基本情報
- CAS
317318-70-0- 標準SMILES
Cc1cc(SCc2sc(-c3ccc(C(F)(F)F)cc3)nc2C)ccc1OCC(=O)O- InChIKey
YDBLKRPLXZNVNB-UHFFFAOYSA-N- 分子式
- C21H18F3NO3S2
- 平均分子量
- 453.5 g/mol
- 単同位体質量
- 453.0680201
概要
GW 501516 is an aromatic ether that is phenoxyacetic acid in which the phenyl group is substituted at position 2 by a methyl group and at position 4 by a (1,3-thiazol-5-ylmethyl)sulfanediyl group, and in which the 1,3-thiazolyl group is substituted at positions 2 and 4 by p-trifluoromethylphenyl and methyl groups, respectively. It has a role as a carcinogenic agent and a PPARbeta/delta agonist. It is a monocarboxylic acid, an aromatic ether, an aryl sulfide, an organofluorine compound and a member of 1,3-thiazoles.
名称と識別子
- 優先名称
- GW 501516
- IUPAC
- 2-[2-methyl-4-[[4-methyl-2-[4-(trifluoromethyl)phenyl]-1,3-thiazol-5-yl]methylsulfanyl]phenoxy]acetic acid
- 現地名
- GW501516
- 英語名
- GW-501516
- 分子式
- C21H18F3NO3S2
- 分子量
- 453.5
名称と別名
名称をさらに表示
データベース識別子
- CAS
317318-70-0- PubChem CID
- 9803963
- DTXSID
DTXSID3041037- ChEMBL
CHEMBL38943- ChEBI
CHEBI:73726- UNII
- 7I2HA1NU22
- Nikkaji
- J1.561.880I
物性
構造計算による物性
- XLogP
- 5.9
- 極性表面積
- 113 Ų
- 水素結合供与体数
- 1
- 水素結合受容体数
- 9
- 回転可能結合数
- 7
- 重原子数
- 30
- 形式電荷
- 0
- 複雑度
- 572
実験および物理化学的性質
物理化学的性質
- 融点
- 134 · 134-136°C
- 沸点
- 584.5 · 584.5±60.0 °C(Predicted)
- 比重(密度)
- 1.42 · 1.42±0.1 g/cm3(Predicted)
- 貯蔵温度
- -20 °C · -20°C
- 溶解性
- 20 mg/mL、透明 · DMSO:可溶20mg/mL、透明
- 外見
- 粉
- 酸解離定数(Pka)
- 3.17 · 3.17±0.10(Predicted)
- 色
- 白からベージュ
- BRN
- 18515150 · 18515150
- 安定性
- 光に敏感
- InChI
- InChI=1S/C21H18F3NO3S2/c1-12-9-16(7-8-17(12)28-10-19(26)27)29-11-18-13(2)25-20(30-18)14-3-5-15(6-4-14)21(22,23)24/h3-9H,10-11H2,1-2H3,(H,26,27)
- InChIKey
- YDBLKRPLXZNVNB-UHFFFAOYSA-N
- SMILES
- C(O)(=O)COC1=CC=C(SCC2SC(C3=CC=C(C(F)(F)F)C=C3)=NC=2C)C=C1C
- CAS データベース
- 317318 · 317318-70-0
化学的性質
化学的特性White Solid
安全と法規制
安全データ
- wgk
- 3
- rtecs
- AI9105500
- ストレージクラス
- 11 - Combustible Solids
化学と産業
薬理情報
Mechanism of Action
This drug regulates fatty acid oxidation in several tissues, such as skeletal muscle and adipose tissue. Overexpression of PPARdelta using a transgenic murine model promotes an increase of muscle oxidative capability. It also plays a major role in the metabolic adaptations to western diet characterized by an excessive amount of saturated fat.
応用分野
説明GW501516, also known as GW-1516 or cardarine and endurobol, is a peroxisome proliferator-activated receptor delta (PPAR-δ) agonist. Activation of the receptor will increase fat-burning capacity and muscle production, as it changes the body's fuel preference from glucose to lipids.
来歴GW501516, also known as Cardarine, was originally discovered in the early 1990s during a research collaboration between two large pharmaceutical companies. The initial proposed use was for the treatment of hyperlipidemia (elevated fats in the blood), though later studies looked at its effectiveness for treating obesity, diabetes, and cardiovascular disease.
使用An experimental drug meant to control lipids and increase the level of HDL, or good cholesterol, in the bloodstream. A cell-permeable, thiazolyl compound that acts as a potent, high affinity, PPARd agonist. Exhibits selectivity for PPARd compared t
一般的な説明GW501516 is the most selective and potent PPARβ (EC50=1.1nM) agonist that has been demonstrated to be 1,000-fold more selective in comparison to existing subtypes. It can regulate expression of genes involved in lipid catabolism and energy uncoupling in skeletal muscle cells and has been shown to block insulin resistance and fatty acid-induced nuclear factor-κB (NF-κB) activation.
サプライヤー100 社
補足説明
定義ChEBI: An aromatic ether that is phenoxyacetic acid in which the phenyl group is substituted at position 2 by a methyl group and at position 4 by a (1,3-thiazol-5-ylmethyl)sulfanediyl group, and in which the 1,3-thiazolyl group is substituted at positions 2 and 4 by p-trifluoromethylphenyl and methyl groups, respectively.
関連反応
化合物ノート
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