基本情報
- CAS
21187-98-4- 標準SMILES
Cc1ccc(S(=O)(=O)NC(=O)NN2CC3CCCC3C2)cc1- InChIKey
BOVGTQGAOIONJV-UHFFFAOYSA-N- 分子式
- C15H21N3O3S
- 平均分子量
- 323.4 g/mol
- 単同位体質量
- 323.13036271
概要
Gliclazide is a N-sulfonylurea. It has a role as a hypoglycemic agent, a radical scavenger and an insulin secretagogue.
名称と識別子
- 優先名称
- Gliclazide
- IUPAC
- 1-(3,3a,4,5,6,6a-hexahydro-1H-cyclopenta[c]pyrrol-2-yl)-3-(4-methylphenyl)sulfonylurea
- 現地名
- グリクラジド
- 英語名
- Gliclazide
- 分子式
- C15H21N3O3S
- 分子量
- 323.41
名称と別名
gliclazide21187-98-4GlimicronDiamicronGliclazidaGlyclazideGliklazidGliclazidumDTXSID9023095SE 17021-(3-Azabicyclo(3.3.0)oct-3-yl)-3-(p-tolylsulfonyl)ureaS-852
名称をさらに表示
ルイメニアダイアグリコキョワクロン1-(3-アザビシクロ[3.3.0]オクタン-3-イル)-3-(4-メチルフェニルスルホニル)尿素グルタミールグリミクロンN-[[3,3a,4,5,6,6a-ヘキサヒドロシクロペンタ[c]ピロール-2(1H)-イル]アミノカルボニル]-4-メチルベンゼンスルホンアミドクラウナート1-(3,3a,4,5,6,6a-ヘキサヒドロシクロペンタ[c]ピロール-2(1H)-イル)-3-トシル尿素ジアミクロングリミクロンHAグリクラジド1-(3,3a,4,5,6,6a-ヘキサヒドロシクロペンタ[c]ピロール-2(1H)-イル)-3-(p-トリルスルホニル)尿素グリミランベネラクサー1-[3-アザビシクロ[3.3.0]オクタ-3-イル]-3-p-トルエンスルホニル尿素グリクラジド (JP17)1-(4-メチルベンゼンスルホニル)-3-{オクタヒドロシクロペンタ[c]ピロール-2-イル}尿素Gliclazide analogue: N-[[(Hexahydrocyclopenta [c]pyrrol-2(1H)-yl)aMino]carbonyl]-2-Methyl benzenesulfonaMide
物性
構造計算による物性
- XLogP
- 1.5
- 極性表面積
- 86.9 Ų
- 水素結合供与体数
- 2
- 水素結合受容体数
- 4
- 回転可能結合数
- 3
- 重原子数
- 22
- 形式電荷
- 0
- 複雑度
- 497
実験および物理化学的性質
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]
物理化学的性質
- 融点
- 163 · 163-169 °C (lit.)
- 比重(密度)
- 1.2205 · 1.2205 (rough estimate)
- 屈折率
- 1.674 · 1.6740 (estimate)
- 貯蔵温度
- 2 · 2-8°C
安全と法規制
安全情報は参考情報です。供給元の安全データシート（SDS）、適用法令、専門家による評価に代わるものではありません。
GHS分類
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.
危険有害性情報
Hazard Classes and CategoriesAcute Tox. 4 (12.7%)
毒性情報
Drug Induced Liver Injury
Drug-Induced Liver Injury Severity and Toxicity (DILIst)
Gliclazide
DILI Positive
Oral
DOI:10.1016/j.drudis.2019.09.022
安全データ
- wgk
- 2
- rtecs
- YT4500000
- ridadr
- 3077
- 毒性
- LD50 orally in mice: >3 g/kg (Duhault)
- hs_code
- 29350090
- risk_code
- 21-36/38-46-62-63
- hazard_code
- Xn,Xi
- safety_code
- 25-26-36/37-53-24/25
- Hazard Classifications
- Acute Tox. 4 Oral
- ストレージクラス
- 11 - Combustible Solids
化学と産業
薬理情報
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.
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