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Tolazamide

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Chemical compound Pharmaceutical compound
Tolazamide
Clinical data
Trade namesTolinase
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
IUPAC name
  • N--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
3D model (JSmol)
SMILES
  • O=S(=O)(c1ccc(cc1)C)NC(=O)NN2CCCCCC2
InChI
  • 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)
  • Key:OUDSBRTVNLOZBN-UHFFFAOYSA-N
  (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: 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:

Azepane proper would lead to .

References

  1. ^ Wright JB, Willette RE (July 1962). "Antidiabetic Agents. N4-Arylsulfonylsemicarbazides". Journal of Medicinal and Pharmaceutical Chemistry. 91 (4): 815–22. doi:10.1021/jm01239a016. PMID 14056414.

External links

  • "Tolazamide". Medline Plus. U.S. National Library of Medicine.
Oral diabetes medication, insulins and insulin analogs, and other drugs used in diabetes (A10)
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