Dexchlorpheniramine

Dexchlorpheniramine
Clinical data
Trade names	Chlor-trimeton, Polaramine
AHFS/Drugs.com	Monograph
MedlinePlus	a682543
Routes of; administration	Oral, Intravenous
ATC code	R06AB02 (WHO) ;
Legal status
Legal status	AU: S3 (Pharmacist only);
Pharmacokinetic data
Elimination half-life	21 to 27 hours
Identifiers
	IUPAC name (3S)-3-(4-chlorophenyl)-N,N-dimethyl-3-pyridin-3-ylpropan-1-amine;
CAS Number	25523-97-1 ;
PubChem CID	33036;
IUPHAR/BPS	1210;
DrugBank	DB13679 ;
ChemSpider	30576 ;
UNII	3Q9Q0B929N;
KEGG	D07803 ;
ChEBI	CHEBI:4464 ;
ChEMBL	ChEMBL1201353 ;
CompTox Dashboard (EPA)	DTXSID50180225 ;
ECHA InfoCard	100.042.779
Chemical and physical data
Formula	C16H19ClN2
Molar mass	274.79 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES Clc1ccc(cc1)[C@@H](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/t15-/m0/s1 ; Key:SOYKEARSMXGVTM-HNNXBMFYSA-N ;
	(verify)

Dexchlorpheniramine (trade name Polaramine) is an antihistamine with anticholinergic properties used to treat allergic conditions such as hay fever or urticaria.^[1]^[2] It is the pharmacologically active dextrorotatory isomer of chlorpheniramine.

It came into medical use in 1959 and was patented in 1962.^[3]

Pharmacology

Dexchlorpheniramine is an antihistamine, or an antagonist of the histamine H₁ receptor. A study found that dexchlorpheniramine had a K_i value of 20 to 30 μM for the muscarinic acetylcholine receptors using rat brain tissue.^[4]

References

^ Theunissen EL, Vermeeren A, Ramaekers JG (January 2006). "Repeated-dose effects of mequitazine, cetirizine and dexchlorpheniramine on driving and psychomotor performance". British Journal of Clinical Pharmacology. 61 (1): 79–86. doi:10.1111/j.1365-2125.2005.02524.x. PMC 1884990. PMID 16390354.
^ Ortíz San Román L, Sanavia Morán E, Campos Domínguez M, Peinador García MM (December 2013). "[Anticholinergic syndrome due to dexchlorpheniramine as a cause of urinary retention]". Anales de Pediatria. 79 (6): 400–401. doi:10.1016/j.anpedi.2013.02.014. PMID 23680058.
^ Fischer J, Ganellin CR (2006). Analogue-based Drug Discovery. John Wiley & Sons. p. 547. ISBN 9783527607495.
^ Yamamura HI, Snyder SH (May 1974). "Muscarinic cholinergic binding in rat brain". Proceedings of the National Academy of Sciences of the United States of America. 71 (5): 1725–1729. Bibcode:1974PNAS...71.1725Y. doi:10.1073/pnas.71.5.1725. PMC 388311. PMID 4151898.

External links

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[pmid16390354-1] Theunissen EL, Vermeeren A, Ramaekers JG (January 2006). "Repeated-dose effects of mequitazine, cetirizine and dexchlorpheniramine on driving and psychomotor performance". British Journal of Clinical Pharmacology. 61 (1): 79–86. doi:10.1111/j.1365-2125.2005.02524.x. PMC 1884990. PMID 16390354.

[pmid23680058-2] Ortíz San Román L, Sanavia Morán E, Campos Domínguez M, Peinador García MM (December 2013). "[Anticholinergic syndrome due to dexchlorpheniramine as a cause of urinary retention]". Anales de Pediatria. 79 (6): 400–401. doi:10.1016/j.anpedi.2013.02.014. PMID 23680058.

[Fis2006-3] Fischer J, Ganellin CR (2006). Analogue-based Drug Discovery. John Wiley & Sons. p. 547. ISBN 9783527607495.

[pmid4151898-4] Yamamura HI, Snyder SH (May 1974). "Muscarinic cholinergic binding in rat brain". Proceedings of the National Academy of Sciences of the United States of America. 71 (5): 1725–1729. Bibcode:1974PNAS...71.1725Y. doi:10.1073/pnas.71.5.1725. PMC 388311. PMID 4151898.

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v t e Antihistamines (R06)
Benzimidazoles (*)	Astemizole Azelastine Bilastine Emedastine Mizolastine Talastine
Diarylmethanes	Diarylmethoxyalkylamines: Bromazine (bromodiphenhydramine) Carbinoxamine Chlorphenoxamine Clemastine Diphenhydramine (+naproxen) Diphenylpyraline Doxylamine Ebastine Orphenadrine Diphenylmethanolpiperidines: Fexofenadine Terfenadine Diphenylmethylpiperazines: Buclizine Cetirizine Levocetirizine Chlorcyclizine Cinnarizine Cyclizine Etodroxizine Hydroxyzine Meclizine Oxatomide Phenylpyridinylpropanamines: Brompheniramine Chlorphenamine Dexbrompheniramine (+pseudoephedrine) Dexchlorpheniramine (+betamethasone) Pheniramine Others: Acrivastine Bamipine Dimetindene Phenyltoloxamine Pyrrobutamine Quifenadine Triprolidine
Ethylenediamines	Antazoline Chloropyramine Histapyrrodine Mepyramine (pyrilamine) Methapyrilene Phenbenzamine Thenalidine Tripelennamine (pyribenzamine)
Tricyclics	Dibenzocycloheptenes: Antidepressants (e.g., amitriptyline) Azatadine Cyproheptadine Deptropine Desloratadine Ketotifen Loratadine Rupatadine Phenothiazines: Alimemazine Fenethazine Hydroxyethylpromethazine Isothipendyl Mequitazine Methdilazine Oxomemazine Promethazine Others: Antidepressants (e.g., doxepin, mirtazapine, trimipramine) Epinastine Latrepirdine Mebhydrolin Olopatadine Perlapine Phenindamine Pimethixene
Others	Phenylpiperazines: Antidepressants (e.g., trazodone) Phenbenzamine
For topical use	Bamipine Chloropyramine Chlorphenoxamine Clemastine Dimetindene Diphenhydramine Doxepin Isothipendyl Mepyramine (pyrilamine) Promethazine