Pheniramine

Pheniramine
Clinical data
AHFS/Drugs.com International Drug Names
MedlinePlus a606008
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
    Metabolism Hepatic hydroxylation, demethylation and glucuronidation
    Excretion Renal
    Identifiers
    CAS Number
    PubChem CID
    IUPHAR/BPS
    DrugBank
    ChemSpider
    UNII
    KEGG
    ChEMBL
    ECHA InfoCard 100.001.506 Edit this at Wikidata
    Chemical and physical data
    Formula C16H20N2
    Molar mass 240.35 g·mol−1
    3D model (JSmol)
      (verify)

    Pheniramine (INN, 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 is generally sold in combination with other medications, rather than as a stand-alone drug, although some formulations are available containing pheniramine by itself. As an example, TheraFlu/Neo Citran contains pheniramine.

    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.

    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.

    Stereoisomerism

    Pheniramine contains a stereocenter and consists of two enantiomers. This is a racemate, a 1: 1 mixture of (R) and the (S) forms:[1]

    Enantiomers of pheniramine

    CAS-Nummer: 56141-72-1
    CAS-Nummer: 23201-92-5

    See also

    References

    1. ↑ 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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