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10238-21-8 molecular structure
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5-chloro-N-[2-(4-{[(cyclohexylcarbamoyl)amino]sulfonyl}phenyl)ethyl]-2-methoxybenzamide

ChemBase ID: 889
Molecular Formular: C23H28ClN3O5S
Molecular Mass: 494.00352
Monoisotopic Mass: 493.14381969
SMILES and InChIs

SMILES:
Clc1cc(C(=O)NCCc2ccc(S(=O)(=O)NC(=O)NC3CCCCC3)cc2)c(OC)cc1
Canonical SMILES:
COc1ccc(cc1C(=O)NCCc1ccc(cc1)S(=O)(=O)NC(=O)NC1CCCCC1)Cl
InChI:
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)
InChIKey:
ZNNLBTZKUZBEKO-UHFFFAOYSA-N

Cite this record

CBID:889 http://www.chembase.cn/molecule-889.html

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NAMES AND DATABASE IDS

NAMES AND DATABASE IDS

Names Database IDs
IUPAC name
5-chloro-N-[2-(4-{[(cyclohexylcarbamoyl)amino]sulfonyl}phenyl)ethyl]-2-methoxybenzamide
IUPAC Traditional name
5-chloro-N-[2-(4-{[(cyclohexylcarbamoyl)amino]sulfonyl}phenyl)ethyl]-2-methoxybenzamide
glyburide
glibenclamide
Brand Name
Abbenclamide
Adiab
Azuglucon
Bastiverit
Benclamin
Betanase
Betanese 5
Calabren
Cytagon
Daonil
Debtan
Dia-basan
Diabeta
Diabiphage
Dibelet
Duraglucon
Euclamin
Euglucan
Euglucon
Euglucon 5
Euglykon
GBN 5
Gen-Glybe
Gewaglucon
Gilemal
Glamide
Glibadone
Gliban
Gliben
Gliben-Puren N
Glibenbeta
Glibenclamid AL
Glibenclamid Basics
Glibenclamid Fabra
Glibenclamid Genericon
Glibenclamid Heumann
Glibenclamid Riker M.
Glibenclamid-Cophar
Glibenclamid-Ratiopharm
Glibenil
Glibens
Glibesyn
Glibet
Glibetic
Glibil
Gliboral
Glicem
Glidiabet
Glimel
Glimide
Glimidstata
Glisulin
Glitisol
Glubate
Gluben
Gluco-Tablimen
Glucobene
Glucohexal
Glucolon
Glucomid
Glucoremed
Glucoven
Glyben
Glybenclamide
Glybenzcyclamide
Glycolande
Glycomin
Glynase
Hexaglucon
Humedia
Lederglib
Libanil
Lisaglucon
Malix
Maninil
Med-Glionil
Melix
Micronase
Miglucan
Nadib
Neogluconin
Norglicem 5
Normoglucon
Novo-Glyburide
Orabetic
Pira
Praeciglucon
PresTab
Prodiabet
Renabetic
Sugril
Suraben
Tiabet
Yuglucon
Semi-Daonil
Synonyms
Glycron
Glynase
Micronase
Glybenzcyclamide
Calabren
DiaBeta
Diabetamide
Gilemal
Libanil
Malix
Semi-Daonil
Glibenclamide
5-Chloro-N-[2-[4-[[[(cyclohexylamino)carbonyl]amino]sulfonyl]phenyl]ethyl]-2-methoxybenzamide
1-[4-[2-(5-Chloro-2-methoxybenzamido)ethyl]phenylsulfonyl]-3-cyclohexylurea N-[4-(β-(2-Methoxy-5-chlorobenzamido)ethyl)benzosulfonyl]-N'-cyclohexylurea
Adiab
Antibet
Azuglucon
Bastiverit
Benclamin
Betanas
Daonil
Euglucon
UR 606
Wuglucon
Yuglucon
Glyburide
glybenclamide
N-p-[2-(5-Chloro-2-methoxybenzamido)-ethyl]benzene-sulfonyl-N'-cyclohexylurea
GLIBENCLAMIDE
Glyburide
5-Chloro-N-[4-(cyclohexylureidosulfonyl)phenethyl]-2-methoxybenzamide
N-p-[2-(5-Chloro-2-methoxybenzamido)ethyl]benzenesulfonyl-N′-cyclohexylurea
Glybenclamide
Glibenclamidum [INN-Latin]
Glibenclamida [INN-Spanish]
Glibenclamide
Apo-Glibenclamide
Glyburide
优降糖
5-氯-N-[4-(环己基脲磺酰)苯乙基]-2-甲氧基苯甲酰胺
N-对[2-(5-氯-2-甲氧基苯甲酰氨基)乙基]苯磺酰基-N′-环己基脲
格列本脲
格列本脲
CAS Number
10238-21-8
EC Number
233-570-6
MDL Number
MFCD00056625
PubChem SID
160964352
24895097
24277838
46509154
PubChem CID
3488
CHEBI ID
5441
ATC CODE
A10BB01
CHEMBL
472
Chemspider ID
3368
DrugBank ID
DB01016
IUPHAR ligand ID
2414
KEGG ID
D00336
Unique Ingredient Identifier
SX6K58TVWC
Wikipedia Title
Glibenclamide
Medline Plus
a684058

CALCULATED PROPERTIES

CALCULATED PROPERTIES

JChem ALOGPS 2.1
Acid pKa 4.3201795  H Acceptors
H Donor LogD (pH = 5.5) 3.0189142 
LogD (pH = 7.4) 2.8509614  Log P 3.79111 
Molar Refractivity 126.9801 cm3 Polarizability 49.538067 Å3
Polar Surface Area 113.6 Å2 Rotatable Bonds
Lipinski's Rule of Five true 
Log P 3.78  LOG S -5.38 
Solubility (Water) 2.06e-03 g/l 

PROPERTIES

PROPERTIES

Physical Property Safety Information Pharmacology Properties Product Information Bioassay(PubChem)
Solubility
4 mg/L expand Show data source
Chloroform expand Show data source
DMSO: soluble expand Show data source
ethanol: soluble2 mg/mL expand Show data source
H2O: insoluble expand Show data source
Methanol expand Show data source
Apperance
White Solid expand Show data source
Melting Point
168-170°C expand Show data source
171-174°C expand Show data source
174-178°C expand Show data source
Hydrophobicity(logP)
4.7 expand Show data source
Storage Condition
-20°C expand Show data source
-20°C Freezer expand Show data source
2-8°C expand Show data source
RTECS
YS4725200 expand Show data source
MSDS Link
Download expand Show data source
Download expand Show data source
Download expand Show data source
Download expand Show data source
German water hazard class
2 expand Show data source
TSCA Listed
expand Show data source
GHS Hazard statements
H303 expand Show data source
GHS Precautionary statements
P312 expand Show data source
Personal Protective Equipment
Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter expand Show data source
Storage Temperature
2-8°C expand Show data source
Admin Routes
Oral expand Show data source
Excretion
Renal and biliary expand Show data source
Half Life
10 hours expand Show data source
Metabolism
Hepatic hydroxylation (CYP2C9-mediated) expand Show data source
Protein Bound
Extensive expand Show data source
Legal Status
POM (UK) expand Show data source
Rx-only (US) expand Show data source
Pregnancy Category
B (US) expand Show data source
C (Australia) expand Show data source
US Licence
Glyburide expand Show data source
Gene Information
human ... KCNH2(3757), KCNJ1(3758), KCNJ11(3767)rat ... Kcnj1(24521) expand Show data source
human ... KCNH2(3757), KCNJ11(3767)rat ... Kcnj1(24521) expand Show data source
Mechanism of Action
ATP-sensitive potassium channels (KATP) blocker in pancreatic beta cells expand Show data source
Purity
≥99% (HPLC) expand Show data source
98% expand Show data source
99% expand Show data source
Salt Data
Free Base expand Show data source
Certificate of Analysis
Download expand Show data source
Download expand Show data source
Suitability
meets USP testing specifications expand Show data source
Application(s)
Antidiabetic drug (type II diabetes) expand Show data source
Inhibits drug-induced coronary vasodilation expand Show data source
Empirical Formula (Hill Notation)
C23H28ClN3O5S expand Show data source

DETAILS

DETAILS

MP Biomedicals MP Biomedicals DrugBank DrugBank Selleck Chemicals Selleck Chemicals Wikipedia Wikipedia Sigma Aldrich Sigma Aldrich TRC TRC
MP Biomedicals - 02157236 external link
Purity: 98%
Selectively blocks ATP-sensitive K+ channels and vascular smooth muscle relaxation.
DrugBank - DB01016 external link
Item Information
Drug Groups approved
Description Glyburide is an oral antihyperglycemic agent used for the treatment of non-insulin-dependent diabetes mellitus (NIDDM). It belongs to the sulfonylurea class of insulin secretagogues, which act by stimulating β cells of the pancreas to release insulin. Sulfonylureas increase both basal insulin secretion and meal-stimulated insulin release. Medications in this class differ in their dose, rate of absorption, duration of action, route of elimination and binding site on their target pancreatic β cell receptor. Sulfonylureas also increase peripheral glucose utilization, decrease hepatic gluconeogenesis and may increase the number and sensitivity of insulin receptors. Sulfonylureas are associated with weight gain, though less so than insulin. Due to their mechanism of action, sulfonylureas may cause hypoglycemia and require consistent food intake to decrease this risk. The risk of hypoglycemia is increased in elderly, debilitated and malnourished individuals. Glyburide has been shown to decrease fasting plasma glucose, postprandial blood glucose and glycosolated hemoglobin (HbA1c) levels (reflective of the last 8-10 weeks of glucose control). Glyburide appears to be completely metabolized, likely in the liver. Although its metabolites exert a small hypoglycemic effect, their contribution to glyburide's hypoglycemic effect is thought to be clinically unimportant. Glyburide metabolites are excreted in urine and feces in approximately equal proportions. The half-life of glyburide appears to be unaffected in those with a creatinine clearance of greater than 29 ml/min/1.73m2.
Indication Indicated as an adjunct to diet to lower the blood glucose in patients with NIDDM whose hyperglycemia cannot be satisfactorily controlled by diet alone.
Pharmacology 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.
Toxicity Oral rat LD50: > 20,000 mg/kg. Oral mouse LD50: 3250 mg/kg.
Affected Organisms
Humans and other mammals
Biotransformation Primarily hepatic (mainly cytochrome P450 3A4). The major metabolite is the 4-trans-hydroxy derivative. A second metabolite, the 3-cis-hydroxy derivative, also occurs. These metabolites do not contribute clinically significant hypoglycemic action in humans as they are only weakly active; however, retention of 4-trans-hydroxyglyburide may prolong the hypoglycemic effect of the agent in those with severe renal impairment.
Absorption Significant absorption within 1 hour and peak plasma levels are reached in 2 to 4 hours. Onset of action occurs within one hour.
Half Life 1.4-1.8 hours (unchanged drug only); 10 hours (metabolites included). Duration of effect is 12-24 hours.
Protein Binding Unchanged drug is ~99% bound to serum proteins; 4-trans-hydroxyglyburide is greater than 97% bound to serum proteins. Protein binding is primarily nonionic making glyburide and is less likely to displace or be displaced by drugs that bind via an ionic mechanism.
Elimination Glyburide is excreted as metabolites in the bile and urine, approximately 50% by each route.
This dual excretory pathway is qualitatively different from that of other sulfonylureas, which are excreted primarily in the urine.
Distribution Steady state Vd=0.125 L/kg; Vd during elimination phase=0.155 L/kg.
Clearance 78 ml/hr/kg in healthy adults. Clearance may be substantially decreased in those with severe renal impairment.
References
Monami M, Luzzi C, Lamanna C, Chiasserini V, Addante F, Desideri CM, Masotti G, Marchionni N, Mannucci E: Three-year mortality in diabetic patients treated with different combinations of insulin secretagogues and metformin. Diabetes Metab Res Rev. 2006 Nov-Dec;22(6):477-82. [Pubmed]
External Links
Wikipedia
RxList
Selleck Chemicals - S1716 external link
Research Area: Endocrinology
Biological Activity:
Glyburide (Diabeta)  is an anti-diabetic drug in a class of medications known as sulfonylureas, closely related to sulfa drugs. The drug works by inhibiting ATP-sensitive potassium channels in pancreatic beta cells. This inhibition causes cell membrane depolarization, which causes voltage-dependent calcium channels to open, which causes an increase in intracellular calcium in the beta cell, which stimulates insulin release. [1, 2]
Sigma Aldrich - G0639 external link
Biochem/physiol Actions
Selectively blocks ATP-sensitive K+ channels; high affinity binding sites found in brain, pancreatic β cells, and cardiovascular system.
Toronto Research Chemicals - G598350 external link
Glyburide is a second generation sulfonylurea with hypoglycemic activity. Glyburide is an antidiabetic.

REFERENCES

REFERENCES

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  • • Monami M, Luzzi C, Lamanna C, Chiasserini V, Addante F, Desideri CM, Masotti G, Marchionni N, Mannucci E: Three-year mortality in diabetic patients treated with different combinations of insulin secretagogues and metformin. Diabetes Metab Res Rev. 2006 Nov-Dec;22(6):477-82. Pubmed
  • • http://en.wikipedia.org/wiki/Glibenclamide
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