Basic information
- CAS
21187-98-4- Standard SMILES
Cc1ccc(S(=O)(=O)NC(=O)NN2CC3CCCC3C2)cc1- InChIKey
BOVGTQGAOIONJV-UHFFFAOYSA-N- Molecular formula
- C15H21N3O3S
- Average molar mass
- 323.4 g/mol
- Monoisotopic mass
- 323.13036271
Overview
Gliclazide is a N-sulfonylurea. It has a role as a hypoglycemic agent, a radical scavenger and an insulin secretagogue.
Names & identifiers
- Preferred name
- Gliclazide
- IUPAC
- 1-(3,3a,4,5,6,6a-hexahydro-1H-cyclopenta[c]pyrrol-2-yl)-3-(4-methylphenyl)sulfonylurea
- English name
- Gliclazide
- Molecular formula
- C15H21N3O3S
- Molecular weight
- 323.41
Names & synonyms
gliclazide21187-98-4GlimicronDiamicronGliclazidaGlyclazideGliklazidGliclazidumDTXSID9023095SE 17021-(3-Azabicyclo(3.3.0)oct-3-yl)-3-(p-tolylsulfonyl)ureaS-852
Show more names
Gliclazide analogue: N-[[(Hexahydrocyclopenta [c]pyrrol-2(1H)-yl)aMino]carbonyl]-2-Methyl benzenesulfonaMides852se1702S-1702DiaprelGlyzideGlinormax
1-(Hexahydrocyclopenta(c)pyrrol-2(1H)-yl)-3-(p-tolylsulfonyl)ureaS 1702DTXCID003095CHEBI:31654NSC-758673J3.151HSE-17021-(Hexahydrocyclopenta[c]pyrrol-2(1H)-yl)-3-[(4-methylphenyl)sulfonyl]urea
Database identifiers
- CAS
21187-98-4- PubChem CID
- 3475
- DTXSID
DTXSID9023095- ChEMBL
CHEMBL427216- ChEBI
CHEBI:31654- EC Number
- 244-260-5
- Nikkaji
- J3.151H
Properties
Computed structural properties
- XLogP
- 1.5
- Topological polar surface area
- 86.9 Ų
- Hydrogen bond donors
- 2
- Hydrogen bond acceptors
- 4
- Rotatable bonds
- 3
- Heavy atoms
- 22
- Formal charge
- 0
- Complexity
- 497
Experimental & physicochemical properties
Drugs
Pharmaceuticals
Pharmaceuticals -> Used in Switzerland
LogP2.6
Solubility
1.90e-01 g/L
42.6 [ug/mL] (The mean of the results at pH 7.4)
Human DrugsHypoglycaemic agents
Melting Point
180-182
181 °C
Physical DescriptionSolid
Collision Cross Section
181.89 Ų [M+K]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]
178 Ų [M+H]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]
Physicochemical properties
- Melting point
- 163 · 163-169 °C (lit.)
- Density
- 1.2205 · 1.2205 (rough estimate)
- refractive index
- 1.674 · 1.6740 (estimate)
- storage temp.
- 2 · 2-8°C
- solubility
- methylene chloride: soluble
- form
- powder
- pka
- 6.07 · 6.07±0.10(Predicted)
- color
- white
- Merck
- 14 · 14,4439
- InChI
- InChI=1S/C15H21N3O3S/c1-11-5-7-14(8-6-11)22(20,21)17-15(19)16-18-9-12-3-2-4-13(12)10-18/h5-8,12-13H,2-4,9-10H2,1H3,(H2,16,17,19)
- InChIKey
- BOVGTQGAOIONJV-UHFFFAOYSA-N
- SMILES
- C1(S(NC(NN2CC3CCCC3C2)=O)(=O)=O)=CC=C(C)C=C1
- CAS DataBase Reference
- 21187 · 21187-98-4(CAS DataBase Reference)
- FDA UNII
- 4 PX8C4HKV · G4PX8C4HKV
- NCI Drug Dictionary
- gliclazide
- ATC code
- 10 BB09 · A10BB09
- EPA Substance Registry System
- Benzenesulfonamide, N-[[(hexahydrocyclopenta[c]pyrrol-2(1H)-yl)amino]carbonyl]-4-methyl (21187-98-4)
- UNSPSC Code
- 41116107 · 41116107
- NACRES
- 77 · NA.77
- Protein binding
- 95 % · Approx 95%
- Excreted unchanged in urine
- 5 % · <5%
- Volume of distribution
- 0.24 · 0.24(L/kg)
- Biological half-life
- 10 · 10-12 (MR: 12-20) / Prolonged
- Symbol(GHS)
- 7 · GHS07
- Signal word
- Warning
- Hazard statements
- 302 · H302
- Precautionary statements
- 301 · P301+P312+P330
- PPE
- 95 · Eyeshields, Gloves, type N95 (US)
- Hazard Codes
- Xn,Xi
- Risk Statements
- 21 · 21-36/38-46-62-63
- Safety Statements
- 25 · 25-26-36/37-53-24/25
- RIDADR
- 3077 · 3077
- WGK Germany
- 2 · 2
- RTECS
- 4500000 · YT4500000
- HS Code
- 29350090 · 29350090
- Storage Class
- 11 · 11 - Combustible Solids
- Hazard Classifications
- 4 Oral · Acute Tox. 4 Oral
- Toxicity
- 50 orally · LD50 orally in mice: >3 g/kg (Duhault)
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
This chemical does not meet GHS hazard criteria for 77.5% (55 of 71) of all reports.
Warning
H302 (12.7%): Harmful if swallowed [Warning Acute toxicity, oral]
P203, P264, P270, P280, P301+P317, P318, P330, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 71 reports by companies from 14 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Hazard information
Hazard Classes and CategoriesAcute Tox. 4 (12.7%)
Toxicology
Drug Induced Liver Injury
Drug-Induced Liver Injury Severity and Toxicity (DILIst)
Gliclazide
DILI Positive
Oral
DOI:10.1016/j.drudis.2019.09.022
Safety data
- PPE
- Eyeshields, Gloves, type N95 (US)
- wgk
- 2
- rtecs
- YT4500000
- ridadr
- 3077
- hs_code
- 29350090
- Toxicity
- LD50 orally in mice: >3 g/kg (Duhault)
- risk_code
- 21-36/38-46-62-63
- Signal word
- Warning
- Symbol(GHS)
- GHS07
- hazard_code
- Xn,Xi
- safety_code
- 25-26-36/37-53-24/25
- Storage Class
- 11 - Combustible Solids
- Hazard statements
- H302
- Hazard Classifications
- Acute Tox. 4 Oral
- Precautionary statements
- P301+P312+P330
Chemistry & industry
Pharmacology
ATC Code
A10BB09
A - Alimentary tract and metabolism
QA - Alimentary tract and metabolism
A10BB09
Protein Binding94%, highly bound to plasma proteins
Pharmacodynamics
Based on the pharmacological properties, gliclazide is a second generation sulphonylurea which acts as a hypoglycemic agent. It stimulates β cells of the islet of Langerhans in the pancreas to release insulin. It also enhances peripheral insulin sensitivity. Overall, it potentiates insulin release and improves insulin dynamics.
Mechanism of Action
Gliclazide binds to the β cell sulfonyl urea receptor (SUR1). This binding subsequently blocks the ATP sensitive potassium channels. The binding results in closure of the channels and leads to a resulting decrease in potassium efflux leads to depolarization of the β cells. This opens voltage-dependent calcium channels in the β cell resulting in calmodulin activation, which in turn leads to exocytosis of insulin containing secretorty granules.
Biological Half-Life10.4 hours. Duration of action is 10-24 hours.
Metabolism/Metabolites
Extensively metabolized in the liver. Less than 1% of the orally administered dose appears unchanged in the urine. Metabolites include oxidized and hydroxylated derivates, as well as glucuronic acid conjugates.
Gliclazide has known human metabolites that include 6-hydroxy-gliclazide, 7-hydroxy-gliclazide, and Methylhydroxygliclazide.
MeSH Pharmacological ClassificationSubstances which lower blood glucose levels.
Absorption, Distribution and Excretion
Rapidly and well absorbed but may have wide inter- and intra-individual variability. Peak plasma concentrations occur within 4-6 hours of oral administration.
Metabolites and conjugates are eliminated primarily by the kidneys (60-70%) and also in the feces (10-20%).
Cellular LocationsExtracellular
Metabolite PathwaysGliclazide Action Pathway
Uses & manufacturing
UsesUse (kg; approx.) in Germany (2009): >10
Applications
DescriptionGliclazide (21187-98-4) is an oral antihyperglycemic agent used for the treatment of diabetes mellitus type II. It belongs to the sulfonylurea class of insulin secretagogues, which stimulates β cells of the pancreas to release insulin. Gliclazide binds to the β cell sulfonyl urea receptor (SUR1), further blocking the ATP sensitive potassium channels. Therefore, the potassium efflux substantially decreases, causing depolarization of the β cells. Then the voltage-dependent calcium channels in the β cell are open, resulting in calmodulin activation, which in turn leads to exocytosis of insulin containing secretorty granules. Recent studies have also shown that gliclazide can effectiveimprove anti-oxidant status and nitric oxide-mediated vasodilation in Type 2 diabetes and protect pancreatic beta-cells from damage by hydrogen peroxide.
UsesGliclazide is an oral hypoglycemic agent used to treat non-insulin-dependent diabetes mellitus.Treatment of diabetes associated with obesity or vascular disease, for adults with type 2 diabetes.Diabetes is a chronic (long-lasting) health condition that affects how your body turns food into energy. Gliclazide reduces blood glucose levels by stimulating insulin secretion from the β-cells of the islets of Langerhans.
General DescriptionChemically, gliclazide, 1-(3-azabicyclo[3.3.0]oct-3-yl)-3-p-tolylsulphonylurea (Diamicron), isvery similar to tolbutamide, with the exception of the bicyclicheterocyclic ring found in gliclazide. The pyrrolidineincreases its lipophilicity over that of tolbutamide,which increases its half-life. Even so, the p-methyl is susceptibleto the same oxidative metabolic fate as observedfor tolbutamide, namely, it will be metabolized to a carboxylicacid.
Upstream & downstream products
Upstream raw materials
Suppliers100 total
北京华美互利生物化工010-56205725 · [email protected]
梯希爱(上海)化成工业发展有限公司021-67121386 · [email protected]
上海阿拉丁生化科技股份有限公司400-6206333 13167063860 · [email protected]
LGM Pharma1-(800)-881-8210 · [email protected]
上海迈瑞尔生化科技有限公司4006356688 18621169109 · [email protected]
武汉易泰科技有限公司上海分公司18930552037 · [email protected]
大连美仑生物技术有限公司0411-62910999 13889544652 · [email protected]
太原市瑞和丰科贸有限公司+86 351 7031519 · [email protected]
上海柯维化学技术有限公司021-64609169 18901607656 · [email protected]
上海诗丹德标准技术服务有限公司021-021-57127007-6622-6622 17621252073 · [email protected]
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Pure Chemistry Scientific Inc.001-857-928-2050 or 1-888-588-9418 · [email protected]
合肥天健化工有限公司551-65418679 15856988503;15837135945 · [email protected]
武汉丰泰威远科技有限公司027-87465837 19945049750 · [email protected]
云南西力生物技术股份有限公司0871-65217109 · [email protected]
天津希恩思生化科技有限公司400 638 7771 · [email protected]
河南多贝化工有限公司0370-2785118 17550508557 · [email protected]
斯百全化学（上海）有限公司021-021-021-67601398-809-809-809 15221380277 · [email protected]
深圳菲斯生物科技有限公司0755-83725681-603
上海思域化工科技有限公司86-21-34053660 · [email protected]
Wuhan NCE Biomedical Co.,Ltd.4000-027-021 |24 +86-13986109188 | +86-15623472865 | +81-08033611988
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TCI AMERICA800-4238616 · [email protected]
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TCI Europe320-37350700 · [email protected]
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Cato Research Chemicals Inc.020-81960175 · [email protected]
上海将来实业股份有限公司021-61552785 · [email protected]
HBCChem, Inc.+1-510-219-6317 · [email protected]
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Sigma-Aldrich西格玛奥德里奇(上海)贸易有限公司021-61415566 800-8193336 · [email protected]
桦特昇生物科技（武汉）有限公司027-59207879 1972026995 18140587686 · [email protected]
南京熙泽医药科技有限公司025-66023220 15250997978 · [email protected]
天津阿尔塔科技有限公司022-6537-8550 15522853686 · [email protected]
TargetMol中国（陶术生物）021-021-33632979 15002134094 · [email protected]
郑州科豫隆化工产品有限公司17319789407 17319789407 · [email protected]
上海昕凯医药科技有限公司21-619849051-1 18521059765 · [email protected]
九鼎化学（上海）科技有限公司4009209199 · [email protected]
EMMX Biotechnology LLC888-539-0666 · [email protected]
上海岚克医药科技发展有限公司0086-21-58956006
成都大道三灵生物科技有限公司18108108965 18108108965 · [email protected]
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广州市齐云生物技术有限公司020-61288194 61288195 · [email protected]
杭州汗科化工有限公司0571-88039185
Additional notes
DefinitionChEBI: Gliclazide is a N-sulfonylurea. It has a role as a hypoglycemic agent, a radical scavenger and an insulin secretagogue.
Related reactions
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Compound notes
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