Chemistry:Brompheniramine

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Brompheniramine, sold under the brand name Dimetapp among others, is a first-generation antihistamine drug of the propylamine (alkylamine) class.[1] It 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. Like the other first-generation drugs of its class, it is considered a sedating antihistamine.[1]

It was patented in 1948 and came into medical use in 1955.[2] In 2023, the combination with dextromethorphan and pseudoephedrine was the 281st most commonly prescribed medication in the United States, with more than 700,000 prescriptions.[3][4]

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 anticholinergic burden, including long-term cognitive impairment.[5]

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[6] similar to other common antihistamines such as diphenhydramine.

Brompheniramine is metabolised by cytochrome P450 isoenzymes in the liver.[6]

Chemistry

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; brompheniramine products contain racemic brompheniramine maleate, whereas dexbrompheniramine (Drixoral) is the dextrorotary (right-handed) stereoisomer.[1][7]

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.[8][9]

History

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.[10]

Names

Brand names include Bromfed, Dimetapp, Bromfenex, Dimetane, and Lodrane. All bromphemiramine preparations are marketed as the maleate salt.[1]

References

  1. ↑ 1.0 1.1 1.2 1.3 Martindale: the complete drug reference (34th ed.). London: Pharmaceutical Press. 2005. p. 569–70. ISBN 0-85369-550-4. OCLC 56903116. 
  2. ↑ Analogue-based Drug Discovery. John Wiley & Sons. 2006. p. 546. ISBN 9783527607495. https://books.google.com/books?id=FjKfqkaKkAAC&pg=PA546. 
  3. ↑ "The Top 300 of 2023". https://clincalc.com/DrugStats/Top300Drugs.aspx. 
  4. ↑ "Brompheniramine; Dextromethorphan; Pseudoephedrine Drug Usage Statistics, United States, 2014 - 2023". https://clincalc.com/DrugStats/Drugs/BrompheniramineDextromethorphanPseudoephedrine. 
  5. ↑ "Anticholinergic burden quantified by anticholinergic risk scales and adverse outcomes in older people: a systematic review". BMC Geriatrics 15 (31). March 2015. doi:10.1186/s12877-015-0029-9. PMID 25879993. 
  6. ↑ 6.0 6.1 "Diphenhydramine: Uses, Interactions, Mechanism of Action". Archived from the original on 22 September 2024. https://web.archive.org/web/20240922051631/https://go.drugbank.com/drugs/DB01075. 
  7. ↑ Remington: The Science and Practice of Pharmacy. Lippincott Williams & Wilkins. 2006. pp. 1546–8. ISBN 9780781746731. 
  8. ↑ Walter LA, US patent 3061517, issued 1962.
  9. ↑ Walter LA, US patent 3030371, issued 1962.
  10. ↑ Better Than Prozac. New York: Oxford University Press. 2003. pp. 39–40. ISBN 0-19-515130-5. https://archive.org/details/betterthanprozac00baro/page/39. 



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