Brompheniramine
Chemical compound
From Wikipedia, the free encyclopedia
Brompheniramine, sold under the brand name Dimetapp among others, is a first-generation antihistamine drug of the propylamine (alkylamine) class.[3] 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.[3]
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| Trade names | Bromfed, Dimetapp, Bromfenex, others |
| AHFS/Drugs.com | Monograph |
| MedlinePlus | a682545 |
| Routes of administration | By mouth |
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| Pharmacokinetic data | |
| Metabolism | Liver |
| Elimination half-life | 24.9 ± 9.3 hours[2] |
| Excretion | Kidney |
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| ECHA InfoCard | 100.001.507 |
| Chemical and physical data | |
| Formula | C16H19BrN2 |
| Molar mass | 319.246 g·mol−1 |
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It was patented in 1948 and came into medical use in 1955.[4] 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.[5][6]
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.[7]
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[8] similar to other common antihistamines such as diphenhydramine.
Brompheniramine is metabolised by cytochrome P450 isoenzymes in the liver.[8]
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.[3][9]
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.[10][11]
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.[12]
