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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=NC=CC=C2

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

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

CNS Penetrant
2554
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

1956
94
Targets

Targets

Primary TargetPharmacologyConditionPotency
Antagonist
2778
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Palliative
Approved
8429
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
Phase III
656
Unknown

Approved Use

Unknown
Palliative
Phase III
656
Unknown

Approved Use

Unknown
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
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

AUC

ValueDoseCo-administeredAnalytePopulation
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
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
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
Sourcing

Sourcing

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

PubMed

TitleDatePubMed
Oral facial dyskinesia associated with prolonged use of antihistaminic decongestants.
1975 Sep 4
Phenylpropanolamine and mental disturbances.
1979 Dec 22-29
[Antimycobacterial antihistaminics].
1989 Aug
Withdrawal symptoms after discontinuation of long-acting brompheniramine maleate.
1994 Dec
Update on medical treatment of ejaculatory disorders.
2002 Dec
First do no harm: managing antihistamine impairment in patients with allergic rhinitis.
2003 May
Antihistamines in the treatment of dermatitis.
2003 Nov-Dec
Fatal cold medication intoxication in an infant.
2003 Oct
Over-the-counter cold medications-postmortem findings in infants and the relationship to cause of death.
2005 Oct
Nimesulide-induced fixed drug eruption.
2005 Sep-Oct
The combined luminol/isoluminol chemiluminescence method for differentiating between extracellular and intracellular oxidant production by neutrophils.
2006
Antiradical effects of antihistamines in human blood. Structure-activity relationship.
2006 Apr
Evaluation of enantioselective binding of antihistamines to human serum albumin by ACE.
2007 Aug
First-generation H1 antihistamines found in pilot fatalities of civil aviation accidents, 1990-2005.
2007 May
The effect of achiral calixarenes on chiral separation of propranolol-HCl and brompheniramine maleate in capillary electrophoresis using cyclodextrin as chiral selector.
2008 Apr
Cough and cold medication use by US children, 1999-2006: results from the slone survey.
2008 Aug
Drug-liposome distribution phenomena studied by capillary electrophoresis-frontal analysis.
2008 Aug
Transient receptor potential vanilloid-1-mediated calcium responses are inhibited by the alkylamine antihistamines dexbrompheniramine and chlorpheniramine.
2008 Dec
Indirect fluorescent determination of selected nitro-aromatic and pharmaceutical compounds via UV-photolysis of 2-phenylbenzimidazole-5-sulfonate.
2008 Feb 15
Surface degradation of composite resins by acidic medicines and pH-cycling.
2008 Jul-Aug
H1-antihistamines and oxidative burst of professional phagocytes.
2009
Pheniramines and oxidative burst of blood phagocytes during ischaemia/reperfusion.
2009 Apr
Protective effect of pheniramines against mesenteric ischaemia/reperfusion-induced injury.
2009 Apr
Acute cough: a diagnostic and therapeutic challenge.
2009 Dec 16
Comparison of chiral separation of basic drugs in capillary electrophoresis and liquid chromatography using neutral and negatively charged cyclodextrins.
2009 Jul 10
A novel flow cytometric high throughput assay for a systematic study on molecular mechanisms underlying T cell receptor-mediated integrin activation.
2009 Jun 25
Enantioseparation of a novel "click" chemistry derived native beta-cyclodextrin chiral stationary phase for high-performance liquid chromatography.
2009 Mar 20
Halogenation effects of pheniramines on the complexation with beta-cyclodextrin.
2009 Oct 15
Treatment of congestion in upper respiratory diseases.
2010 Apr 8
Commonly prescribed medications and potential false-positive urine drug screens.
2010 Aug 15
Arvid Carlsson, and the story of dopamine.
2010 Jan
Trace determination of pharmaceuticals and other wastewater-derived micropollutants by solid phase extraction and gas chromatography/mass spectrometry.
2010 Jan 22
Determination of chlorpheniramine in human plasma by HPLC-ESI-MS/MS: application to a dexchlorpheniramine comparative bioavailability study.
2010 Jul
Profiling of a prescription drug library for potential renal drug-drug interactions mediated by the organic cation transporter 2.
2011 Jul 14
Patents

Patents

JPS63243024A
4

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.
Name Type Language
BROMPHENIRAMINE
HSDB   INN   MI   VANDF   WHO-DD  
INN  
Official Name English
Brompheniramine [WHO-DD]
Common Name English
BROTANE
Brand 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 Sat Dec 16 16:45:06 GMT 2023 , Edited by admin on Sat Dec 16 16:45:06 GMT 2023
LIVERTOX 124
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WHO-VATC QR06AB51
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NCI_THESAURUS C29578
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WHO-ATC R06AB01
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WHO-ATC R06AB51
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Code System Code Type Description
MESH
D001977
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PRIMARY
CAS
86-22-6
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PRIMARY
WIKIPEDIA
BROMPHENIRAMINE
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PRIMARY
PUBCHEM
6834
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PRIMARY
NCI_THESAURUS
C61655
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PRIMARY
DRUG CENTRAL
408
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PRIMARY
ChEMBL
CHEMBL811
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PRIMARY
HSDB
3017
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PRIMARY
DRUG BANK
DB00835
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PRIMARY
CAS
32188-07-1
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SUPERSEDED
ECHA (EC/EINECS)
201-657-8
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PRIMARY
DAILYMED
H57G17P2FN
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PRIMARY
FDA UNII
H57G17P2FN
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PRIMARY
EPA CompTox
DTXSID5022691
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PRIMARY
CAS
156428-33-0
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SUPERSEDED
IUPHAR
7133
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PRIMARY
EVMPD
SUB05924MIG
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PRIMARY
SMS_ID
100000092553
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PRIMARY
MERCK INDEX
m2723
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PRIMARY Merck Index
RXCUI
1767
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PRIMARY RxNorm
INN
770
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PRIMARY
CHEBI
3183
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PRIMARY
LACTMED
Brompheniramine
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PRIMARY
ACTIVE MOIETY
Structure of BROMPHENIRAMINE
SALT/SOLVATE (PARENT)
Structure of BROMPHENIRAMINE MALEATE
NIH
NCATS
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ACCESSIBILITY
DISCLAIMER
HHS VULNERABILITY DISCLOSURE
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