Brompheniramine

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 cat. C (USA)
Legal status Unscheduled, OTC
Routes Oral
Pharmacokinetic data
Bioavailability  ?
Metabolism Hepatic
Half-life  ?
Excretion Urine
Identifiers
CAS number 86-22-6
ATC code R06AB01
PubChem CID 6834
DrugBank APRD00832
ChemSpider 6573 YesY
UNII H57G17P2FN YesY
KEGG D07543 YesY
ChEBI CHEBI:3183 YesY
ChEMBL CHEMBL811 YesY
Chemical data
Formula C16H19BrN2 
Mol. mass 319.24
SMILES eMolecules & PubChem
 YesY(what is this?)  (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.[1]

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.

Contents

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. ^ 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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Look at other dictionaries:

  • brompheniramine maleate — A potent antihistaminic agent. * * * [USP] the maleate salt of brompheniramine, used in the treatment of allergic rhinitis, allergic conjunctivitis, and cutaneous manifestations of allergic reactions; administered orally or by intramuscular,… …   Medical dictionary

  • brompheniramine — /brohm feuh near euh meen , min/, n. Pharm. a substance, C16H19BrN2, used as an antihistamine in the management of various allergies, as hay fever. [presumably coined from contr. of the component names bromophenyl, pyridinepropanamine; see BROMO …   Universalium

  • brompheniramine — noun An antihistamine drug of the propylamine class …   Wiktionary

  • brompheniramine — brom·phen·ir·a·mine .brōm fen ir ə .mēn, fən n an H1 antagonist of histamine administered in the form of its maleate C16H19BrN2·C4H4O4 esp. to treat allergies and the common cold * * * n. an antihistamine given by mouth to relieve the symptoms of …   Medical dictionary

  • brompheniramine — /brohm feuh near euh meen , min/, n. Pharm. a substance, C16H19BrN2, used as an antihistamine in the management of various allergies, as hay fever. [presumably coined from contr. of the component names bromophenyl, pyridinepropanamine; see BROMO …   Useful english dictionary

  • brompheniramine maleate — noun antihistamine (trade name Dimetane) used to treat hypersensitivity reactions (as rhinitis) • Syn: ↑Dimetane • Hypernyms: ↑antihistamine • Substance Holonyms: ↑Dimetapp …   Useful english dictionary

  • Бромфенирамин (Brompheniramine) — антигистаминный лекарственный препарат; назначается внутрь для уменьшения симптомов аллергических реакций, особенно в случае сенной лихорадки и ринита. Наиболее типичные побочные эффекты: сонливость, головокружение, сухость во рту и расстройство… …   Медицинские термины

  • BROMPHEN — Brompheniramine Maleate (Medical » Physiology) …   Abbreviations dictionary

  • БРОМФЕНИРАМИН — (brompheniramine) антигистаминный лекарственный препарат; назначается внутрь для уменьшения симптомов аллергических реакций, особенно в случае сенной лихорадки и ринита. Наиболее типичные побочные эффекты: сонливость, головокружение, сухость во… …   Толковый словарь по медицине

  • Diphenhydramine — Systematic (IUPAC) name 2 (diphenylmethoxy) N,N dimethylethanamine Clinical data Trade names Benadryl …   Wikipedia

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