Brompheniramine

{{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 / S3 / S2

| legal_AU_comment =

| legal_US = Rx-only / OTC

| bioavailability =

| metabolism = 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

| 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.{{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 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.

It was patented in 1948 and came into medical use in 1955.{{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 2022, the combination with dextromethorphan and pseudoephedrine was the 265th most commonly prescribed medication in the United States, with more than 1{{nbsp}}million prescriptions.{{cite web | title=The Top 300 of 2022 | url=https://clincalc.com/DrugStats/Top300Drugs.aspx | website=ClinCalc | access-date=30 August 2024 | archive-date=30 August 2024 | archive-url=https://web.archive.org/web/20240830202410/https://clincalc.com/DrugStats/Top300Drugs.aspx | url-status=live }}{{cite web | title = Brompheniramine; Dextromethorphan; Pseudoephedrine Drug Usage Statistics, United States, 2013 - 2022 | website = ClinCalc | url = https://clincalc.com/DrugStats/Drugs/BrompheniramineDextromethorphanPseudoephedrine | access-date = 30 August 2024 }}

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 anticholinergenic 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 | pages = 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 of histamine H₁ receptors. It also functions as a moderately effective anticholinergic agent, and is likely an antimuscarinic agent{{cite web | title = Diphenhydramine: Uses, Interactions, Mechanism of Action | website = DrugBank Online | url=https://go.drugbank.com/drugs/DB01075 | access-date = 2024-11-26 | archiveurl = https://web.archive.org/web/20240922051631/https://go.drugbank.com/drugs/DB01075 | archivedate = 2024-09-22 | url-status = live}} similar to other common antihistamines such as diphenhydramine.

Brompheniramine is metabolised by cytochrome P450 isoenzymes in the liver.

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.{{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 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.{{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 and his colleagues, working at the Swedish company Astra AB, were able to derive the first marketed selective serotonin reuptake inhibitor, 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 salt.

References

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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