Movatterモバイル変換

[0]ホーム
URL:

Jump to content
WikipediaThe Free Encyclopedia
Search

Clemizole

From Wikipedia, the free encyclopedia
Chemical compound

Pharmaceutical compound
Clemizole
Clinical data
Trade namesAllercur, Histacur
Other namesEPX-100
ATC code
  • None
Identifiers
  • 1-[(4-Chlorophenyl)methyl]-2-(pyrrolidin-1-ylmethyl)benzimidazole
CAS Number
PubChemCID
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
NIAID ChemDB
CompTox Dashboard(EPA)
ECHA InfoCard100.006.486Edit this at Wikidata
Chemical and physical data
FormulaC19H20ClN3
Molar mass325.84 g·mol−1
3D model (JSmol)
  • Clc1ccc(cc1)Cn3c(nc2ccccc23)CN4CCCC4
  • InChI=1S/C19H20ClN3/c20-16-9-7-15(8-10-16)13-23-18-6-2-1-5-17(18)21-19(23)14-22-11-3-4-12-22/h1-2,5-10H,3-4,11-14H2
  • Key:CJXAEXPPLWQRFR-UHFFFAOYSA-N

Clemizole, sold under the brand namesAllercur and Histacur, is ahistamine H1 receptor antagonist of thebenzimidazole group described as anantihistamine,antipruritic, andsedative which is no longer marketed.[1][2][3][4]

It is also aserotonin receptoragonist and is being studied for the potential treatment ofDravet syndrome,Lennox–Gastaut syndrome, andepilepsy under the development code nameEPX-100.[5][4][6]

The drug was first described in thescientific literature by 1952.[1] Its serotonin receptor agonist andanticonvulsant properties were discovered in 2017.[5][4]

Synthesis

[edit]

Benzimidazoles substituted with an alkylamine at position 2 have a venerable history as H1 antihistaminic agents. The standard starting material for many benzimidazoles consists ofphenylenediamine, or its derivatives.

Clemizole synthesis:[7][8][9]

Reaction of that compound withchloroacetic acid can be rationalized by invoking initial formation of the chloromethyl amide.Imide formation with the remaining free amino group closes the ring to afford 2-chloromethyl benzimidazole (3). Displacement of halogen withpyrrolidine affords the alkylation product. The proton on the fused imidazole nitrogen is then removed by reaction withsodium hydride. Treatment of the resulting anion with α,4-dichlorotoluene gives the H1 antihistaminic agent clemizole (5).

See also

[edit]

References

[edit]
  1. ^abElks J (2014).The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies. Springer US. p. 288.ISBN 978-1-4757-2085-3. Retrieved29 October 2024.
  2. ^Schweizerischer Apotheker-Verein (2004).Index Nominum: International Drug Directory. Medpharm Scientific Publishers. p. 291.ISBN 978-3-88763-101-7. Retrieved29 October 2024.
  3. ^Morton IK, Hall JM (2012).Concise Dictionary of Pharmacological Agents: Properties and Synonyms. Springer Netherlands. p. 78.ISBN 978-94-011-4439-1. Retrieved29 October 2024.
  4. ^abcGriffin A, Hamling KR, Knupp K, Hong S, Lee LP, Baraban SC (March 2017)."Clemizole and modulators of serotonin signalling suppress seizures in Dravet syndrome".Brain.140 (3):669–683.doi:10.1093/brain/aww342.PMC 6075536.PMID 28073790.
  5. ^abSills GJ (2023)."Pharmacological diversity amongst approved and emerging antiseizure medications for the treatment of developmental and epileptic encephalopathies".Ther Adv Neurol Disord.16 17562864231191000.doi:10.1177/17562864231191000.PMC 10467199.PMID 37655228.
  6. ^"Clemizole - Epygenix Therapeutics/University of California at San Francisco".AdisInsight. 9 October 2024. Retrieved29 October 2024.
  7. ^Jerchel D, Fischer H, Kracht M (1952). "Zur Darstellung der Benzimidazole".Justus Liebigs Annalen der Chemie.575 (2):162–173.doi:10.1002/jlac.19525750204.
  8. ^GB 703272, Schenck M, Heinz W, issued 1954, assigned to Schering AG 
  9. ^US 2689853, Schenck M, Heinz W, issued 1954, assigned to Schering AG 
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-HT3–7
5-HT3
5-HT4
5-HT5A
5-HT6
5-HT7
Retrieved from "https://en.wikipedia.org/w/index.php?title=Clemizole&oldid=1328685442"
Categories:
Hidden categories:
[8]ページ先頭
©2009-2026 Movatter.jp