Tolazamide
Chemical compound
- US FDA: Tolazamide
category
- AU: C
administration
- A10BB05 (WHO)
- US: ℞-only
- N-[(azepan-1-ylamino)carbonyl]-4-methylbenzenesulfonamide
- 1156-19-0
- 5503
- 6847
- DB00839
Y
- 5302 Y
- 9LT1BRO48Q
- D00379 Y
- CHEBI:9613
- ChEMBL817 Y
- DTXSID3021358
- 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)Y
- Key:OUDSBRTVNLOZBN-UHFFFAOYSA-NY
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
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
- ^ 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
- "Tolazamide". Medline Plus. U.S. National Library of Medicine.
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