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Chlorphenamine

Chlorphenamine
Chlorphenamine.svg
Clinical data
Trade names Chlor-Trimeton; Piriton
AHFS/Drugs.com Monograph
MedlinePlus a682543
Pregnancy
category
  • AU: A
  • US: B (No risk in non-human studies)
Routes of
administration
Oral, IV, IM, SC
ATC code
Legal status
Legal status
Pharmacokinetic data
Bioavailability 25 to 50%
Protein binding 72%
Metabolism Hepatic (CYP2D6)
Biological half-life 21–27 hours
Excretion Renal
Identifiers
CAS Number
PubChem CID
IUPHAR/BPS
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
ECHA InfoCard 100.004.596
Chemical and physical data
Formula C16H19ClN2
Molar mass 274.788 g/mol
3D model (Jmol)
Solubility in water 0.55 g/100 mL, liquid mg/mL (20 °C)
 NYesY (what is this?)  

Chlorphenamine (INN), also called chlorpheniramine (USAN and former BAN), commonly marketed in the form of chlorphenamine maleate, is a first-generation alkylamine antihistamine used in the prevention of the symptoms of allergic conditions such as rhinitis and urticaria. Its sedative effects are relatively weak compared to other first-generation antihistamines. Chlorphenamine is one of the most commonly used antihistamines in small-animal veterinary practice. Although not generally approved as an antidepressant or anti-anxiety medication, chlorphenamine appears to have these properties as well.

Chlorphenamine is part of a series of antihistamines including pheniramine (Naphcon) and its halogenated derivatives and others including fluorpheniramine, dexchlorpheniramine (Polaramine), brompheniramine (Dimetapp), dexbrompheniramine (Drixoral), deschlorpheniramine, triprolidine (Actifed), and iodopheniramine.

The halogenated alkylamine antihistamines all exhibit optical isomerism, and chlorphenamine in the indicated products is racemic chlorphenamine maleate, whereas dexchlorpheniramine is the dextrorotary stereoisomer.


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