Thenalidine

Thenalidine
Clinical data
ATC code	D04AA03 (WHO) R06AX03 (WHO) ; R06AX53 (WHO) (combinations);
Identifiers
	IUPAC name 1-Methyl-N-phenyl-N-(2-thienylmethyl)piperidin-4-amine;
CAS Number	86-12-4 ;
PubChem CID	27901;
DrugBank	DB04826 ;
ChemSpider	25957 ;
UNII	6U94N2D00F;
KEGG	D07194 ;
CompTox Dashboard (EPA)	DTXSID1048835 ;
ECHA InfoCard	100.001.501
Chemical and physical data
Formula	C17H22N2S
Molar mass	286.44 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES s1c(ccc1)CN(c2ccccc2)C3CCN(C)CC3;
	InChI InChI=1S/C17H22N2S/c1-18-11-9-16(10-12-18)19(14-17-8-5-13-20-17)15-6-3-2-4-7-15/h2-8,13,16H,9-12,14H2,1H3 ; Key:KLOHYVOVXOUKQI-UHFFFAOYSA-N ;
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Thenalidine is an antihistamine with anticholinergic properties used as an antipruritic drug.^[1] It was withdrawn from the US, Canadian, and UK markets in 1963 due to a risk of neutropenia.^[2]

References

^ Getzler NA, Ereaux LP (March 1959). "Evaluation of thenalidine tratrate (sandostene) in dermatological disorders". Canadian Medical Association Journal. 80 (6): 445–8. PMC 1830689. PMID 13629433.
^ "Thenalidine". DrugBank.

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[1] Getzler NA, Ereaux LP (March 1959). "Evaluation of thenalidine tratrate (sandostene) in dermatological disorders". Canadian Medical Association Journal. 80 (6): 445–8. PMC 1830689. PMID 13629433.

[2] "Thenalidine". DrugBank.

[1]

[2]

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