Details
| Stereochemistry | RACEMIC |
| Molecular Formula | C16H19BrN2 |
| Molecular Weight | 319.2396 |
| Optical Activity | ( + / - ) |
| Defined Stereocenters | 0 / 1 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
CN(C)CCC(c1ccc(cc1)Br)c2ccccn2
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
| Molecular Formula | C16H19BrN2 |
| Molecular Weight | 319.2396 |
| Charge | 0 |
| Count |
|
| Stereochemistry | RACEMIC |
| Additional Stereochemistry | No |
| Defined Stereocenters | 0 / 1 |
| E/Z Centers | 0 |
| Optical Activity | ( + / - ) |
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 Date4.86950404E11 |
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| Palliative | Unknown Approved UseUnknown |
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| 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 |
PubMed
| Title | Date | PubMed |
|---|---|---|
| Oral facial dyskinesia accociated with prolonged use of antihistaminic decongestants. | 1975 Sep 4 |
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| Phenylpropanolamine and mental disturbances. | 1979 Dec 22-29 |
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| [Antimycobacterial antihistaminics]. | 1989 Aug |
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| Toxicity of over-the-counter cough and cold medications. | 2001 Sep |
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| Update on medical treatment of ejaculatory disorders. | 2002 Dec |
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| Involvement of calmodulin inhibition in analgesia induced with low doses of intrathecal trifluoperazine. | 2002 Feb |
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| Spermine-induced negative inotropic effect in isolated rat heart, is mediated through the release of ATP. | 2003 Jul 1 |
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| First do no harm: managing antihistamine impairment in patients with allergic rhinitis. | 2003 May |
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| Antihistamines in the treatment of dermatitis. | 2003 Nov-Dec |
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| Retentivity and enantioselectivity of uniformly sized molecularly imprinted polymers for d-chlorpheniramine and -brompheniramine in hydro-organic mobile phases. | 2004 May 5 |
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| Role of chemical structure in stereoselective recognition of beta-blockers and H1-antihistamines by human serum transferrin in capillary zone electrophoresis. | 2006 Apr |
|
| Analysis of pharmaceutical preparations containing antihistamine drugs by micellar liquid chromatography. | 2006 Feb 13 |
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| Optimization by factorial design of a capillary zone electrophoresis method for the simultaneous separation of antihistamines. | 2006 May 1 |
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| Characterization of antihistamine-human serum protein interactions by capillary electrophoresis. | 2007 Apr 20 |
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| Evaluation of enantioselective binding of basic drugs to plasma by ACE. | 2007 Aug |
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| Evaluation of enantioselective binding of antihistamines to human serum albumin by ACE. | 2007 Aug |
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| Medication administered to children from 0 to 7.5 years in the Avon Longitudinal Study of Parents and Children (ALSPAC). | 2007 Feb |
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| Enantiomeric quality control of antihistamines in pharmaceuticals by affinity electrokinetic chromatography with human serum albumin as chiral selector. | 2007 Jun 5 |
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| Possible role of pseudoephedrine and other over-the-counter cold medications in the deaths of very young children. | 2007 Mar |
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| First-generation H1 antihistamines found in pilot fatalities of civil aviation accidents, 1990-2005. | 2007 May |
|
| 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 |
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| 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 |
|
| Protective effect of pheniramines against mesenteric ischaemia/reperfusion-induced injury. | 2009 Apr |
|
| Comparison of chiral separation of basic drugs in capillary electrophoresis and liquid chromatography using neutral and negatively charged cyclodextrins. | 2009 Jul 10 |
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| Enantioseparation of a novel "click" chemistry derived native beta-cyclodextrin chiral stationary phase for high-performance liquid chromatography. | 2009 Mar 20 |
|
| 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 |
|
| Profiling of a prescription drug library for potential renal drug-drug interactions mediated by the organic cation transporter 2. | 2011 Jul 14 |
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
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on
Fri Jun 25 22:57:46 UTC 2021
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| Record UNII |
H57G17P2FN
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| Record Status |
Validated (UNII)
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WHO-VATC |
QR06AB01
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LIVERTOX |
124
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WHO-VATC |
QR06AB51
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NCI_THESAURUS |
C29578
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WHO-ATC |
R06AB01
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WHO-ATC |
R06AB51
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D001977
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86-22-6
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BROMPHENIRAMINE
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6834
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C61655
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408
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CHEMBL811
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3017
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DB00835
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32188-07-1
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201-657-8
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H57G17P2FN
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86-22-6
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156428-33-0
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7133
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SUB05924MIG
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M2723
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1767
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770
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Brompheniramine
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BINDER->LIGAND |
BINDING
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ENANTIOMER -> RACEMATE | |||
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ENANTIOMER -> RACEMATE | |||
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TARGET -> INHIBITOR | |||
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SALT/SOLVATE -> PARENT |
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ACTIVE MOIETY |
| Name | Property Type | Amount | Referenced Substance | Defining | Parameters | References |
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| Volume of Distribution | PHARMACOKINETIC |
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| Biological Half-life | PHARMACOKINETIC |
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