Brompheniramine

Brompheniramine, sold under the brand name Dimetapp among others, is a first-generation antihistamine drug of the propylamine (alkylamine) class.[2] 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.[2]

Brompheniramine
Clinical data
Trade namesBromfed, Dimetapp, Bromfenex, and others
AHFS/Drugs.comMonograph
MedlinePlusa682545
Routes of
administration		By mouth
ATC code
Legal status
Legal status
  • AU: S4 / S3 / S2
  • US: Rx-only / OTC
Pharmacokinetic data
MetabolismHepatic
Elimination half-life24.9 ± 9.3 hours[1]
ExcretionUrine
Identifiers
IUPAC name
  • (R/S)-3-(4-Bromophenyl)-N,N-dimethyl-3-pyridin-2-yl-propan-1-amine
CAS Number
PubChem CID
IUPHAR/BPS
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.001.507
Chemical and physical data
FormulaC16H19BrN2
Molar mass319.246 g·mol−1
3D model (JSmol)
SMILES
  • Brc1ccc(cc1)C(c2ncccc2)CCN(C)C
InChI
  • 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 Y
  • Key:ZDIGNSYAACHWNL-UHFFFAOYSA-N Y
  (verify)

It was patented in 1948 and came into medical use in 1955.[3]

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.[4]

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 P450 isoenzymes in the liver.

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.[2][5]

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.[6][7]

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.[8]

Names

Brand names include Bromfed, Dimetapp, Bromfenex, Dimetane, and Lodrane. All bromphemiramine preparations are marketed as the maleate salt.[2]

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. Sweetman, Sean C., ed. (2005). Martindale: the complete drug reference (34th ed.). London: Pharmaceutical Press. p. 569–70. ISBN 0-85369-550-4. OCLC 56903116.
  3. Fischer, Jnos; Ganellin, C. Robin (2006). Analogue-based Drug Discovery. John Wiley & Sons. p. 546. ISBN 9783527607495.
  4. 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): 31. doi:10.1186/s12877-015-0029-9. PMC 4377853. PMID 25879993.
  5. Troy, David B.; Beringer, Paul (2006). Remington: The Science and Practice of Pharmacy. Lippincott Williams & Wilkins. pp. 1546–8. ISBN 9780781746731.
  6. L.A. Walter, U.S. Patent 3,061,517 (1962)
  7. L.A. Walter, U.S. Patent 3,030,371 (1962)
  8. Barondes, Samuel H. (2003). Better Than Prozac. New York: Oxford University Press. pp. 39–40. ISBN 0-19-515130-5.
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