DEXBROMPHENIRAMINE MALEATE

US Approved OTC

First approved in 1956

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C16H19BrN2.C4H4O4
Molecular Weight	435.312
Optical Activity	UNSPECIFIED
Defined Stereocenters	1 / 1
E/Z Centers	1
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

OC(=O)\C=C/C(O)=O.CN(C)CC[C@@H](C1=CC=C(Br)C=C1)C2=CC=CC=N2

InChI

InChIKey=SRGKFVAASLQVBO-DASCVMRKSA-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-/t15-;/m0./s1

HIDE SMILES / InChI

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

Molecular Formula	C16H19BrN2
Molecular Weight	319.239
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	1 / 1
E/Z Centers	0
Optical Activity	UNSPECIFIED

Description
Sources: https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=e241d83e-996c-494d-b3fe-97f1ef4809ed
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

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Histamine H1 receptor 315 Target ID: CHEMBL231 Sources: https://www.ncbi.nlm.nih.gov/pubmed/10212017	Antagonist 2778

Conditions

Condition	Modality	Highest Phase	Product
Common cold 58 Sources: https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=06db369d-09fe-4ca2-b98c-705356b7c403	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
Nasal congestion and inflammations 4 Sources: https://clinicaltrials.gov/ct2/show/NCT01393561	Palliative	Phase III 656	Unknown Approved Use Unknown
Rhinitis 20 Sources: https://clinicaltrials.gov/ct2/show/NCT01393561	Palliative	Phase III 656	Unknown Approved Use Unknown

C_max

Value	Dose	Co-administered	Analyte	Population
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

Value	Dose	Co-administered	Analyte	Population
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

T_1/2

Value	Dose	Co-administered	Analyte	Population
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

Vendor/Aggregator	ID	URL
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

Title	Date	PubMed
Oral facial dyskinesia associated with prolonged use of antihistaminic decongestants.	1975 Sep 4	239337
Phenylpropanolamine and mental disturbances.	1979 Dec 22-29	92706
[Antimycobacterial antihistaminics].	1989 Aug	2513793
Withdrawal symptoms after discontinuation of long-acting brompheniramine maleate.	1994 Dec	7857852
Update on medical treatment of ejaculatory disorders.	2002 Dec	12406365
Spermine-induced negative inotropic effect in isolated rat heart, is mediated through the release of ATP.	2003 Jul 1	12818376
First do no harm: managing antihistamine impairment in patients with allergic rhinitis.	2003 May	12743547
Antihistamines in the treatment of dermatitis.	2003 Nov-Dec	15926215
Fatal cold medication intoxication in an infant.	2003 Oct	14607011
Retentivity and enantioselectivity of uniformly sized molecularly imprinted polymers for d-chlorpheniramine and -brompheniramine in hydro-organic mobile phases.	2004 May 5	15093155
Laboratory exposures to staphylococcal enterotoxin B.	2004 Sep	15498154
Over-the-counter cold medications-postmortem findings in infants and the relationship to cause of death.	2005 Oct	16419411
Nimesulide-induced fixed drug eruption.	2005 Sep-Oct	16287549
The combined luminol/isoluminol chemiluminescence method for differentiating between extracellular and intracellular oxidant production by neutrophils.	2006	16805965
Role of chemical structure in stereoselective recognition of beta-blockers and H1-antihistamines by human serum transferrin in capillary zone electrophoresis.	2006 Apr	16609932
Antiradical effects of antihistamines in human blood. Structure-activity relationship.	2006 Apr	16547801
Extra- and intracellular formation of reactive oxygen species by human neutrophils in the presence of pheniramine, chlorpheniramine and brompheniramine.	2006 Dec	17159800
Electrophysiological effects of brompheniramine on cardiac ion channels and action potential.	2006 Dec	17010640
Analysis of pharmaceutical preparations containing antihistamine drugs by micellar liquid chromatography.	2006 Feb 13	16182504
Optimization by factorial design of a capillary zone electrophoresis method for the simultaneous separation of antihistamines.	2006 May 1	16549055
Characterization of antihistamine-human serum protein interactions by capillary electrophoresis.	2007 Apr 20	17339039
Evaluation of enantioselective binding of basic drugs to plasma by ACE.	2007 Aug	17661317
Evaluation of enantioselective binding of antihistamines to human serum albumin by ACE.	2007 Aug	17605150
Medication administered to children from 0 to 7.5 years in the Avon Longitudinal Study of Parents and Children (ALSPAC).	2007 Feb	17200835
Enantiomeric quality control of antihistamines in pharmaceuticals by affinity electrokinetic chromatography with human serum albumin as chiral selector.	2007 Jun 5	17512827
Possible role of pseudoephedrine and other over-the-counter cold medications in the deaths of very young children.	2007 Mar	17316256
First-generation H1 antihistamines found in pilot fatalities of civil aviation accidents, 1990-2005.	2007 May	17539447
The effect of achiral calixarenes on chiral separation of propranolol-HCl and brompheniramine maleate in capillary electrophoresis using cyclodextrin as chiral selector.	2008 Apr	18468383
Uniformly sized molecularly imprinted polymers for d-chlorpheniramine: influence of a porogen on their morphology and enantioselectivity.	2008 Apr 14	17644298
Potentialities of ITP-CZE method with diode array detection for enantiomeric purity control of dexbrompheniramine in pharmaceuticals.	2008 Apr 14	17618074
Cough and cold medication use by US children, 1999-2006: results from the slone survey.	2008 Aug	18676518
Drug-liposome distribution phenomena studied by capillary electrophoresis-frontal analysis.	2008 Aug	18651665
Transient receptor potential vanilloid-1-mediated calcium responses are inhibited by the alkylamine antihistamines dexbrompheniramine and chlorpheniramine.	2008 Dec	19085565
Indirect fluorescent determination of selected nitro-aromatic and pharmaceutical compounds via UV-photolysis of 2-phenylbenzimidazole-5-sulfonate.	2008 Feb 15	18371796
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	17905259
Surface degradation of composite resins by acidic medicines and pH-cycling.	2008 Jul-Aug	19089257
Blockade of HERG K+ channel by an antihistamine drug brompheniramine requires the channel binding within the S6 residue Y652 and F656.	2008 Mar	17516459
Pheniramines and oxidative burst of blood phagocytes during ischaemia/reperfusion.	2009 Apr	19271141
Protective effect of pheniramines against mesenteric ischaemia/reperfusion-induced injury.	2009 Apr	19271140
Comparison of chiral separation of basic drugs in capillary electrophoresis and liquid chromatography using neutral and negatively charged cyclodextrins.	2009 Jul 10	19481637
A novel flow cytometric high throughput assay for a systematic study on molecular mechanisms underlying T cell receptor-mediated integrin activation.	2009 Jun 25	19557182
Enantioseparation of a novel "click" chemistry derived native beta-cyclodextrin chiral stationary phase for high-performance liquid chromatography.	2009 Mar 20	19185873
Halogenation effects of pheniramines on the complexation with beta-cyclodextrin.	2009 Oct 15	19540697
Treatment of congestion in upper respiratory diseases.	2010 Apr 8	20463825
Trace determination of pharmaceuticals and other wastewater-derived micropollutants by solid phase extraction and gas chromatography/mass spectrometry.	2010 Jan 22	20015510
Profiling of a prescription drug library for potential renal drug-drug interactions mediated by the organic cation transporter 2.	2011 Jul 14	21599003

Patents

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 `Fri Dec 15 14:58:49 GMT 2023` Edited by `admin` on `Fri Dec 15 14:58:49 GMT 2023`
Record UNII	BPA9UT29BS
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

DEXBROMPHENIRAMINE MALEATE

Common Name

English

DEXBROMPHENIRAMINE MALEATE [USP MONOGRAPH]

Common Name

English

(+)-2-(P-BROMO-.ALPHA.-(2-(DIMETHYLAMINO)ETHYL)BENZYL)PYRIDINE MALEATE (1:1)

Common Name

English

DEXBROMPHENIRAMINE MALEATE COMPONENT OF BROMPHERIL

Common Name

English

DISOMER

Brand Name

English

BROMPHERIL COMPONENT DEXBROMPHENIRAMINE MALEATE

Common Name

English

BROMPHENIRAMINE D-FORM MALEATE [MI]

Common Name

English

DEXBROMPHENIRAMINE MALEATE [MART.]

Common Name

English

DEXBROMPHENIRAMINE MALEATE COMPONENT OF RESPORAL

Common Name

English

DRIXORAL PLUS COMPONENT DEXBROMPHENIRAMINE MALEATE

Common Name

English

DEXBROMPHENIRAMINE MALEATE COMPONENT OF DRIXORAL

Common Name

English

DEXBROMPHENIRAMINE MALEATE COMPONENT OF DISOBROM

Common Name

English

DISOPHROL COMPONENT DEXBROMPHENIRAMINE MALEATE

Common Name

English

BROMPHENIRAMINE D-FORM MALEATE

Common Name

English

DEXBROMPHENIRAMINE MALEATE [VANDF]

Common Name

English

DEXBROMPHENIRAMINE MALEATE [USP-RS]

Common Name

English

DISOBROM COMPONENT DEXBROMPHENIRAMINE MALEATE

Common Name

English

DRIXORAL COMPONENT DEXBROMPHENIRAMINE MALEATE

Common Name

English

DEXBROMPHENIRAMINE MALEATE [ORANGE BOOK]

Common Name

English

DEXBROMPHENIRAMINE MALEATE COMPONENT OF DRIXORAL PLUS

Common Name

English

2-PYRIDINEPROPANAMINE, G-(4-BROMOPHENYL)-N,N-DIMETHYL-, (S)-, (Z)-2-BUTENEDIOATE (1:1)

Common Name

English

Dexbrompheniramine maleate [WHO-DD]

Common Name

English

DEXBROMPHENIRAMINE MALEATE COMPONENT OF DISOPHROL

Common Name

English

RESPORAL COMPONENT DEXBROMPHENIRAMINE MALEATE

Common Name

English

Classification Tree Code System Code

CFR

21 CFR 341.12