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 ;
PubChem CID	6834;
IUPHAR/BPS	7133;
DrugBank	DB00835 ;
ChemSpider	6573 ;
UNII	H57G17P2FN;
KEGG	D07543 ;
ChEBI	CHEBI:3183 ;
ChEMBL	CHEMBL811 ;
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 ; Key:ZDIGNSYAACHWNL-UHFFFAOYSA-N ;
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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.^[2]

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.

Pharmacology[edit]

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[edit]

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.^[3]

Chemistry[edit]

Brompheniramine is a 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.^[4]^[5]

References[edit]

^ 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.
^ Barondes, Samuel H. (2003). Better Than Prozac. New York: Oxford University Press. pp. 39–40. ISBN 0-19-515130-5.
^ 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). doi:10.1186/s12877-015-0029-9. PMC 4377853. PMID 25879993.
^ L.A. Walter, U.S. Patent 3,061,517 (1962)
^ L.A. Walter, U.S. Patent 3,030,371 (1962)

External links[edit]

[pmid6128358-1] 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.

[Barondes-2] Barondes, Samuel H. (2003). Better Than Prozac. New York: Oxford University Press. pp. 39–40. ISBN 0-19-515130-5.

[3] 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). doi:10.1186/s12877-015-0029-9. PMC 4377853. PMID 25879993.

[4] L.A. Walter, U.S. Patent 3,061,517 (1962)

[5] L.A. Walter, U.S. Patent 3,030,371 (1962)

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v t e Antihistamines (R06)

Aminoalkyl ethers	Bromazine (bromodiphenhydramine) Carbinoxamine Clemastine Chlorphenoxamine Diphenylpyraline Diphenhydramine Doxylamine Orphenadrine Phenyltoloxamine

Substituted alkylamines	Brompheniramine Chlorphenamine Dexbrompheniramine (+pseudoephedrine) Dexchlorpheniramine (+betamethasone) Dimetindene Pheniramine Talastine

Substituted ethylenediamines	Chloropyramine Histapyrrodine Mepyramine Methapyrilene Tripelennamine (pyribenzamine)

Phenothiazine derivatives	Alimemazine Fenethazine Hydroxyethylpromethazine Isothipendyl Mequitazine Methdilazine Oxomemazine Promethazine

Piperazine derivatives	Buclizine Cetirizine Levocetirizine Chlorcyclizine Cinnarizine Cyclizine Hydroxyzine Meclizine Oxatomide

Others for systemic use	Antazoline Azanator Azatadine Bamipine Cyproheptadine Deptropine Ebastine Emedastine Epinastine Ketotifen Latrepirdine Mebhydrolin Mizolastine Olopatadine Phenindamine Pimethixene Pyrrobutamine Quifenadine Rupatadine Triprolidine selective (Acrivastine Astemizole Azelastine Bilastine Desloratadine Fexofenadine Loratadine Terfenadine)

For topical use	Bamipine Chloropyramine Chlorphenoxamine Clemastine Dimetindene Diphenhydramine Isothipendyl Mepyramine Promethazine Thenalidine

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Predecessors and acquired companies	Astra AB Cambridge Antibody Technology MedImmune Zeneca

People	Tom McKillop Louis Schweitzer

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Brompheniramine

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Pharmacology[edit]

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Chemistry[edit]

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References[edit]

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