Oxatomide
Chemical compound
From Wikipedia, the free encyclopedia
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] Oxatomide was also found to have antiviral activity against Venezuelan equine encephalitis virus (VEEV).[6]
Above: molecular structure of oxatomide
Below: 3D representation of an oxatomide molecule | |
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| Trade names | Tinset, others |
| Other names | KW-4354; McN-JR 35443; R-35443 |
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| Routes of administration | By mouth |
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| ECHA InfoCard | 100.056.637 |
| Chemical and physical data | |
| Formula | C27H30N4O |
| Molar mass | 426.564 g·mol−1 |
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It was patented in 1976 and came into medical use in 1981.[7]
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.