Chemistry:Brompheniramine

Short description: Chemical compound

Brompheniramine

Clinical data
Trade names	Bromfed, Dimetapp, Bromfenex, and others
AHFS/Drugs.com	Monograph
MedlinePlus	a682545
Pregnancy category	US: C (Risk not ruled out)
Routes of administration	By mouth
ATC code	R06AB01 (WHO)
Legal status
Legal status	AU: S4 / S3 / S2 US: Rx-only / OTC
Pharmacokinetic data
Metabolism	Hepatic
Elimination half-life	24.9 ± 9.3 hours
Excretion	Urine
Identifiers
IUPAC name (R/S)-3-(4-Bromophenyl)-N,N-dimethyl-3-pyridin-2-yl-propan-1-amine
CAS Number	86-22-6 Y
PubChem CID	6834
IUPHAR/BPS	7133
DrugBank	DB00835 Y
ChemSpider	6573 Y
UNII	H57G17P2FN
KEGG	D07543 Y
ChEBI	CHEBI:3183 Y
ChEMBL	ChEMBL811 Y
Chemical and physical data
Formula	C16H19BrN2
Molar mass	319.246 g·mol−1
3D model (JSmol)	Interactive image
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
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Brompheniramine, sold under the brand name Dimetapp among others, is a first-generation antihistamine drug of the propylamine (alkylamine) class. 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.

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

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.

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.

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.

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.

Names

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

See also

• Pheniramine
• Zimelidine

External links

• "Brompheniramine". Drug Information Portal. U.S. National Library of Medicine. https://druginfo.nlm.nih.gov/drugportal/name/brompheniramine.