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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
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

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

4.86950404E11
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
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
Retentivity and enantioselectivity of uniformly sized molecularly imprinted polymers for d-chlorpheniramine and -brompheniramine in hydro-organic mobile phases.
2004 May 5
Over-the-counter cold medications-postmortem findings in infants and the relationship to cause of death.
2005 Oct
The combined luminol/isoluminol chemiluminescence method for differentiating between extracellular and intracellular oxidant production by neutrophils.
2006
Role of chemical structure in stereoselective recognition of beta-blockers and H1-antihistamines by human serum transferrin in capillary zone electrophoresis.
2006 Apr
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
Electrophysiological effects of brompheniramine on cardiac ion channels and action potential.
2006 Dec
Characterization of antihistamine-human serum protein interactions by capillary electrophoresis.
2007 Apr 20
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
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
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
Enantioseparation of a novel "click" chemistry derived native beta-cyclodextrin chiral stationary phase for high-performance liquid chromatography.
2009 Mar 20
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

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.
Substance Class Chemical
Created
by admin
on Sat Dec 16 16:45:05 UTC 2023
Edited
by admin
on Sat Dec 16 16:45:05 UTC 2023
Record UNII
H57G17P2FN
Record Status Validated (UNII)
Record Version
  • Download
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 UTC 2023 , Edited by admin on Sat Dec 16 16:45:06 UTC 2023
LIVERTOX 124
Created by admin on Sat Dec 16 16:45:06 UTC 2023 , Edited by admin on Sat Dec 16 16:45:06 UTC 2023
WHO-VATC QR06AB51
Created by admin on Sat Dec 16 16:45:06 UTC 2023 , Edited by admin on Sat Dec 16 16:45:06 UTC 2023
NCI_THESAURUS C29578
Created by admin on Sat Dec 16 16:45:06 UTC 2023 , Edited by admin on Sat Dec 16 16:45:06 UTC 2023
WHO-ATC R06AB01
Created by admin on Sat Dec 16 16:45:06 UTC 2023 , Edited by admin on Sat Dec 16 16:45:06 UTC 2023
WHO-ATC R06AB51
Created by admin on Sat Dec 16 16:45:06 UTC 2023 , Edited by admin on Sat Dec 16 16:45:06 UTC 2023
Code System Code Type Description
MESH
D001977
Created by admin on Sat Dec 16 16:45:06 UTC 2023 , Edited by admin on Sat Dec 16 16:45:06 UTC 2023
PRIMARY
CAS
86-22-6
Created by admin on Sat Dec 16 16:45:06 UTC 2023 , Edited by admin on Sat Dec 16 16:45:06 UTC 2023
PRIMARY
WIKIPEDIA
BROMPHENIRAMINE
Created by admin on Sat Dec 16 16:45:06 UTC 2023 , Edited by admin on Sat Dec 16 16:45:06 UTC 2023
PRIMARY
PUBCHEM
6834
Created by admin on Sat Dec 16 16:45:06 UTC 2023 , Edited by admin on Sat Dec 16 16:45:06 UTC 2023
PRIMARY
NCI_THESAURUS
C61655
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PRIMARY
DRUG CENTRAL
408
Created by admin on Sat Dec 16 16:45:06 UTC 2023 , Edited by admin on Sat Dec 16 16:45:06 UTC 2023
PRIMARY
ChEMBL
CHEMBL811
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PRIMARY
HSDB
3017
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PRIMARY
DRUG BANK
DB00835
Created by admin on Sat Dec 16 16:45:06 UTC 2023 , Edited by admin on Sat Dec 16 16:45:06 UTC 2023
PRIMARY
CAS
32188-07-1
Created by admin on Sat Dec 16 16:45:06 UTC 2023 , Edited by admin on Sat Dec 16 16:45:06 UTC 2023
SUPERSEDED
ECHA (EC/EINECS)
201-657-8
Created by admin on Sat Dec 16 16:45:06 UTC 2023 , Edited by admin on Sat Dec 16 16:45:06 UTC 2023
PRIMARY
DAILYMED
H57G17P2FN
Created by admin on Sat Dec 16 16:45:06 UTC 2023 , Edited by admin on Sat Dec 16 16:45:06 UTC 2023
PRIMARY
FDA UNII
H57G17P2FN
Created by admin on Sat Dec 16 16:45:06 UTC 2023 , Edited by admin on Sat Dec 16 16:45:06 UTC 2023
PRIMARY
EPA CompTox
DTXSID5022691
Created by admin on Sat Dec 16 16:45:06 UTC 2023 , Edited by admin on Sat Dec 16 16:45:06 UTC 2023
PRIMARY
CAS
156428-33-0
Created by admin on Sat Dec 16 16:45:06 UTC 2023 , Edited by admin on Sat Dec 16 16:45:06 UTC 2023
SUPERSEDED
IUPHAR
7133
Created by admin on Sat Dec 16 16:45:06 UTC 2023 , Edited by admin on Sat Dec 16 16:45:06 UTC 2023
PRIMARY
EVMPD
SUB05924MIG
Created by admin on Sat Dec 16 16:45:06 UTC 2023 , Edited by admin on Sat Dec 16 16:45:06 UTC 2023
PRIMARY
SMS_ID
100000092553
Created by admin on Sat Dec 16 16:45:06 UTC 2023 , Edited by admin on Sat Dec 16 16:45:06 UTC 2023
PRIMARY
MERCK INDEX
m2723
Created by admin on Sat Dec 16 16:45:06 UTC 2023 , Edited by admin on Sat Dec 16 16:45:06 UTC 2023
PRIMARY Merck Index
RXCUI
1767
Created by admin on Sat Dec 16 16:45:06 UTC 2023 , Edited by admin on Sat Dec 16 16:45:06 UTC 2023
PRIMARY RxNorm
INN
770
Created by admin on Sat Dec 16 16:45:06 UTC 2023 , Edited by admin on Sat Dec 16 16:45:06 UTC 2023
PRIMARY
CHEBI
3183
Created by admin on Sat Dec 16 16:45:06 UTC 2023 , Edited by admin on Sat Dec 16 16:45:06 UTC 2023
PRIMARY
LACTMED
Brompheniramine
Created by admin on Sat Dec 16 16:45:06 UTC 2023 , Edited by admin on Sat Dec 16 16:45:06 UTC 2023
PRIMARY
Related Record Type Details
PLASMA PROTEIN FRACTION (HUMAN)
BINDER->LIGAND
BINDING
Structure of DEXBROMPHENIRAMINE
ENANTIOMER -> RACEMATE
Structure of BROMPHENIRAMINE, (R)-
ENANTIOMER -> RACEMATE
HISTAMINE H1 RECEPTOR
TARGET -> INHIBITOR
Structure of BROMPHENIRAMINE MALEATE
SALT/SOLVATE -> PARENT
Related Record Type Details
Structure of BROMPHENIRAMINE
ACTIVE MOIETY
Name Property Type Amount Referenced Substance Defining Parameters References
Volume of Distribution PHARMACOKINETIC
Biological Half-life PHARMACOKINETIC
NIH
NCATS
PRIVACY ACT
ACCESSIBILITY
DISCLAIMER
HHS VULNERABILITY DISCLOSURE
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