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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 of BROMPHENIRAMINE

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
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

Curator's Comment: first-generation antihistamines (FGAs) such as chlorpheniramine, diphenhydramine, and brompheniramine, are lipophilic and readily cross the blood–brain barrier, resulting in sedation and cognitive impairment.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Palliative
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
Palliative
Unknown

Approved Use

Unknown
Palliative
Unknown

Approved Use

Unknown
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
11.6 ng/mL
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

AUC

ValueDoseCo-administeredAnalytePopulation
284 ng × h/mL
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
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
24.9 h
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

Overview

OverviewOther

Other InhibitorOther SubstrateOther Inducer




Drug as perpetrator​

Drug as perpetrator​

TargetModalityActivityMetaboliteClinical evidence
no [IC50 >100 uM]
Drug as victimTox targets

Tox targets

TargetModalityActivityMetaboliteClinical evidence
PubMed

PubMed

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

Patents

Sample Use Guides

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
  • Download
Name Type Language
BROTANE
Preferred Name English
BROMPHENIRAMINE
HSDB   INN   MI   VANDF   WHO-DD  
INN  
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 QR06AB01
Created by admin on Wed Apr 02 08:20:59 GMT 2025 , Edited by admin on Wed Apr 02 08:20:59 GMT 2025
LIVERTOX 124
Created by admin on Wed Apr 02 08:20:59 GMT 2025 , Edited by admin on Wed Apr 02 08:20:59 GMT 2025
WHO-VATC QR06AB51
Created by admin on Wed Apr 02 08:20:59 GMT 2025 , Edited by admin on Wed Apr 02 08:20:59 GMT 2025
NCI_THESAURUS C29578
Created by admin on Wed Apr 02 08:20:59 GMT 2025 , Edited by admin on Wed Apr 02 08:20:59 GMT 2025
WHO-ATC R06AB01
Created by admin on Wed Apr 02 08:20:59 GMT 2025 , Edited by admin on Wed Apr 02 08:20:59 GMT 2025
WHO-ATC R06AB51
Created by admin on Wed Apr 02 08:20:59 GMT 2025 , Edited by admin on Wed Apr 02 08:20:59 GMT 2025
Code System Code Type Description
MESH
D001977
Created by admin on Wed Apr 02 08:20:59 GMT 2025 , Edited by admin on Wed Apr 02 08:20:59 GMT 2025
PRIMARY
CAS
86-22-6
Created by admin on Wed Apr 02 08:20:59 GMT 2025 , Edited by admin on Wed Apr 02 08:20:59 GMT 2025
PRIMARY
WIKIPEDIA
BROMPHENIRAMINE
Created by admin on Wed Apr 02 08:20:59 GMT 2025 , Edited by admin on Wed Apr 02 08:20:59 GMT 2025
PRIMARY
PUBCHEM
6834
Created by admin on Wed Apr 02 08:20:59 GMT 2025 , Edited by admin on Wed Apr 02 08:20:59 GMT 2025
PRIMARY
NCI_THESAURUS
C61655
Created by admin on Wed Apr 02 08:20:59 GMT 2025 , Edited by admin on Wed Apr 02 08:20:59 GMT 2025
PRIMARY
DRUG CENTRAL
408
Created by admin on Wed Apr 02 08:20:59 GMT 2025 , Edited by admin on Wed Apr 02 08:20:59 GMT 2025
PRIMARY
ChEMBL
CHEMBL811
Created by admin on Wed Apr 02 08:20:59 GMT 2025 , Edited by admin on Wed Apr 02 08:20:59 GMT 2025
PRIMARY
HSDB
3017
Created by admin on Wed Apr 02 08:20:59 GMT 2025 , Edited by admin on Wed Apr 02 08:20:59 GMT 2025
PRIMARY
DRUG BANK
DB00835
Created by admin on Wed Apr 02 08:20:59 GMT 2025 , Edited by admin on Wed Apr 02 08:20:59 GMT 2025
PRIMARY
CAS
32188-07-1
Created by admin on Wed Apr 02 08:20:59 GMT 2025 , Edited by admin on Wed Apr 02 08:20:59 GMT 2025
SUPERSEDED
ECHA (EC/EINECS)
201-657-8
Created by admin on Wed Apr 02 08:20:59 GMT 2025 , Edited by admin on Wed Apr 02 08:20:59 GMT 2025
PRIMARY
DAILYMED
H57G17P2FN
Created by admin on Wed Apr 02 08:20:59 GMT 2025 , Edited by admin on Wed Apr 02 08:20:59 GMT 2025
PRIMARY
FDA UNII
H57G17P2FN
Created by admin on Wed Apr 02 08:20:59 GMT 2025 , Edited by admin on Wed Apr 02 08:20:59 GMT 2025
PRIMARY
EPA CompTox
DTXSID5022691
Created by admin on Wed Apr 02 08:20:59 GMT 2025 , Edited by admin on Wed Apr 02 08:20:59 GMT 2025
PRIMARY
CAS
156428-33-0
Created by admin on Wed Apr 02 08:20:59 GMT 2025 , Edited by admin on Wed Apr 02 08:20:59 GMT 2025
SUPERSEDED
IUPHAR
7133
Created by admin on Wed Apr 02 08:20:59 GMT 2025 , Edited by admin on Wed Apr 02 08:20:59 GMT 2025
PRIMARY
EVMPD
SUB05924MIG
Created by admin on Wed Apr 02 08:20:59 GMT 2025 , Edited by admin on Wed Apr 02 08:20:59 GMT 2025
PRIMARY
SMS_ID
100000092553
Created by admin on Wed Apr 02 08:20:59 GMT 2025 , Edited by admin on Wed Apr 02 08:20:59 GMT 2025
PRIMARY
MERCK INDEX
m2723
Created by admin on Wed Apr 02 08:20:59 GMT 2025 , Edited by admin on Wed Apr 02 08:20:59 GMT 2025
PRIMARY Merck Index
RXCUI
1767
Created by admin on Wed Apr 02 08:20:59 GMT 2025 , Edited by admin on Wed Apr 02 08:20:59 GMT 2025
PRIMARY RxNorm
INN
770
Created by admin on Wed Apr 02 08:20:59 GMT 2025 , Edited by admin on Wed Apr 02 08:20:59 GMT 2025
PRIMARY
CHEBI
3183
Created by admin on Wed Apr 02 08:20:59 GMT 2025 , Edited by admin on Wed Apr 02 08:20:59 GMT 2025
PRIMARY
LACTMED
Brompheniramine
Created by admin on Wed Apr 02 08:20:59 GMT 2025 , Edited by admin on Wed Apr 02 08:20:59 GMT 2025
PRIMARY
Related Record Type Details
BINDER->LIGAND
BINDING
ENANTIOMER -> RACEMATE
ENANTIOMER -> RACEMATE
TARGET -> INHIBITOR
SALT/SOLVATE -> PARENT
Related Record Type Details
ACTIVE MOIETY
Name Property Type Amount Referenced Substance Defining Parameters References
Volume of Distribution PHARMACOKINETIC
Biological Half-life PHARMACOKINETIC