Brompheniramine

Brompheniramine

Clinical data
AHFS/Drugs.com	Monograph
MedlinePlus	a682545
Pregnancy category	US: C (Risk not ruled out)
Routes of administration	Oral
ATC code	R06AB01 (WHO)
Legal status
Legal status	AU: S2 (Pharmacy only) – 4, depending on formulation and usage Unscheduled, OTC
Pharmacokinetic data
Metabolism	Hepatic
Biological half-life	24.9 ± 9.3 hours
Excretion	Urine
Identifiers
IUPAC name 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
ECHA InfoCard	100.001.507
Chemical and physical data
Formula	C16H19BrN2
Molar mass	319.24 g/mol
3D model (Jmol)	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

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), triprolidine (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 and norepinephrine. 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.