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Tolazamide

Summary

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

Tolazamide
Clinical data
Trade namesTolinase
AHFS/Drugs.comMonograph
MedlinePlusa682482
License data
  • US FDA: Tolazamide
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
  • 1156-19-0
PubChem CID
  • 5503
IUPHAR/BPS
  • 6847
DrugBank
  • DB00839 checkY
ChemSpider
  • 5302 checkY
UNII
  • 9LT1BRO48Q
KEGG
  • D00379 checkY
ChEBI
  • CHEBI:9613
ChEMBL
  • ChEMBL817 checkY
CompTox Dashboard (EPA)
  • DTXSID3021358 Edit this at Wikidata
ECHA InfoCard100.013.262 Edit this at Wikidata
Chemical and physical data
FormulaC14H21N3O3S
Molar mass311.40 g·mol−1
3D model (JSmol)
  • Interactive image
  • 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)

Synthesis edit

 
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 edit

  1. ^ a b 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 edit

  • "Tolazamide". Medline Plus. U.S. National Library of Medicine.