BROMPHENIRAMINE

US Approved OTC

First approved in 1956

Details

Stereochemistry	RACEMIC
Molecular Formula	C16H19BrN2
Molecular Weight	319.239
Optical Activity	( + / - )
Defined Stereocenters	0 / 1
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CN(C)CCC(C1=CC=C(Br)C=C1)C2=CC=CC=N2

InChI

InChIKey=ZDIGNSYAACHWNL-UHFFFAOYSA-N

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

HIDE SMILES / InChI

Molecular Formula	C16H19BrN2
Molecular Weight	319.239
Charge	0
Count

Stereochemistry	RACEMIC
Additional Stereochemistry	No
Defined Stereocenters	0 / 1
E/Z Centers	0
Optical Activity	( + / - )

Description
Sources: https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=e241d83e-996c-494d-b3fe-97f1ef4809ed
Curator's Comment: description was created based on several sources, including https://www.drugs.com/mtm/brompheniramine.html

Brompheniramine is an antihistaminergic medication of the propylamine class. It is a first-generation antihistamine, which is used for the treatment of the symptoms of the common cold and allergic rhinitis, such as runny nose, itchy eyes, watery eyes, and sneezing. In allergic reactions, an allergen interacts with and cross-links surface IgE antibodies on mast cells and basophils. Once the mast cell-antibody-antigen complex is formed, a complex series of events occurs that eventually leads to cell-degranulation and the release of histamine (and other chemical mediators) from the mast cell or basophil. Once released, histamine can react with local or widespread tissues through histamine receptors. Brompheniramine is a histamine H1 antagonist of the alkylamine class. It provides effective, temporary relief of sneezing, watery and itchy eyes, and runny nose due to hay fever and other upper respiratory allergies. Brompheniramine is metabolised by cytochrome P450s. The halogenated alkylamine antihistamines all exhibit optic isomerism and brompheniramine products contain racemic brompheniramine maleate whereas dexbrompheniramine (Drixoral) is the dextrorotary (right-handed) stereoisomer.

CNS Activity

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Histamine H1 receptor 316 Target ID: CHEMBL231 Sources: https://www.ncbi.nlm.nih.gov/pubmed/10212017	Antagonist 2849

Conditions

Condition	Modality	Highest Phase	Product
Common cold 58 Sources: https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=06db369d-09fe-4ca2-b98c-705356b7c403	Palliative	Approved 8583	BROMFED-DM (BROMPHENIRAMINE MALEATE; DEXTROMETHORPHAN HYDROBROMIDE; PSEUDOEPHEDRINE HYDROCHLORIDE) Approved Use For relief of coughs and upper respiratory symptoms, including nasal congestion, associated with allergy or the common cold. Launch Date 1985
Nasal congestion and inflammations 3 Sources: https://clinicaltrials.gov/ct2/show/NCT01393561	Palliative	Phase III 665	Unknown Approved Use Unknown
Rhinitis 19 Sources: https://clinicaltrials.gov/ct2/show/NCT01393561	Palliative	Phase III 665	Unknown Approved Use Unknown

C_max

Value	Dose	Co-administered	Analyte	Population
11.6 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/6128358/	0.13 mg/kg single, oral dose: 0.13 mg/kg route of administration: Oral experiment type: SINGLE co-administered:		BROMPHENIRAMINE plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED

AUC

Value	Dose	Co-administered	Analyte	Population
284 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/6128358/	0.13 mg/kg single, oral dose: 0.13 mg/kg route of administration: Oral experiment type: SINGLE co-administered:		BROMPHENIRAMINE plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED

T_1/2

Value	Dose	Co-administered	Analyte	Population
24.9 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/6128358/	0.13 mg/kg single, oral dose: 0.13 mg/kg route of administration: Oral experiment type: SINGLE co-administered:		BROMPHENIRAMINE plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED

Overview

CYP3A4	CYP2C9	CYP2D6	hERG
substrate 1946	substrate 1193	substrate 1388	inhibitor 2217

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
BSEP 550	P-gp 2052 pCYP 3 FMO 34

Drug as perpetrator

Target	Modality	Activity	Metabolite	Clinical evidence
BSEP 554	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/24799086/	no [IC50 >100 uM]

Drug as victim

Target	Modality	Activity
CYP3A4 1946	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/27397500/	likely
CYP2C9 1193	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/29136286/ \| https://pubmed.ncbi.nlm.nih.gov/27397500/	no
CYP2D6 1388	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/29136286/ \| https://pubmed.ncbi.nlm.nih.gov/27397500/	yes
FMO 34	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/15701578/	yes
P-gp 2052	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/17180728/	yes
pCYP 3	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/406849/	yes

Tox targets

Target	Modality	Activity	Metabolite	Clinical evidence
hERG 2263	inhibitor 2237 Sources: https://pubmed.ncbi.nlm.nih.gov/17516459/

Sourcing

Vendor/Aggregator	ID	URL
ChEBI	CHEBI:3183	https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:3183
eMolecules	901744	https://www.emolecules.com/cgi-bin/more?vid=901744
MolPort	MolPort-005-935-546	https://www.molport.com/shop/molecule-link/MolPort-005-935-546

PubMed

Title	Date	PubMed
Profiling of a prescription drug library for potential renal drug-drug interactions mediated by the organic cation transporter 2.	2011-07-14	21599003
Commonly prescribed medications and potential false-positive urine drug screens.	2010-08-15	20689123
Determination of chlorpheniramine in human plasma by HPLC-ESI-MS/MS: application to a dexchlorpheniramine comparative bioavailability study.	2010-07	19924675
Treatment of congestion in upper respiratory diseases.	2010-04-08	20463825
Trace determination of pharmaceuticals and other wastewater-derived micropollutants by solid phase extraction and gas chromatography/mass spectrometry.	2010-01-22	20015510
Arvid Carlsson, and the story of dopamine.	2010-01	20174530
Acute cough: a diagnostic and therapeutic challenge.	2009-12-16	20015366
Halogenation effects of pheniramines on the complexation with beta-cyclodextrin.	2009-10-15	19540697
Comparison of chiral separation of basic drugs in capillary electrophoresis and liquid chromatography using neutral and negatively charged cyclodextrins.	2009-07-10	19481637
A novel flow cytometric high throughput assay for a systematic study on molecular mechanisms underlying T cell receptor-mediated integrin activation.	2009-06-25	19557182
Pheniramines and oxidative burst of blood phagocytes during ischaemia/reperfusion.	2009-04	19271141
Protective effect of pheniramines against mesenteric ischaemia/reperfusion-induced injury.	2009-04	19271140
Enantioseparation of a novel "click" chemistry derived native beta-cyclodextrin chiral stationary phase for high-performance liquid chromatography.	2009-03-20	19185873
H1-antihistamines and oxidative burst of professional phagocytes.	2009	20027159
Transient receptor potential vanilloid-1-mediated calcium responses are inhibited by the alkylamine antihistamines dexbrompheniramine and chlorpheniramine.	2008-12	19085565
Cough and cold medication use by US children, 1999-2006: results from the slone survey.	2008-08	18676518
Drug-liposome distribution phenomena studied by capillary electrophoresis-frontal analysis.	2008-08	18651665
Uniformly sized molecularly imprinted polymers for d-chlorpheniramine: influence of a porogen on their morphology and enantioselectivity.	2008-04-14	17644298
Potentialities of ITP-CZE method with diode array detection for enantiomeric purity control of dexbrompheniramine in pharmaceuticals.	2008-04-14	17618074
The effect of achiral calixarenes on chiral separation of propranolol-HCl and brompheniramine maleate in capillary electrophoresis using cyclodextrin as chiral selector.	2008-04	18468383
Blockade of HERG K+ channel by an antihistamine drug brompheniramine requires the channel binding within the S6 residue Y652 and F656.	2008-03	17516459
Indirect fluorescent determination of selected nitro-aromatic and pharmaceutical compounds via UV-photolysis of 2-phenylbenzimidazole-5-sulfonate.	2008-02-15	18371796
Surface degradation of composite resins by acidic medicines and pH-cycling.	2008-02-08	19089257
Possibilities of column coupling electrophoresis provided with a fiber-based diode array detection in enantioselective analysis of drugs in pharmaceutical and clinical samples.	2008-01-25	17905259
Evaluation of enantioselective binding of basic drugs to plasma by ACE.	2007-08	17661317
Evaluation of enantioselective binding of antihistamines to human serum albumin by ACE.	2007-08	17605150
Enantiomeric quality control of antihistamines in pharmaceuticals by affinity electrokinetic chromatography with human serum albumin as chiral selector.	2007-06-05	17512827
First-generation H1 antihistamines found in pilot fatalities of civil aviation accidents, 1990-2005.	2007-05	17539447
Characterization of antihistamine-human serum protein interactions by capillary electrophoresis.	2007-04-20	17339039
Possible role of pseudoephedrine and other over-the-counter cold medications in the deaths of very young children.	2007-03	17316256
Medication administered to children from 0 to 7.5 years in the Avon Longitudinal Study of Parents and Children (ALSPAC).	2007-02	17200835
Extra- and intracellular formation of reactive oxygen species by human neutrophils in the presence of pheniramine, chlorpheniramine and brompheniramine.	2006-12	17159800
Electrophysiological effects of brompheniramine on cardiac ion channels and action potential.	2006-12	17010640
Optimization by factorial design of a capillary zone electrophoresis method for the simultaneous separation of antihistamines.	2006-05-01	16549055
Role of chemical structure in stereoselective recognition of beta-blockers and H1-antihistamines by human serum transferrin in capillary zone electrophoresis.	2006-04	16609932
Antiradical effects of antihistamines in human blood. Structure-activity relationship.	2006-04	16547801
Analysis of pharmaceutical preparations containing antihistamine drugs by micellar liquid chromatography.	2006-02-13	16182504
The combined luminol/isoluminol chemiluminescence method for differentiating between extracellular and intracellular oxidant production by neutrophils.	2006	16805965
Nimesulide-induced fixed drug eruption.	2005-11-17	16287549
Over-the-counter cold medications-postmortem findings in infants and the relationship to cause of death.	2005-10	16419411
Antihistamines in the treatment of dermatitis.	2005-06-01	15926215
Laboratory exposures to staphylococcal enterotoxin B.	2004-09	15498154
Retentivity and enantioselectivity of uniformly sized molecularly imprinted polymers for d-chlorpheniramine and -brompheniramine in hydro-organic mobile phases.	2004-05-05	15093155
Fatal cold medication intoxication in an infant.	2003-10	14607011
Spermine-induced negative inotropic effect in isolated rat heart, is mediated through the release of ATP.	2003-07-01	12818376
First do no harm: managing antihistamine impairment in patients with allergic rhinitis.	2003-05	12743547
Withdrawal symptoms after discontinuation of long-acting brompheniramine maleate.	1994-12	7857852
[Antimycobacterial antihistaminics].	1989-08	2513793
Phenylpropanolamine and mental disturbances.	1979-12-22	92706
Oral facial dyskinesia associated with prolonged use of antihistaminic decongestants.	1975-09-04	239337

Patents

Sample Use Guides

In Vivo Use Guide

Adults and pediatric patients 12 years of age and over: 10 mL (2 teaspoonfuls) every 4 hours. Children 6 to under 12 years of age: 5 mL (1 teaspoonful) every 4 hours. Children 2 to under 6 years of age: 2.5 mL (½ teaspoonful) every 4 hours. Infants 6 months to under 2 years of age:

Route of Administration: Oral

In Vitro Use Guide

The anticholinergic properties of brompheniramine was assessed in an in vitro model of human nasal mucosal glandular secretion. The effective dose reducing methacholine-induced secretion (ED50) was determined. ED50 was 4.10 microM for rompheniramine.

Substance Class	Chemical Created by `admin` on `Wed Apr 02 08:20:59 GMT 2025` Edited by `admin` on `Wed Apr 02 08:20:59 GMT 2025`
Record UNII	H57G17P2FN
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

BROTANE

Preferred Name

English

BROMPHENIRAMINE

Official Name

English

Brompheniramine [WHO-DD]

Common Name

English

brompheniramine [INN]

Common Name

English

BROMPHENIRAMINE [HSDB]

Common Name

English

BROMPHENIRAMINE [VANDF]

Common Name

English

BROMPHENIRAMINE [MI]

Common Name

English

Classification Tree Code System Code

WHO-VATC

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