Tolazamide

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Tolazamide
Tolazamide.svg
Tolazamide ball-and-stick.png
Clinical data
AHFS/Drugs.com Monograph
MedlinePlus a682482
License data
Pregnancy
category
  • AU: C
  • US: C (Risk not ruled out)
Routes of
administration
Oral
ATC code
Legal status
Legal status
Pharmacokinetic data
Bioavailability ?
Metabolism metabolized in the liver to active metabolites
Biological half-life 7 hours
Excretion Renal (85%) and fecal (7%)
Identifiers
CAS Number
PubChem CID
IUPHAR/BPS
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
ECHA InfoCard 100.013.262
Chemical and physical data
Formula C14H21N3O3S
Molar mass 311.401 g/mol
3D model (Jmol)
  (verify)

Tolazamide is an oral blood glucose lowering drug used for people with Type 2 diabetes. It is part of the sulfonylurea family (ATC A10BB).

Synthesis[edit]

para-Toluenesulfonamide is converted to its carbamate with ethyl chloroformate in the presence of a base. Heating that intermediate with azepane leads to the displacement of the ethoxy group and the formation of tolazemide:[1]

Tolazemide synthesis:[2] U.S. Patent 3,063,903 GB 887886  DE 1196200 

References[edit]

  1. ^ Wright, J. B.; Willette, R. E. (1962). J. Med. Chem. 5 (4): 815–822. doi:10.1021/jm01239a016.  Missing or empty |title= (help)
  2. ^ Wright, J. B.; Willette, R. E. (1962). "Antidiabetic Agents. N4-Arylsulfonylsemicarbazides". Journal of medicinal and pharmaceutical chemistry. 91: 815–22. PMID 14056414. 

External links[edit]