Tolazamide

Tolazamide

Systematic (IUPAC) name
N-[(azepan-1-ylamino)carbonyl]-4-methylbenzenesulfonamide
Clinical data
AHFS/Drugs.com	monograph
MedlinePlus	a682482
Licence data	US FDA:link
Pregnancy cat.	C(AU) C(US)
Legal status	℞-only (US)
Routes	Oral
Pharmacokinetic data
Bioavailability	?
Metabolism	?
Half-life	7 hours
Excretion	Renal (85%) and fecal (7%)
Identifiers
CAS number	1156-19-0
ATC code	A10BB05
PubChem	CID 5503
DrugBank	APRD01267
ChemSpider	5302 Y
UNII	9LT1BRO48Q Y
KEGG	D00379 Y
ChEMBL	CHEMBL817 Y
Chemical data
Formula	C14H21N3O3S
Mol. mass	311.401 g/mol
SMILES	eMolecules & PubChem
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
Y(what is this?)  (verify)

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:

External links

• NIH/Medline