Oxatomide

From Wikipedia, the free encyclopedia

This is an old revision of this page, as edited by Klbrain (talk | contribs) at 10:31, 28 June 2017 (Undid revision 787746613 by 203.205.34.102 (talk)Consensus view is that drugs are inventions; see Wikipedia talk:WikiProject Pharmacology#Are pharmaceutical drugs inventions?). The present address (URL) is a permanent link to this revision, which may differ significantly from the current revision.

Oxatomide
Clinical data
Trade namesTinset, Cedlips, Atoxan
AHFS/Drugs.comInternational Drug Names
Routes of
administration		Oral
ATC code
Legal status
Legal status
  • In general: ℞ (Prescription only)
Identifiers
  • 1-{3-[4-(diphenylmethyl)piperazin-1-yl]propyl}-1,3-dihydro-2H-benzimidazol-2-one
CAS Number
PubChem CID
ChemSpider
UNII
KEGG
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.056.637 Edit this at Wikidata
Chemical and physical data
FormulaC27H30N4O
Molar mass426.553 g/mol g·mol−1
3D model (JSmol)
  • O=C2Nc1ccccc1N2CCCN5CCN(C(c3ccccc3)c4ccccc4)CC5
  • 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) checkY
  • Key:BAINIUMDFURPJM-UHFFFAOYSA-N checkY
 ☒NcheckY (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

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

References

  1. ^ 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.
  2. ^ J. Vandenberk et al., DE 2714437 ; eidem, U.S. patent 4,250,176 (1977, 1981 both to Janssen).


Stub icon

This drug article relating to the respiratory system is a stub. You can help Wikipedia by expanding it.

Retrieved from "https://en.wikipedia.org/w/index.php?title=Oxatomide&oldid=787917641"