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Oxatomide

From Wikipedia, the free encyclopedia
Chemical compound

Pharmaceutical compound
Oxatomide
Above: molecular structure of oxatomideBelow: 3D representation of an oxatomide molecule
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
  • 1-{3-[4-(diphenylmethyl)piperazin-1-yl]propyl}-1,3-dihydro-2H-benzimidazol-2-one
CAS Number
PubChemCID
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard(EPA)
ECHA InfoCard100.056.637Edit this at Wikidata
Chemical and physical data
FormulaC27H30N4O
Molar mass426.564 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, sold under the brand nameTinset among others, is aantihistamine of thediphenylmethylpiperazine family which is marketed inEurope,Japan, and a number of other countries.[1][2][3][4] It was discovered atJanssen Pharmaceutica in 1975.[5] Oxatomide lacks anyanticholinergic effects.[2] In addition to itsH1 receptorantagonism, it also possessesantiserotonergic activity similarly tohydroxyzine.[2] Oxatomide was also found to haveantiviral activity against Venezuelan equine encephalitis virus (VEEV).[6]

It was patented in 1976 and came into medical use in 1981.[7]

Chemistry

[edit]

Synthesis

[edit]
Oxatomide synthesis:[8][9]

Reaction of2-Benzimidazolinone withisopropenyl acetate leads to the singly protected imidazolone derivative (2).Alkylation of this with3-chloro-1-bromopropane affords the functionalized derivative (3). Alkylation of themonobenzhydryl derivative ofpiperazine (4) with3 gives oxatomide (5), after hydrolytic removal of theprotecting group.

References

[edit]
  1. ^Elks J (14 November 2014).The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies. Springer. pp. 912–.ISBN 978-1-4757-2085-3.
  2. ^abcOhmori K, Ishii H, Nito M, Shuto K, Nakamizo N (May 1983)."[Pharmacological studies on oxatomide (KW-4354). (7) Antagonistic effects on chemical mediators]".Nihon Yakurigaku Zasshi. Folia Pharmacologica Japonica (in Japanese).81 (5):399–409.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.
  4. ^"Oxatomide".Drugs.com.
  5. ^Schwartz H (August 1989).Breakthrough: the discovery of modern medicines at Janssen. Skyline Pub. Group. p. 149.ISBN 978-1-56019-100-1.
  6. ^Hu X, Morazzani E, Compton JR, Harmon M, Soloveva V, Glass PJ, et al. (July 2023)."In Silico Screening of Inhibitors of the Venezuelan Equine Encephalitis Virus Nonstructural Protein 2 Cysteine Protease".Viruses.15 (7): 1503.doi:10.3390/v15071503.PMC 10385868.PMID 37515189.
  7. ^Fischer J, Ganellin CR (2006).Analogue-based Drug Discovery. John Wiley & Sons. p. 548.ISBN 9783527607495.
  8. ^DE 2714437, 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]", published 1977-10-20, assigned toJanssen Pharmaceutica 
  9. ^US 4250176, Vandenberk J, Kennis LE, Van der Aa MJ, Van Heertum AH, issued 10 February 1981, assigned to Janssen Pharmaceutica NV. 
Benzimidazoles(*)
Diarylmethanes
Ethylenediamines
Tricyclics
Others
Fortopical use
H1
Agonists
Antagonists
H2
Agonists
Antagonists
H3
Agonists
Antagonists
H4
Agonists
Antagonists
5-HT1
5-HT1A
5-HT1B
5-HT1D
5-HT1E
5-HT1F
5-HT2
5-HT2A
5-HT2B
5-HT2C
5-HT37
5-HT3
5-HT4
5-HT5A
5-HT6
5-HT7
CARTooltip Constitutive androstane receptor
PXRTooltip Pregnane X receptor
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