Tolazamide

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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	metabolized in the liver to active metabolites
Half-life	7 hours
Excretion	Renal (85%) and fecal (7%)
Identifiers
CAS number	1156-19-0
ATC code	A10BB05
PubChem	CID 5503
DrugBank	DB00839
ChemSpider	5302^Y
UNII	9LT1BRO48Q^Y
KEGG	D00379^Y
ChEBI	CHEBI:9613
ChEMBL	CHEMBL817^Y
Chemical data
Formula	C₁₄H₂₁N₃O₃S
Mol. 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
Y (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

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]

References

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

External links

NIH/Medline

Oral anti-diabetic drugs and Insulin analogs (A10)

Insulin

Sensitizers

Biguanides	Metformin^# Buformin^‡ Phenformin^‡

TZDs/"glitazones" (PPAR)	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^‡

Other

Alpha-glucosidase inhibitors	Acarbose Miglitol Voglibose

Amylin analog	Pramlintide

SGLT2 inhibitors	Canagliflozin Dapagliflozin Empagliflozin^† Remogliflozin^§ Sergliflozin^§ Tofogliflozin^†

Other	Bromocriptine Benfluorex^‡ Tolrestat^‡

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^‡Withdrawn from market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

M: END

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

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