Brompheniramine

{{Short description|Chemical compound}} {{Use dmy dates|date=August 2025}} {{cs1 config |name-list-style=vanc |display-authors=6}} {{Drugbox| Watchedfields = changed | verifiedrevid = 459984520 | image = Brompheniramine structure.svg | image_class = skin-invert-image | width = 222 | alt =

| tradename = Bromfed, Dimetapp, Bromfenex, others | Drugs.com = {{drugs.com|monograph|brompheniramine-maleate-dexbrompheniramine-maleate}} | MedlinePlus = a682545 | routes_of_administration = By mouth

| legal_AU = S4 | legal_AU_comment = /{{nbsp}}Schedule 4; Schedule 3; Schedule 2; Appendix K, clause 1<ref>{{cite web | title=Therapeutic Goods (Poisons Standard— June 2025) Instrument 2025 | website=Therapeutic Goods Administration (TGA) | date=May 2025 | url=https://www.legislation.gov.au/F2025L00599/asmade/2025-05-28/text/original/pdf | format=pdf | access-date=31 August 2025}}</ref> | legal_US = Rx-only | legal_US_comment = /{{nbsp}}OTC

| bioavailability = | metabolism = Liver | elimination_half-life = 24.9 ± 9.3 hours<ref name="pmid6128358">{{cite journal |vauthors=Simons FE, Frith EM, Simons KJ | title = The pharmacokinetics and antihistaminic effects of brompheniramine | journal = The Journal of Allergy and Clinical Immunology | volume = 70 | issue = 6 | pages = 458–64 |date=December 1982 | pmid = 6128358 | doi = 10.1016/0091-6749(82)90009-4| doi-access = free }}</ref> | excretion = Kidney

| IUPHAR_ligand = 7133 | CAS_number_Ref = {{cascite|correct|??}} | CAS_number = 86-22-6 | ATC_prefix = R06 | ATC_suffix = AB01 | PubChem = 6834 | DrugBank_Ref = {{drugbankcite|correct|drugbank}} | DrugBank = DB00835 | ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} | ChemSpiderID = 6573 | UNII_Ref = {{fdacite|correct|FDA}} | UNII = H57G17P2FN | KEGG_Ref = {{keggcite|correct|kegg}} | KEGG = D07543 | ChEBI_Ref = {{ebicite|correct|EBI}} | ChEBI = 3183 | ChEMBL_Ref = {{ebicite|correct|EBI}} | ChEMBL = 811

| IUPAC_name = (''R''/''S'')-3-(4-Bromophenyl)-''N'',''N''-dimethyl-3-pyridin-2-yl-propan-1-amine | C = 16 | H = 19 | Br = 1 | N = 2 | smiles = Brc1ccc(cc1)C(c2ncccc2)CCN(C)C | StdInChI_Ref = {{stdinchicite|correct|chemspider}} | StdInChI = 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 | StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} | StdInChIKey = ZDIGNSYAACHWNL-UHFFFAOYSA-N }}

'''Brompheniramine''', sold under the brand name '''Dimetapp''' among others, is a first-generation antihistamine drug of the propylamine (alkylamine) class.<ref name="Martindale34">{{Cite book| veditors = Sweetman SC |title=Martindale: the complete drug reference |edition=34th |publisher=Pharmaceutical Press |location=London |year=2005 |isbn=0-85369-550-4 |oclc=56903116 |page=569–70}}</ref> 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.<ref name="Martindale34"/>

It was patented in 1948 and came into medical use in 1955.<ref name=Fis2006>{{cite book | vauthors = Fischer J, Ganellin CR |title=Analogue-based Drug Discovery |date=2006 |publisher=John Wiley & Sons |isbn=9783527607495 |page=546 |url=https://books.google.com/books?id=FjKfqkaKkAAC&pg=PA546 }}</ref> 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.<ref>{{cite web | title=The Top 300 of 2023 | url=https://clincalc.com/DrugStats/Top300Drugs.aspx | website=ClinCalc | access-date=17 August 2025 | archive-date=17 August 2025 | archive-url=https://web.archive.org/web/20250817043812/https://clincalc.com/DrugStats/Top300Drugs.aspx | url-status=live }}</ref><ref>{{cite web | title = Brompheniramine; Dextromethorphan; Pseudoephedrine Drug Usage Statistics, United States, 2014 - 2023 | website = ClinCalc | url = https://clincalc.com/DrugStats/Drugs/BrompheniramineDextromethorphanPseudoephedrine | access-date = 17 August 2025 }}</ref>

==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.<ref>{{cite journal | vauthors = Salahudeen MS, Duffull SB, Nishtala PS | title = Anticholinergic burden quantified by anticholinergic risk scales and adverse outcomes in older people: a systematic review | journal = BMC Geriatrics | volume = 15 | issue = 31 | article-number = 31 | date = March 2015 | pmid = 25879993 | pmc = 4377853 | doi = 10.1186/s12877-015-0029-9 | doi-access = free }}</ref>

==Pharmacology== Brompheniramine works by acting as an antagonist of histamine H<sub>1</sub> receptors. It also functions as a moderately effective anticholinergic agent, and is likely an antimuscarinic agent<ref name=DBO>{{cite web | title = Diphenhydramine: Uses, Interactions, Mechanism of Action | website = DrugBank Online | url=https://go.drugbank.com/drugs/DB01075 | access-date = 26 November 2024 | archiveurl = https://web.archive.org/web/20240922051631/https://go.drugbank.com/drugs/DB01075 | archivedate = 22 September 2024 | url-status = live}}</ref> similar to other common antihistamines such as diphenhydramine.

Brompheniramine is metabolised by cytochrome P450 isoenzymes in the liver.<ref name=DBO />

==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.<ref name="Martindale34"/><ref name="Remington21">{{cite book| vauthors = Troy DB, Beringer P |title=Remington: The Science and Practice of Pharmacy|date=2006|publisher=Lippincott Williams & Wilkins|pages=1546–8|isbn=9780781746731}}</ref>

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.<ref>{{cite patent | country = US | number = 3061517 | inventor = Walter LA | gdate = 1962 | postscript = . }}</ref><ref>{{cite patent | country = US | number = 3030371 | inventor = Walter LA | gdate = 1962 | postscript = . }}</ref>

==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.<ref name="Barondes">{{cite book | vauthors = Barondes SH | year= 2003 | title= Better Than Prozac| pages= [https://archive.org/details/betterthanprozac00baro/page/39 39–40] | location= New York | publisher= Oxford University Press | isbn= 0-19-515130-5 | url-access= registration |url=https://archive.org/details/betterthanprozac00baro/page/39}}</ref>

==Names== Brand names include Bromfed, Dimetapp, Bromfenex, Dimetane, and Lodrane. All bromphemiramine preparations are marketed as the maleate salt.<ref name="Martindale34"/>

==References== {{Reflist}}

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Category:Drugs developed by AstraZeneca Category:Drugs developed by Pfizer Category:Drugs developed by Wyeth Category:H1 receptor antagonists Category:Muscarinic antagonists Category:4-Bromophenyl compounds Category:2-Pyridyl compounds Category:Serotonin–norepinephrine reuptake inhibitors