Tolazamide - Misplaced Pages

This is an old revision of this page, as edited by CheMoBot (talk | contribs) at 07:54, 30 August 2011 (Updating {{drugbox}} (no changed fields - updated 'DrugBank_Ref', 'ChEBI_Ref', 'ChEBI_Ref') per Chem/Drugbox validation (report errors or bugs)). The present address (URL) is a permanent link to this revision, which may differ significantly from the current revision.

Revision as of 07:54, 30 August 2011 by CheMoBot (talk | contribs) (Updating {{drugbox}} (no changed fields - updated 'DrugBank_Ref', 'ChEBI_Ref', 'ChEBI_Ref') per Chem/Drugbox validation (report errors or bugs))(diff) ← Previous revision | Latest revision (diff) | Newer revision → (diff) Pharmaceutical compound

Tolazamide
Clinical data

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	?
Elimination half-life	7 hours
Excretion	Renal (85%) and fecal (7%)
Identifiers
IUPAC name N--4-methylbenzenesulfonamide
CAS Number	1156-19-0
PubChem CID	5503
DrugBank	APRD01267
ChemSpider	5302
UNII	9LT1BRO48Q
KEGG	D00379
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
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
(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

para-Toluenesulfonamide is converted to its 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:

Wright, J. B.; Willette, R. E. (1962). J. Med. Chem. 5 (4): 815–822. doi:10.1021/jm01239a016. {{cite journal}}: Missing or empty |title= (help)CS1 maint: multiple names: authors list (link)

Oral diabetes medication, insulins and insulin analogs, and other drugs used in diabetes (A10)

fast-acting	Insulin aspart Insulin glulisine Insulin lispro
short-acting	Regular insulin
long-acting	Insulin detemir Insulin glargine (+lixisenatide) NPH insulin Lente insulin Ultralente insulin
ultra-long-acting	Insulin degludec (+insulin aspart, +liraglutide) Insulin icodec (+semaglutide)
inhalable	Exubera Afrezza

Non-insulins

Biguanides	Buformin Metformin Phenformin
TZDs/"glitazones" (PPAR)	Ciglitazone Darglitazone Englitazone Lobeglitazone Netoglitazone Pioglitazone Rivoglitazone Rosiglitazone Troglitazone
Dual PPAR agonists	Aleglitazar Muraglitazar Saroglitazar Tesaglitazar
Amylin analogs and DACRAs	Cagrilintide Pramlintide

GLP1 poly-agonist peptides	Mazdutide (GLP-1/GCGR) Retatrutide (GLP-1/GIP/GCGR) Tirzepatide (GLP-1/GIP)

Other

Aldose reductase inhibitors	Epalrestat Fidarestat Ranirestat Tolrestat Zenarestat
Alpha-glucosidase inhibitors	Acarbose Miglitol Voglibose
SGLT2 inhibitors/"gliflozins"	Canagliflozin Dapagliflozin Empagliflozin Ertugliflozin Ipragliflozin Luseogliflozin Remogliflozin Sergliflozin Sotagliflozin Tofogliflozin Velagliflozin
Other	Benfluorex Bromocriptine Imeglimin

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