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
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 ;
ChemSpider	5302 ;
UNII	9LT1BRO48Q;
KEGG	D00379 ;
ChEBI	CHEBI:9613;
ChEMBL	ChEMBL817 ;
CompTox Dashboard (EPA)	DTXSID3021358 ;
ECHA InfoCard	100.013.262
Chemical and physical data
Formula	C14H21N3O3S
Molar mass	311.401 g/mol 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) ; Key:OUDSBRTVNLOZBN-UHFFFAOYSA-N ;
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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

Tolazemide synthesis:[1] U.S. Patent 3,063,903 GB 887886 DE 1196200

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:[2]

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

References

Wright, J. B.; Willette, R. E. (1962). "Antidiabetic Agents. N4-Arylsulfonylsemicarbazides". Journal of Medicinal and Pharmaceutical Chemistry. 91: 815–22. PMID 14056414.
Wright, John B.; Willette, Robert E. (1962). "Antidiabetic Agents. N4-Arylsulfonylsemicarbazides". Journal of Medicinal and Pharmaceutical Chemistry. 5 (4): 815–822. doi:10.1021/jm01239a016. ISSN 0095-9065.

External links

NIH/Medline

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[1] Wright, J. B.; Willette, R. E. (1962). "Antidiabetic Agents. N4-Arylsulfonylsemicarbazides". Journal of Medicinal and Pharmaceutical Chemistry. 91: 815–22. PMID 14056414.

[WrightWillette1962-2] Wright, John B.; Willette, Robert E. (1962). "Antidiabetic Agents. N4-Arylsulfonylsemicarbazides". Journal of Medicinal and Pharmaceutical Chemistry. 5 (4): 815–822. doi:10.1021/jm01239a016. ISSN 0095-9065.