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Brompheniramine

From Wikipedia, the free encyclopedia
Chemical compound

Pharmaceutical compound
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 (Prescription only) / Schedule 4; Schedule 3; Schedule 2; Appendix K, clause 1[1]
  • US: ℞-only / OTC
Pharmacokinetic data
MetabolismLiver
Eliminationhalf-life24.9 ± 9.3 hours[2]
ExcretionKidney
Identifiers
  • (R/S)-3-(4-Bromophenyl)-N,N-dimethyl-3-pyridin-2-yl-propan-1-amine
CAS Number
PubChemCID
IUPHAR/BPS
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard(EPA)
ECHA InfoCard100.001.507Edit 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 nameDimetapp among others, is a first-generationantihistamine drug of thepropylamine (alkylamine) class.[3] It is indicated for the treatment of the symptoms of thecommon cold andallergic rhinitis, such as runny nose, itchy eyes, watery eyes, and sneezing. Like the other first-generation drugs of its class, it is considered asedating antihistamine.[3]

It was patented in 1948 and came into medical use in 1955.[4] In 2023, the combination withdextromethorphan andpseudoephedrine was the 281st most commonly prescribed medication in the United States, with more than 700,000 prescriptions.[5][6]

Side effects

[edit]

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.[7]

Pharmacology

[edit]

Brompheniramine works by acting as anantagonist ofhistamine H1 receptors. It also functions as a moderately effectiveanticholinergic agent, and is likely anantimuscarinic agent[8] similar to other common antihistamines such asdiphenhydramine.

Brompheniramine is metabolised bycytochrome P450isoenzymes in the liver.[8]

Chemistry

[edit]

Brompheniramine is part of a series of antihistamines includingpheniramine (Naphcon) and its halogenated derivatives and others includingfluorpheniramine,chlorpheniramine,dexchlorpheniramine (Polaramine),triprolidine (Actifed), and iodopheniramine. The halogenated alkylamine antihistamines all exhibitoptical isomerism; brompheniramine products contain racemic brompheniramine maleate, whereasdexbrompheniramine (Drixoral) is the dextrorotary (right-handed) stereoisomer.[3][9]

Brompheniramine is ananalog ofchlorpheniramine. 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

[edit]

Arvid Carlsson and his colleagues, working at theSwedish companyAstra AB, were able to derive the first marketedselective serotonin reuptake inhibitor,zimelidine, from brompheniramine.[12]

Names

[edit]

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

References

[edit]
  1. ^"Therapeutic Goods (Poisons Standard— June 2025) Instrument 2025"(pdf).Therapeutic Goods Administration (TGA). May 2025. Retrieved31 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. ^abcdSweetman 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. Retrieved17 August 2025.
  6. ^"Brompheniramine; Dextromethorphan; Pseudoephedrine Drug Usage Statistics, United States, 2014 - 2023".ClinCalc. Retrieved17 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. ^ab"Diphenhydramine: Uses, Interactions, Mechanism of Action".DrugBank Online.Archived from the original on 22 September 2024. Retrieved26 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 1962. 
  11. ^US 3030371, Walter LA, issued 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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