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Details

Stereochemistry RACEMIC
Molecular Formula C16H19BrN2
Molecular Weight 319.2396
Optical Activity ( + / - )
Defined Stereocenters 0 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of BROMPHENIRAMINE

SMILES

CN(C)CCC(c1ccc(cc1)Br)c2ccccn2

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 319.2396
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

4.86950404E11
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
PubMed

PubMed

TitleDatePubMed
Oral facial dyskinesia accociated with prolonged use of antihistaminic decongestants.
1975 Sep 4
Phenylpropanolamine and mental disturbances.
1979 Dec 22-29
[Antimycobacterial antihistaminics].
1989 Aug
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
Antihistamines in the treatment of dermatitis.
2003 Nov-Dec
Retentivity and enantioselectivity of uniformly sized molecularly imprinted polymers for d-chlorpheniramine and -brompheniramine in hydro-organic mobile phases.
2004 May 5
Role of chemical structure in stereoselective recognition of beta-blockers and H1-antihistamines by human serum transferrin in capillary zone electrophoresis.
2006 Apr
Analysis of pharmaceutical preparations containing antihistamine drugs by micellar liquid chromatography.
2006 Feb 13
Optimization by factorial design of a capillary zone electrophoresis method for the simultaneous separation of antihistamines.
2006 May 1
Characterization of antihistamine-human serum protein interactions by capillary electrophoresis.
2007 Apr 20
Evaluation of enantioselective binding of basic drugs to plasma by ACE.
2007 Aug
Evaluation of enantioselective binding of antihistamines to human serum albumin by ACE.
2007 Aug
Medication administered to children from 0 to 7.5 years in the Avon Longitudinal Study of Parents and Children (ALSPAC).
2007 Feb
Enantiomeric quality control of antihistamines in pharmaceuticals by affinity electrokinetic chromatography with human serum albumin as chiral selector.
2007 Jun 5
Possible role of pseudoephedrine and other over-the-counter cold medications in the deaths of very young children.
2007 Mar
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
Potentialities of ITP-CZE method with diode array detection for enantiomeric purity control of dexbrompheniramine in pharmaceuticals.
2008 Apr 14
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
Possibilities of column coupling electrophoresis provided with a fiber-based diode array detection in enantioselective analysis of drugs in pharmaceutical and clinical samples.
2008 Jan 25
Surface degradation of composite resins by acidic medicines and pH-cycling.
2008 Jul-Aug
Blockade of HERG K+ channel by an antihistamine drug brompheniramine requires the channel binding within the S6 residue Y652 and F656.
2008 Mar
H1-antihistamines and oxidative burst of professional phagocytes.
2009
Protective effect of pheniramines against mesenteric ischaemia/reperfusion-induced injury.
2009 Apr
Comparison of chiral separation of basic drugs in capillary electrophoresis and liquid chromatography using neutral and negatively charged cyclodextrins.
2009 Jul 10
Enantioseparation of a novel "click" chemistry derived native beta-cyclodextrin chiral stationary phase for high-performance liquid chromatography.
2009 Mar 20
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
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 Fri Jun 25 22:57:46 UTC 2021
Edited
by admin
on Fri Jun 25 22:57:46 UTC 2021
Record UNII
H57G17P2FN
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
BROMPHENIRAMINE
HSDB   INN   MI   VANDF   WHO-DD  
INN  
Official Name English
BROTANE
Brand 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 Fri Jun 25 22:57:46 UTC 2021 , Edited by admin on Fri Jun 25 22:57:46 UTC 2021
LIVERTOX 124
Created by admin on Fri Jun 25 22:57:46 UTC 2021 , Edited by admin on Fri Jun 25 22:57:46 UTC 2021
WHO-VATC QR06AB51
Created by admin on Fri Jun 25 22:57:46 UTC 2021 , Edited by admin on Fri Jun 25 22:57:46 UTC 2021
NCI_THESAURUS C29578
Created by admin on Fri Jun 25 22:57:46 UTC 2021 , Edited by admin on Fri Jun 25 22:57:46 UTC 2021
WHO-ATC R06AB01
Created by admin on Fri Jun 25 22:57:46 UTC 2021 , Edited by admin on Fri Jun 25 22:57:46 UTC 2021
WHO-ATC R06AB51
Created by admin on Fri Jun 25 22:57:46 UTC 2021 , Edited by admin on Fri Jun 25 22:57:46 UTC 2021
Code System Code Type Description
MESH
D001977
Created by admin on Fri Jun 25 22:57:46 UTC 2021 , Edited by admin on Fri Jun 25 22:57:46 UTC 2021
PRIMARY
CAS
86-22-6
Created by admin on Fri Jun 25 22:57:46 UTC 2021 , Edited by admin on Fri Jun 25 22:57:46 UTC 2021
PRIMARY
WIKIPEDIA
BROMPHENIRAMINE
Created by admin on Fri Jun 25 22:57:46 UTC 2021 , Edited by admin on Fri Jun 25 22:57:46 UTC 2021
PRIMARY
PUBCHEM
6834
Created by admin on Fri Jun 25 22:57:46 UTC 2021 , Edited by admin on Fri Jun 25 22:57:46 UTC 2021
PRIMARY
NCI_THESAURUS
C61655
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PRIMARY
DRUG CENTRAL
408
Created by admin on Fri Jun 25 22:57:46 UTC 2021 , Edited by admin on Fri Jun 25 22:57:46 UTC 2021
PRIMARY
ChEMBL
CHEMBL811
Created by admin on Fri Jun 25 22:57:46 UTC 2021 , Edited by admin on Fri Jun 25 22:57:46 UTC 2021
PRIMARY
HSDB
3017
Created by admin on Fri Jun 25 22:57:46 UTC 2021 , Edited by admin on Fri Jun 25 22:57:46 UTC 2021
PRIMARY
DRUG BANK
DB00835
Created by admin on Fri Jun 25 22:57:46 UTC 2021 , Edited by admin on Fri Jun 25 22:57:46 UTC 2021
PRIMARY
CAS
32188-07-1
Created by admin on Fri Jun 25 22:57:46 UTC 2021 , Edited by admin on Fri Jun 25 22:57:46 UTC 2021
SUPERSEDED
ECHA (EC/EINECS)
201-657-8
Created by admin on Fri Jun 25 22:57:46 UTC 2021 , Edited by admin on Fri Jun 25 22:57:46 UTC 2021
PRIMARY
FDA UNII
H57G17P2FN
Created by admin on Fri Jun 25 22:57:46 UTC 2021 , Edited by admin on Fri Jun 25 22:57:46 UTC 2021
PRIMARY
EPA CompTox
86-22-6
Created by admin on Fri Jun 25 22:57:46 UTC 2021 , Edited by admin on Fri Jun 25 22:57:46 UTC 2021
PRIMARY
CAS
156428-33-0
Created by admin on Fri Jun 25 22:57:46 UTC 2021 , Edited by admin on Fri Jun 25 22:57:46 UTC 2021
SUPERSEDED
IUPHAR
7133
Created by admin on Fri Jun 25 22:57:46 UTC 2021 , Edited by admin on Fri Jun 25 22:57:46 UTC 2021
PRIMARY
EVMPD
SUB05924MIG
Created by admin on Fri Jun 25 22:57:46 UTC 2021 , Edited by admin on Fri Jun 25 22:57:46 UTC 2021
PRIMARY
MERCK INDEX
M2723
Created by admin on Fri Jun 25 22:57:46 UTC 2021 , Edited by admin on Fri Jun 25 22:57:46 UTC 2021
PRIMARY Merck Index
RXCUI
1767
Created by admin on Fri Jun 25 22:57:46 UTC 2021 , Edited by admin on Fri Jun 25 22:57:46 UTC 2021
PRIMARY RxNorm
INN
770
Created by admin on Fri Jun 25 22:57:46 UTC 2021 , Edited by admin on Fri Jun 25 22:57:46 UTC 2021
PRIMARY
LACTMED
Brompheniramine
Created by admin on Fri Jun 25 22:57:46 UTC 2021 , Edited by admin on Fri Jun 25 22:57:46 UTC 2021
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