Tolazamide

Tolazamide
Clinical data
Trade names	Tolinase
AHFS/Drugs.com	Monograph
MedlinePlus	a682482
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	?
Metabolism	metabolized in the liver to active metabolites
Elimination half-life	7 hours
Excretion	Renal (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 ;
ChemSpider	5302 ;
UNII	9LT1BRO48Q;
KEGG	D00379 ;
ChEBI	CHEBI:9613;
ChEMBL	ChEMBL817 ;
CompTox Dashboard (EPA)	DTXSID3021358 ;
ECHA InfoCard	100.013.262
Chemical and physical data
Formula	C14H21N3O3S
Molar mass	311.40 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) ; Key:OUDSBRTVNLOZBN-UHFFFAOYSA-N ;
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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].

^ ^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.