GLYBURIDE

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

Structure Search

SMILES

COC1=CC=C(Cl)C=C1C(=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)

HIDE SMILES / InChI

Molecular Formula	C23H28ClN3O5S
Molecular Weight	494.004
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Description
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

Originator

Approval Year

Targets

Primary Target	Pharmacology	Potency
Sulfonylurea receptor 1 5 Target ID: CHEMBL2071 Sources: https://www.ncbi.nlm.nih.gov/pubmed/11716850	Agonist 2752	7.1 nM [IC50]
Sulfonylurea receptor 2 9 Target ID: CHEMBL3244 Sources: https://www.ncbi.nlm.nih.gov/pubmed/15294453	Modulator 846	5.2 nM [IC50]
Cytochrome P450 2C9 50 Target ID: CHEMBL3397 Sources: https://www.ncbi.nlm.nih.gov/pubmed/12920163	Inhibitor 8504	2.4 µM [Ki]
Cytochrome P450 3A4 127 Target ID: CHEMBL340 Sources: https://www.ncbi.nlm.nih.gov/pubmed/12920163	Inhibitor 8504	42.5 µM [Ki]
Acyl coenzyme A:cholesterol acyltransferase 15 Target ID: CHEMBL2265 Sources: https://www.ncbi.nlm.nih.gov/pubmed/11032738	Inhibitor 8504	20.0 µM [IC50]
Sulfonylurea receptor 1, Kir6.2 13 Target ID: CHEMBL2096972 Sources: http://www.genome.jp/dbget-bin/www_bget?D00336	Agonist 2752	4.3 nM [IC50]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Type 2 diabetes mellitus 262 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2013/017532Orig1s034lbl.pdf	Primary		Approved 8583	Diaßeta Approved Use Diaßeta is indicated as an adjunct to diet and exercise to improve glycemic control in adults with type 2 diabetes mellitus. Launch Date 1984

C_max

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

T_1/2

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: https://pubmed.ncbi.nlm.nih.gov/4927607/	unhealthy, adult Health Status: unhealthy Age Group: adult Sex: M+F Sources: https://pubmed.ncbi.nlm.nih.gov/4927607/	Sources: https://pubmed.ncbi.nlm.nih.gov/4927607/
5 mg 1 times / day multiple, oral Recommended Dose: 5 mg, 1 times / day Route: oral Route: multiple Dose: 5 mg, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/16021069/	unhealthy, mean age 32.8 years Health Status: unhealthy Age Group: mean age 32.8 years Sex: F Sources: https://pubmed.ncbi.nlm.nih.gov/16021069/	Disc. AE: Hypoglycemia... AEs leading to discontinuation/dose reduction: Hypoglycemia (5%) Sources: https://pubmed.ncbi.nlm.nih.gov/16021069/
2.5 mg 1 times / day steady, oral Dose: 2.5 mg, 1 times / day Route: oral Route: steady Dose: 2.5 mg, 1 times / day Sources: https://clinicaltrials.gov/ct2/show/NCT00744965	unhealthy\|pregnant Health Status: unhealthy\|pregnant Sex: F Sources: https://clinicaltrials.gov/ct2/show/NCT00744965	Other AEs: Facial swelling... Other AEs: Facial swelling (serious, 1 patient) Sources: https://clinicaltrials.gov/ct2/show/NCT00744965

AEs

AE	Significance	Dose	Population
Hypoglycemia	5% Disc. AE	5 mg 1 times / day multiple, oral Recommended Dose: 5 mg, 1 times / day Route: oral Route: multiple Dose: 5 mg, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/16021069/	unhealthy, mean age 32.8 years Health Status: unhealthy Age Group: mean age 32.8 years Sex: F Sources: https://pubmed.ncbi.nlm.nih.gov/16021069/
Facial swelling	serious, 1 patient	2.5 mg 1 times / day steady, oral Dose: 2.5 mg, 1 times / day Route: oral Route: steady Dose: 2.5 mg, 1 times / day Sources: https://clinicaltrials.gov/ct2/show/NCT00744965	unhealthy\|pregnant Health Status: unhealthy\|pregnant Sex: F Sources: https://clinicaltrials.gov/ct2/show/NCT00744965

Overview

CYP3A4	CYP2C9	CYP2D6	hERG
substrate 1946 inhibitor 2252	substrate 1193 inhibitor 2438	substrate 1388

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
MRP5 31 BSEP 550 OCT1 620 OATP1B1 1079	CYP2C19 1119 OATP2B1 122

Drug as perpetrator

Target	Modality	Activity	Clinical evidence
CYP3A4 2633	inhibitor 4027 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
CYP2C9 2497	inhibitor 4027 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
MRP5 80	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/15897250/	yes [IC50 15 uM]
BSEP 554	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/19520776/	yes [IC50 18.8 uM]
OCT1 656	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/20567254/	yes [IC50 199 uM]
OATP1B1 1095	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/16595711/	yes [Ki 0.75 uM]

Drug as victim

Target	Modality	Activity	Clinical evidence
CYP2C9 1193	substrate 4014 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/017532s038lbl.pdf#page=5; https://pubmed.ncbi.nlm.nih.gov/9069698/ Page: 5.0	major	yes (co-administration study) Comment: Coadministration with rifampin (inducer) increased blood sugar levels in 17 of 29 patients (595) Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/017532s038lbl.pdf#page=5; https://pubmed.ncbi.nlm.nih.gov/9069698/ Page: 5.0
CYP2C19 1119	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/11956508/	minor
CYP3A4 1946	substrate 4014 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/017532s038lbl.pdf#page=5; https://pubmed.ncbi.nlm.nih.gov/9069698/ Page: 5.0	minor	yes (co-administration study) Comment: Coadministration with rifampin (inducer) increased blood sugar levels in 17 of 29 patients (595) Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/017532s038lbl.pdf#page=5; https://pubmed.ncbi.nlm.nih.gov/9069698/ Page: 5.0
CYP2D6 1388	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/11956508/	no
OATP2B1 122	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/15640378/	yes

Sourcing

Vendor/Aggregator	ID	URL
ChEBI	CHEBI:5441	https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:5441
ChemicalBook	CB1737679	https://www.chemicalbook.com/ChemicalProductProperty_EN_CB1737679
eMolecules	27520402	https://www.emolecules.com/cgi-bin/more?vid=27520402
eMolecules	538570	https://www.emolecules.com/cgi-bin/more?vid=538570
MolPort	MolPort-000-784-850	https://www.molport.com/shop/molecule-link/MolPort-000-784-850
Selleck Chemicals	Glyburide(Diabeta)	http://www.selleckchem.com/products/Glyburide(Diabeta).html
ZINC	ZINC000000537805	http://zinc15.docking.org/substances/ZINC000000537805

PubMed

Title	Date	PubMed
Glibenclamide induced chronic cholestasis simulating primary biliary cirrhosis: a case report.	1996 Mar	10967995
Glyburide-ciprofloxacin interaction with resistant hypoglycemia.	2000 Aug	10918110
Drug interaction: omeprazole and phenprocoumon.	2001	11313000
Troglitazone prevents the rise in visceral adiposity and improves fatty liver associated with sulfonylurea therapy--a randomized controlled trial.	2001 Apr	11288035
The Arabidopsis thaliana ABC transporter AtMRP5 controls root development and stomata movement.	2001 Apr 17	11296221
Effects of phosphodiesterase inhibitors on hypoxic pulmonary vasoconstriction. Influence of K(+) channels and nitric oxide.	2001 Apr 6	11301069
State-dependent modification of ATP-sensitive K+ channels by phosphatidylinositol 4,5-bisphosphate.	2001 Feb	11208525
Nitric oxide activates the sarcolemmal K(ATP) channel in normoxic and chronically hypoxic hearts by a cyclic GMP-dependent mechanism.	2001 Feb	11162137
Functional and molecular characterization of receptor subtypes mediating coronary microvascular dilation to adenosine.	2001 Feb	11162132
The sulphonylurea glibenclamide inhibits multidrug resistance protein (MRP1) activity in human lung cancer cells.	2001 Feb	11159731
Mechanism of prolonged vasorelaxation to ATP in the rat isolated mesenteric arterial bed.	2001 Feb	11159721
Assessment of CFTR chloride channel openers in intact normal and cystic fibrosis murine epithelia.	2001 Feb	11159718
Protein kinase C and G(i/o) proteins are involved in adenosine- and ischemic preconditioning-mediated renal protection.	2001 Feb	11158213
Altered effects of potassium channel modulation in the coronary circulation in experimental hypercholesterolemia.	2001 Feb 1	11166765
Potassium channel openers depolarize hippocampal mitochondria.	2001 Feb 16	11172747
Functional evidence for an inward rectifier potassium current in rat renal afferent arterioles.	2001 Feb 2	11157666
Ibuprofen-related hypoglycemia in a patient receiving sulfonylurea.	2001 Feb 20	11182854
Activation of Na(+), K(+), Cl(-)-cotransport mediates intracellular Ca(2+) increase and apoptosis induced by Pinacidil in HepG2 human hepatoblastoma cells.	2001 Feb 23	11181077
Effect of glibenclamide in gabapentin antinociception.	2001 Jan	11211568
Near-normoglycaemic remission in African-Americans with Type 2 diabetes mellitus is associated with recovery of beta cell function.	2001 Jan	11168335
Vascular effects of metabolic inhibition by 2-deoxy-D-glucose in humans.	2001 Jan	11152379
Involvement of Ca2+ -activated K+ channels in ginsenosides-induced aortic relaxation in rats.	2001 Jan	11152372
Effect of oral administration of bark extracts of Pterocarpus santalinus L. on blood glucose level in experimental animals.	2001 Jan	11137350
Protection of cardiac myocytes via delta(1)-opioid receptors, protein kinase C, and mitochondrial K(ATP) channels.	2001 Jan	11123254
Role of mitochondrial and sarcolemmal K(ATP) channels in ischemic preconditioning of the canine heart.	2001 Jan	11123240
Cause of high variability in drug dissolution testing and its impact on setting tolerances.	2001 Jan	11113646
Intrahippocampal infusions of k-atp channel modulators influence spontaneous alternation performance: relationships to acetylcholine release in the hippocampus.	2001 Jan 15	11160440
Insulin-induced relaxation of rat mesenteric artery is mediated by Ca(2+)-activated K(+) channels.	2001 Jan 5	11137870
Hypoglycemic and antihyperglycemic activity of Syzygium alternifolium (Wt.) Walp. seed extracts in normal and diabetic rats.	2001 Mar	11315761
Hemodynamic, metabolic and hormonal responses to oral glibenclamide in patients with cirrhosis receiving glucose.	2001 Mar	11305519
Improvement of glycemic control by 1 year of insulin therapy leads to a sustained decrease in sE-selectin concentrations in type 2 diabetes.	2001 Mar	11289483
Inhibitory effects of nicorandil on rat mesangial cell proliferation via the protein kinase G pathway.	2001 Mar	11287762
The mechanism of gentisic acid-induced relaxation of the guinea pig isolated trachea: the role of potassium channels and vasoactive intestinal peptide receptors.	2001 Mar	11262590
Mechanism of CGRP-induced relaxation in rat intramural coronary arteries.	2001 Mar	11250874
Functional characterisation of human TASK-3, an acid-sensitive two-pore domain potassium channel.	2001 Mar	11249964
Characterization of secretory and morphologic properties of primary cultured endocrine cells from porcine pancreata.	2001 Mar	11249067
Concentration of the complement activation product, acylation-stimulating protein, is related to C-reactive protein in patients with type 2 diabetes.	2001 Mar	11230779
Regulation of an outwardly rectifying chloride conductance in renal epithelial cells by external and internal calcium.	2001 Mar 1	11284203
Gramicidin-perforated patch analysis on HCO3- secretion through a forskolin-activated anion channel in rat parotid intralobular duct cells.	2001 Mar 1	11284200
Profile of moxifloxacin drug interactions.	2001 Mar 15	11249829
Functional roles of cardiac and vascular ATP-sensitive potassium channels clarified by Kir6.2-knockout mice.	2001 Mar 30	11282890
Characteristics of pancreatic beta-cell secretion in Type 2 diabetic patients treated with gliclazide and glibenclamide.	2001 May	11311964

Patents

Sample Use Guides

In Vivo Use Guide

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

Inhibition of ABCA1 by glibenclamide (Glyburide) has been reported to occur in the concentration range of 100 to 1,000 uM

Substance Class	Chemical Created by `admin` on `Mon Mar 31 17:46:19 GMT 2025` Edited by `admin` on `Mon Mar 31 17:46:19 GMT 2025`
Record UNII	SX6K58TVWC
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

GLYBURIDE

Official Name

English

GLIBENCLAMIDE

Preferred Name

English

U-26452

Code

English

CIRARA

Brand Name

English

HB-419

Code

English

GLIBENCLAMIDE [EP MONOGRAPH]

Common Name

English

GLYBURIDE [WHO-IP]

Common Name

English

GLYBURIDE [MI]

Common Name

English

GLYBENCLAMIDE

Common Name

English

U-26,45

Code

English

GLYBURIDE [USP MONOGRAPH]

Common Name

English

GLUCOVANCE COMPONENT GLYBURIDE

Common Name

English

MICRONASE

Brand Name

English

HB 419

Code

English

GLYBURIDE [USAN]

Common Name

English

NSC-759618

Code

English

GLIBENCLAMIDUM [WHO-IP LATIN]

Common Name

English

GLYBURIDE [VANDF]

Common Name

English

BENZAMIDE, 5-CHLORO-N-(2-(4-((((CYCLOHEXYLAMINO)CARBONYL)AMINO)SULFONYL)PHENYL)ETHYL)-2-METHOXY-

Systematic Name

English

GLIBENCLAMIDE [MART.]

Common Name

English

GLIBENCLAMIDE [WHO-IP]

Common Name

English

U-26,452

Code

English

GLYBURIDE [USP-RS]

Common Name

English

glibenclamide [INN]

Common Name

English

Glibenclamide [WHO-DD]

Common Name

English

GLYNASE

Brand Name

English

GLIBENCLAMIDE [JAN]

Common Name

English

DIABETA

Brand Name

English

1-((P-(2-(5-CHLORO-O-ANISAMIDO)ETHYL)PHENYL)SULFONYL)-3-CYCLOHEXYLUREA

Common Name

English

GLYBURIDE [ORANGE BOOK]

Common Name

English

Classification Tree Code System Code

NDF-RT

N0000008054