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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 of DEXBROMPHENIRAMINE MALEATE

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

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

1985
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 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
Toxicity of over-the-counter cough and cold medications.
2001 Sep
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
Antihistamines in the treatment of dermatitis.
2003 Nov-Dec
Fatal cold medication intoxication in an infant.
2003 Oct
Laboratory exposures to staphylococcal enterotoxin B.
2004 Sep
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
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
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
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
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
Pheniramines and oxidative burst of blood phagocytes during ischaemia/reperfusion.
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
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

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.
Name Type Language
DEXBROMPHENIRAMINE MALEATE
MART.   ORANGE BOOK   USP   USP-RS   VANDF   WHO-DD  
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
MI  
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
Created by admin on Fri Dec 15 14:58:49 GMT 2023 , Edited by admin on Fri Dec 15 14:58:49 GMT 2023
NCI_THESAURUS C29578
Created by admin on Fri Dec 15 14:58:49 GMT 2023 , Edited by admin on Fri Dec 15 14:58:49 GMT 2023
Code System Code Type Description
CAS
2391-03-9
Created by admin on Fri Dec 15 14:58:49 GMT 2023 , Edited by admin on Fri Dec 15 14:58:49 GMT 2023
PRIMARY
MESH
C015121
Created by admin on Fri Dec 15 14:58:49 GMT 2023 , Edited by admin on Fri Dec 15 14:58:49 GMT 2023
PRIMARY
ECHA (EC/EINECS)
219-236-2
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PRIMARY
DRUG BANK
DBSALT001411
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PRIMARY
EVMPD
SUB01626MIG
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PRIMARY
MERCK INDEX
m2723
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PRIMARY Merck Index
RS_ITEM_NUM
1178002
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PRIMARY
SMS_ID
100000087764
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PRIMARY
DAILYMED
BPA9UT29BS
Created by admin on Fri Dec 15 14:58:49 GMT 2023 , Edited by admin on Fri Dec 15 14:58:49 GMT 2023
PRIMARY
ChEMBL
CHEMBL1201287
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PRIMARY
NCI_THESAURUS
C61706
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PRIMARY
PUBCHEM
6433334
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PRIMARY
FDA UNII
BPA9UT29BS
Created by admin on Fri Dec 15 14:58:49 GMT 2023 , Edited by admin on Fri Dec 15 14:58:49 GMT 2023
PRIMARY
RXCUI
48936
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PRIMARY RxNorm
EPA CompTox
DTXSID6047818
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PRIMARY