Oxatomide
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Clinical data | |
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Trade names | Tinset, Cedlips, Atoxan |
AHFS/Drugs.com | International Drug Names |
Routes of administration |
Oral |
ATC code | R06AE06 (WHO) |
Legal status | |
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Identifiers | |
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CAS Number | 60607-34-3 ![]() |
PubChem (CID) | 4615 |
ChemSpider | 4454 ![]() |
UNII | J31IL9Z2EE ![]() |
KEGG | D01773 ![]() |
ChEMBL | CHEMBL13828 ![]() |
ECHA InfoCard | 100.056.637 |
Chemical and physical data | |
Formula | C27H30N4O |
Molar mass | 426.553 g/mol |
3D model (Jmol) | Interactive image |
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Oxatomide (R35443) is a first-generation antihistamine of the diphenylmethylpiperazine (benzhydrylpiperazine) class.[1] It was discovered at Janssen Pharmaceutica in 1975. Oxatomide lacks any anticholinergic effects.[1] In addition to its H1 receptor antagonism, it also possesses antiserotonergic actions.[1]
Synthesis[edit]
![](http://web.archive.org./web/20170210235914im_/https://upload.wikimedia.org/wikipedia/commons/thumb/7/79/Oxatomide_synthesis.svg/500px-Oxatomide_synthesis.svg.png)
Oxatomide synthesis:[2]
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.
See also[edit]
References[edit]
- ^ 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]". Nippon Yakurigaku Zasshi. Folia Pharmacologica Japonica (in Japanese). 81 (5): 399–409. doi:10.1254/fpj.81.399. PMID 6138301.
- ^ J. Vandenberk et al., DE 2714437 ; eidem, U.S. Patent 4,250,176 (1977, 1981 both to Janssen).
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Substituted alkylamines | |
Substituted ethylenediamines |
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Phenothiazine derivatives | |
Piperazine derivatives | |
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Simple piperazines (no additional rings) |
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Phenylpiperazines |
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Benzylpiperazines | |
Diphenylalkylpiperazines (benzhydrylalkylpiperazines) |
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Pyrimidinylpiperazines | |
Pyridinylpiperazines | |
Benzo(iso)thiazolylpiperazines | |
Tricyclics (piperazine attached via side chain) |
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Others/Uncategorized |
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