Brompheniramine

Brompheniramine
Clinical data
Trade namesBromfed, Dimetapp, Bromfenex, others
AHFS/Drugs.comMonograph
MedlinePlusa682545
Routes of
administration		By mouth
ATC code
Legal status
Legal status
  • AU: S4 / S3 / S2
  • US: Rx-only / OTC
Pharmacokinetic data
MetabolismLiver
Elimination half-life24.9 ± 9.3 hours[1]
ExcretionKidney
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 InfoCard100.001.507 Edit this at Wikidata
Chemical and physical data
FormulaC16H19BrN2
Molar mass319.246 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 checkY
  • Key:ZDIGNSYAACHWNL-UHFFFAOYSA-N checkY
  (verify)

Brompheniramine, sold under the brand name Dimetapp among others, is a first-generation antihistamine drug of the propylamine (alkylamine) class.[2] 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.[2]

It was patented in 1948 and came into medical use in 1955.[3] In 2022, the combination with dextromethorphan and pseudoephedrine was the 265th most commonly prescribed medication in the United States, with more than 1 million prescriptions.[4][5]

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.[6]

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

Brompheniramine is metabolised by cytochrome P450 isoenzymes in the liver.[7]

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.[2][8]

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.[9][10]

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.[11]

Names

Brand names include Bromfed, Dimetapp, Bromfenex, Dimetane, and Lodrane. All bromphemiramine preparations are marketed as the maleate salt.[2]

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. ^ a b c d Sweetman SC, ed. (2005). Martindale: the complete drug reference (34th ed.). London: Pharmaceutical Press. p. 569–70. ISBN 0-85369-550-4. OCLC 56903116.
  3. ^ Fischer J, Ganellin CR (2006). Analogue-based Drug Discovery. John Wiley & Sons. p. 546. ISBN 9783527607495.
  4. ^ "The Top 300 of 2022". ClinCalc. Archived from the original on 30 August 2024. Retrieved 30 August 2024.
  5. ^ "Brompheniramine; Dextromethorphan; Pseudoephedrine Drug Usage Statistics, United States, 2013 - 2022". ClinCalc. Retrieved 30 August 2024.
  6. ^ 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.
  7. ^ a b "Diphenhydramine: Uses, Interactions, Mechanism of Action". DrugBank Online. Archived from the original on 22 September 2024. Retrieved 26 November 2024.
  8. ^ Troy DB, Beringer P (2006). Remington: The Science and Practice of Pharmacy. Lippincott Williams & Wilkins. pp. 1546–8. ISBN 9780781746731.
  9. ^ US 3061517, Walter LA, issued 1962. 
  10. ^ US 3030371, Walter LA, issued 1962. 
  11. ^ Barondes SH (2003). Better Than Prozac. New York: Oxford University Press. pp. 39–40. ISBN 0-19-515130-5.