Last updated
Tolazamide ball-and-stick.png
Clinical data
Trade names Tolinase
AHFS/ Monograph
MedlinePlus a682482
License data
  • AU:C
Routes of
ATC code
Legal status
Legal status
Pharmacokinetic data
Bioavailability ?
Metabolism metabolized in the liver to active metabolites
Elimination half-life 7 hours
Excretion Renal (85%) and fecal (7%)
  • N-[(azepan-1-ylamino)carbonyl]-4-methylbenzenesulfonamide
CAS Number
PubChem CID
CompTox Dashboard (EPA)
ECHA InfoCard 100.013.262 OOjs UI icon edit-ltr-progressive.svg
Chemical and physical data
Formula C14H21N3O3S
Molar mass 311.40 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) Yes check.svgY

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



Tolazemide synthesis: 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 Tolazamide synthesis.png
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: [1]

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

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  1. 1 2 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.