From Wikipedia, the free encyclopedia
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]
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.
[6]
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 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.
[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]
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.
[10]
Names
Brand names include Bromfed, Dimetapp, Bromfenex, Dimetane, and Lodrane. All bromphemiramine preparations are marketed as the
maleate salt.
[2]
References
^ 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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