Tolazamide

Tolazamide
Systematic (IUPAC) name


N-[(azepan-1-ylamino)carbonyl]-4-methylbenzenesulfonamide
Clinical data
AHFS/Drugs.com	monograph
MedlinePlus	a682482
Licence data	US FDA: Tolazamide
Pregnancy category	AU: C US: C (Risk not ruled out)
Legal status	US: ℞-only
Routes of administration	Oral
Pharmacokinetic data
Bioavailability	?
Metabolism	metabolized in the liver to active metabolites
Biological half-life	7 hours
Excretion	Renal (85%) and fecal (7%)
Identifiers
CAS Number	1156-19-0
ATC code	A10BB05
PubChem	CID 5503
IUPHAR/BPS	6847
DrugBank	DB00839^Y
ChemSpider	5302^Y
UNII	9LT1BRO48Q^Y
KEGG	D00379^Y
ChEBI	CHEBI:9613
ChEMBL	CHEMBL817^Y
Chemical data
Formula	C₁₄H₂₁N₃O₃S
Molar mass	311.401 g/mol
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)^Y Key:OUDSBRTVNLOZBN-UHFFFAOYSA-N^Y
(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:^[1]

Tolazemide synthesis:^[2] U.S. Patent 3,063,903 GB 887886 DE 1196200

References

↑ Wright, J. B.; Willette, R. E. (1962). J. Med. Chem. 5 (4): 815–822. doi:10.1021/jm01239a016. Missing or empty |title= (help)
↑ Wright, J. B.; Willette, R. E. (1962). "Antidiabetic Agents. N4-Arylsulfonylsemicarbazides". Journal of medicinal and pharmaceutical chemistry 91: 815–22. PMID 14056414.

External links

NIH/Medline

Oral anti-diabetic drugs, insulins and insulin analogs, and other drugs used in diabetes (A10)

Insulin

Sensitizers

Biguanides	Metformin^# Buformin<sp>‡ Phenformin^‡

TZDs/"glitazones" (PPAR)	Ciglitazone^§ Darglitazone^§ Englitazone^§ Lobeglitazone Netoglitazone^§ Pioglitazone Rivoglitazone^† Rosiglitazone Troglitazone^‡

Dual PPAR agonists	Aleglitazar^† Muraglitazar^§ Saroglitazar Tesaglitazar^§

Secretagogues

K+ ATP

Sulfonylureas	1st generation: Acetohexamide Carbutamide Chlorpropamide Metahexamide Tolbutamide Tolazamide 2nd generation: Glibenclamide (Glyburide)^# Glibornuride Glipizide Gliquidone Glisoxepide Glyclopyramide Glimepiride Gliclazide

Meglitinides/"glinides"	Nateglinide Repaglinide Mitiglinide

GLP-1 agonists

DPP-4 inhibitors

GPR40 Free fatty acid receptor 1

Fasiglifam^†

Analogs/other insulins

fast-acting (Insulin lispro
Insulin aspart
Insulin glulisine)
short-acting (Regular insulin)
long-acting (Insulin glargine
Insulin detemir
NPH insulin)
ultra-long-acting (Insulin degludec^†)
inhalable Exubera^‡
Afrezza

Other

Aldose reductase inhibitors	Epalrestat Fidarestat^§ Ranirestat^† Tolrestat^‡ Zenarestat^§

Alpha-glucosidase inhibitors	Acarbose Miglitol Voglibose

Amylin analog	Pramlintide

Sodium glucose transporter (SGLT2) inhibitors	Canagliflozin Dapagliflozin Empagliflozin Remogliflozin^§ Sergliflozin^§ Tofogliflozin^†

Other	Benfluorex^‡ Bromocriptine

^#WHO-EM
^‡Withdrawn from market
Clinical trials:
- ^†Phase III
- ^§Never to phase III

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