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
Phenylpropanolamine and mental disturbances.	1979 Dec 22-29	92706
[Antimycobacterial antihistaminics].	1989 Aug	2513793
Withdrawal symptoms after discontinuation of long-acting brompheniramine maleate.	1994 Dec	7857852
pH-independent large-volume sample stacking of positive or negative analytes in capillary electrophoresis.	2001 Jan	11197179
Toxicity of over-the-counter cough and cold medications.	2001 Sep	11533370
Update on medical treatment of ejaculatory disorders.	2002 Dec	12406365
Involvement of calmodulin inhibition in analgesia induced with low doses of intrathecal trifluoperazine.	2002 Feb	11928715
Spermine-induced negative inotropic effect in isolated rat heart, is mediated through the release of ATP.	2003 Jul 1	12818376
First do no harm: managing antihistamine impairment in patients with allergic rhinitis.	2003 May	12743547
Retentivity and enantioselectivity of uniformly sized molecularly imprinted polymers for d-chlorpheniramine and -brompheniramine in hydro-organic mobile phases.	2004 May 5	15093155
Laboratory exposures to staphylococcal enterotoxin B.	2004 Sep	15498154
Nimesulide-induced fixed drug eruption.	2005 Sep-Oct	16287549
Antiradical effects of antihistamines in human blood. Structure-activity relationship.	2006 Apr	16547801
Extra- and intracellular formation of reactive oxygen species by human neutrophils in the presence of pheniramine, chlorpheniramine and brompheniramine.	2006 Dec	17159800
Medication administered to children from 0 to 7.5 years in the Avon Longitudinal Study of Parents and Children (ALSPAC).	2007 Feb	17200835
Potentialities of ITP-CZE method with diode array detection for enantiomeric purity control of dexbrompheniramine in pharmaceuticals.	2008 Apr 14	17618074
Profiling of a prescription drug library for potential renal drug-drug interactions mediated by the organic cation transporter 2.	2011 Jul 14	21599003

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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