Tolazamide

Tolazamide

Clinical data
AHFS/Drugs.com	Monograph
MedlinePlus	a682482
License data	US FDA: Tolazamide
Pregnancy category	AU: C US: C (Risk not ruled out)
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
Biological 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 Y
KEGG	D00379 Y
ChEBI	CHEBI:9613
ChEMBL	CHEMBL817 Y
ECHA InfoCard	100.013.262
Chemical and physical data
Formula	C14H21N3O3S
Molar mass	311.401 g/mol
3D model (Jmol)	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 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 azepane leads to the displacement of the ethoxy group and the formation of tolazemide:

Tolazemide synthesis: U.S. Patent 3,063,903 GB 887886  DE 1196200 

External links

• NIH/Medline