Oxatomide
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Systematic (IUPAC) name | |
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1-{3-[4-(diphenylmethyl)piperazin-1-yl]propyl}-1,3-dihydro-2H-benzimidazol-2-one
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Clinical data | |
Trade names | Tinset, Cedlips, Atoxan |
AHFS/Drugs.com | International Drug Names |
Routes of administration |
Oral |
Legal status | |
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Identifiers | |
CAS Number | 60607-34-3 N |
ATC code | R06AE06 (WHO) |
PubChem | CID 4615 |
ChemSpider | 4454 Y |
UNII | J31IL9Z2EE Y |
KEGG | D01773 Y |
ChEMBL | CHEMBL13828 Y |
Chemical data | |
Formula | C27H30N4O |
Molar mass | 426.553 g/mol |
3D model (Jmol) | Interactive image |
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NY (what is this?) (verify) |
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]
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).
Aminoalkyl ethers |
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Substituted alkylamines | |
Substituted ethylenediamines |
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Phenothiazine derivatives | |
Piperazine derivatives | |
Others for systemic use |
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For topical use |
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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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