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
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 an

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].

References

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