Details
Stereochemistry | ACHIRAL |
Molecular Formula | C23H28ClN3O5S |
Molecular Weight | 494.004 |
Optical Activity | NONE |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
COC1=C(C=C(Cl)C=C1)C(=O)NCCC2=CC=C(C=C2)S(=O)(=O)NC(=O)NC3CCCCC3
InChI
InChIKey=ZNNLBTZKUZBEKO-UHFFFAOYSA-N
InChI=1S/C23H28ClN3O5S/c1-32-21-12-9-17(24)15-20(21)22(28)25-14-13-16-7-10-19(11-8-16)33(30,31)27-23(29)26-18-5-3-2-4-6-18/h7-12,15,18H,2-6,13-14H2,1H3,(H,25,28)(H2,26,27,29)
DescriptionSources: http://www.drugbank.ca/drugs/DB01016Curator's Comment: Description was created based on several sources, including
http://www.accessdata.fda.gov/drugsatfda_docs/label/2013/017532Orig1s034lbl.pdf
Sources: http://www.drugbank.ca/drugs/DB01016
Curator's Comment: Description was created based on several sources, including
http://www.accessdata.fda.gov/drugsatfda_docs/label/2013/017532Orig1s034lbl.pdf
Glyburide, a second-generation sulfonylurea antidiabetic agent, lowers blood glucose acutely by stimulating the release of insulin from the pancreas, an effect dependent upon functioning beta cells in the pancreatic islets. 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 sulfonyl-urea hypoglycemic drugs. The combination of glibenclamide and metformin may have a synergistic effect, since both agents act to improve glucose tolerance by different but complementary mechanisms. In addition to its blood glucose lowering actions, glyburide produces a mild diuresis by enhancement of renal free water clearance. Glyburide is twice as potent as the related second-generation agent glipizide. Sulfonylureas such as glyburide bind to ATP-sensitive potassium channels 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. Glyburide is indicated as an adjunct to diet to lower the blood glucose in patients with NIDDM whose hyperglycemia cannot be satisfactorily controlled by diet alone. Glyburide is available as a generic, is manufactured by many pharmaceutical companies and is sold in doses of 1.25, 2.5 and 5 mg under many brand names including Gliben-J, Daonil, Diabeta, Euglucon, Gilemal, Glidanil, Glybovin, Glynase, Maninil, Micronase and Semi-Daonil. It is also available in a fixed-dose combination drug with metformin that is sold under various trade names, e.g. Bagomet Plus, Benimet, Glibomet, Gluconorm, Glucored, Glucovance, Metglib and many others.
CNS Activity
Sources: https://www.ncbi.nlm.nih.gov/pubmed/26225433
Curator's Comment: Weak penetration in rodents was shown. Glyburide reaches the central nervous system when given systemically, is rapidly removed across the BBB when given intracranioventricularly, and any Glyburide that does enter (and is below detection limit) is insufficient to influence neuronal function
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: CHEMBL2071 Sources: https://www.ncbi.nlm.nih.gov/pubmed/11716850 |
7.1 nM [IC50] | ||
Target ID: CHEMBL3244 Sources: https://www.ncbi.nlm.nih.gov/pubmed/15294453 |
5.2 nM [IC50] | ||
Target ID: CHEMBL3397 Sources: https://www.ncbi.nlm.nih.gov/pubmed/12920163 |
2.4 µM [Ki] | ||
Target ID: CHEMBL340 Sources: https://www.ncbi.nlm.nih.gov/pubmed/12920163 |
42.5 µM [Ki] | ||
Target ID: CHEMBL2265 Sources: https://www.ncbi.nlm.nih.gov/pubmed/11032738 |
20.0 µM [IC50] | ||
Target ID: CHEMBL2096972 Sources: http://www.genome.jp/dbget-bin/www_bget?D00336 |
4.3 nM [IC50] |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Primary | Diaßeta Approved UseDiaßeta is indicated as an adjunct to diet and exercise to improve glycemic control in adults with type 2 diabetes mellitus. Launch Date4.52131193E11 |
Cmax
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
91.1 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/11406737/ |
1.75 mg single, oral dose: 1.75 mg route of administration: Oral experiment type: SINGLE co-administered: |
GLYBURIDE plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED |
AUC
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
323.9 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/11406737/ |
1.75 mg single, oral dose: 1.75 mg route of administration: Oral experiment type: SINGLE co-administered: |
GLYBURIDE plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED |
T1/2
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
2 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/11406737/ |
1.75 mg single, oral dose: 1.75 mg route of administration: Oral experiment type: SINGLE co-administered: |
GLYBURIDE plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED |
Doses
Dose | Population | Adverse events |
---|---|---|
40 mg 1 times / day multiple, oral Highest studied dose Dose: 40 mg, 1 times / day Route: oral Route: multiple Dose: 40 mg, 1 times / day Sources: |
unhealthy, adult n = 23 Health Status: unhealthy Condition: diabetes Age Group: adult Sex: M+F Population Size: 23 Sources: |
|
5 mg 1 times / day multiple, oral (median) Recommended Dose: 5 mg, 1 times / day Route: oral Route: multiple Dose: 5 mg, 1 times / day Sources: |
unhealthy, mean age 32.8 years n = 236 Health Status: unhealthy Condition: gestational diabetes mellitus Age Group: mean age 32.8 years Sex: F Population Size: 236 Sources: |
Disc. AE: Hypoglycemia... AEs leading to discontinuation/dose reduction: Hypoglycemia (5%) Sources: |
2.5 mg 1 times / day steady, oral (starting) Dose: 2.5 mg, 1 times / day Route: oral Route: steady Dose: 2.5 mg, 1 times / day Sources: |
unhealthy|pregnant n = 189 Health Status: unhealthy|pregnant Condition: Mild Gestational Diabetes Sex: F Population Size: 189 Sources: |
Other AEs: Facial swelling... Other AEs: Facial swelling (serious, 1 patient) Sources: |
AEs
AE | Significance | Dose | Population |
---|---|---|---|
Hypoglycemia | 5% Disc. AE |
5 mg 1 times / day multiple, oral (median) Recommended Dose: 5 mg, 1 times / day Route: oral Route: multiple Dose: 5 mg, 1 times / day Sources: |
unhealthy, mean age 32.8 years n = 236 Health Status: unhealthy Condition: gestational diabetes mellitus Age Group: mean age 32.8 years Sex: F Population Size: 236 Sources: |
Facial swelling | serious, 1 patient | 2.5 mg 1 times / day steady, oral (starting) Dose: 2.5 mg, 1 times / day Route: oral Route: steady Dose: 2.5 mg, 1 times / day Sources: |
unhealthy|pregnant n = 189 Health Status: unhealthy|pregnant Condition: Mild Gestational Diabetes Sex: F Population Size: 189 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/12920163/ Page: 2.0 |
weak [IC50 90 uM] | weak (co-administration study) Comment: Glyburide reduced the mean AUCτ of bosentan and the phenol, hydroxy, and hydroxy-phenol metabolites 29%, 26%, 25%, and 22% (all P < .05), respectively Sources: https://pubmed.ncbi.nlm.nih.gov/12920163/ Page: 2.0 |
||
Sources: https://pubmed.ncbi.nlm.nih.gov/12920163/ Page: 2.0 |
yes [IC50 11.3 uM] | weak (co-administration study) Comment: Glyburide reduced the mean AUCτ of bosentan and the phenol, hydroxy, and hydroxy-phenol metabolites 29%, 26%, 25%, and 22% (all P < .05), respectively Sources: https://pubmed.ncbi.nlm.nih.gov/12920163/ Page: 2.0 |
||
yes [IC50 15 uM] | ||||
yes [IC50 18.8 uM] | ||||
yes [IC50 199 uM] | ||||
yes [Ki 0.75 uM] |
Drug as victim
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
major | yes (co-administration study) Comment: Coadministration with rifampin (inducer) increased blood sugar levels in 17 of 29 patients (595) Page: 5.0 |
|||
minor | ||||
minor | yes (co-administration study) Comment: Coadministration with rifampin (inducer) increased blood sugar levels in 17 of 29 patients (595) Page: 5.0 |
|||
no | ||||
yes |
PubMed
Title | Date | PubMed |
---|---|---|
The structure and function of the ATP-sensitive K+ channel in insulin-secreting pancreatic beta-cells. | 1999 Apr |
|
Drug interaction: omeprazole and phenprocoumon. | 2001 |
|
Role of pertussis toxin-sensitive G-proteins in intracellular Ca2+ release and apoptosis induced by inhibiting cystic fibrosis transmembrane conductance regulator (CFTR) Cl- channels in HepG2 human hepatoblastoma cells. | 2001 |
|
Nitrooxy alkyl apovincaminate activates K+ currents in rat neocortical neurons. | 2001 Feb |
|
Changes in cell volume induced by activation of the cyclic amp-dependent chloride channel in guinea-pig cardiac myocytes. | 2001 Feb |
|
Effects of K+ channel openers on I K(ATP) of human atrial myocytes at physiological temperatures. | 2001 Feb |
|
Functional and molecular characterization of receptor subtypes mediating coronary microvascular dilation to adenosine. | 2001 Feb |
|
Assessment of CFTR chloride channel openers in intact normal and cystic fibrosis murine epithelia. | 2001 Feb |
|
Ethanol enhances the functional recovery of stunned myocardium independent of K(ATP) channels in dogs. | 2001 Feb |
|
Mitochondrial ATP dependent potassium channels mediate non-ischemic preconditioning by tachycardia in dogs. | 2001 Jan |
|
Verapamil prevents stretch-induced shortening of atrial effective refractory period in langendorff-perfused rabbit heart. | 2001 Jan |
|
Vasopressin regulates water flow in a rat cortical collecting duct cell line not containing known aquaporins. | 2001 Jan 1 |
|
Intrahippocampal infusions of k-atp channel modulators influence spontaneous alternation performance: relationships to acetylcholine release in the hippocampus. | 2001 Jan 15 |
|
K(ATP) channel blockers selectively interact with A(1)-adenosine receptor mediated modulation of acetylcholine release in the rat hippocampus. | 2001 Jan 19 |
|
Insulin-induced relaxation of rat mesenteric artery is mediated by Ca(2+)-activated K(+) channels. | 2001 Jan 5 |
|
Formulation, characterization, and in vitro release of glyburide from proliposomal beads. | 2001 Jan-Mar |
|
Hypoglycemic and antihyperglycemic activity of Syzygium alternifolium (Wt.) Walp. seed extracts in normal and diabetic rats. | 2001 Mar |
|
Characterization of secretory and morphologic properties of primary cultured endocrine cells from porcine pancreata. | 2001 Mar |
|
Concentration of the complement activation product, acylation-stimulating protein, is related to C-reactive protein in patients with type 2 diabetes. | 2001 Mar |
|
Profile of moxifloxacin drug interactions. | 2001 Mar 15 |
|
Characteristics of pancreatic beta-cell secretion in Type 2 diabetic patients treated with gliclazide and glibenclamide. | 2001 May |
Sample Use Guides
The usual starting dose is 2.5 to 5 mg daily, administered
with breakfast or the first main meal. Those patients who may be more sensitive to hypoglycemic drugs should be started at 1.25 mg daily. The usual maintenance dose is in the range of 1.25 to 20 mg daily, which may be given as a single dose or in divided doses.
Route of Administration:
Oral
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/22399138
Inhibition of ABCA1 by glibenclamide (Glyburide) has been reported to
occur in the concentration range of 100 to 1,000 uM
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Classification Tree | Code System | Code | ||
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NDF-RT |
N0000008054
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NDF-RT |
N0000008054
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FDA ORPHAN DRUG |
502615
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FDA ORPHAN DRUG |
518816
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LIVERTOX |
463
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WHO-VATC |
QA10BB01
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NDF-RT |
N0000175608
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FDA ORPHAN DRUG |
539316
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NDF-RT |
N0000008054
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FDA ORPHAN DRUG |
491215
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WHO-ESSENTIAL MEDICINES LIST |
18.5
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EU-Orphan Drug |
EU/3/15/1589
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NCI_THESAURUS |
C97936
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WHO-ATC |
A10BB01
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Code System | Code | Type | Description | ||
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SUB07916MIG
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2386
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GLYBURIDE
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PRIMARY | Description: A white or almost white, crystalline powder; odourless or almost odourless. Solubility: Practically insoluble in water and ether R; slightly soluble in ethanol (~750 g/l) TS and methanol R. Category: Antidiabetic agent. Storage: Glibenclamide should be kept in a well-closed container. Definition: Glibenclamide contains not less than 98.5% and not more than 101.0% of C23H28ClN3O5S, calculated with reference to the dried substance. | ||
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1314
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759618
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m5784
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SX6K58TVWC
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5441
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Glyburide
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3488
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10238-21-8
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SX6K58TVWC
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233-570-6
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100000080403
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D005905
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1295505
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2414
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GLIBENCLAMIDE
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DB01016
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4815
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PRIMARY | RxNorm | ||
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DTXSID0037237
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C29076
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CHEMBL472
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ACTIVE MOIETY
METABOLITE (PARENT)
METABOLITE (PARENT)