Brompheniramine Explained

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 2021, the combination with dextromethorphan and pseudoephedrine was the 294th most commonly prescribed medication in the United States with more than 500,000 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 anticholinergenic 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.

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]

Notes and References

  1. Book: Sweetman SC . Martindale: the complete drug reference . 34th . Pharmaceutical Press . London . 2005 . 0-85369-550-4 . 56903116 . 569–70.
  2. Book: Fischer J, Ganellin CR . Analogue-based Drug Discovery . 2006 . John Wiley & Sons . 9783527607495 . 546 .
  3. Web site: The Top 300 of 2021 . ClinCalc . 14 January 2024 . 15 January 2024 . https://web.archive.org/web/20240115223848/https://clincalc.com/DrugStats/Top300Drugs.aspx . live .
  4. Web site: Brompheniramine; Dextromethorphan; Pseudoephedrine - Drug Usage Statistics . ClinCalc . 14 January 2024 .
  5. Salahudeen MS, Duffull SB, Nishtala PS . Anticholinergic burden quantified by anticholinergic risk scales and adverse outcomes in older people: a systematic review . BMC Geriatrics . 15 . 31 . 31 . March 2015 . 25879993 . 4377853 . 10.1186/s12877-015-0029-9 . free .
  6. Web site: Diphenhydramine: Uses, Interactions, Mechanism of Action . DrugBank Online . 2024-11-26 . https://web.archive.org/web/20240922051631/https://go.drugbank.com/drugs/DB01075 . 2024-09-22 . live.
  7. Book: Troy DB, Beringer P . Remington: The Science and Practice of Pharmacy. 2006. Lippincott Williams & Wilkins. 1546–8. 9780781746731.
  8. US . 3061517 . Walter LA . 1962 . . .
  9. US . 3030371 . Walter LA . 1962 . . .
  10. Book: Barondes SH . 2003 . Better Than Prozac. 39–40 . New York . Oxford University Press . 0-19-515130-5 . registration .