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

File:Tolazamide synthesis.png

The reaction between p-toluenesulfonamide (1) and ethyl chloroformate (2) in the presence of base gives tosylurethane [5577-13-9] (3). Heating that intermediate with azepane (4) leads to the displacement of the ethoxy group and the formation of tolazemide (5).{{cite book | vauthors=((Vardanyan, Ṛuben)), ((Hruby, V. J.)) | date= 2006 | title=Synthesis of essential drugs | publisher=Elsevier | isbn=9780444521668}}{{cite journal | vauthors = Wright JB, Willette RE | title = Antidiabetic Agents. N4-Arylsulfonylsemicarbazides | journal = Journal of Medicinal and Pharmaceutical Chemistry | volume = 91 | pages = 815–22 | date = July 1962 | issue = 4 | pmid = 14056414 | doi = 10.1021/jm01239a016 }}John B Wright, {{US patent|3063903}} (1962 to Upjohn Co).Wright John Brenton, {{Cite patent|country=GB|number=887886}} (1962 to Upjohn).DE1196200 idem Korger Gerhard, Weber Helmut, Aumuller Walter, {{US patent|3248384}} (1966 to Hoechst Ag).

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

References

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