Brompheniramine: Difference between revisions

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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 drug|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''' ('''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 drug|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.
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.

Revision as of 22:23, 15 April 2012

Brompheniramine
Clinical data
AHFS/Drugs.comMonograph
MedlinePlusa682545
Pregnancy
category
Routes of
administration
Oral
ATC code
Legal status
Legal status
  • Unscheduled, OTC
Pharmacokinetic data
Bioavailability?
MetabolismHepatic
Elimination half-life24.9 ± 9.3 hours[1]
ExcretionUrine
Identifiers
  • 3-(4-bromophenyl)-N,N-dimethyl-3-pyridin-2-yl-propan-1-amine
CAS Number
PubChem CID
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.001.507 Edit this at Wikidata
Chemical and physical data
FormulaC16H19BrN2
Molar mass319.24 g/mol g·mol−1
3D model (JSmol)
  • Brc1ccc(cc1)C(c2ncccc2)CCN(C)C
  • InChI=1S/C16H19BrN2/c1-19(2)12-10-15(16-5-3-4-11-18-16)13-6-8-14(17)9-7-13/h3-9,11,15H,10,12H2,1-2H3 checkY
  • Key:ZDIGNSYAACHWNL-UHFFFAOYSA-N checkY
  (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), 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. 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.

References

  1. ^ Simons FE, Frith EM, Simons KJ (1982). "The pharmacokinetics and antihistaminic effects of brompheniramine". The Journal of Allergy and Clinical Immunology. 70 (6): 458–64. PMID 6128358. {{cite journal}}: Unknown parameter |month= ignored (help)CS1 maint: multiple names: authors list (link)
  2. ^ Barondes, Samuel H. (2003). Better Than Prozac. New York: Oxford University Press. pp. 39–40. ISBN 0-19-515130-5. {{cite book}}: Cite has empty unknown parameter: |month= (help)

External links