Brompheniramine

Brompheniramine
Clinical data
AHFS/Drugs.com Monograph
MedlinePlus a682545
Pregnancy
category
  • US: C (Risk not ruled out)
    Routes of
    administration    		 Oral
    ATC code
    Legal status
    Legal status
    • AU: S2 (Pharmacy only) – 4, depending on formulation and usage
    • Unscheduled, OTC
    Pharmacokinetic data
    Metabolism Hepatic
    Elimination half-life 24.9 ± 9.3 hours[1]
    Excretion Urine
    Identifiers
    CAS Number
    PubChem CID
    IUPHAR/BPS
    DrugBank
    ChemSpider
    UNII
    KEGG
    ChEBI
    ChEMBL
    ECHA InfoCard 100.001.507 Edit this at Wikidata
    Chemical and physical data
    Formula C16H19BrN2
    Molar mass 319.24 g/mol
    3D model (JSmol)
      (verify)

    Brompheniramine (Bromfed, Dimetapp, Bromfenex, Dimetane, BPN, Lodrane), commonly marketed as its salt brompheniramine maleate, is an antihistamine drug of the propylamine (alkylamine) class. It is readily available over the counter and is indicated for the treatment of the symptoms of the common cold and allergic rhinitis, such as runny nose, itchy eyes, watery eyes, and sneezing. It is a first-generation antihistamine.

    Brompheniramine is part of a series of antihistamines including pheniramine (Naphcon) and its halogenated derivatives and others including fluorpheniramine, chlorpheniramine, dexchlorpheniramine (Polaramine), triprolidine (Actifed), and iodopheniramine.

    The halogenated alkylamine antihistamines all exhibit optical isomerism and brompheniramine products contain racemic brompheniramine maleate whereas dexbrompheniramine (Drixoral) is the dextrorotary (right-handed) stereoisomer.

    Brompheniramine has antidepressant properties, inhibiting reuptake of the neurotransmitter serotonin and norepinephrine. Based on this knowledge, Arvid Carlsson and his colleagues, working at the Swedish company Astra AB, were able to derive the first marketed selective serotonin reuptake inhibitor, zimelidine, from brompheniramine.[2]

    Like other agents of this type, brompheniramine also has analgesic-sparing (potentiating) effects on opioid analgesics, commonly reducing codeine, dihydrocodeine, and hydrocodone requirements by 10 to 35 percent.

    Pharmacology

    Brompheniramine works by acting as an antagonist of histamine H1 receptors. It also functions as a moderately effective anticholinergic agent, and is likely an antimuscarinic agent similar to other common antihistamines such as diphenhydramine.

    Brompheniramine is metabolised by cytochrome P450s.

    The halogenated alkylamine antihistamines all exhibit optic isomerism and brompheniramine products contain racaemic brompheniramine maleate whereas dexbrompheniramine (Drixoral) is the dextrorotary (right-handed) stereoisomer.

    Side effects

    Brompheniramine's effects on the cholinergic system may include side-effects such as drowsiness, sedation, dry mouth, dry throat, blurred vision, and increased heart rate. It is listed as one of the drugs of highest anticholinergic activity in a study of anticholinergenic burden, including long-term cognitive impairment.[3]

    Chemistry

    Brompheniramine is an analog of chlorpheniramine. The only difference is that the chlorine atom in the benzene ring is replaced with a bromine atom. It is also synthesized in an analogous manner.[4][5]

    See also

    References

    1. ↑ Simons FE, Frith EM, Simons KJ (December 1982). "The pharmacokinetics and antihistaminic effects of brompheniramine". The Journal of Allergy and Clinical Immunology. 70 (6): 458–64. doi:10.1016/0091-6749(82)90009-4. PMID 6128358.
    2. ↑ Barondes, Samuel H. (2003). Better Than Prozac. New York: Oxford University Press. pp. 39–40. ISBN 0-19-515130-5.
    3. ↑ Salahudeen MJ; Duffull SB; Nishtala PS; et al. (2015-03-25). "Anticholinergic burden quantified by anticholinergic risk scales and adverse outcomes in older people: a systematic review". BMC Geriatrics. 15 (31). doi:10.1186/s12877-015-0029-9. PMC 4377853. PMID 25879993.
    4. ↑ L.A. Walter, U.S. Patent 3,061,517 (1962)
    5. ↑ L.A. Walter, U.S. Patent 3,030,371 (1962)
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