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
Eliminationhalf-life	7 hours
Excretion	Renal (85%) and fecal (7%)
Identifiers
IUPAC name N-[(azepan-1-ylamino)carbonyl]-4-methylbenzenesulfonamide
CAS Number	1156-19-0
PubChemCID	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
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Tolazamide is anoralblood glucose loweringdrug used for people withType 2 diabetes. It is part of thesulfonylurea family (ATC A10BB).

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

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

• "Tolazamide".Medline Plus. U.S. National Library of Medicine.

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