Tolazamide

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 YesY
UNII 9LT1BRO48Q YesY
KEGG D00379 YesY
ChEMBL CHEMBL817 YesY
Chemical data
Formula C14H21N3O3S 
Mol. mass 311.401 g/mol
SMILES eMolecules & PubChem
 YesY(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

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:[1]

Tolazemide.png

References

  1. ^ Wright, J. B.; Willette, R. E. (1962). J. Med. Chem. 5 (4): 815–822. doi:10.1021/jm01239a016. 

External links


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M: END

anat/phys/devp/horm

noco(d)/cong/tumr, sysi/epon

proc, drug (A10/H1/H2/H3/H5)


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