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 liver
Excretion	kidney
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 ;
CompTox Dashboard (EPA)	DTXSID5022805 ;
ECHA InfoCard	100.115.538
Chemical and physical data
Formula	C18H22ClNO
Molar mass	303.83 g·mol−1
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. 58: 447–50. PMID 13967113.
^ Uldall PR, Walton JN, Newell DJ (June 1961). "Chlorphenoxamine hydrochloride in parkinsonism. A controlled trial". British Medical Journal. 1 (5240): 1649–52. doi:10.1136/bmj.1.5240.1649. PMC 1954253. PMID 13779077.
^ Arnold H, Brock N, Kuhas E, Lorenz D (January 1954). "Beitrag Zur Wirkung Von Antihistamin-Substanzen. 1. Chemische Konstitution Und Pharmakologische Wirkung in Der Gruppe Der Basischen Benzhydrylaether" [Contribution to the Effect Of Antihistamine Substances. 1. Chemical constitution and pharmacological activity in the group of basic benzhydrylethers]. Arzneimittel-Forschung [Drug Research] (in German). 4 (3): 189–94. PMID 13159698.

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[1] Bazex A, Dupre A, Christol B (1963). "[Trial treatment of urticaria with chlorphenoxamine]". Clinique. 58: 447–50. PMID 13967113.

[2] Uldall PR, Walton JN, Newell DJ (June 1961). "Chlorphenoxamine hydrochloride in parkinsonism. A controlled trial". British Medical Journal. 1 (5240): 1649–52. doi:10.1136/bmj.1.5240.1649. PMC 1954253. PMID 13779077.

[3] Arnold H, Brock N, Kuhas E, Lorenz D (January 1954). "Beitrag Zur Wirkung Von Antihistamin-Substanzen. 1. Chemische Konstitution Und Pharmakologische Wirkung in Der Gruppe Der Basischen Benzhydrylaether" [Contribution to the Effect Of Antihistamine Substances. 1. Chemical constitution and pharmacological activity in the group of basic benzhydrylethers]. Arzneimittel-Forschung [Drug Research] (in German). 4 (3): 189–94. PMID 13159698.

[1]

[2]

[3]

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

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

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 liver
Excretion	kidney
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
CompTox Dashboard (EPA)	DTXSID5022805
ECHA InfoCard	100.115.538
Chemical and physical data
Formula	C₁₈H₂₂ClNO
Molar mass	303.83 g·mol⁻¹
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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