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

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 Y
ChemSpider	5302 Y
UNII	9LT1BRO48Q
KEGG	D00379 Y
ChEBI	CHEBI:9613
ChEMBL	ChEMBL817 Y
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) Y Key:OUDSBRTVNLOZBN-UHFFFAOYSA-N Y
(verify)

Synthesis

The reaction between p-toluenesulfonamide (1) and ethyl chloroformate (2) in the presence of base gives tosylurethane [5577-13-9] (3). Heating that intermediate with azepane (4) leads to the displacement of the ethoxy group and the formation of tolazemide (5).^{[1][2][3][4][5]}

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