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Chemical compound
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 2021, the combination with dextromethorphan and pseudoephedrine was the 294th most commonly prescribed medication in the United States with more than 500,000 prescriptions.[ 4] [ 5]
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]
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.
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] [ 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]
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]
Brand names include Bromfed, Dimetapp, Bromfenex, Dimetane, and Lodrane. All bromphemiramine preparations are marketed as the maleate salt.[ 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 .
^ 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 .
^ Fischer J, Ganellin CR (2006). Analogue-based Drug Discovery . John Wiley & Sons. p. 546. ISBN 9783527607495 .
^ "The Top 300 of 2021" . ClinCalc . Archived from the original on 15 January 2024. Retrieved 14 January 2024 .
^ "Brompheniramine; Dextromethorphan; Pseudoephedrine - Drug Usage Statistics" . ClinCalc . Retrieved 14 January 2024 .
^ 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 .
^ Troy DB, Beringer P (2006). Remington: The Science and Practice of Pharmacy . Lippincott Williams & Wilkins. pp. 1546–8. ISBN 9780781746731 .
^ US 3061517 , Walter LA, issued 1962.
^ US 3030371 , Walter LA, issued 1962.
^ Barondes SH (2003). Better Than Prozac . New York: Oxford University Press. pp. 39–40 . ISBN 0-19-515130-5 .
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