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Tolazamide

Tolazamide
Tolazamide.svg
Tolazamide ball-and-stick.png
Clinical data
AHFS/Drugs.comMonograph
MedlinePlusa682482
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?
Metabolismmetabolized in the liver to active metabolites
Elimination half-life7 hours
ExcretionRenal (85%) and fecal (7%)
Identifiers
CAS Number
PubChem CID
IUPHAR/BPS
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.013.262 Edit this at Wikidata
Chemical and physical data
FormulaC14H21N3O3S
Molar mass311.401 g/mol g·mol−1
3D model (JSmol)
  (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

para-Toluenesulfonamide is converted to its carbamate with ethyl chloroformate in the presence of a base. Heating that intermediate with 1-amino-azepane leads to the displacement of the ethoxy group and the formation of tolazemide:[2]

Azepane proper would lead to [13078-23-4].

References

  1. ^ Wright, J. B.; Willette, R. E. (1962). "Antidiabetic Agents. N4-Arylsulfonylsemicarbazides". Journal of Medicinal and Pharmaceutical Chemistry. 91: 815–22. PMID 14056414.
  2. ^ Wright, John B.; Willette, Robert E. (1962). "Antidiabetic Agents. N4-Arylsulfonylsemicarbazides". Journal of Medicinal and Pharmaceutical Chemistry. 5 (4): 815–822. doi:10.1021/jm01239a016. ISSN 0095-9065.

External links