Chlorpheniramine

Chlorphenamine

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	R06AB04 (WHO)
Legal status
Legal status	AU: S3 (Pharmacist only) UK: P (Pharmacy medicines) US: OTC (for oral forms)
Pharmacokinetic data
Bioavailability	25 to 50%
Protein binding	72%
Metabolism	Hepatic (CYP2D6)
Biological half-life	21–27 hours
Excretion	Renal
Identifiers
IUPAC name 3-(4-chlorophenyl)-N,N-dimethyl- 3-pyridin-2-yl-propan-1-amine
CAS Number	113-92-8 N
PubChem CID	2725
IUPHAR/BPS	1210
DrugBank	DB01114 Y
ChemSpider	2624 Y
UNII	3U6IO1965U
KEGG	D07398 Y
ChEBI	CHEBI:52010 Y
ChEMBL	CHEMBL505 Y
ECHA InfoCard	100.004.596
Chemical and physical data
Formula	C16H19ClN2
Molar mass	274.788 g/mol
3D model (Jmol)	Interactive image
Solubility in water	0.55 g/100 mL, liquid mg/mL (20 °C)
SMILES Clc1ccc(cc1)C(c2ncccc2)CCN(C)C
InChI InChI=1S/C16H19ClN2/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 Y Key:SOYKEARSMXGVTM-UHFFFAOYSA-N Y
NY (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.