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Brompheniramine

Chemical compound

Summary

Chemical compound

| Drugs.com =

| elimination_half-life = 24.9 ± 9.3 hours

Brompheniramine, sold under the brand name Dimetapp among others, is a first-generation antihistamine drug of the propylamine (alkylamine) class. 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.

It was patented in 1948 and came into medical use in 1955. 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.

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.

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 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.

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.

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.

Names

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

References

References

  1. (May 2025). "Therapeutic Goods (Poisons Standard— June 2025) Instrument 2025".
  2. (December 1982). "The pharmacokinetics and antihistaminic effects of brompheniramine". The Journal of Allergy and Clinical Immunology.
  3. (2005). "Martindale: the complete drug reference". Pharmaceutical Press.
  4. (2006). "Analogue-based Drug Discovery". John Wiley & Sons.
  5. "The Top 300 of 2023".
  6. "Brompheniramine; Dextromethorphan; Pseudoephedrine Drug Usage Statistics, United States, 2014 - 2023".
  7. (March 2015). "Anticholinergic burden quantified by anticholinergic risk scales and adverse outcomes in older people: a systematic review". BMC Geriatrics.
  8. "Diphenhydramine: Uses, Interactions, Mechanism of Action".
  9. (2006). "Remington: The Science and Practice of Pharmacy". Lippincott Williams & Wilkins.
  10. {{cite patent
  11. {{cite patent
  12. (2003). "Better Than Prozac". Oxford University Press.
Wikipedia Source

This article was imported from Wikipedia and is available under the Creative Commons Attribution-ShareAlike 4.0 License. Content has been adapted to SurfDoc format. Original contributors can be found on the article history page.

drugs-developed-by-astrazeneca drugs-developed-by-pfizer drugs-developed-by-wyeth h1-receptor-antagonists muscarinic-antagonists 4-bromophenyl-compounds 2-pyridyl-compounds serotonin–norepinephrine-reuptake-inhibitors
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