Brompheniramine

Last updated

Brompheniramine
Brompheniramine structure.svg
Clinical data
Trade names Bromfed, Dimetapp, Bromfenex, others
AHFS/Drugs.com Monograph
MedlinePlus a682545
Routes of
administration 		By mouth
ATC code
Legal status
Legal status
  • AU: S4 (Prescription only)/ Schedule 4; Schedule 3; Schedule 2; Appendix K, clause 1 [1]
  • US: ℞-only / OTC
Pharmacokinetic data
Metabolism Liver
Elimination half-life 24.9 ± 9.3 hours [2]
Excretion Kidney
Identifiers
  • (R/S)-3-(4-Bromophenyl)-N,N-dimethyl-3-pyridin-2-yl-propan-1-amine
CAS Number
PubChem CID
IUPHAR/BPS
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard 100.001.507 OOjs UI icon edit-ltr-progressive.svg
Chemical and physical data
Formula C16H19BrN2
Molar mass 319.246 g·mol−1
3D model (JSmol)
  • Brc1ccc(cc1)C(c2ncccc2)CCN(C)C
  • InChI=1S/C16H19BrN2/c1-19(2)12-10-15(16-5-3-4-11-18-16)13-6-8-14(17)9-7-13/h3-9,11,15H,10,12H2,1-2H3 Yes check.svgY
  • Key:ZDIGNSYAACHWNL-UHFFFAOYSA-N Yes check.svgY
   (verify)

Brompheniramine, sold under the brand name Dimetapp among others, is a first-generation antihistamine drug of the propylamine (alkylamine) class. [3] 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. [3]

Contents

It was patented in 1948 and came into medical use in 1955. [4] 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. [5] [6]

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. [7]

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

Brompheniramine is metabolised by cytochrome P450 isoenzymes in the liver. [8]

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. [3] [9]

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. [10] [11]

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. [12]

Names

Brand names include Bromfed, Dimetapp, Bromfenex, Dimetane, and Lodrane. All bromphemiramine preparations are marketed as the maleate salt. [3]

References

  1. ↑ "Therapeutic Goods (Poisons Standard— June 2025) Instrument 2025" (pdf). Therapeutic Goods Administration (TGA). May 2025. Retrieved 31 August 2025.
  2. ↑ 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.
  3. 1 2 3 4 Sweetman SC, ed. (2005). Martindale: the complete drug reference (34th ed.). London: Pharmaceutical Press. p. 569–70. ISBN   0-85369-550-4. OCLC   56903116.
  4. ↑ Fischer J, Ganellin CR (2006). Analogue-based Drug Discovery. John Wiley & Sons. p. 546. ISBN   9783527607495.
  5. ↑ "The Top 300 of 2023". ClinCalc. Archived from the original on 17 August 2025. Retrieved 17 August 2025.
  6. ↑ "Brompheniramine; Dextromethorphan; Pseudoephedrine Drug Usage Statistics, United States, 2014 - 2023". ClinCalc. Retrieved 17 August 2025.
  7. ↑ Salahudeen MS, Duffull SB, Nishtala PS (March 2015). "Anticholinergic burden quantified by anticholinergic risk scales and adverse outcomes in older people: a systematic review". BMC Geriatrics. 15 (31) 31. doi: 10.1186/s12877-015-0029-9 . PMC   4377853 . PMID   25879993.
  8. 1 2 "Diphenhydramine: Uses, Interactions, Mechanism of Action". DrugBank Online. Archived from the original on 22 September 2024. Retrieved 26 November 2024.
  9. ↑ Troy DB, Beringer P (2006). Remington: The Science and Practice of Pharmacy. Lippincott Williams & Wilkins. pp. 1546–8. ISBN   9780781746731.
  10. ↑ US 3061517,Walter LA,issued 6 September 1962.
  11. ↑ US 3030371,Walter LA,issued 6 September 1962.
  12. ↑ Barondes SH (2003). Better Than Prozac . New York: Oxford University Press. pp.  39–40. ISBN   0-19-515130-5.
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