Brompheniramine
Encyclopedia
Brompheniramine commonly marketed as its salt brompheniramine maleate is an antihistamine
drug of the propylamine
(alkylamine) class. It is readily available over the counter
and is indicated for the treatment of the symptoms of the common cold
and allergic rhinitis
, such as runny nose, itchy eyes, watery eyes, and sneezing. It is a first-generation antihistamine.
Brompheniramine is part of a series of antihistamines including pheniramine
(Naphcon) and its halogenated derivatives and others including fluorpheniramine, chlorpheniramine, dexchlorpheniramine
(Polaramine), deschlorpheniramine, dipheniramine (also known as triprolidine
with the trade name Actifed), and iodopheniramine.
The halogenated alkylamine antihistamines all exhibit optical isomerism and brompheniramine products contain racemic brompheniramine maleate whereas dexbrompheniramine
(Drixoral) is the dextrorotary (right-handed) stereoisomer.
Brompheniramine has antidepressant
properties, inhibiting reuptake
of the neurotransmitter
serotonin
. Based on this knowledge, Arvid Carlsson
and his colleagues, working at the Swedish
company Astra AB
, were able to derive the first marketed selective serotonin reuptake inhibitor
, zimelidine
, from brompheniramine.
Like other agents of this type, brompheniramine also has analgesic-sparing (potentiating) effects on opioid analgesics, commonly reducing codeine, dihydrocodeine, and hydrocodone requirements by 10 to 35 percent.
of histamine H1 receptors. It also functions as a moderately effective anticholinergic
agent, and is likely an antimuscarinic agent similar to other common antihistamines such as diphenhydramine
.
Brompheniramine is metabolised by cytochrome P450s.
The halogenated alkylamine antihistamines all exhibit optic isomerism and brompheniramine products contain racaemic brompheniramine maleate whereas dexbrompheniramine
(Drixoral) is the dextrorotary (right-handed) stereoisomer.
Antihistamine
An H1 antagonist is a histamine antagonist of the H1 receptor that serves to reduce or eliminate effects mediated by histamine, an endogenous chemical mediator released during allergic reactions...
drug of the propylamine
Propylamine
Propylamine, also known as n-propylamine, is an amine with the chemical formula C3H9N.Propylamine is a weak base with its Kb equaling 4.7 × 10-4.-Preparation:...
(alkylamine) class. It is readily available over the counter
Over-the-counter drug
Over-the-counter drugs are medicines that may be sold directly to a consumer without a prescription from a healthcare professional, as compared to prescription drugs, which may be sold only to consumers possessing a valid prescription...
and is indicated for the treatment of the symptoms of the common cold
Common cold
The common cold is a viral infectious disease of the upper respiratory system, caused primarily by rhinoviruses and coronaviruses. Common symptoms include a cough, sore throat, runny nose, and fever...
and allergic rhinitis
Allergic rhinitis
Allergic rhinitis, also known as pollenosis or hay fever, is an allergic inflammation of the nasal airways.It occurs when an allergen, such as pollen, dust or animal dander is inhaled by an individual with a sensitized immune system...
, such as runny nose, itchy eyes, watery eyes, and sneezing. It is a first-generation antihistamine.
Brompheniramine is part of a series of antihistamines including pheniramine
Pheniramine
Pheniramine is an antihistamine with anticholinergic properties used to treat allergic conditions such as hay fever or urticaria. It has relatively strong sedative effects, and may sometimes be used off-label as an over-the-counter sleeping pill in a similar manner to other sedating antihistamines...
(Naphcon) and its halogenated derivatives and others including fluorpheniramine, chlorpheniramine, dexchlorpheniramine
Dexchlorpheniramine
Dexchlorpheniramine is an antihistamine with anticholinergic properties used to treat allergic conditions such as hay fever or urticaria...
(Polaramine), deschlorpheniramine, dipheniramine (also known as triprolidine
Triprolidine
Triprolidine is an over-the-counter antihistamine with anticholinergic properties. It is used to combat the symptoms associated with allergies and is sometimes combined with other cold medications designed to provide general relief for flu-like symptoms. Like many over-the-counter antihistamines,...
with the trade name Actifed), and iodopheniramine.
The halogenated alkylamine antihistamines all exhibit optical isomerism and brompheniramine products contain racemic brompheniramine maleate whereas dexbrompheniramine
Dexbrompheniramine
Dexbrompheniramine is an antihistamine with anticholinergic properties used to treat allergic conditions such as hay fever or urticaria. It is the pharmacologically active dextrorotatory isomer of brompheniramine...
(Drixoral) is the dextrorotary (right-handed) stereoisomer.
Brompheniramine has antidepressant
Antidepressant
An antidepressant is a psychiatric medication used to alleviate mood disorders, such as major depression and dysthymia and anxiety disorders such as social anxiety disorder. According to Gelder, Mayou &*Geddes people with a depressive illness will experience a therapeutic effect to their mood;...
properties, inhibiting reuptake
Reuptake
Reuptake, or re-uptake, is the reabsorption of a neurotransmitter by a neurotransmitter transporter of a pre-synaptic neuron after it has performed its function of transmitting a neural impulse....
of the neurotransmitter
Neurotransmitter
Neurotransmitters are endogenous chemicals that transmit signals from a neuron to a target cell across a synapse. Neurotransmitters are packaged into synaptic vesicles clustered beneath the membrane on the presynaptic side of a synapse, and are released into the synaptic cleft, where they bind to...
serotonin
Serotonin
Serotonin or 5-hydroxytryptamine is a monoamine neurotransmitter. Biochemically derived from tryptophan, serotonin is primarily found in the gastrointestinal tract, platelets, and in the central nervous system of animals including humans...
. Based on this knowledge, Arvid Carlsson
Arvid Carlsson
Arvid Carlsson is a Swedish scientist who is best known for his work with the neurotransmitter dopamine and its effects in Parkinson's disease...
and his colleagues, working at the Swedish
Sweden
Sweden , officially the Kingdom of Sweden , is a Nordic country on the Scandinavian Peninsula in Northern Europe. Sweden borders with Norway and Finland and is connected to Denmark by a bridge-tunnel across the Öresund....
company Astra AB
AstraZeneca
AstraZeneca plc is a global pharmaceutical and biologics company headquartered in London, United Kingdom. It is the world's seventh-largest pharmaceutical company measured by revenues and has operations in over 100 countries...
, were able to derive the first marketed selective serotonin reuptake inhibitor
Selective serotonin reuptake inhibitor
Selective serotonin re-uptake inhibitors or serotonin-specific reuptake inhibitor are a class of compounds typically used as antidepressants in the treatment of depression, anxiety disorders, and some personality disorders. The efficacy of SSRIs is disputed...
, zimelidine
Zimelidine
Zimelidine was the first selective serotonin reuptake inhibitor antidepressant to be marketed. It is a pyridylallylamine, and is structurally different from other antidepressants....
, from brompheniramine.
Like other agents of this type, brompheniramine also has analgesic-sparing (potentiating) effects on opioid analgesics, commonly reducing codeine, dihydrocodeine, and hydrocodone requirements by 10 to 35 percent.
Pharmacology
Brompheniramine works by acting as an antagonistCompetitive inhibition
Competitive inhibition is a form of enzyme inhibition where binding of the inhibitor to the active site on the enzyme prevents binding of the substrate and vice versa.-Mechanism:...
of histamine H1 receptors. It also functions as a moderately effective anticholinergic
Anticholinergic
An anticholinergic agent is a substance that blocks the neurotransmitter acetylcholine in the central and the peripheral nervous system. An example of an anticholinergic is dicycloverine, and the classic example is atropine....
agent, and is likely an antimuscarinic agent similar to other common antihistamines such as diphenhydramine
Diphenhydramine
Diphenhydramine hydrochloride is a first-generation antihistamine possessing anticholinergic, antitussive, antiemetic, and sedative properties which is mainly used to treat allergies. Like most other first-generation antihistamines, the drug also has a powerful hypnotic effect, and for this reason...
.
Brompheniramine is metabolised by cytochrome P450s.
The halogenated alkylamine antihistamines all exhibit optic isomerism and brompheniramine products contain racaemic brompheniramine maleate whereas dexbrompheniramine
Dexbrompheniramine
Dexbrompheniramine is an antihistamine with anticholinergic properties used to treat allergic conditions such as hay fever or urticaria. It is the pharmacologically active dextrorotatory isomer of brompheniramine...
(Drixoral) is the dextrorotary (right-handed) stereoisomer.
Side effects
Its effects on the cholinergic system may include side-effects such as drowsiness, sedation, dry mouth, dry throat, blurred vision, and increased heart rate.Chemistry
Brompheniramine, 3-(p-bromophenyl)-3-(2-pyridyl)propyldimethylamine, is an analog of chlorpheniramine. The only difference is that the chlorine atom in the benzene ring is replaced with a bromine atom. It is also synthesized in an analogous manner.- L.A. Walter, (1962).
- L.A. Walter, (1962).