ピオグリタゾン塩酸塩

Pioglitazone Hydrochloride

HCID 60560

基本情報

CAS
112529-15-4
標準SMILES
CCc1ccc(CCOc2ccc(CC3SC(=O)NC3=O)cc2)nc1.Cl
InChIKey
GHUUBYQTCDQWRA-UHFFFAOYSA-N
分子式
C19H21ClN2O3S
平均分子量
392.9 g/mol
単同位体質量
392.09614121

概要

Pioglitazone hydrochloride is an aromatic ether.

名称と識別子

優先名称
Pioglitazone Hydrochloride
IUPAC
5-[[4-[2-(5-ethyl-2-pyridinyl)ethoxy]phenyl]methyl]-1,3-thiazolidine-2,4-dione;hydrochloride
現地名
ピオグリタゾン塩酸塩
英語名
Pioglitazone hydrochloride
分子式
C19H21ClN2O3S
分子量
392.9

名称と別名

pioglitazone hydrochloride112529-15-4Pioglitazone HClPiomedDiabiomGlidipionGlizofarPioglitazone (as hydrochloride)DTXSID3044203JQT35NPK6CSTR-001Pioglitazonehydrochloride
名称をさらに表示
ピオグリタゾン塩酸塩5-[4-[2-(5-エチル-2-ピリジル)エトキシ]ベンジル]-2,4-チアゾリジンジオン塩酸塩ピオグリタゾン 塩酸塩ピオグリタゾン塩酸塩, 98%ピオグリタゾン塩酸塩 (JP17)ピオグリタゾン・塩酸rac-(5R*)-5-[4-[2-(5-エチル-2-ピリジニル)エトキシ]ベンジル]チアゾリジン-2,4-ジオン・塩酸塩ピオグリタゾン・塩酸塩塩酸ピオグリタゾンアクトスアクトスOD(5R)-5-[4-[2-(5-エチル-2-ピリジニル)エトキシ]ベンジル]チアゾリジン-2,4-ジオン(5R)-5-({4-[2-(5-エチルピリジン-2-イル)エトキシ]フェニル}メチル)-1,3-チアゾリジン-2,4-ジオン(5R)-5-[4-[2-(5-エチル-2-ピリジル)エトキシ]ベンジル]チアゾリジン-2,4-ジオンACTOSPioglitazone hydrochlorid[5-[[4-[2-(5-ethyl-2-pyridinyl)ethoxy]phenyl]methyl]-2,4-] thiazolidinedione hydrochloridePiogPiogLAD-4833U-72107ECAS:112529-15-4
NSC-758876DTXCID1024203OSENI COMPONENT PIOGLITAZONE HYDROCHLORIDEPioglitazone.HClRefChem:56526(5RS)-5-(4-(2-(5-Ethylpyridin-2-yl)ethoxy)benzyl)thiazolidine-2,4-dione monohydrochloride5-(4-(2-(5-Ethylpyridin-2-yl)ethoxy)benzyl)thiazolidine-2,4-dione hydrochlorideU-72107A

データベース識別子

CAS
112529-15-4
PubChem CID
60560
DTXSID
DTXSID3044203
ChEMBL
CHEMBL1715
ChEBI
CHEBI:8229
UNII
JQT35NPK6C
EC Number
629-731-9

物性

構造計算による物性

極性表面積
93.6 Ų
水素結合供与体数
2
水素結合受容体数
5
回転可能結合数
7
重原子数
26

実験および物理化学的性質

Solubility1.8 [ug/mL] (The mean of the results at pH 7.4)
Human Drugs · 5 件

FDA approved drugs -> Active ingredient

EMA approved medicines: Human medicine

EMA approved medicines: Human medicine

EMA approved medicines: Human medicine

FDA approved drugs -> Active ingredient

Collision Cross Section178 Ų [M+H]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]

物理化学的性質

融点
193 · 193-194°C
貯蔵温度
2 · 2-8°C
溶解性
10 mg/mL以上 · DMSO:10mg/mL以上
外見
粉
色
ホワイトからオフホワイト
水溶解度
水 (<1mg/ml、25°C)、DMF、メタノール、エタノール (4mg/ml、25°C)、DMSO (79mg/ml、25°C) に可溶。

化学的性質

化学的特性Colourless Prisms

安全と法規制

GHS分類

GHS Classification · 4 件

Warning

H302 (12.3%): Harmful if swallowed [Warning Acute toxicity, oral]

P203, P264, P264+P265, P270, P280, P301+P317, P305+P351+P338, P318, P330, P337+P317, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 57 reports by companies from 16 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 (12.3%)

毒性情報

Exposure Routes · 1 件

Following oral administration, in the fasting state, pioglitazone is first measurable in serum within 30 minutes, with peak concentrations observed within 2 hours. Food slightly delays the time to peak serum concentration to 3 to 4 hours, but does not alter the extent of absorption.

Toxicity Summary · 1 件

Pioglitazone acts as an agonist at peroxisome proliferator activated receptors (PPAR) in target tissues for insulin action such as adipose tissue, skeletal muscle, and liver. Activation of PPAR-gamma receptors increases the transcription of insulin-responsive genes involved in the control of glucose production, transport, and utilization. In this way, pioglitazone both enhances tissue sensitivity to insulin and reduces hepatic gluconeogenesis. Thus, insulin resistance associated with type 2 diabetes mellitus is improved without an increase in insulin secretion by pancreatic β cells.

Carcinogen Classification2A, probably carcinogenic to humans. (L135)
Drug Induced Liver Injury · 6 件

Drug Induced Liver Injury Rank (DILIrank 2.0)

Pioglitazone hydrochloride

vLess-DILI-concern

3

Warnings & precautions

DOI:10.1016/j.drudis.2016.02.015

Toxicity DataHypogycemia; LD<sub>50</sub>=mg/kg (orally in rat)

安全データ

wgk
3
hs_code
29341000
risk_code
36/38-36
hazard_code
Xi
safety_code
22-24/25-26
hazard_class
IRRITANT

化学と産業

薬理情報

Metabolism/MetabolitesHepatic
FDA Pharmacological Classification · 2 件

PIOGLITAZONE HYDROCHLORIDE

Peroxisome Proliferator Receptor gamma Agonist [EPC]; Peroxisome Proliferator-activated Receptor gamma Agonists [MoA]; Peroxisome Proliferator Receptor alpha Agonist [EPC]; Thiazolidinediones [CS]; Thiazolidinedione [EPC]; Peroxisome Proliferator-activated Receptor alpha Agonists [MoA]

MeSH Pharmacological ClassificationSubstances which lower blood glucose levels.

用途と製造

UsesTreatment of Type II diabetes mellitus
応用分野 · 5 件

用途チアゾリジン系PPARγ 作用 剤です。インスリン抵抗性を改善し、血糖低 下作用を示します。

用途チアゾリジン系PPARγ作用 剤です。インスリン抵抗性を改善し、血糖低 下作用を示します。

説明Pioglitazone is a new orally active thiazolidinedione (TZD) launched in the US for the treatment of non-insulin dependent diabetes mellitus (NIDDM). It can be synthesized in 4 steps, the last one transforming an alphabromoester into thiazolidine with thiourea. As with other representatives in this class, it potently activates the nuclear receptor peroxisome proliferator-activated receptor gamma which is believed to be involved in the regulation of insulin resistance and adipogenesis. In several obese and obese diabetic animal models, treatment with Pioglitazone resulted in reductions in plasma glucose and serum lipids. In clinical studies, Pioglitazone at a once daily oral dose of 15-45 mg, as monotherapy or in combination with non-TZDs or insulin, was shown to significantly improve glycemic control in type-2 diabetes and demonstrated a beneficial effect on insulin resistance and other clinically relevant parameters as plasma levels of triglycerides or HDL-cholesterol. Pioglitazone is reported to be safe and well tolerated and is said to have a lower occurrence of hepatic toxicity as well as a low probability for drug interaction.

使用Pioglitazone hydrochloride is a euglycemic agent,used as an antidiabetic.

一般的な説明Pioglitazone hydrochloride is an oral antidiabetic agent used in the treatment of type 2 diabetes mellitus (also known as non-insulin-dependent diabetes mellitus (NIDDM) or adult-onset diabetes.

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関連反応

9 件

化合物ノート

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