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
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-
| 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 |
DescriptionSources: https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=e241d83e-996c-494d-b3fe-97f1ef4809edCurator's Comment: description was created based on several sources, including
https://www.drugs.com/mtm/brompheniramine.html
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.
Approval Year
Targets
| Primary Target | Pharmacology | Condition | Potency |
|---|---|---|---|
Target ID: CHEMBL231 |
Conditions
| Condition | Modality | Targets | Highest Phase | Product |
|---|---|---|---|---|
| Palliative | BROMFED-DM (BROMPHENIRAMINE MALEATE; DEXTROMETHORPHAN HYDROBROMIDE; PSEUDOEPHEDRINE HYDROCHLORIDE) Approved UseFor relief of coughs and upper respiratory symptoms, including nasal congestion, associated with allergy or the common cold. Launch Date1985 |
|||
| Palliative | Unknown Approved UseUnknown |
|||
| Palliative | Unknown Approved UseUnknown |
Cmax
| 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 |
T1/2
| 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 |
Overview
| CYP3A4 | CYP2C9 | CYP2D6 | hERG |
|---|---|---|---|
Drug as perpetrator
| Target | Modality | Activity | Metabolite | Clinical evidence |
|---|---|---|---|---|
| no [IC50 >100 uM] |
Drug as victim
| Target | Modality | Activity | Metabolite | Clinical evidence |
|---|---|---|---|---|
| likely | ||||
| no | ||||
| yes | ||||
| yes | ||||
| yes | ||||
| yes |
Tox targets
| Target | Modality | Activity | Metabolite | Clinical evidence |
|---|---|---|---|---|
PubMed
| Title | Date | PubMed |
|---|---|---|
| Profiling of a prescription drug library for potential renal drug-drug interactions mediated by the organic cation transporter 2. | 2011-07-14 |
|
| Commonly prescribed medications and potential false-positive urine drug screens. | 2010-08-15 |
|
| Determination of chlorpheniramine in human plasma by HPLC-ESI-MS/MS: application to a dexchlorpheniramine comparative bioavailability study. | 2010-07 |
|
| Treatment of congestion in upper respiratory diseases. | 2010-04-08 |
|
| Trace determination of pharmaceuticals and other wastewater-derived micropollutants by solid phase extraction and gas chromatography/mass spectrometry. | 2010-01-22 |
|
| Arvid Carlsson, and the story of dopamine. | 2010-01 |
|
| Acute cough: a diagnostic and therapeutic challenge. | 2009-12-16 |
|
| Halogenation effects of pheniramines on the complexation with beta-cyclodextrin. | 2009-10-15 |
|
| Comparison of chiral separation of basic drugs in capillary electrophoresis and liquid chromatography using neutral and negatively charged cyclodextrins. | 2009-07-10 |
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| A novel flow cytometric high throughput assay for a systematic study on molecular mechanisms underlying T cell receptor-mediated integrin activation. | 2009-06-25 |
|
| Pheniramines and oxidative burst of blood phagocytes during ischaemia/reperfusion. | 2009-04 |
|
| Protective effect of pheniramines against mesenteric ischaemia/reperfusion-induced injury. | 2009-04 |
|
| Enantioseparation of a novel "click" chemistry derived native beta-cyclodextrin chiral stationary phase for high-performance liquid chromatography. | 2009-03-20 |
|
| H1-antihistamines and oxidative burst of professional phagocytes. | 2009 |
|
| Transient receptor potential vanilloid-1-mediated calcium responses are inhibited by the alkylamine antihistamines dexbrompheniramine and chlorpheniramine. | 2008-12 |
|
| Cough and cold medication use by US children, 1999-2006: results from the slone survey. | 2008-08 |
|
| Drug-liposome distribution phenomena studied by capillary electrophoresis-frontal analysis. | 2008-08 |
|
| Uniformly sized molecularly imprinted polymers for d-chlorpheniramine: influence of a porogen on their morphology and enantioselectivity. | 2008-04-14 |
|
| Potentialities of ITP-CZE method with diode array detection for enantiomeric purity control of dexbrompheniramine in pharmaceuticals. | 2008-04-14 |
|
| The effect of achiral calixarenes on chiral separation of propranolol-HCl and brompheniramine maleate in capillary electrophoresis using cyclodextrin as chiral selector. | 2008-04 |
|
| Blockade of HERG K+ channel by an antihistamine drug brompheniramine requires the channel binding within the S6 residue Y652 and F656. | 2008-03 |
|
| Indirect fluorescent determination of selected nitro-aromatic and pharmaceutical compounds via UV-photolysis of 2-phenylbenzimidazole-5-sulfonate. | 2008-02-15 |
|
| Surface degradation of composite resins by acidic medicines and pH-cycling. | 2008-02-08 |
|
| Possibilities of column coupling electrophoresis provided with a fiber-based diode array detection in enantioselective analysis of drugs in pharmaceutical and clinical samples. | 2008-01-25 |
|
| Evaluation of enantioselective binding of basic drugs to plasma by ACE. | 2007-08 |
|
| Evaluation of enantioselective binding of antihistamines to human serum albumin by ACE. | 2007-08 |
|
| Enantiomeric quality control of antihistamines in pharmaceuticals by affinity electrokinetic chromatography with human serum albumin as chiral selector. | 2007-06-05 |
|
| First-generation H1 antihistamines found in pilot fatalities of civil aviation accidents, 1990-2005. | 2007-05 |
|
| Characterization of antihistamine-human serum protein interactions by capillary electrophoresis. | 2007-04-20 |
|
| Possible role of pseudoephedrine and other over-the-counter cold medications in the deaths of very young children. | 2007-03 |
|
| Medication administered to children from 0 to 7.5 years in the Avon Longitudinal Study of Parents and Children (ALSPAC). | 2007-02 |
|
| Extra- and intracellular formation of reactive oxygen species by human neutrophils in the presence of pheniramine, chlorpheniramine and brompheniramine. | 2006-12 |
|
| Electrophysiological effects of brompheniramine on cardiac ion channels and action potential. | 2006-12 |
|
| Optimization by factorial design of a capillary zone electrophoresis method for the simultaneous separation of antihistamines. | 2006-05-01 |
|
| Role of chemical structure in stereoselective recognition of beta-blockers and H1-antihistamines by human serum transferrin in capillary zone electrophoresis. | 2006-04 |
|
| Antiradical effects of antihistamines in human blood. Structure-activity relationship. | 2006-04 |
|
| Analysis of pharmaceutical preparations containing antihistamine drugs by micellar liquid chromatography. | 2006-02-13 |
|
| The combined luminol/isoluminol chemiluminescence method for differentiating between extracellular and intracellular oxidant production by neutrophils. | 2006 |
|
| Nimesulide-induced fixed drug eruption. | 2005-11-17 |
|
| Over-the-counter cold medications-postmortem findings in infants and the relationship to cause of death. | 2005-10 |
|
| Antihistamines in the treatment of dermatitis. | 2005-06-01 |
|
| Laboratory exposures to staphylococcal enterotoxin B. | 2004-09 |
|
| Retentivity and enantioselectivity of uniformly sized molecularly imprinted polymers for d-chlorpheniramine and -brompheniramine in hydro-organic mobile phases. | 2004-05-05 |
|
| Fatal cold medication intoxication in an infant. | 2003-10 |
|
| Spermine-induced negative inotropic effect in isolated rat heart, is mediated through the release of ATP. | 2003-07-01 |
|
| First do no harm: managing antihistamine impairment in patients with allergic rhinitis. | 2003-05 |
|
| Withdrawal symptoms after discontinuation of long-acting brompheniramine maleate. | 1994-12 |
|
| [Antimycobacterial antihistaminics]. | 1989-08 |
|
| Phenylpropanolamine and mental disturbances. | 1979-12-22 |
|
| Oral facial dyskinesia associated with prolonged use of antihistaminic decongestants. | 1975-09-04 |
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
| Substance Class |
Chemical
Created
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admin
on
Edited
Mon Mar 31 18:45:17 GMT 2025
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| Record UNII |
IXA7C9ZN03
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| Record Status |
Validated (UNII)
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CFR |
21 CFR 341.12
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NCI_THESAURUS |
C29578
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C47422
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m2723
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DBSALT000940
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| Related Record | Type | Details | ||
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ENANTIOMER -> RACEMATE | |||
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ENANTIOMER -> RACEMATE | |||
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PARENT -> SALT/SOLVATE |
| Related Record | Type | Details | ||
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IMPURITY -> PARENT |
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
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| Related Record | Type | Details | ||
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ACTIVE MOIETY |