90%
MetabolismHepatic (CYP2D6)
Elimination half-life4–6 hours
ExcretionRenal
Identifiers
IUPAC name
  • 2-[(E)-1-(4-methylphenyl)-3-pyrrolidin-1-yl-
    prop-1-enyl]pyridine
CAS Number
PubChem CID
IUPHAR/BPS
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.006.934
Chemical and physical data
FormulaC19H22N2
Molar mass278.399 g·mol−1
3D model (JSmol)
Melting point60 °C (140 °F)
Solubility in water500 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+ checkY
  • Key:CBEQULMOCCWAQT-WOJGMQOQSA-N checkY
 ☒NcheckY (what is this?)  (verify)

Triprolidine is an over-the-counter antihistamine with anticholinergic properties.[1] It is used to combat the symptoms associated with allergies and is sometimes combined with other cold medications designed to provide general relief for flu-like symptoms.[2] As with many antihistamines, the most common side effect is drowsiness.[1]

Today, Triprolidine is used less frequently and has been replaced in popular medications by other antihistamines like Diphenhydramine, Promethazine, Chlorpheniramine, as well as second generation antihistamines like Loratadine and Fexofenadine. Triprolidine remains an ingredient in the cold medicine Actifed in many territories.

It was patented in 1948 and came into medical use in 1953.[3]

See also

References

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