Structure via PubChem · Public domain (PubChem)
sematilide
Sign in to saveSematilide is an antiarrhythmic agent. It is the same structure as for procainamide, differing only by the placement of a mesyl sulfonamide moiety to the anilino nitrogen.
In the Vinony graph
Within Vinony's link graph, sematilide is referenced by 5 other articles, and connects out to digital object identifier, chemical formula and molar mass.
Vinony files it under Antiarrhythmic agents, Benzamides and Chembox image size set.
Its subject is documented across 5 Wikipedia language editions.
Chemical data
- Formula
- C14H23N3O3S
- Molecular weight
- 313.42 g/mol
- IUPAC name
- N-[2-(diethylamino)ethyl]-4-(methanesulfonamido)benzamide
- SMILES
- CCN(CC)CCNC(=O)C1=CC=C(C=C1)NS(=O)(=O)C
- InChIKey
- KHYPYQZQJSBPIX-UHFFFAOYSA-N
- XLogP
- 0.5
- Polar surface area
- 86.9 Ų
- H-bond donors
- 2
- H-bond acceptors
- 5
- Formal charge
- 0
via PubChem
Drug data · ChEMBL
- Max clinical phase
- Phase 2
- Molecule type
- Small molecule
via ChEMBL · EBI
Research
56 papersvia PubMed
Wikidata facts
- Subclass of
- chemical compound
- Mass
- 313.146
Show 3 more facts
- chemical formula
- C₁₄H₂₃N₃O₃S
- canonical SMILES
- CCN(CC)CCNC(=O)C1=CC=C(C=C1)NS(=O)(=O)C
- subject has role
- antiarrhythmic agent
via Wikidata · CC0
~1 min read
Encyclopedic overview
2 sectionsContents
- Synthesis
- References
Sematilide is an antiarrhythmic agent. It is the same structure as for procainamide, differing only by the placement of a mesyl sulfonamide moiety to the anilino nitrogen.
==Synthesis== class=skin-invert-image|thumb|center|500px|Synthesis of sematilide Sematilide can be synthesized from benzocaine (1). Reaction with mesyl chloride, followed by saponification and removal of the water from the reaction mixture, gives sodium 4-[(methylsulfonyl)amino]benzoate (2). Chlorination with thionyl chloride gives 4-[(methylsulfonyl)amino]benzoyl chloride. Amide formation with N,N-diethylethylenediamine (3) then concludes the synthesis of sematilide (4).
Excerpted from Wikipedia’s “sematilide” article, available under the CC BY-SA 4.0 licence.