Details
Stereochemistry | RACEMIC |
Molecular Formula | C16H19BrN2 |
Molecular Weight | 319.239 |
Optical Activity | ( + / - ) |
Defined Stereocenters | 0 / 1 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
CN(C)CCC(C1=CC=C(Br)C=C1)C2=CC=CC=N2
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 | 319.239 |
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 |
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Target ID: CHEMBL231 Sources: https://www.ncbi.nlm.nih.gov/pubmed/10212017 |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
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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 |
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Palliative | Unknown Approved UseUnknown |
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Palliative | Unknown Approved UseUnknown |
Cmax
Value | Dose | Co-administered | Analyte | Population |
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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 |
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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 | ||||
Sources: https://pubmed.ncbi.nlm.nih.gov/406849/ |
yes |
Tox targets
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
PubMed
Title | Date | PubMed |
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Phenylpropanolamine and mental disturbances. | 1979 Dec 22-29 |
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[Antimycobacterial antihistaminics]. | 1989 Aug |
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Withdrawal symptoms after discontinuation of long-acting brompheniramine maleate. | 1994 Dec |
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pH-independent large-volume sample stacking of positive or negative analytes in capillary electrophoresis. | 2001 Jan |
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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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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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Laboratory exposures to staphylococcal enterotoxin B. | 2004 Sep |
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Nimesulide-induced fixed drug eruption. | 2005 Sep-Oct |
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Antiradical effects of antihistamines in human blood. Structure-activity relationship. | 2006 Apr |
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Extra- and intracellular formation of reactive oxygen species by human neutrophils in the presence of pheniramine, chlorpheniramine and brompheniramine. | 2006 Dec |
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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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Potentialities of ITP-CZE method with diode array detection for enantiomeric purity control of dexbrompheniramine in pharmaceuticals. | 2008 Apr 14 |
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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
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/9578932
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
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H57G17P2FN
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Brompheniramine
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Related Record | Type | Details | ||
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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 |
Related Record | Type | Details | ||
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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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