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Glibenclamide

HCID 3488
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Basic information

CAS
10238-21-8
Standard SMILES
COc1ccc(Cl)cc1C(=O)NCCc1ccc(S(=O)(=O)NC(=O)NC2CCCCC2)cc1
InChIKey
ZNNLBTZKUZBEKO-UHFFFAOYSA-N
Molecular formula
C23H28ClN3O5S
Average molar mass
494 g/mol
Monoisotopic mass
493.1438199

Overview

Glyburide is an N-sulfonylurea that is acetohexamide in which the acetyl group is replaced by a 2-(5-chloro-2-methoxybenzamido)ethyl group. It has a role as an EC 3.6.3.49 (channel-conductance-controlling ATPase) inhibitor, a hypoglycemic agent, an anti-arrhythmia drug and an EC 2.7.1.33 (pantothenate kinase) inhibitor. It is a N-sulfonylurea and a member of monochlorobenzenes.

Names & identifiers

Preferred name
Glibenclamide
IUPAC
5-chloro-N-[2-[4-(cyclohexylcarbamoylsulfamoyl)phenyl]ethyl]-2-methoxybenzamide
English name
Glibenclamide
Molecular formula
C23H28ClN3O5S
Molecular weight
494

Names & synonyms

Glibenclamideglyburide10238-21-8GlynaseEugluconSemi-daonilLibanilLederglibCalabrenGlibenclamidaGlibenclamidumGlyburide (micronized)
Show more names
GLYBENCLAMIDE5-Chloro-N-(4-(N-(cyclohexylcarbaMoyl)sulfaMoyl)phenethyl)-2-MethoxybenzaMideDiabetaGIBENCLAMIDEGlibenclamidGLYBENZCYCLAMIDEadiabMalix
HB 4191-(p-(2-(5-Chloro-2-methoxybenzamido)ethyl)benzenesulfonyl)-3-cyclohexylurea5-chloro-N-[2-[4-(cyclohexylcarbamoylsulfamoyl)phenyl]ethyl]-2-methoxybenzamideGlikenDiabetamide 5SX6K58TVWC5-Chloro-N-(2-(4-((((cyclohexylamino)carbonyl)amino)sulfonyl)phenyl)ethyl)-2-methoxybenzamideDiabetamide 2.5

Database identifiers

CAS
10238-21-8
PubChem CID
3488
DTXSID
DTXSID0037237
ChEMBL
CHEMBL472
ChEBI
CHEBI:5441

Properties

Computed structural properties

XLogP
4.8
Topological polar surface area
122 Ų
Hydrogen bond donors
3
Hydrogen bond acceptors
5
Rotatable bonds
8
Heavy atoms
33
Formal charge
0
Complexity
746

Experimental & physicochemical properties

Chemical ClassesPharmaceutical
Drugs · 2 items

Pharmaceuticals

Pharmaceuticals -> Listed in ZINC15

LogP · 2 items

4.7

3.09

Solubility2.06e-03 g/L
Human Drugs · 4 items

Breast Feeding; Lactation; Milk, Human; Hypoglycemic Agents; Sulfonylurea Compounds

FDA approved drugs -> Active ingredient

EMA approved medicines: Human medicine (Orphan designations)

FDA approved drugs -> Active ingredient

Melting Point169 - 170 °C
Physical DescriptionSolid
Collision Cross Section · 4 items

213.2 Ų [M-H]- [CCS Type: DT; Buffer gas: N2; Ionization: ESI-; Dataset: TOXCAST; Source Identifier: DTXSID0037237]

204.7 Ų [M+H]+ [CCS Type: TW; Method: Major Mix IMS/Tof Calibration Kit (Waters)]

216.96 Ų [M+K]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]

Safety & regulation

Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.

GHS classification

GHS Classification · 5 items

This chemical does not meet GHS hazard criteria for 1.1% (1 of 95) of reports.

Warning

H302 (89.5%): Harmful if swallowed [Warning Acute toxicity, oral]

P264, P270, P273, P301+P317, P330, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 95 reports by companies from 11 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Hazard information

Regulatory InformationGlyburide: Does not have an individual approval but may be used under an appropriate group standard
Other Safety InformationIMAP assessments - Benzamide, 5-chloro-N-[2-[4-[[[(cyclohexylamino)carbonyl]amino]sulfonyl]phenyl]ethyl]-2-methoxy-: Environment tier I assessment
Hazard Classes and CategoriesAcute Tox. 4 (89.5%)

Toxicology

Adverse EffectsAdverse Drug Reactions
Toxicity Summary · 1 item

Glyburide toxicity is primarily associated with the risk of severe hypoglycemia due to an excessive dosage, whether it occurs accidentally or intentionally. Due to duplicate metabolism involving the CYP2C9 enzyme, drug-drug interactions between glyburide and other sulfonylureas can also potentiate hypoglycemia.

Drug Induced Liver Injury · 6 items

Drug Induced Liver Injury Rank (DILIrank 2.0)

Glyburide

Chemistry & industry

Pharmacology

ATC Code · 3 items

A10BB01

A - Alimentary tract and metabolism

QA - Alimentary tract and metabolism

Protein BindingGlyburide is 99.9% bound to protein in plasma with >98% accounted for by binding to serum albumin.
Pharmacodynamics · 1 item

Glyburide is a second generation sulfonylurea that stimulates insulin secretion through the closure of ATP-sensitive potassium channels on beta cells, raising intracellular potassium and calcium ion concentrations. Glibenclamide has a long duration of action as it is given once daily, and a wide therapeutic index as patients are started at doses as low as 0.75mg but that can increase as high as 10mg or more. Patients taking glyburide should be cautioned regarding an increased risk of cardiovascular mortality as seen with tolbutamide, another sulfonylurea.

Mechanism of Action · 1 item

Glyburide belongs to a class of drugs known as sulfonylureas. These drugs act by closing ATP-sensitive potassium channels on pancreatic beta cells. The ATP-sensitive potassium channels on beta cells are known as sulfonylurea receptor 1 (SUR1). Under low glucose concentrations, SUR1 remains open, allowing for potassium ion efflux to create a -70mV membrane potential. Normally SUR1 closes in response to high glucose concentrations, the membrane potential of the cells becomes less negative, the cell depolarizes, voltage gated calcium channels open, calcium ions enter the cell, and the increased intracellular calcium concentration stimulates the release of insulin containing granules. Glyburide bypasses this process by forcing SUR1 closed and stimulating increased insulin secretion.

Biological Half-LifeElderly patients have a terminal elimination half life of 4.0-13.4h, while younger patients have a terminal elimination half life of 4.0-13.9h.
Metabolism/Metabolites · 2 items

Glyburide is metabolized mainly by CYP3A4, followed by CYP2C9, CYP2C19, CYP3A7, and CYP3A5. These enzymes metabolize glyburide to 4-trans-hydroxycyclohexyl glyburide (M1), 4-cis-hydroxycyclohexyl glyburide (M2a), 3-cis-hydroxycyclohexyl glyburide (M2b), 3-trans-hydroxycyclohexyl glyburide (M3), 2-trans-hydroxycyclohexyl glyburide (M4), and ethylhydroxycyclohexyl glyburide (M5). The M1 and M2b metabolites are considered active, along with the parent molecule.

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Compound notes

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On this pageBasic informationOverviewNames & identifiersPropertiesSafety & regulationChemistry & industryRelated reactionsCompound notes
UNII
SX6K58TVWC
EC Number
233-570-6
Nikkaji
J3.430D

205.9 Ų [M+H]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]

Physicochemical properties

Melting point
173 · 173-175°C
Density
1.1805 · 1.1805 (rough estimate)
refractive index
1.61 · 1.6100 (estimate)
storage temp.
2 · 2-8°C
solubility
2 mg/mL · ethanol: soluble2mg/mL
pka
5.3 · 5.3(at 25℃)
form
White solid
color
White
Water Solubility
Soluble in ethanol (5 mg/mL), DMSO (25 mg/mL), chloroform (1:36), methanol (1:250), and DMF. Insoluble in water.
Merck
14 · 14,4478
BCS Class
2 · 2
Stability
1 year · Stable for 1 year from date of purchase as supplied. Solutions in DMSO or ethanol may be stored at -20° for up to 3 months.
Major Application
pharmaceutical (small molecule)
InChIKey
ZNNLBTZKUZBEKO-UHFFFAOYSA-N
SMILES
COc1ccc(Cl)cc1C(=O)NCCc2ccc(cc2)S(=O)(=O)NC(=O)NC3CCCCC3
CAS DataBase Reference
10238 · 10238-21-8(CAS DataBase Reference)
EWG's Food Scores
1 · 1
FDA UNII
6 K58TVWC · SX6K58TVWC
NCI Drug Dictionary
Diabeta
ATC code
10 BB01 · A10BB01
NIST Chemistry Reference
Glyburide(10238-21-8)
EPA Substance Registry System
5 · Benzamide, 5-chloro-N-[2-[4-[[[(cyclohexylamino)carbonyl]amino]sulfonyl]phenyl]ethyl]-2-methoxy- (10238-21-8)
UNSPSC Code
41116107 · 41116107
NACRES
77 · NA.77
Protein binding
97 % · 97%
Excreted unchanged in urine
5 % · <5%
Volume of distribution
0.125 · 0.125(L/kg)
Biological half-life
2.1 · 2.1-10 / -
Symbol(GHS)
8 · GHS08
Signal word
Danger
Hazard statements
370 · H370
Precautionary statements
260 · P260-P264-P270-P308+P311-P405-P501
PPE
95 · Eyeshields, Gloves, type N95 (US)
Hazard Codes
Xn
Risk Statements
20 · 20/21/22
Safety Statements
22 · 22-36/37/39-36-24/25
WGK Germany
2 · 2
RTECS
4725200 · YS4725200
HS Code
29350090 · 29350090
Storage Class
11 · 11 - Combustible Solids
Hazard Classifications
4 · Aquatic Chronic 4
Toxicity
50 in · LD50 in rats and mice (g/kg): >20 orally; >12.5 i.p.; >20 s.c. (Mizukami)

vLess-DILI-concern

3

Adverse reactions

DOI:10.1016/j.drudis.2016.02.015

Effects During Pregnancy and Lactation◉ Summary of Use during Lactation
USGS Health-Based Screening Levels for Evaluating Water-Quality · 3 items

Glyburide

Pharmaceutical

Smith, C.D. and Nowell, L.H., 2024. Health-Based Screening Levels for evaluating water-quality data (3rd ed.). DOI:10.5066/F71C1TWP

EPA Human Health Benchmarks for Pharmaceuticals · 6 items

Glyburide

0.03

0.1

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.

Data used to generate the benchmarks include the following: Lowest Daily Dose (LDD): 1.25 mg/day, Lowest Therapeutic Dose (LTD): 0.02 mg/kg-day, and Screening Dose: 0.000005 mg/kg-day.

27-Dec-19

Safety data

PPE
Eyeshields, Gloves, type N95 (US)
wgk
2
rtecs
YS4725200
hs_code
29350090
Toxicity
LD50 in rats and mice (g/kg): >20 orally; >12.5 i.p.; >20 s.c. (Mizukami)
risk_code
20/21/22
Signal word
Danger
Symbol(GHS)
GHS08
hazard_code
Xn
safety_code
22-36/37/39-36-24/25
Storage Class
11 - Combustible Solids
Hazard statements
H370
Hazard Classifications
Aquatic Chronic 4
Precautionary statements
P260-P264-P270-P308+P311-P405-P501

Glyburide has known human metabolites that include 3-cis-Hydroxycyclohexyl glyburide, 3-trans-Hydroxycyclohexyl glyburide, 4-cis-hydroxycyclohexyl glyburide, and 2-trans-hydroxycyclohexyl glyburide.

FDA Pharmacological Classification · 6 items

SX6K58TVWC

GLYBURIDE

Established Pharmacologic Class [EPC] - Sulfonylurea

Chemical Structure [CS] - Sulfonylurea Compounds

Glyburide is a Sulfonylurea.

GLYBURIDE

MeSH Pharmacological ClassificationSubstances which lower blood glucose levels.
Absorption, Distribution and Excretion · 4 items

Elderly patients taking glyburide reached a Cmax of 211-315ng/mL with a Tmax of 0.9-1.0h, while younger patients reached a Cmax of 144-302ng/mL with a Tmax of 1.3-3.0h. Patients taking glyburide have and AUC of 348ng*h/mL.

Unlike other sulfonylureas, glyburide is 50% excreted in the urine and 50% in the feces. Glyburide is mainly excreted as the metabolite 4-trans-hydroxyglyburide.

Elderly patients have a volume of distribution of 19.3-52.6L, while younger patients have a volume of distribution of 21.5-49.3L.

Elderly patients have a clearance of 2.70-3.55L/h, while younger patients have a clearance of 2.47-4.11L/h.

Cellular LocationsCytoplasm
Metabolite PathwaysGlibenclamide Action Pathway

Uses & manufacturing

UsesUse (kg; approx.) in Germany (2009): >750
Applications · 8 items

UsesHypoglycemic agents with stronger effect than toluene sulfonylurea; used for the treatment of mild, non-insulin-dependent diabetes;

DescriptionGlyburide (10238-21-8) is a second generation oral hypoglycemic agent. Acts via ATP-dependent K+ channel (Kir6, KATP) block.1Inhibits Kir6 currents in the pancreas, causing an increase in intracellular Ca2+ and insulin secretion. Glyburide also inhibits recombinant CFTR Cl- channels with an IC50 of 20 μM.2Cell permeable.

Usesantihyperglycemic

UsesAn ATP-dependent KIR6 and CFTR Cl- channel blocker

UsesGlyburide (Glibenclamide) is a sulfonylurea compound that modulates insulin production. Sulfonylureas bind to ATP-dependent K+ channels in beta cells of the pancreas, depolarizing them and stimulating the release of Ca2+, which in turn stimulates insulin production. Glyburide (Glibenclamide) is an ATP-dependent K+ channel (KIR6, KATP) and CFTR Cl- channel blocker. This compound inhibits recombinant CFTR Cl- channels (IC50 = 20 M).

UsesGlyburide is a second generation sulfonylurea with hypoglycemic activity. Glyburide is an antidiabetic.

General DescriptionGlyburide (glibenclamide) is 5-chloro-N-[2-[4-[[[(cyclohexylamino)carbonyl]amino]sulfonyl]phenyl]ethyl]-2-methoxybenzamide; this compound can also be named asthe urea—see preceding discussion (Diabeta, Glynase,generic). Some tablet formulations contain micronized drug(formerly Micronase, now only generic). Combinations areavailable with metformin in the United States (Glucovance,generic; tablets, mg glipizide/mg metformin as hydrochloride:1.25/250, 2.5/500, 5/500).

General DescriptionSimilar to glipizide, glyburide, 1-[[p-[2-(5-chloro-o-anisamido)ethyl]-phenyl]sulfonyl]-3-cyclohexylurea(DiaBeta, Micronase, Glynase), is a second-generationoral hypoglycemic agent. The drug has a half-life eliminationof 10 hours, but its hypoglycemic effect remains for upto 24 hours.

Upstream & downstream products

Upstream raw materials

IsocyanatocyclohexaneSodium hydroxide4-(2-(5-Chloro-2-methoxybenzamido)ethyl)benzenesulfamide18-Crown-6N,N-DimethylformamidePotassium tert-butoxide

Additional notes

DefinitionChEBI: An N-sulfonylurea that is acetohexamide in which the acetyl group is replaced by a 2-(5-chloro-2-methoxybenzamido)ethyl group.