# Brompheniramine
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> Markdown URL: https://mediated.wiki/source/Brompheniramine.md
> Source: https://en.wikipedia.org/wiki/Brompheniramine
> Source revision: 1312520050
> License: Creative Commons Attribution-ShareAlike 4.0 International (https://creativecommons.org/licenses/by-sa/4.0/)
{{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](/source/Oral_administration)
| legal_AU = S4
| legal_AU_comment = /{{nbsp}}Schedule 4; Schedule 3; Schedule 2; Appendix K, clause 1[{{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}}]
| legal_US = Rx-only
| legal_US_comment = /{{nbsp}}OTC
| bioavailability =
| metabolism = [Liver](/source/Liver)
| elimination_half-life = 24.9 ± 9.3 hours[{{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 }}]
| excretion = [Kidney](/source/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](/source/antihistamine) drug of the [propylamine](/source/propylamine) (alkylamine) class.[{{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}}] It is indicated for the treatment of the symptoms of the [common cold](/source/common_cold) and [allergic rhinitis](/source/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](/source/sedative) antihistamine.[{{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 }}] In 2023, the combination with [dextromethorphan](/source/dextromethorphan) and [pseudoephedrine](/source/pseudoephedrine) was the 281st most commonly prescribed medication in the United States, with more than 700,000 prescriptions.[{{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 }}][{{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 }}]
==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.[{{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 }}]
==Pharmacology==
Brompheniramine works by acting as an [antagonist](/source/competitive_inhibition) of [histamine H1 receptor](/source/histamine_H1_receptor)s. It also functions as a moderately effective [anticholinergic](/source/anticholinergic) agent, and is likely an [antimuscarinic](/source/antimuscarinic) agent[{{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}}] similar to other common antihistamines such as [diphenhydramine](/source/diphenhydramine).
Brompheniramine is metabolised by [cytochrome P450](/source/cytochrome_P450) [isoenzyme](/source/isoenzyme)s in the liver.[{{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}}]
Brompheniramine is an [analog](/source/structural_analog) of [chlorpheniramine](/source/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.[{{cite patent | country = US | number = 3061517 | inventor = Walter LA | gdate = 1962 | postscript = . }}][{{cite patent | country = US | number = 3030371 | inventor = Walter LA | gdate = 1962 | postscript = . }}]
==History==
[Arvid Carlsson](/source/Arvid_Carlsson) and his colleagues, working at the [Swedish](/source/Sweden) company [Astra AB](/source/AstraZeneca), were able to derive the first marketed [selective serotonin reuptake inhibitor](/source/selective_serotonin_reuptake_inhibitor), [zimelidine](/source/zimelidine), from brompheniramine.[{{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}}]
==Names==
Brand names include Bromfed, Dimetapp, Bromfenex, Dimetane, and Lodrane. All bromphemiramine preparations are marketed as the [maleate](/source/maleate) salt.