Pheniramine

Pheniramine (trade name Avil among others) is an antihistamine with anticholinergic properties used to treat allergic conditions such as hay fever or urticaria. It has relatively strong sedative effects, and may sometimes be used off-label as an over-the-counter sleeping pill in a similar manner to other sedating antihistamines such as diphenhydramine. Pheniramine is also commonly found in eyedrops used for the treatment of allergic conjunctivitis.

Pheniramine
Clinical data
AHFS/Drugs.comInternational Drug Names
MedlinePlusa606008
Pregnancy
category
  • AU: A
  • US: C (Risk not ruled out)
    Routes of
    administration    		Oral; injection (intramuscular or slow intravenous); topical (ophthalmic/nasal solution)
    ATC code
    Pharmacokinetic data
    MetabolismHepatic hydroxylation, demethylation and glucuronidation
    ExcretionRenal
    Identifiers
    CAS Number
    PubChem CID
    IUPHAR/BPS
    DrugBank
    ChemSpider
    UNII
    KEGG
    ChEMBL
    CompTox Dashboard (EPA)
    ECHA InfoCard100.001.506
    Chemical and physical data
    FormulaC16H20N2
    Molar mass240.350 g·mol−1
    3D model (JSmol)
      (verify)

    It was patented in 1948.[1] Pheniramine is generally sold in combination with other medications, rather than as a stand-alone drug, although some formulations are available containing pheniramine by itself.

    Side effects

    Pheniramine may cause drowsiness or bradycardia, and over-dosage may lead to sleep disorders.

    Overdose may lead to seizures, especially in combination with alcohol.

    People combining with cortisol in the long term should avoid pheniramine as it may decrease levels of adrenaline (epinephrine) which may lead to loss of consciousness.

    Pheniramine is a deliriant (hallucinogen) in toxic doses. Recreational use of Coricidin for the dissociative (hallucinogenic) effect of its dextromethorphan is hazardous because it also contains chlorpheniramine.

    Chemical relatives

    Halogenation of pheniramine increases its potency 20-fold. Halogenated derivatives of pheniramine include chlorphenamine, brompheniramine, dexchlorpheniramine, dexbrompheniramine, and zimelidine. Two other halogenated derivatives, fluorpheniramine and iodopheniramine, are currently in use for research on combination therapies for malaria and some cancers.

    Other analogs include triprolidine. Similar molecules include diphenhydramine, doxylamine, and tripelennamine.

    Stereoisomerism

    Pheniramine contains a stereocenter and can exists as either of two enantiomers. The pharmaceutical drug is a racemate, an equal mixture of the (R)- and (S)-forms.[2]

    Enantiomers of pheniramine

    (R)-Pheniramine
    CAS number: 56141-72-1
    (S)-Pheniramine
    CAS number: 23201-92-5

    See also

    References
    1. Fischer, Jnos; Ganellin, C. Robin (2006). Analogue-based Drug Discovery. John Wiley & Sons. p. 546. ISBN 9783527607495.
    2. F. v. Bruchhausen, G. Dannhardt, S. Ebel, A. W. Frahm, E. Hackenthal, U. Holzgrabe (Hrsg.): Hagers Handbuch der Pharmazeutischen Praxis: Band 9: Stoffe P-Z, Springer Verlag, Berlin, Aufl. 5, 2014, S. 121, ISBN 978-3-642-63389-8.
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