Tolazamide

Tolazamide
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 A10BB05 (WHO)
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 1156-19-0
PubChem (CID) 5503
IUPHAR/BPS 6847
DrugBank DB00839 YesY
ChemSpider 5302 YesY
UNII 9LT1BRO48Q YesY
KEGG D00379 YesY
ChEBI CHEBI:9613
ChEMBL CHEMBL817 YesY
ECHA InfoCard 100.013.262
Chemical and physical data
Formula C14H21N3O3S
Molar mass 311.401 g/mol
3D model (Jmol) Interactive image
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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

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]

References

  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.


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