Tolazamide
Tolazamide.svg
Tolazamide ball-and-stick.png
Clinical data
AHFS/Drugs.comMonograph
MedlinePlusa682482
License data
Pregnancy
category
  • AU: C
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
  • N-[(azepan-1-ylamino)carbonyl]-4-methylbenzenesulfonamide
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 mass311.40 g·mol−1
3D model (JSmol)
  • O=S(=O)(c1ccc(cc1)C)NC(=O)NN2CCCCCC2
  • InChI=1S/C14H21N3O3S/c1-12-6-8-13(9-7-12)21(19,20)16-14(18)15-17-10-4-2-3-5-11-17/h6-9H,2-5,10-11H2,1H3,(H2,15,16,18) checkY
  • Key:OUDSBRTVNLOZBN-UHFFFAOYSA-N checkY
  (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

Tolazemide synthesis:[1] U.S. Patent 3,063,903 .mw-parser-output .citation{word-wrap:break-word}.mw-parser-output .citation:target{background-color:rgba(0,127,255,0.133)}GB 887886  DE 1196200 
Tolazemide synthesis:[1] U.S. Patent 3,063,903 GB 887886  DE 1196200 

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:[1]

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

References

  1. ^ a b Wright JB, Willette RE (July 1962). "Antidiabetic Agents. N4-Arylsulfonylsemicarbazides". Journal of Medicinal and Pharmaceutical Chemistry. 91: 815–22. doi:10.1021/jm01239a016. PMID 14056414.