Triprolidine

Triprolidine
Clinical data
Trade namesFlonase Nighttime Allergy Relief, Actidil, others
AHFS/Drugs.comMonograph
Pregnancy
category
  • C (US)
Routes of
administration		By mouth
ATC code
Legal status
Legal status
Pharmacokinetic data
BioavailabilityOral: 4%
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. ^ a b 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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