Chlorpheniramine Trade names Chlor-trimeton AHFS /Drugs.com Monograph MedlinePlus a682543 Routes of Oral ATC code Legal status
(3S )-3-(4-chlorophenyl)-N ,N -dimethyl-3-pyridin-3-ylpropan-1-amine
CAS Number PubChem CID IUPHAR/BPS DrugBank ChemSpider UNII KEGG ChEBI ChEMBL CompTox Dashboard (EPA ) ECHA InfoCard 100.042.779 Formula C 16 H 19 Cl N 2 Molar mass −1 3D model (JSmol )
Clc1ccc(cc1)[C@@H](c2ncccc2)CCN(C)C
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
Y Key:SOYKEARSMXGVTM-HNNXBMFYSA-N
Y
Dexchlorpheniramine (trade name Polaramine ) is an antihistamine with anticholinergic properties used to treat allergic conditions such as hay fever or urticaria .[1] [2] 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 Ki value of 20 to 30 μM for the muscarinic acetylcholine receptors using rat brain tissue.[4]
References [ ]
^ Theunissen, E. L.; Vermeeren, A.; Ramaekers, J. G. (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, M. M. (2013). "Síndrome anticolinérgico por dexclorfeniramina como causa de retención urinaria". Anales de Pediatría . 79 (6): 400–1. doi :10.1016/j.anpedi.2013.02.014 . PMID 23680058 . ^ Fischer, Jnos; Ganellin, C. Robin (2006). Analogue-based Drug Discovery ISBN 9783527607495 ^ Yamamura HI, Snyder SH (1974). "Muscarinic cholinergic binding in rat brain" . Proc. Natl. Acad. Sci. U.S.A . 71 (5): 1725–9. Bibcode :1974PNAS...71.1725Y . doi :10.1073/pnas.71.5.1725 PMC 388311 PMID 4151898 .
External links [ ]
Antihistamines (R06 )
Benzimidazoles (* )
Astemizole Azelastine Bilastine Emedastine Mizolastine Talastine Diarylmethanes Ethylenediamines Tricyclics Others
Phenylpiperazines : Antidepressants (e.g., trazodone )Phenbenzamine For topical use
Bamipine Chloropyramine Chlorphenoxamine Clemastine Dimetindene Diphenhydramine Doxepin Isothipendyl Mepyramine (pyrilamine) Promethazine
H1
Agonists
2-Pyridylethylamine Betahistine Histamine HTMT L -HistidineUR-AK49 Antagonists
Others: Atypical antipsychotics (e.g., aripiprazole , asenapine , brexpiprazole , brilaroxazine , clozapine , iloperidone , olanzapine , paliperidone , quetiapine , risperidone , ziprasidone , zotepine )Phenylpiperazine antidepressants (e.g., hydroxynefazodone , nefazodone , trazodone , triazoledione )Tetracyclic antidepressants (e.g., amoxapine , loxapine , maprotiline , mianserin , mirtazapine , oxaprotiline )Tricyclic antidepressants (e.g., amitriptyline , butriptyline , clomipramine , desipramine , dosulepin (dothiepin) , doxepin , imipramine , iprindole , lofepramine , nortriptyline , protriptyline , trimipramine )Typical antipsychotics (e.g., chlorpromazine , flupenthixol , fluphenazine , loxapine , perphenazine , prochlorperazine , thioridazine , thiothixene )
H2
H3
Agonists
α-Methylhistamine Cipralisant Histamine Imetit Immepip Immethridine L -HistidineMethimepip Proxyfan Antagonists
H4
Agonists
4-Methylhistamine α-Methylhistamine Histamine L -HistidineOUP-16 VUF-8430 Antagonists
See also: Receptor/signaling modulators • Monoamine metabolism modulators • Monoamine reuptake inhibitors
mAChRs
Agonists Antagonists
3-Quinuclidinyl benzilate 4-DAMP Aclidinium bromide (+formoterol )Abediterol AF-DX 384 Ambutonium bromide Anisodamine Anisodine Antihistamines (first-generation) (e.g., brompheniramine , buclizine , captodiame , chlorphenamine (chlorpheniramine) , cinnarizine , clemastine , cyproheptadine , dimenhydrinate , dimetindene , diphenhydramine , doxylamine , meclizine , mequitazine , perlapine , phenindamine , pheniramine , phenyltoloxamine , promethazine , propiomazine , triprolidine )Atropine Atropine methonitrate Atypical antipsychotics (e.g., clozapine , fluperlapine , olanzapine (+fluoxetine ), , quetiapine , tenilapine , zotepine )Benactyzine Benzatropine (benztropine) Benzilone Benzilylcholine mustard Benzydamine Biperiden Bornaprine Camylofin CAR-226,086 CAR-301,060 CAR-302,196 CAR-302,282 CAR-302,668 Caramiphen Cimetropium bromide Clidinium bromide Cloperastine CS-27349 Cyclobenzaprine Cyclopentolate Darifenacin Desfesoterodine Dexetimide Dicycloverine (dicyclomine) Dihexyverine Difemerine Diphemanil metilsulfate Ditran Drofenine EA-3167 EA-3443 EA-3580 EA-3834 Emepronium bromide Etanautine Etybenzatropine (ethybenztropine) Fenpiverinium Fentonium bromide Fesoterodine Flavoxate Glycopyrronium bromide (+beclometasone/formoterol , +indacaterol )Hexocyclium Himbacine Homatropine Imidafenacin Ipratropium bromide (+salbutamol )Isopropamide Hyoscyamine Mamba toxin 3 Mamba toxin 7 Mazaticol Mebeverine Meladrazine Mepenzolate Methantheline Methoctramine Methylatropine Methylhomatropine Methylscopolamine Metixene Muscarinic toxin 7 N-Ethyl-3-piperidyl benzilate N-Methyl-3-piperidyl benzilate Nefopam Octatropine methylbromide (anisotropine methylbromide) Orphenadrine Otenzepad (AF-DX 116) Otilonium bromide Oxapium iodide Oxitropium bromide Oxybutynin Oxyphencyclimine Oxyphenonium bromide PD-102,807 PD-0298029 Penthienate Pethidine Phenglutarimide Phenyltoloxamine Pipenzolate bromide Piperidolate Pirenzepine Piroheptine Pizotifen Poldine Pridinol Prifinium bromide Procyclidine Profenamine (ethopropazine) Propantheline bromide Propiverine Quinidine 3-Quinuclidinyl thiochromane-4-carboxylate Revefenacin Rociverine Scopolamine (hyoscine) Scopolamine butylbromide (hyoscine butylbromide) Sofpironium bromide Solifenacin SSRIs femoxetine , paroxetine )Telenzepine Terodiline Tetracyclic antidepressants (e.g., amoxapine , maprotiline , mianserin , mirtazapine )Tiemonium iodide Timepidium bromide Tiotropium bromide Tofenacin Tolterodine Tricyclic antidepressants (e.g., amitriptyline (+perphenazine ), amitriptylinoxide , butriptyline , cidoxepin , clomipramine , desipramine , , dibenzepin , dosulepin (dothiepin) , doxepin , imipramine , lofepramine , nitroxazepine , northiaden (desmethyldosulepin) , nortriptyline , protriptyline , quinupramine , trimipramine )Tridihexethyl Trihexyphenidyl Trimebutine Tropatepine Tropicamide Trospium chloride Typical antipsychotics (e.g., chlorpromazine , chlorprothixene , cyamemazine (cyamepromazine) , loxapine , mesoridazine , thioridazine )Umeclidinium bromide (+vilanterol )WIN-2299 Xanomeline
Precursors (and prodrugs )
Acetyl-coA Adafenoxate Choline (lecithin )Citicoline Cyprodenate Dimethylethanolamine Glycerophosphocholine Meclofenoxate (centrophenoxine) Phosphatidylcholine Phosphatidylethanolamine Phosphorylcholine Pirisudanol See also: Receptor/signaling modulators • Nicotinic acetylcholine receptor modulators • Acetylcholine metabolism/transport modulators
