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Details

Stereochemistry RACEMIC
Molecular Formula C16H19BrN2.C4H4O4
Molecular Weight 435.312
Optical Activity ( + / - )
Defined Stereocenters 0 / 1
E/Z Centers 1
Charge 0

SHOW SMILES / InChI
Structure of BROMPHENIRAMINE MALEATE

SMILES

OC(=O)\C=C/C(O)=O.CN(C)CCC(C1=CC=C(Br)C=C1)C2=CC=CC=N2

InChI

InChIKey=SRGKFVAASLQVBO-BTJKTKAUSA-N
InChI=1S/C16H19BrN2.C4H4O4/c1-19(2)12-10-15(16-5-3-4-11-18-16)13-6-8-14(17)9-7-13;5-3(6)1-2-4(7)8/h3-9,11,15H,10,12H2,1-2H3;1-2H,(H,5,6)(H,7,8)/b;2-1-

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 ( + / - )
Molecular Formula C4H4O4
Molecular Weight 116.0722
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 1
Optical Activity NONE

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
2588
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
2849
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
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
Palliative
Phase III
665
Unknown

Approved Use

Unknown
Palliative
Phase III
665
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
Overview

Overview

CYP3A4CYP2C9CYP2D6hERG
substrate
1946
substrate
1193
substrate
1388
inhibitor
2217

OverviewOther

Other InhibitorOther SubstrateOther Inducer
BSEP
550
P-gp
2052

pCYP
3

FMO
34
Drug as perpetrator​

Drug as perpetrator​

TargetModalityActivityMetaboliteClinical evidence
BSEP
554
 no [IC50 >100 uM]
Drug as victim

Drug as victim

TargetModalityActivityMetaboliteClinical evidence
CYP3A4
1946
 likely
CYP2C9
1193
 no
CYP2D6
1388
 yes
FMO
34
 yes
P-gp
2052
 yes
pCYP
3
 yes
Tox targets

Tox targets

TargetModalityActivityMetaboliteClinical evidence
hERG
2263
Sourcing

Sourcing

Vendor/AggregatorIDURL
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

PubMed

TitleDatePubMed
Phenylpropanolamine and mental disturbances.
1979 Dec 22-29
Spermine-induced negative inotropic effect in isolated rat heart, is mediated through the release of ATP.
2003 Jul 1
Antihistamines in the treatment of dermatitis.
2003 Nov-Dec
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
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
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
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
Blockade of HERG K+ channel by an antihistamine drug brompheniramine requires the channel binding within the S6 residue Y652 and F656.
2008 Mar
Protective effect of pheniramines against mesenteric ischaemia/reperfusion-induced injury.
2009 Apr
Treatment of congestion in upper respiratory diseases.
2010 Apr 8
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
3

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 Mon Mar 31 18:45:17 GMT 2025
Edited
by admin
on Mon Mar 31 18:45:17 GMT 2025
Record UNII
IXA7C9ZN03
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
BROMPHENIRAMINE MALEATE
EP   MART.   MI   ORANGE BOOK   USP   USP-RS   VANDF   WHO-DD  
Common Name English
BIPHETAP COMPONENT BROMPHENIRAMINE MALEATE
Preferred Name English
BROMANATE DM COMPONENT BROMPHENIRAMINE MALEATE
Common Name English
BROMPHENIRAMINE MALEATE [MART.]
Common Name English
BROMPHENIRAMINE MALEATE [EP IMPURITY]
Common Name English
DIMETAPP COMPONENT BROMPHENIRAMINE MALEATE
Common Name English
Brompheniramine maleate [WHO-DD]
Common Name English
BROMATAPP COMPONENT BROMPHENIRAMINE MALEATE
Common Name English
DIMETANE
Brand Name English
2-PYRIDINEPROPANAMINE, .GAMMA.-(4-BROMOPHENYL)-N,N-DIMETHYL-, (±)-, (Z)-BUTENEDIOATE (1:1)
Systematic Name English
BROMPHENIRAMINE MALEATE [EP MONOGRAPH]
Common Name English
BROMPHENIRAMINE MALEATE [USP-RS]
Common Name English
DIMETANE-DC COMPONENT BROMPHENIRAMINE MALEATE
Common Name English
NSC-758652
Code English
BROMPHENIRAMINE MALEATE [USP MONOGRAPH]
Common Name English
MYPHETANE DC COMPONENT BROMPHENIRAMINE MALEATE
Common Name English
BROMANATE DC COMPONENT BROMPHENIRAMINE MALEATE
Common Name English
BROMPHENIRAMINE MALEATE [ORANGE BOOK]
Common Name English
BROMFED-DM COMPONENT BROMPHENIRAMINE MALEATE
Common Name English
BROMPHENIRAMINE MALEATE [VANDF]
Common Name English
(±)-2-P-BROMO-.ALPHA.-2-(DIMETHYLAMINO)ETHYLBENZYLPYRIDINE MALEATE (1:1)
Common Name English
BROMANATE COMPONENT BROMPHENIRAMINE MALEATE
Common Name English
DIMETANE-DX COMPONENT BROMPHENIRAMINE MALEATE
Common Name English
Classification Tree Code System Code
CFR 21 CFR 341.12
Created by admin on Mon Mar 31 18:45:17 GMT 2025 , Edited by admin on Mon Mar 31 18:45:17 GMT 2025
NCI_THESAURUS C29578
Created by admin on Mon Mar 31 18:45:17 GMT 2025 , Edited by admin on Mon Mar 31 18:45:17 GMT 2025
Code System Code Type Description
DAILYMED
IXA7C9ZN03
Created by admin on Mon Mar 31 18:45:17 GMT 2025 , Edited by admin on Mon Mar 31 18:45:17 GMT 2025
PRIMARY
CHEBI
3184
Created by admin on Mon Mar 31 18:45:17 GMT 2025 , Edited by admin on Mon Mar 31 18:45:17 GMT 2025
PRIMARY
NCI_THESAURUS
C47422
Created by admin on Mon Mar 31 18:45:17 GMT 2025 , Edited by admin on Mon Mar 31 18:45:17 GMT 2025
PRIMARY
FDA UNII
IXA7C9ZN03
Created by admin on Mon Mar 31 18:45:17 GMT 2025 , Edited by admin on Mon Mar 31 18:45:17 GMT 2025
PRIMARY
PUBCHEM
5281067
Created by admin on Mon Mar 31 18:45:17 GMT 2025 , Edited by admin on Mon Mar 31 18:45:17 GMT 2025
PRIMARY
ECHA (EC/EINECS)
213-562-9
Created by admin on Mon Mar 31 18:45:17 GMT 2025 , Edited by admin on Mon Mar 31 18:45:17 GMT 2025
PRIMARY
CAS
2664-17-7
Created by admin on Mon Mar 31 18:45:17 GMT 2025 , Edited by admin on Mon Mar 31 18:45:17 GMT 2025
NON-SPECIFIC STOICHIOMETRY
EVMPD
SUB00881MIG
Created by admin on Mon Mar 31 18:45:17 GMT 2025 , Edited by admin on Mon Mar 31 18:45:17 GMT 2025
PRIMARY
CAS
980-71-2
Created by admin on Mon Mar 31 18:45:17 GMT 2025 , Edited by admin on Mon Mar 31 18:45:17 GMT 2025
PRIMARY
EPA CompTox
DTXSID2052657
Created by admin on Mon Mar 31 18:45:17 GMT 2025 , Edited by admin on Mon Mar 31 18:45:17 GMT 2025
PRIMARY
RXCUI
142427
Created by admin on Mon Mar 31 18:45:17 GMT 2025 , Edited by admin on Mon Mar 31 18:45:17 GMT 2025
PRIMARY RxNorm
SMS_ID
100000088205
Created by admin on Mon Mar 31 18:45:17 GMT 2025 , Edited by admin on Mon Mar 31 18:45:17 GMT 2025
PRIMARY
RS_ITEM_NUM
1078008
Created by admin on Mon Mar 31 18:45:17 GMT 2025 , Edited by admin on Mon Mar 31 18:45:17 GMT 2025
PRIMARY
ChEMBL
CHEMBL811
Created by admin on Mon Mar 31 18:45:17 GMT 2025 , Edited by admin on Mon Mar 31 18:45:17 GMT 2025
PRIMARY
NSC
758652
Created by admin on Mon Mar 31 18:45:17 GMT 2025 , Edited by admin on Mon Mar 31 18:45:17 GMT 2025
PRIMARY
MERCK INDEX
m2723
Created by admin on Mon Mar 31 18:45:17 GMT 2025 , Edited by admin on Mon Mar 31 18:45:17 GMT 2025
PRIMARY Merck Index
DRUG BANK
DBSALT000940
Created by admin on Mon Mar 31 18:45:17 GMT 2025 , Edited by admin on Mon Mar 31 18:45:17 GMT 2025
PRIMARY
Related Record Type Details
Structure of BROMPHENIRAMINE MALEATE, (R)-
ENANTIOMER -> RACEMATE
Structure of DEXBROMPHENIRAMINE MALEATE
ENANTIOMER -> RACEMATE
Structure of BROMPHENIRAMINE
PARENT -> SALT/SOLVATE
Related Record Type Details
Structure of N-nitroso-desmethyl-brompheniramine
IMPURITY -> PARENT
Structure of CHLORPHENIRAMINE
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
Structure of PHENIRAMINE
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
Related Record Type Details
Structure of BROMPHENIRAMINE
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