Brompheniramine

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Brompheniramine
Brompheniramine structure.svg
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)
Routes of
administration
Oral
Legal status
Legal status
  • AU: S2 (Pharmacy only) – 4, depending on formulation and usage
  • Unscheduled, OTC
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 (WHO)
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
  (verify)

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), triprolidine (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[edit]

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[edit]

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.[3]

Chemistry[edit]

Brompheniramine is a 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.[4][5]

See also[edit]

References[edit]

  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. 
  3. ^ Salahudeen MJ; Duffull SB; Nishtala PS; et al. (2015-03-25). "Anticholinergic burden quantified by anticholinergic risk scales and adverse outcomes in older people: a systematic review". BMC Geriatrics. 15 (31). doi:10.1186/s12877-015-0029-9. PMC 4377853free to read. PMID 25879993. 
  4. ^ L.A. Walter, U.S. Patent 3,061,517 (1962)
  5. ^ L.A. Walter, U.S. Patent 3,030,371 (1962)

External links[edit]