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Dexbrompheniramine

Dexbrompheniramine structure

CAS No:
132-21-8
Formula:
C16H19BrN2
Chemical Name:
Dexbrompheniramine
Synonyms:
2-Pyridinepropanamine,γ-(4-bromophenyl)-N,N-dimethyl-,(γS)-;Pyridine,2-[p-bromo-α-[2-(dimethylamino)ethyl]benzyl]-,(S)-;2-Pyridinepropanamine,γ-(4-bromophenyl)-N,N-dimethyl-,(S)-;(γS)-γ-(4-Bromophenyl)-N,N-dimethyl-2-pyridinepropanamine;(+)-2-[p-Bromo-α-[2-(dimethylamino)ethyl]benzyl]pyridine;Dexbrompheniramine;(+)-Parabromdylamine;d-Brompheniramine;(+)-Brompheniramine;(S)-Brompheniramine;2-Pyridinepropanamine γ-(4-bromophenyl)-N,N-dimethyl-,(γS)-;156428-34-1
Categories:
Active Pharmaceutical Ingredients > Antiallergic Drugs

Description

ChEBI: The (pharmacologically active) (S)-(+)-enantiomer of brompheniramine. A histamine H1 receptor antagonist, it is used (commonly as its maleate salt) for the symptomatic relief of allergic conditions, including rhinitis nd conjunctivitis.

Solid

Dexbrompheniramine is the (pharmacologically active) (S)-(+)-enantiomer of brompheniramine. A histamine H1 receptor antagonist, it is used (commonly as its maleate salt) for the symptomatic relief of allergic conditions, including rhinitis and conjunctivitis. It has a role as a H1-receptor antagonist and an anti-allergic agent.|Dexbrompheniramine maleate is an antihistamine agent that is used for the treatment of allergic conditions, such as hay fever or urticaria.|Brompheniramine and chlorpheniramine maleate are first generation antihistamines that are widely used to treat symptoms of allergic rhinitis and the common cold. Clinically apparent liver injury from brompheniramine or chlorpheniramine must be exceeding rare, if it occurs at all.|Dexbrompheniramine is an alkylamine derivative with anticholinergic and sedative properties. Dexbrompheniramine is a histamine H1-receptor antagonist that competes with histamine for the H1-receptor sites on effector cells in the gastrointestinal tract, blood vessels and respiratory tract. The antagonistic action of this agent blocks the activities of endogenous histamine, which subsequently leads to temporary relief from the negative histamine-mediated symptoms of allergic reaction such as bronchoconstriction, vasodilation, increased capillary permeability and spasmodic contractions of gastrointestinal smooth muscle.

Dexbrompheniramine Basic Attributes

Molecular Weight：

319.24

Exact Mass：

319.24

EC Number：

201-657-8

UNII：

75T64B71RP

DSSTox ID：

DTXSID8022905

NCI Thesaurus Code：

C61705

ATC Code：

R - Respiratory system

Characteristics

PSA：

16.1

XLogP3：

3.4

Appearance：

Solid

Density：

1.265g/cm3

Melting Point：

113-115

Boiling Point：

147-152 °C @ Press: 0.5 Torr

Flash Point：

197.5ºC

Refractive Index：

1.577

Water Solubility：

1.27e-02 g/L

Storage Conditions：

Preparations containing brompheniramine maleate generally should be stored in tight, light-resistant containers at a controlled room temperature between 15 - 30 deg C.

Vapor Pressure：

4.63X10-5 mm Hg at 25 deg C (est)

Specific rotation：

D25 +42.7° (c = 1 in DMF)

Safety Information

Stability/Shelf Life：

SENSITIVE TO LIGHT /BROMPHENIIRAMINE MALEATE/

Toxicity

Toxicity Summary：

Signs of an overdose include fast or irregular heartbeat, mental or mood changes, tightness in the chest, and unusual tiredness or weakness.

Hepatotoxicity：

Despite widespread use, the first generation antihistamines such as brompheniramine and chlorpheniramine have rarely been linked to liver test abnormalities or to clinically apparent liver injury. A single case report of clinically apparent liver injury with jaundice attributed to dexchlorpheniramine was reported from France. The time to onset was 10 days, and the clinical presentation resembled acute viral hepatitis, with marked elevations in serum aminotransferase levels and jaundice. Recovery was rapid and complete, but jaundice and hepatitis recurred within 10 days of restarting. Immunoallergic features (rash, fever, eosinophilia) were absent as were autoantibodies. Interestingly, the patient tolerated other antihistamines (cetirizine) without difficulty.

Drug Information

Drug Indication：

For treatment and relief of symptoms of allergies, hay fever, and colds

LiverTox Summary：

Brompheniramine and chlorpheniramine maleate are first generation antihistamines that are widely used to treat symptoms of allergic rhinitis and the common cold. Clinically apparent liver injury from brompheniramine or chlorpheniramine must be exceeding rare, if it occurs at all.

Drug Classes：

Antihistamines

Pharmacology：

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. Histamine, acting on H₁-receptors, produces pruritis, vasodilatation, hypotension, flushing, headache, tachycardia, and bronchoconstriction. Histamine also increases vascular permeability and potentiates pain. Dexbrompheniramine is a histamine H1 antagonist (or more correctly, an inverse histamine agonist) 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.

MeSH：

Drugs that selectively bind to but do not activate histamine H1 receptors, thereby blocking the actions of endogenous histamine. Included here are the classical antihistaminics that antagonize or prevent the action of histamine mainly in immediate hypersensitivity. They act in the bronchi, capillaries, and some other smooth muscles, and are used to prevent or allay motion sickness, seasonal rhinitis, and allergic dermatitis and to induce somnolence. The effects of blocking central nervous system H1 receptors are not as well understood. (See all compounds classified as Histamine H1 Antagonists.)

Absorption：

Antihistamines are well absorbed from the gastrointestinal tract after oral administration.

Metabolism/Metabolites：

Hepatic (cytochrome P-450 system), some renal.

Biological Half-Life：

25 hours

Mechanism of Action：

Dexbrompheniramine competitively binds to the histamine H₁-receptor. It competes with histamine for the normal H₁-receptor sites on effector cells of the gastrointestinal tract, blood vessels and respiratory tract. This blocks the action of endogenous histamine, which subsequently leads to temporary relief of the negative symptoms brought on by histamine.

MeSH Entry Terms：

dexbrompheniramine

Dexbrompheniramine Use and Manufacturing

Uses

Antihistaminic.

Use Classification：

Human Drugs -> FDA Approved Drug Products with Therapeutic Equivalence Evaluations (Orange Book) -> Active Ingredients

Computed Properties

Molecular Weight:319.24
XLogP3:3.5
Hydrogen Bond Acceptor Count:2
Rotatable Bond Count:5
Exact Mass:318.07316
Monoisotopic Mass:318.07316
Topological Polar Surface Area:16.1
Heavy Atom Count:19
Complexity:249
Defined Atom Stereocenter Count:1
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes