Chlorphenoxamine

Chlorphenoxamine
Clinical data
AHFS/Drugs.com	International Drug Names
Routes of; administration	Oral, topical
ATC code	D04AA34 (WHO) R06AA06 (WHO);
Pharmacokinetic data
Bioavailability	Well absorbed
Metabolism	Likely hepatic
Excretion	Renal
Identifiers
	IUPAC name {2-[1-(4-chlorophenyl)-1-phenylethoxy]ethyl}dimethylamine;
CAS Number	77-38-3 562-09-4;
PubChem CID	6475;
DrugBank	DB09007 ;
ChemSpider	6230 ;
UNII	3UVD77BP8R;
KEGG	D07198 ;
ChEMBL	CHEMBL2110774 ;
ECHA InfoCard	100.115.538
Chemical and physical data
Formula	C18H22ClNO
Molar mass	303.826 g/mol
3D model (JSmol)	Interactive image;
	SMILES Clc1ccc(cc1)C(OCCN(C)C)(c2ccccc2)C;
	InChI InChI=1S/C18H22ClNO/c1-18(21-14-13-20(2)3,15-7-5-4-6-8-15)16-9-11-17(19)12-10-16/h4-12H,13-14H2,1-3H3 ; Key:KKHPNPMTPORSQE-UHFFFAOYSA-N ;
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Chlorphenoxamine (Phenoxene) is an antihistamine and anticholinergic used as an antipruritic^[1] and antiparkinsonian^[2] agent. It is an analog of diphenhydramine.^[3]

References

↑ Bazex, A.; Dupre, A.; Christol, B. (1963). "Trial treatment of urticaria with chlorphenoxamine". Clinique (Paris, France). 58: 447–450. PMID 13967113.
↑ Uldall, P. R.; Walton, J. N.; Newell, D. J. (1961). "Chlorphenoxamine hydrochloride in parkinsonism. A controlled trial". British Medical Journal. 1 (5240): 1649–1652. doi:10.1136/bmj.1.5240.1649. PMC 1954253. PMID 13779077.
↑ H. Arnold, N. Brock, E. Kuhas, and D. Lorenz, Arzneimittel Forsch., 4, 189 (1954).

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[1] Bazex, A.; Dupre, A.; Christol, B. (1963). "Trial treatment of urticaria with chlorphenoxamine". Clinique (Paris, France). 58: 447–450. PMID 13967113.

[2] Uldall, P. R.; Walton, J. N.; Newell, D. J. (1961). "Chlorphenoxamine hydrochloride in parkinsonism. A controlled trial". British Medical Journal. 1 (5240): 1649–1652. doi:10.1136/bmj.1.5240.1649. PMC 1954253. PMID 13779077.

[3] H. Arnold, N. Brock, E. Kuhas, and D. Lorenz, Arzneimittel Forsch., 4, 189 (1954).

Antipruritics (D04)
Antihistamines for topical use	Thonzylamine Mepyramine Thenalidine Tripelennamine Chloropyramine Promethazine Tolpropamine Dimetindene Clemastine Bamipine Isothipendyl Diphenhydramine Chlorphenoxamine
Anesthetics for topical use	Lidocaine Dibucaine Oxybuprocaine Benzocaine Quinisocaine Tetracaine Pramocaine
Others	Corticosteroids (e.g., hydrocortisone) Counterirritants (e.g., mint oil, menthol, camphor) Nalfurafine

Antihistamines (R06)
Benzimidazoles (*)	Astemizole Azelastine Bilastine Emedastine Mizolastine Talastine
Diarylmethanes	Diarylmethoxyalkylamines: Bromazine (bromodiphenhydramine) Carbinoxamine Chlorphenoxamine Clemastine Diphenhydramine 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

Histamine receptor modulators
H₁	Agonists: 2-Pyridylethylamine Betahistine Histamine HTMT L-Histidine UR-AK49 Antagonists: First-generation: 4-Methyldiphenhydramine Alimemazine Antazoline Azatadine Bamipine Benzatropine (benztropine) Bepotastine Bromazine Brompheniramine Buclizine Captodiame Carbinoxamine Chlorcyclizine Chloropyramine Chlorothen Chlorphenamine Chlorphenoxamine Cinnarizine Clemastine Clobenzepam Clocinizine Cloperastine Cyclizine Cyproheptadine Dacemazine Decloxizine Deptropine Dexbrompheniramine Dexchlorpheniramine Dimenhydrinate Dimetindene Diphenhydramine Diphenylpyraline Doxylamine Embramine Etodroxizine Etybenzatropine (ethylbenztropine) Etymemazine Fenethazine Flunarizine Histapyrrodine Homochlorcyclizine Hydroxyethylpromethazine Hydroxyzine Isopromethazine Isothipendyl Meclozine Medrylamine Mepyramine (pyrilamine) Mequitazine Methafurylene Methapyrilene Methdilazine Moxastine Orphenadrine Oxatomide Oxomemazine Perlapine Phenindamine Pheniramine Phenyltoloxamine Pimethixene Piperoxan Pipoxizine Promethazine Propiomazine Pyrrobutamine Talastine Thenalidine Thenyldiamine Thiazinamium Thonzylamine Tolpropamine Tripelennamine Triprolidine Second/third-generation: Acrivastine Alinastine Astemizole Azelastine Bamirastine Barmastine Bepiastine Bepotastine Bilastine Cabastinen Carebastine Cetirizine Clemastine Clemizole Clobenztropine Desloratadine Dorastine Ebastine Efletirizine Emedastine Epinastine Fexofenadine Flezelastine Ketotifen Latrepirdine Levocabastine Levocetirizine Linetastine Loratadine Mapinastine Mebhydrolin Mizolastine Moxastine Noberastine Octastine Olopatadine Perastine Pibaxizine Piclopastine Quifenadine (phencarol) Rocastine Rupatadine Setastine Sequifenadine (bicarphen) Talastine Temelastine Terfenadine Vapitadine Zepastine Others: Atypical antipsychotics (e.g., aripiprazole, asenapine, brexpiprazole, clozapine, iloperidone, olanzapine, paliperidone, quetiapine, risperidone, RP-5063, 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) Unknown/unsorted: Azanator Belarizine Elbanizine Flotrenizine GSK1004723 Napactadine Tagorizine Trelnarizine Trenizine
H₂	Agonists: Amthamine Betazole Dimaprit Histamine HTMT Impromidine L-Histidine UR-AK49 Antagonists: Bisfentidine Burimamide Cimetidine Dalcotidine Donetidine Ebrotidine Etintidine Famotidine Isolamtidine Lafutidine Lamtidine Lavoltidine (loxtidine) Lupitidine Metiamide Mifentidine Niperotidine Nizatidine Osutidine Oxmetidine Pibutidine Quisultazine (quisultidine) Ramixotidine Ranitidine Roxatidine Sufotidine Tiotidine Tuvatidine Venritidine Xaltidine Zolantidine
H₃	Agonists: α-Methylhistamine Cipralisant Histamine Imetit Immepip Immethridine L-Histidine Methimepip Proxyfan Antagonists: A-349,821 A-423,579 ABT-239 ABT-652 AZD5213 Bavisant Betahistine Burimamide Ciproxifan Clobenpropit Conessine Enerisant GSK-189,254 Impentamine Iodophenpropit Irdabisant JNJ-5207852 MK-0249 NNC 38-1049 PF-03654746 Pitolisant SCH-79687 Thioperamide VUF-5681
H₄	Agonists: 4-Methylhistamine α-Methylhistamine Histamine L-Histidine OUP-16 VUF-8430 Antagonists: JNJ-7777120 Mianserin Seliforant Thioperamide Toreforant VUF-6002
See also: Receptor/signaling modulators • Monoamine metabolism modulators • Monoamine reuptake inhibitors

Clinical data

AHFS/Drugs.com	International Drug Names
Routes of administration	Oral, topical
ATC code	D04AA34 (WHO) R06AA06 (WHO)
Pharmacokinetic data
Bioavailability	Well absorbed
Metabolism	Likely hepatic
Excretion	Renal
Identifiers
IUPAC name {2-[1-(4-chlorophenyl)-1-phenylethoxy]ethyl}dimethylamine
CAS Number	77-38-3^Y 562-09-4
PubChem CID	6475
DrugBank	DB09007^N
ChemSpider	6230^Y
UNII	3UVD77BP8R
KEGG	D07198^Y
ChEMBL	CHEMBL2110774^N
ECHA InfoCard	100.115.538
Chemical and physical data
Formula	C₁₈H₂₂ClNO
Molar mass	303.826 g/mol
3D model (JSmol)	Interactive image
SMILES Clc1ccc(cc1)C(OCCN(C)C)(c2ccccc2)C
InChI InChI=1S/C18H22ClNO/c1-18(21-14-13-20(2)3,15-7-5-4-6-8-15)16-9-11-17(19)12-10-16/h4-12H,13-14H2,1-3H3^Y Key:KKHPNPMTPORSQE-UHFFFAOYSA-N^Y
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