Brompheniramine, sold under the brand name Dimetapp among others, is a first-generation antihistamine drug of the

propylamine Propylamine, also known as ''n''-propylamine, is an amine with the chemical formula CH3(CH2)2NH2. It is a colorless volatile liquid.Karsten Eller, Erhard Henkes, Roland Rossbacher, Hartmut Höke "Amines, Aliphatic" in ''Ullmann's Encyclopedia of I ...

(alkylamine) class. 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.

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.

Pharmacology

Brompheniramine works by acting as an antagonist of histamine H₁ receptors. It also functions as a moderately effective

anticholinergic Anticholinergics (anticholinergic agents) are substances that block the action of the neurotransmitter called acetylcholine (ACh) at synapses in the central and peripheral nervous system. These agents inhibit the parasympathetic nervous sys ...

agent, and is likely an

antimuscarinic A muscarinic receptor antagonist (MRA) is a type of anticholinergic agent that blocks the activity of the muscarinic acetylcholine receptor. The muscarinic receptor is a protein involved in the transmission of signals through certain parts of th ...

agent similar to other common antihistamines such as diphenhydramine. Brompheniramine is metabolised by cytochrome P450

isoenzyme In biochemistry, isozymes (also known as isoenzymes or more generally as multiple forms of enzymes) are enzymes that differ in amino acid sequence but catalyze the same chemical reaction. Isozymes usually have different kinetic parameters (e.g. dif ...

s in the liver.

Chemistry

Brompheniramine is part of a series of antihistamines including

pheniramine Pheniramine (trade name Avil among others) is an antihistamine with anticholinergic properties used to treat allergic conditions such as hay fever or urticaria. It has relatively strong sedative effects, and may sometimes be used off-label as an ...

(Naphcon) and its halogenated derivatives and others including fluorpheniramine, chlorpheniramine,

dexchlorpheniramine Dexchlorpheniramine (trade name Polaramine) is an antihistamine with anticholinergic properties used to treat allergic conditions such as hay fever or urticaria. It is the pharmacologically active dextrorotatory isomer of chlorpheniramine. It c ...

(Polaramine),

triprolidine Triprolidine is an over-the-counter antihistamine with anticholinergic properties. It is used to combat the symptoms associated with allergies and is sometimes combined with other cold medications designed to provide general relief for flu-like ...

(Actifed), and iodopheniramine. The halogenated alkylamine antihistamines all exhibit

optical isomerism In chemistry, an enantiomer ( /ɪˈnænti.əmər, ɛ-, -oʊ-/ ''ih-NAN-tee-ə-mər''; from Ancient Greek ἐνάντιος ''(enántios)'' 'opposite', and μέρος ''(méros)'' 'part') – also called optical isomer, antipode, or optical anti ...

; brompheniramine products contain racemic brompheniramine maleate ,whereas

dexbrompheniramine Dexbrompheniramine is an antihistamine with anticholinergic properties used to treat allergic conditions such as hay fever or urticaria. It is the pharmacologically active dextrorotatory isomer of brompheniramine. It was formerly marketed in comb ...

(Drixoral) is the dextrorotary (right-handed) stereoisomer. Brompheniramine is an

analog Analog or analogue may refer to: Computing and electronics * Analog signal, in which information is encoded in a continuous variable ** Analog device, an apparatus that operates on analog signals *** Analog electronics, circuits which use 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.L.A. Walter, (1962)

History

Arvid Carlsson and his colleagues, working at the

Swedish Swedish or ' may refer to: Anything from or related to Sweden, a country in Northern Europe. Or, specifically: * Swedish language, a North Germanic language spoken primarily in Sweden and Finland ** Swedish alphabet, the official alphabet used by ...

company Astra AB, were able to derive the first marketed

selective serotonin reuptake inhibitor Selective serotonin reuptake inhibitors (SSRIs) are a class of drugs that are typically used as antidepressants in the treatment of major depressive disorder, anxiety disorders, and other psychological conditions. SSRIs increase the extracellul ...

, zimelidine, from brompheniramine.

Names

Brand names include Bromfed, Dimetapp, Bromfenex, Dimetane, and Lodrane. All bromphemiramine preparations are marketed as the maleate salt.

References

External links

* {{Portal bar , Medicine AstraZeneca brands Pfizer brands Wyeth brands H1 receptor antagonists Muscarinic antagonists Bromoarenes 2-Pyridyl compounds Serotonin–norepinephrine reuptake inhibitors