Tolazamide
{{short description|Chemical compound}}
{{Drugbox
| verifiedrevid = 408966679
| IUPAC_name = N-[(azepan-1-ylamino)carbonyl]-4-methylbenzenesulfonamide
| image = Tolazamide.svg
| image2 = Tolazamide ball-and-stick.png
| tradename = Tolinase
| Drugs.com = {{drugs.com|monograph|tolazamide}}
| MedlinePlus = a682482
| licence_US = Tolazamide
| pregnancy_AU = C
| pregnancy_US = C
| legal_US = Rx-only
| routes_of_administration = Oral
| bioavailability = ?
| metabolism = metabolized in the liver to active metabolites
| elimination_half-life = 7 hours
| excretion = Renal (85%) and fecal (7%)
| IUPHAR_ligand = 6847
| CAS_number = 1156-19-0
| ATC_prefix = A10
| ATC_suffix = BB05
| PubChem = 5503
| DrugBank_Ref = {{drugbankcite|correct|drugbank}}
| DrugBank = DB00839
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 5302
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = 9LT1BRO48Q
| KEGG_Ref = {{keggcite|correct|kegg}}
| KEGG = D00379
| ChEBI = 9613
| ChEMBL_Ref = {{ebicite|correct|EBI}}
| ChEMBL = 817
| C=14 | H=21 | N=3 | O=3 | S=1
| SMILES = O=S(=O)(c1ccc(cc1)C)NC(=O)NN2CCCCCC2
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 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)
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = OUDSBRTVNLOZBN-UHFFFAOYSA-N
}}
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 1-amino-azepane leads to the displacement of the ethoxy group and the formation of tolazemide:
Azepane proper would lead to [13078-23-4].
References
{{reflist}}
External links
- {{cite web | title = Tolazamide | url = https://medlineplus.gov/druginfo/meds/a682482.html | work = Medline Plus | publisher = U.S. National Library of Medicine }}
{{Oral hypoglycemics}}
{{Ion channel modulators}}
Category:Potassium channel blockers
{{gastrointestinal-drug-stub}}