U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ACHIRAL
Molecular Formula C12H18N2O3S
Molecular Weight 270.348
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of TOLBUTAMIDE

SMILES

CCCCNC(=O)NS(=O)(=O)C1=CC=C(C)C=C1

InChI

InChIKey=JLRGJRBPOGGCBT-UHFFFAOYSA-N
InChI=1S/C12H18N2O3S/c1-3-4-9-13-12(15)14-18(16,17)11-7-5-10(2)6-8-11/h5-8H,3-4,9H2,1-2H3,(H2,13,14,15)

HIDE SMILES / InChI

Molecular Formula C12H18N2O3S
Molecular Weight 270.348
Charge 0
Count
MOL RATIO 1 MOL RATIO (average)
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Description

Tolbutamide is an oral antihyperglycemic agent used for the treatment of non-insulin-dependent diabetes mellitus (NIDDM). It is structurally similar to acetohexamide, chlorpropamide and tolazamide and belongs to the sulfonylurea class of insulin secretagogues, which act by stimulating β cells of the pancreas to release insulin. Sulfonylureas lower blood glucose in patients with NIDDM by directly stimulating the acute release of insulin from functioning beta cells of pancreatic islet tissue by an unknown process that involves a sulfonylurea receptor (receptor 1) on the beta cell. Sulfonylureas inhibit the ATP-potassium channels on the beta cell membrane and potassium efflux, which results in depolarization and calcium influx, calcium-calmodulin binding, kinase activation, and release of insulin-containing granules by exocytosis, an effect similar to that of glucose.

CNS Activity

Originator

Approval Year

Targets

Primary TargetPharmacologyConditionPotency
0.8 µM [IC50]
1.15 µM [IC50]

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Tolbutamide

Cmax

ValueDoseCo-administeredAnalytePopulation
51.1 μg/mL
1 g single, oral
TOLBUTAMIDE plasma
Homo sapiens

AUC

ValueDoseCo-administeredAnalytePopulation
998.42 μg × h/mL
1 g single, oral
TOLBUTAMIDE plasma
Homo sapiens

T1/2

ValueDoseCo-administeredAnalytePopulation
418 min
20 mg/kg bw single, intravenous
TOLBUTAMIDE plasma
Homo sapiens

Funbound

ValueDoseCo-administeredAnalytePopulation
5%
20 mg/kg bw single, intravenous
TOLBUTAMIDE plasma
Homo sapiens

Overview

CYP3A4CYP2C9CYP2D6hERG

OverviewOther

Drug as perpetrator​

Drug as victim

PubMed

Sample Use Guides

In Vivo Use Guide
Usual Adult Dose for Diabetes Type 2 Initial dose: 1 to 2 g orally once a day or in divided doses through the day -Adjust dose based on blood glucose response Maintenance dose: 0.25 to 3 g orally once a day or in divided doses through the day Maximum dose: 3 g per day
Route of Administration: Oral
In Vitro Use Guide
Insulin effects were eliminated in the presence of a ATP-dependent K+ (K(ATP)) channel antagonist tolbutamide (200 uM) in brain stem slices
Substance Class Chemical
Record UNII
982XCM1FOI
Record Status Validated (UNII)
Record Version