Oxatomide

Oxatomide
Clinical data
Trade names	Tinset, others
Other names	KW-4354; McN-JR 35443; R-35443
AHFS/Drugs.com	International Drug Names
Routes of; administration	By mouth
ATC code	R06AE06 (WHO) ;
Legal status
Legal status	In general: ℞ (Prescription only);
Identifiers
	IUPAC name 1-{3-[4-(diphenylmethyl)piperazin-1-yl]propyl}-1,3-dihydro-2H-benzimidazol-2-one;
CAS Number	60607-34-3 ;
PubChem CID	4615;
ChemSpider	4454 ;
UNII	J31IL9Z2EE;
KEGG	D01773 ;
ChEBI	CHEBI:31943;
ChEMBL	ChEMBL13828 ;
CompTox Dashboard (EPA)	DTXSID4045181 ;
ECHA InfoCard	100.056.637
Chemical and physical data
Formula	C27H30N4O
Molar mass	426.564 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES O=C2Nc1ccccc1N2CCCN5CCN(C(c3ccccc3)c4ccccc4)CC5;
	InChI InChI=1S/C27H30N4O/c32-27-28-24-14-7-8-15-25(24)31(27)17-9-16-29-18-20-30(21-19-29)26(22-10-3-1-4-11-22)23-12-5-2-6-13-23/h1-8,10-15,26H,9,16-21H2,(H,28,32) ; Key:BAINIUMDFURPJM-UHFFFAOYSA-N ;
	(what is this?) (verify)

Oxatomide, sold under the brand name Tinset among others, is a antihistamine of the diphenylmethylpiperazine family which is marketed in Europe, Japan, and a number of other countries.^[1]^[2]^[3]^[4] It was discovered at Janssen Pharmaceutica in 1975.^[5] Oxatomide lacks any anticholinergic effects.^[2] In addition to its H₁ receptor antagonism, it also possesses antiserotonergic activity similarly to hydroxyzine.^[2]

It was patented in 1976 and came into medical use in 1981.^[6]

Chemistry

Synthesis

Reaction of 2-Benzimidazolinone with isopropenyl acetate leads to the singly protected imidazolone derivative (2). Alkylation of this with 3-chloro-1-bromopropane affords the functionalized derivative (3). Alkylation of the monobenzhydryl derivative of piperazine (4) with 3 gives oxatomide (5), after hydrolytic removal of the protecting group.

References

^ Elks J (14 November 2014). The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies. Springer. pp. 912–. ISBN 978-1-4757-2085-3.
^ ^a ^b ^c Ohmori K, Ishii H, Nito M, Shuto K, Nakamizo N (May 1983). "[Pharmacological studies on oxatomide (KW-4354). (7) Antagonistic effects on chemical mediators]". Nihon Yakurigaku Zasshi. Folia Pharmacologica Japonica (in Japanese). 81 (5): 399–409. doi:10.1254/fpj.81.399. PMID 6138301.
^ Index Nominum 2000: International Drug Directory. Taylor & Francis. 2000. pp. 768–. ISBN 978-3-88763-075-1.
^ "Oxatomide". Drugs.com.
^ Schwartz H (August 1989). Breakthrough: the discovery of modern medicines at Janssen. Skyline Pub. Group. p. 149. ISBN 978-1-56019-100-1.
^ Fischer J, Ganellin CR (2006). Analogue-based Drug Discovery. John Wiley & Sons. p. 548. ISBN 9783527607495.
^ DE 2714437, Vandenberk J, Kennis LE, Van der Aa MJ, Van Heertum AH, "Piperazin- und Piperidinderivate, Verfahren zu ihrer Herstellung und Arzneipräparate [Piperazine and piperide derivatives, procedures for their manufacturing and medicinal preparations]", published 1977-10-20, assigned to Janssen Pharmaceutica
^ US 4250176, Vandenberk J, Kennis LE, Van der Aa MJ, Van Heertum AH, issued 10 February 1981, assigned to Janssen Pharmaceutica NV.

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[Elks2014-1] Elks J (14 November 2014). The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies. Springer. pp. 912–. ISBN 978-1-4757-2085-3.

[pmid6138301-2] Ohmori K, Ishii H, Nito M, Shuto K, Nakamizo N (May 1983). "[Pharmacological studies on oxatomide (KW-4354). (7) Antagonistic effects on chemical mediators]". Nihon Yakurigaku Zasshi. Folia Pharmacologica Japonica (in Japanese). 81 (5): 399–409. doi:10.1254/fpj.81.399. PMID 6138301.

[IndexNominum2000-3] Index Nominum 2000: International Drug Directory. Taylor & Francis. 2000. pp. 768–. ISBN 978-3-88763-075-1.

[Drugs.com-4] "Oxatomide". Drugs.com.

[Schwartz1989-5] Schwartz H (August 1989). Breakthrough: the discovery of modern medicines at Janssen. Skyline Pub. Group. p. 149. ISBN 978-1-56019-100-1.

[Fis2006-6] Fischer J, Ganellin CR (2006). Analogue-based Drug Discovery. John Wiley & Sons. p. 548. ISBN 9783527607495.

[7] DE 2714437, Vandenberk J, Kennis LE, Van der Aa MJ, Van Heertum AH, "Piperazin- und Piperidinderivate, Verfahren zu ihrer Herstellung und Arzneipräparate [Piperazine and piperide derivatives, procedures for their manufacturing and medicinal preparations]", published 1977-10-20, assigned to Janssen Pharmaceutica

[8] US 4250176, Vandenberk J, Kennis LE, Van der Aa MJ, Van Heertum AH, issued 10 February 1981, assigned to Janssen Pharmaceutica NV.

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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