Tolazamide

 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
Tolazamide.svg
Tolazamide ball-and-stick.png
Clinical data
AHFS/Drugs.comMonograph
MedlinePlusa682482
License data
  • US FDA: Tolazamide
Pregnancy
category
  • AU: C
Routes of
administration		Oral
ATC code
  • A10BB05 (WHO)
Legal status
Legal status
  • US: ℞-only
Pharmacokinetic data
Bioavailability?
Metabolismmetabolized in the liver to active metabolites
Elimination half-life7 hours
ExcretionRenal (85%) and fecal (7%)
Identifiers
IUPAC name
  • N-[(azepan-1-ylamino)carbonyl]-4-methylbenzenesulfonamide
CAS Number
  • 1156-19-0
PubChem CID
  • 5503
IUPHAR/BPS
  • 6847
DrugBank
  • DB00839 check
ChemSpider
  • 5302 check
UNII
  • 9LT1BRO48Q
KEGG
  • D00379 check
ChEBI
  • CHEBI:9613
ChEMBL
  • ChEMBL817 check
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
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) check
  • Key:OUDSBRTVNLOZBN-UHFFFAOYSA-N check
  (verify)

SynthesisEdit

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].

This article uses material from the Wikipedia article
 Metasyntactic variable, which is released under the 
Creative Commons
Attribution-ShareAlike 3.0 Unported License.