https://wiki.sarg.dev/index.php?action=history&feed=atom&title=BrompheniramineBrompheniramine - Revision history2026-06-25T22:32:02ZRevision history for this page on the wikiMediaWiki 1.44.2https://wiki.sarg.dev/index.php?title=Brompheniramine&diff=352588&oldid=previmported>Kyleandbusse: /* Side effects */ corrected anticholinergenic to anticholinergic2025-09-21T03:54:33Z<p><span class="autocomment">Side effects: </span> corrected anticholinergenic to anticholinergic</p>
<p><b>New page</b></p><div>{{Short description|Chemical compound}}<br />
{{Use dmy dates|date=August 2025}}<br />
{{cs1 config |name-list-style=vanc |display-authors=6}}<br />
{{Drugbox| Watchedfields = changed<br />
| verifiedrevid = 459984520<br />
| image = Brompheniramine structure.svg<br />
| image_class = skin-invert-image<br />
| width = 222<br />
| alt = <br />
<br />
<!-- Clinical data --><br />
| tradename = Bromfed, Dimetapp, Bromfenex, others<br />
| Drugs.com = {{drugs.com|monograph|brompheniramine-maleate-dexbrompheniramine-maleate}}<br />
| MedlinePlus = a682545<br />
| routes_of_administration = [[Oral administration|By mouth]]<br />
<br />
| legal_AU = S4<br />
| 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><br />
| legal_US = Rx-only<br />
| legal_US_comment = /{{nbsp}}OTC<br />
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<!-- Pharmacokinetic data --><br />
| bioavailability =<br />
| metabolism = [[Liver]]<br />
| 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><br />
| excretion = [[Kidney]]<br />
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<!-- Identifiers --><br />
| IUPHAR_ligand = 7133<br />
| CAS_number_Ref = {{cascite|correct|??}}<br />
| CAS_number = 86-22-6<br />
| ATC_prefix = R06<br />
| ATC_suffix = AB01<br />
| PubChem = 6834<br />
| DrugBank_Ref = {{drugbankcite|correct|drugbank}}<br />
| DrugBank = DB00835<br />
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}<br />
| ChemSpiderID = 6573<br />
| UNII_Ref = {{fdacite|correct|FDA}}<br />
| UNII = H57G17P2FN<br />
| KEGG_Ref = {{keggcite|correct|kegg}}<br />
| KEGG = D07543<br />
| ChEBI_Ref = {{ebicite|correct|EBI}}<br />
| ChEBI = 3183<br />
| ChEMBL_Ref = {{ebicite|correct|EBI}}<br />
| ChEMBL = 811<br />
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<!-- Chemical data --><br />
| IUPAC_name = (''R''/''S'')-3-(4-Bromophenyl)-''N'',''N''-dimethyl-3-pyridin-2-yl-propan-1-amine<br />
| C = 16 | H = 19 | Br = 1 | N = 2 <br />
| smiles = Brc1ccc(cc1)C(c2ncccc2)CCN(C)C<br />
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}<br />
| 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<br />
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}<br />
| StdInChIKey = ZDIGNSYAACHWNL-UHFFFAOYSA-N<br />
}}<br />
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<!-- Definition and medical uses --><br />
'''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 [[sedative|sedating]] antihistamine.<ref name="Martindale34"/><br />
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<!-- Society and culture --><br />
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><br />
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==Side effects==<br />
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><br />
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==Pharmacology==<br />
Brompheniramine works by acting as an [[competitive inhibition|antagonist]] of [[histamine H1 receptor|histamine H<sub>1</sub> receptor]]s. 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]].<br />
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Brompheniramine is metabolised by [[cytochrome P450]] [[isoenzyme]]s in the liver.<ref name=DBO /><br />
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==Chemistry==<br />
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><br />
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Brompheniramine is an [[structural analog|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><br />
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==History==<br />
[[Arvid Carlsson]] and his colleagues, working at the [[Sweden|Swedish]] company [[AstraZeneca|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><br />
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==Names==<br />
Brand names include Bromfed, Dimetapp, Bromfenex, Dimetane, and Lodrane. All bromphemiramine preparations are marketed as the [[maleate]] salt.<ref name="Martindale34"/><br />
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==References==<br />
{{Reflist}}<br />
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{{Antihistamines}}<br />
{{AstraZeneca}}<br />
{{Hallucinogens}}<br />
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[[Category:Drugs developed by AstraZeneca]]<br />
[[Category:Drugs developed by Pfizer]]<br />
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[[Category:Serotonin–norepinephrine reuptake inhibitors]]</div>imported>Kyleandbusse