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.
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.