Tolazamide

From Wikipedia, the free encyclopedia
Jump to: navigation, search
Tolazamide
Tolazamide.svg
Tolazamide ball-and-stick.png
Systematic (IUPAC) name
N-[(azepan-1-ylamino)carbonyl]-4-methylbenzenesulfonamide
Clinical data
AHFS/Drugs.com monograph
MedlinePlus a682482
Licence data US FDA:link
Pregnancy cat.
Legal status
Routes Oral
Pharmacokinetic data
Bioavailability ?
Metabolism metabolized in the liver to active metabolites
Half-life 7 hours
Excretion Renal (85%) and fecal (7%)
Identifiers
CAS number 1156-19-0
ATC code A10BB05
PubChem CID 5503
DrugBank DB00839
ChemSpider 5302 YesY
UNII 9LT1BRO48Q YesY
KEGG D00379 YesY
ChEBI CHEBI:9613
ChEMBL CHEMBL817 YesY
Chemical data
Formula C14H21N3O3S 
Mol. mass 311.401 g/mol
 YesY (what is this?)  (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[edit]

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

Tolazemide synthesis:[2] U.S. Patent 3,063,903 GB 887886  DE 1196200 

References[edit]

  1. ^ Wright, J. B.; Willette, R. E. (1962). J. Med. Chem. 5 (4): 815–822. doi:10.1021/jm01239a016. 
  2. ^ Wright, J. B.; Willette, R. E. (1962). "Antidiabetic Agents. N4-Arylsulfonylsemicarbazides". Journal of medicinal and pharmaceutical chemistry 91: 815–22. PMID 14056414.  edit

External links[edit]