Brompheniramine

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Brompheniramine
Brompheniramine structure.svg
Clinical data
Trade names Bromfed, Dimetapp, Bromfenex, others
AHFS/Drugs.com Monograph
MedlinePlus a682545
Routes of
administration
By mouth
ATC code
Legal status
Legal status
  • AU:S4 / S3 / S2
  • US:Rx-only / OTC
Pharmacokinetic data
Metabolism Liver
Elimination half-life 24.9 ± 9.3 hours [1]
Excretion Kidney
Identifiers
  • (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 InfoCard 100.001.507 OOjs UI icon edit-ltr-progressive.svg
Chemical and physical data
Formula C16H19BrN2
Molar mass 319.246 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 Yes check.svgY
  • Key:ZDIGNSYAACHWNL-UHFFFAOYSA-N Yes check.svgY
   (verify)

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]

Contents

It was patented in 1948 and came into medical use in 1955. [3] In 2021, the combination with dextromethorphan and pseudoephedrine was the 294th most commonly prescribed medication in the United States with more than 500,000 prescriptions. [4] [5]

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. [6]

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 [7] similar to other common antihistamines such as diphenhydramine.

Brompheniramine is metabolised by cytochrome P450 isoenzymes in the liver. [7]

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] [8]

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. [9] [10]

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. [11]

Names

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

Related Research Articles

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Triprolidine is an over-the-counter antihistamine with anticholinergic properties. It is used to combat the symptoms associated with allergies and is sometimes combined with other cold medications designed to provide general relief for flu-like symptoms. As with many antihistamines, the most common side effect is drowsiness.

<span class="mw-page-title-main">Cold medicine</span> Medication taken to relieve cold symptoms

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<span class="mw-page-title-main">Diphenhydramine</span> Antihistamine medication

Diphenhydramine, sold under the brand name Benadryl among others, is an antihistamine and sedative. It is a first-generation H1-antihistamine and it works by blocking certain effects of histamine, which produces its antihistamine and sedative effects. Diphenhydramine is also a potent anticholinergic. It is mainly used to treat allergies, insomnia, and symptoms of the common cold. It is also less commonly used for tremors in parkinsonism, and nausea. It is taken by mouth, injected into a vein, injected into a muscle, or applied to the skin. Maximal effect is typically around two hours after a dose, and effects can last for up to seven hours.

Vicks NyQuil is a brand of over-the-counter medication manufactured by Procter & Gamble intended for the relief of various symptoms of the common cold. All medications within the NyQuil imprint contain sedating antihistamines, hypnotics, and/or alcohol, and are intended to be taken before sleep. Its daytime counterpart is antihistamine-free DayQuil, formulated to avoid drowsiness. NyQuil is also used as a sleep aid. NyQuil was first marketed in the United States in 1966.

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<span class="mw-page-title-main">Chlorphenamine</span> Antihistamine used to treat allergies

Chlorphenamine (CP, CPM), also known as chlorpheniramine, is an antihistamine used to treat the symptoms of allergic conditions such as allergic rhinitis (hay fever). It is taken orally (by mouth). The medication takes effect within two hours and lasts for about 4–6 hours. It is a first-generation antihistamine and works by blocking the histamine H1 receptor.

<span class="mw-page-title-main">Cetirizine</span> Antihistamine medication

Cetirizine is a second-generation antihistamine used to treat allergic rhinitis, dermatitis, and urticaria (hives). It is taken by mouth. Effects generally begin within thirty minutes and last for about a day. The degree of benefit is similar to other antihistamines such as diphenhydramine, which is a first-generation antihistamine.

<span class="mw-page-title-main">Fexofenadine</span> Antihistamine medication

Fexofenadine, sold under the brand name Allegra among others, is an antihistamine pharmaceutical drug used in the treatment of allergy symptoms, such as hay fever and urticaria.

<span class="mw-page-title-main">Promethazine</span> Sedating antihistamine

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Doxylamine is an antihistamine medication used to treat insomnia and allergies, and—in combination with pyridoxine (vitamin B6)—to treat morning sickness in pregnant women. It is available over-the-counter and is typically sold under such brand names as Equate or Unisom, among others; and it is used in nighttime cold medicines (e.g., NyQuil) and pain medications containing acetaminophen and/or codeine to help with sleep. The medication is delivered chemically by the salt doxylamine succinate and is taken by mouth. Doxylamine and other first-generation antihistamines are the most widely used sleep medications in the world. Typical side effects of doxylamine (at recommended doses) include dizziness, drowsiness, grogginess, and dry mouth, among others.

Dimetapp is an American brand of over-the-counter cold and allergy medicines that is manufactured by Foundation Consumer Brands. At one point, Dimetapp as a household word referred to a single combination preparation marketed to relieve symptoms of the common cold, containing brompheniramine and phenylephrine. Variants were created, including Dimetapp DM with the addition of dextromethorphan. Dimetapp Elixir and Colour Free Elixir are intended to relieve nasal congestion, runny nose, itchy watery eyes and sneezing, whereas Dimetapp DM and Dimetapp DM Colour Free Elixir are intended for colds with dry coughs and also to treat whooping cough. Early Dimetapp was flavored with cherry and plum as they were readily available during the time, setting a precedent for its purple color; however, the flavor has been described as a grape candy.

<span class="mw-page-title-main">Orphenadrine</span> Muscle relaxant drug

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<span class="mw-page-title-main">Phenyltoloxamine</span> Chemical compound

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<span class="mw-page-title-main">Zimelidine</span> SSRI antidepressant drug

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<span class="mw-page-title-main">Dexbrompheniramine</span> Chemical compound

Dexbrompheniramine is an antihistamine with anticholinergic properties used to treat allergic conditions such as hay fever or urticaria. It is the pharmacologically active dextrorotatory isomer of brompheniramine. It was formerly marketed in combination with pseudoephedrine under the name Drixoral in the US and Canada. It is an alkylamine antihistamine.

<span class="mw-page-title-main">Pheniramine</span> Chemical compound

Pheniramine is an antihistamine with anticholinergic properties used to treat allergic conditions such as hay fever or urticaria. It has relatively strong sedative effects, and may sometimes be used off-label as an over-the-counter sleeping pill in a similar manner to other sedating antihistamines such as diphenhydramine. Pheniramine is also commonly found in eyedrops used for the treatment of allergic conjunctivitis.

<span class="mw-page-title-main">Tripelennamine</span> Chemical compound

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<span class="mw-page-title-main">Bromazine</span> Chemical compound

Bromazine, sold under the brand names Ambodryl, Ambrodil, and Deserol among others, also known as bromodiphenhydramine, is an antihistamine and anticholinergic medication of the ethanolamine class. It is an analogue of diphenhydramine with a bromine substitution on one of the phenyl rings.

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. 1 2 3 4 Sweetman SC, ed. (2005). Martindale: the complete drug reference (34th ed.). London: Pharmaceutical Press. p. 569–70. ISBN   0-85369-550-4. OCLC   56903116.
  3. Fischer J, Ganellin CR (2006). Analogue-based Drug Discovery. John Wiley & Sons. p. 546. ISBN   9783527607495.
  4. "The Top 300 of 2021". ClinCalc. Archived from the original on 15 January 2024. Retrieved 14 January 2024.
  5. "Brompheniramine; Dextromethorphan; Pseudoephedrine - Drug Usage Statistics". ClinCalc. Retrieved 14 January 2024.
  6. Salahudeen MS, Duffull SB, Nishtala PS (March 2015). "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.
  7. 1 2 "Diphenhydramine: Uses, Interactions, Mechanism of Action". DrugBank Online. Archived from the original on 22 September 2024. Retrieved 26 November 2024.
  8. Troy DB, Beringer P (2006). Remington: The Science and Practice of Pharmacy. Lippincott Williams & Wilkins. pp. 1546–8. ISBN   9780781746731.
  9. US 3061517,Walter LA,issued 1962.
  10. US 3030371,Walter LA,issued 1962.
  11. Barondes SH (2003). Better Than Prozac . New York: Oxford University Press. pp.  39–40. ISBN   0-19-515130-5.