Brompheniramine

Brompheniramine
Systematic (IUPAC) name
3-(4-bromophenyl)-N,N-dimethyl-3-pyridin-2-yl-propan-1-amine
Clinical data
AHFS/Drugs.com monograph
MedlinePlus a682545
Pregnancy
category
  • US: C (Risk not ruled out)
Legal status
  • AU: S2 (Pharmacy only) – 4, depending on formulation and usage
  • Unscheduled, OTC
Routes of
administration		 Oral
Pharmacokinetic data
Metabolism Hepatic
Biological half-life 24.9 ± 9.3 hours[1]
Excretion Urine
Identifiers
CAS Number 86-22-6 YesY
ATC code R06AB01
PubChem CID 6834
IUPHAR/BPS 7133
DrugBank DB00835 YesY
ChemSpider 6573 YesY
UNII H57G17P2FN YesY
KEGG D07543 YesY
ChEBI CHEBI:3183 YesY
ChEMBL CHEMBL811 YesY
Chemical data
Formula C16H19BrN2
Molar mass 319.24 g/mol
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Brompheniramine (Bromfed, Dimetapp, Bromfenex, Dimetane, BPN, Lodrane), commonly marketed as its salt brompheniramine maleate, is an antihistamine drug of the propylamine (alkylamine) class. It is readily available over the counter and 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. It is a first-generation antihistamine.

Brompheniramine is part of a series of antihistamines including pheniramine (Naphcon) and its halogenated derivatives and others including fluorpheniramine, chlorpheniramine, dexchlorpheniramine (Polaramine), deschlorpheniramine, dipheniramine (also known as triprolidine with the trade name Actifed), and iodopheniramine.

The halogenated alkylamine antihistamines all exhibit optical isomerism and brompheniramine products contain racemic brompheniramine maleate whereas dexbrompheniramine (Drixoral) is the dextrorotary (right-handed) stereoisomer.

Brompheniramine has antidepressant properties, inhibiting reuptake of the neurotransmitter serotonin and norepinephrine. Based on this knowledge, 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.[2]

Like other agents of this type, brompheniramine also has analgesic-sparing (potentiating) effects on opioid analgesics, commonly reducing codeine, dihydrocodeine, and hydrocodone requirements by 10 to 35 percent.

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 P450s.

The halogenated alkylamine antihistamines all exhibit optic isomerism and brompheniramine products contain racaemic brompheniramine maleate whereas dexbrompheniramine (Drixoral) is the dextrorotary (right-handed) stereoisomer.

Side effects

Its effects on the cholinergic system may include side-effects such as drowsiness, sedation, dry mouth, dry throat, blurred vision, and increased heart rate.

Chemistry

Brompheniramine, 3-(p-bromophenyl)-3-(2-pyridyl)propyldimethylamine, 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.

See also

References

  1. ↑ 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.
  2. ↑ Barondes, Samuel H. (2003). Better Than Prozac. New York: Oxford University Press. pp. 39–40. ISBN 0-19-515130-5.

External links

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