Details
Stereochemistry | ACHIRAL |
Molecular Formula | C14H21N3O3S |
Molecular Weight | 311.4 |
Optical Activity | NONE |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
CC1=CC=C(C=C1)S(=O)(=O)NC(=O)NN2CCCCCC2
InChI
InChIKey=OUDSBRTVNLOZBN-UHFFFAOYSA-N
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)
Molecular Formula | C14H21N3O3S |
Molecular Weight | 311.4 |
Charge | 0 |
Count |
|
Stereochemistry | ACHIRAL |
Additional Stereochemistry | No |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Optical Activity | NONE |
DescriptionSources: http://www.drugbank.ca/drugs/DB00839Curator's Comment: Description was created based on several sources, including
https://www.drugs.com/pro/tolinase.html
Sources: http://www.drugbank.ca/drugs/DB00839
Curator's Comment: Description was created based on several sources, including
https://www.drugs.com/pro/tolinase.html
Tolazamide is an oral blood glucose lowering drug of the sulfonylurea class. Tolazamide appears to lower the blood glucose acutely by stimulating the release of insulin from the pancreas, an effect dependent upon functioning beta cells in the pancreatic islets. The mechanism by which tolazamide lowers blood glucose during long-term administration has not been clearly established. With chronic administration in Type II diabetic patients, the blood glucose lowering effect persists despite a gradual decline in the insulin secretory response to the drug. Extrapancreatic effects may be involved in the mechanism of action of oral sulfonylurea hypoglycemic drugs. Some patients who are initially responsive to oral hypoglycemic drugs, including tolazamide, may become unresponsive or poorly responsive over time. Alternatively, tolazamide may be effective in some patients who have become unresponsive to one or more other sulfonylurea drugs. In addition to its blood glucose lowering actions, tolazamide produces a mild diuresis by enhancement of renal free water clearance. Sulfonylureas likely bind to ATP-sensitive potassium-channel receptors on the pancreatic cell surface, reducing potassium conductance and causing depolarization of the membrane. Depolarization stimulates calcium ion influx through voltage-sensitive calcium channels, raising intracellular concentrations of calcium ions, which induces the secretion, or exocytosis, of insulin. Tolazamide is used for use as an adjunct to diet to lower the blood glucose in patients with non-insulin dependent diabetes mellitus (Type II) whose hyperglycemia cannot be satisfactorily controlled by diet alone.
Originator
Sources: http://en.pharmacodia.com/web/drug/1_7746.html
Curator's Comment: was developed and marketed as Tolinase® by Pharmacia and Upjohn
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: CHEMBL2096972 Sources: http://www.genome.jp/dbget-bin/www_bget?D00379 |
5.861 nM [Ki] | ||
Target ID: CHEMBL1293292 Sources: http://www.drugbank.ca/drugs/DB00839 |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Primary | Tolazamide Approved UseIndicated as an adjunct to diet to lower the blood glucose in patients with noninsulin dependent diabetes mellitus (Type II) whose hyperglycemia cannot be satisfactorily controlled by diet alone. Launch Date1984 |
Cmax
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
21.8 μg/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/7175719/ |
500 mg single, oral dose: 500 mg route of administration: Oral experiment type: SINGLE co-administered: |
TOLAZAMIDE serum | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
AUC
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
260 μg × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/7175719/ |
500 mg single, oral dose: 500 mg route of administration: Oral experiment type: SINGLE co-administered: |
TOLAZAMIDE serum | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
T1/2
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
4.6 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/7175719/ |
500 mg single, oral dose: 500 mg route of administration: Oral experiment type: SINGLE co-administered: |
TOLAZAMIDE serum | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
Doses
Dose | Population | Adverse events |
---|---|---|
0.5 g 2 times / day multiple, oral Recommended Dose: 0.5 g, 2 times / day Route: oral Route: multiple Dose: 0.5 g, 2 times / day Sources: |
unhealthy, 50 n = 8 Health Status: unhealthy Condition: diabetes mellitus Age Group: 50 Sex: M+F Population Size: 8 Sources: |
|
0.75 g 1 times / day single, oral Overdose Dose: 0.75 g, 1 times / day Route: oral Route: single Dose: 0.75 g, 1 times / day Sources: |
unhealthy, 59 n = 1 Health Status: unhealthy Condition: diabetes mellitus Age Group: 59 Sex: F Population Size: 1 Sources: |
Other AEs: Shakiness... |
1 g 1 times / day single, oral Overdose Dose: 1 g, 1 times / day Route: oral Route: single Dose: 1 g, 1 times / day Sources: |
unhealthy, 62 n = 1 Health Status: unhealthy Condition: diabetes mellitus Age Group: 62 Sex: F Population Size: 1 Sources: |
Other AEs: Dizziness... |
0.5 g 1 times / day single, oral Overdose Dose: 0.5 g, 1 times / day Route: oral Route: single Dose: 0.5 g, 1 times / day Sources: |
unhealthy, 69 n = 1 Health Status: unhealthy Condition: diabetes mellitus Age Group: 69 Sex: F Population Size: 1 Sources: |
Other AEs: Dizziness... |
AEs
AE | Significance | Dose | Population |
---|---|---|---|
Shakiness | 0.75 g 1 times / day single, oral Overdose Dose: 0.75 g, 1 times / day Route: oral Route: single Dose: 0.75 g, 1 times / day Sources: |
unhealthy, 59 n = 1 Health Status: unhealthy Condition: diabetes mellitus Age Group: 59 Sex: F Population Size: 1 Sources: |
|
Dizziness | 1 g 1 times / day single, oral Overdose Dose: 1 g, 1 times / day Route: oral Route: single Dose: 1 g, 1 times / day Sources: |
unhealthy, 62 n = 1 Health Status: unhealthy Condition: diabetes mellitus Age Group: 62 Sex: F Population Size: 1 Sources: |
|
Dizziness | 0.5 g 1 times / day single, oral Overdose Dose: 0.5 g, 1 times / day Route: oral Route: single Dose: 0.5 g, 1 times / day Sources: |
unhealthy, 69 n = 1 Health Status: unhealthy Condition: diabetes mellitus Age Group: 69 Sex: F Population Size: 1 Sources: |
Overview
CYP3A4 | CYP2C9 | CYP2D6 | hERG |
---|---|---|---|
OverviewOther
Other Inhibitor | Other Substrate | Other Inducer |
---|---|---|
Drug as perpetrator
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
Sources: https://pubmed.ncbi.nlm.nih.gov/2661591/ |
yes |
Drug as victim
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
major | ||||
minor |
PubMed
Title | Date | PubMed |
---|---|---|
Tolazamide-induced cholestasis. | 1980 Aug |
|
Wernicke's encephalopathy induced by tolazamide. | 1983 Sep 8 |
|
Reconstitution of IKATP: an inward rectifier subunit plus the sulfonylurea receptor. | 1995 Nov 17 |
|
Screening, library-assisted identification and validated quantification of oral antidiabetics of the sulfonylurea-type in plasma by atmospheric pressure chemical ionization liquid chromatography-mass spectrometry. | 2002 Jun 15 |
|
[A 50-year history of new drugs in Japan-the development and progress of anti-diabetic drugs and the epidemiological aspects of diabetes mellitus]. | 2003 |
|
Selection of drugs to test the specificity of the Tg.AC assay by screening for induction of the gadd153 promoter in vitro. | 2003 Aug |
|
Cardiovascular risk factors associated with insulin resistance: effects of oral antidiabetic agents. | 2005 |
|
Effects of sulfonylureas, alpha-endosulfine counterparts, on glomerulosclerosis in type 1 and type 2 models of diabetes. | 2005 Feb |
|
Risk of cardiovascular disease and all cause mortality among patients with type 2 diabetes prescribed oral antidiabetes drugs: retrospective cohort study using UK general practice research database. | 2009 Dec 3 |
Sample Use Guides
In Vivo Use Guide
Sources: https://www.drugs.com/pro/tolinase.html
The usual starting dose of Tolinase Tablets (Tolazamide) for the mild to moderately severe Type II diabetic patient is 100–250 mg daily administered with breakfast or the first main meal. Generally, if the fasting blood glucose is less than 200 mg/dl, the starting dose is 100 mg/day as a single daily dose. If the fasting blood glucose value is greater than 200 mg/dl, the starting dose is 250 mg/day as a single dose. If the patient is malnourished, underweight, elderly, or not eating properly, the initial therapy should be 100 mg once a day.
Route of Administration:
Oral
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/9151937
Tolazamide (1 mM) block contractions induced by prostaglandin F2alpha and the thromboxane A2 mimetic U-46619 in rat aorta
Substance Class |
Chemical
Created
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Record UNII |
9LT1BRO48Q
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Validated (UNII)
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NCI_THESAURUS |
C97936
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N0000008054
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N0000008054
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Tolazamide
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C29502
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Tolazamide
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1156-19-0
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DB00839
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1668001
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CHROMATOGRAPHIC PURITY (HPLC/UV)
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