Chemistry:Oxatomide

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Short description: Chemical compound
Oxatomide
Oxatomide.png
Clinical data
Trade namesTinset, others
Other namesKW-4354; McN-JR 35443; R-35443
AHFS/Drugs.comInternational Drug Names
Routes of
administration		By mouth
ATC code
Legal status
Legal status
  • In general: ℞ (Prescription only)
Identifiers
CAS Number
PubChem CID
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
Chemical and physical data
FormulaC27H30N4O
Molar mass426.564 g·mol−1
3D model (JSmol)
 ☒N☑Y (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

Oxatomide synthesis:[7][8]

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

  1. ↑ The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies. Springer. 14 November 2014. pp. 912–. ISBN 978-1-4757-2085-3. https://books.google.com/books?id=0vXTBwAAQBAJ&pg=PA912. 
  2. ↑ 2.0 2.1 2.2 "[Pharmacological studies on oxatomide (KW-4354). (7) Antagonistic effects on chemical mediators]" (in ja). Nihon Yakurigaku Zasshi. Folia Pharmacologica Japonica 81 (5): 399–409. May 1983. doi:10.1254/fpj.81.399. PMID 6138301. 
  3. ↑ Index Nominum 2000: International Drug Directory. Taylor & Francis. 2000. pp. 768–. ISBN 978-3-88763-075-1. https://books.google.com/books?id=5GpcTQD_L2oC&pg=PA768. 
  4. ↑ "Oxatomide". Drugs.com. https://www.drugs.com/international/oxatomide.html. 
  5. ↑ Breakthrough: the discovery of modern medicines at Janssen. Skyline Pub. Group. August 1989. p. 149. ISBN 978-1-56019-100-1. https://archive.org/details/breakthroughdisc0000schw. 
  6. ↑ (in en) Analogue-based Drug Discovery. John Wiley & Sons. 2006. p. 548. ISBN 9783527607495. https://books.google.com/books?id=FjKfqkaKkAAC&pg=PA548. 
  7. ↑ 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]", DE patent 2714437, published 1977-10-20
  8. ↑ Vandenberk J, Kennis LE, Van der Aa MJ, Van Heertum AH, US patent 4250176, issued 10 February 1981, assigned to Janssen Pharmaceutica NV.



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