5-(2,5-dimethylphenoxy)-2,2-dimethylpentanoic acid

• ChemBase编号: 1110
• 分子式: C15H22O3
• 平均质量: 250.33338
• 单一同位素质量: 250.15689456
• SMILES: O(CCCC(C)(C)C(=O)O)c1c(ccc(c1)C)C
• Canonical SMILES: Cc1ccc(c(c1)OCCCC(C(=O)O)(C)C)C
• InChI: InChI=1S/C15H22O3/c1-11-6-7-12(2)13(10-11)18-9-5-8-15(3,4)14(16)17/h6-7,10H,5,8-9H2,1-4H3,(H,16,17)
• InChIKey: HEMJJKBWTPKOJG-UHFFFAOYSA-N

名称和登记号

名称

• IUPAC标准名: 5-(2,5-dimethylphenoxy)-2,2-dimethylpentanoic acid
• IUPAC传统名: gemfibrozil; 5-(2,5-dimethylphenoxy)-2,2-dimethylpentanoic acid
• 商标名: Apo-Gemfibrozil; Bolutol; Cholespid; Decrelip; Fibratol; Fibrocit; Gemfibril; Gemfibromax; Gemlipid; Gen-Fibro; Genlip; Gevilon; Hipolixan; Jezil; Lipozid; Lipur; Lopid; Novo-Gemfibrozil; Nu-Gemfibrozil
• 别名: 2,2-Dimethyl-5-(2,5-dimethylphenoxy)pentanoic acid; Gemfibrozil; Gemfibrozil; 5-(2,5-Dimethylphenoxy)-2,2-dimethylpentanoic acid; 5-(2,5-Dimethylphenoxy)-2,2-dimethylpentanoic Acid; 2,2-Dimethyl-5-(2,5-xylyloxy)valeric Acid; CI-7; Decrelip; Genlip; Gevilon; Lipozid; Emfib; Hipolixan; Lipur; Organolipid; Gemcor; Lopid; Jezil; Gen-Fibro

登记号

• CAS号: 25812-30-0
• EC号: 247-280-2
• MDL号: MFCD00079335
• PubChem SID: 24895377; 160964573; 46508264
• PubChem CID: 3463

理论计算性质

JChem

• Acid pKa: 4.4168005
• 质子受体: 3
• 质子供体: 1
• LogD (pH = 5.5): 3.2735415
• LogD (pH = 7.4): 1.5146497
• Log P: 4.3896437
• 摩尔折射率: 71.8191 cm^3
• 极化性: 27.933592 Å^3
• 极化表面积: 46.53 Å^2
• 可自由旋转的化学键: 6
• 里宾斯基五规则: true

ALOGPS 2.1

• Log P: 3.61
• LOG S: -3.95
• 溶解度: 2.78e-02 g/l

分子性质

理化性质

• 溶解度: 10 mg/mL (in base); Chloroform; Ethyl Acetate; Hexane
• 外观: White Solid
• 熔点: 61-63°C
• 疏水性(logP): 3.4

安全信息

• 保存条件: -20°C; -20°C Freezer
• 保存注意事项: IRRITANT
• RTECS编号: YV7120000
• 欧盟危险性物质标志: 有害性(Harmful) (Xn)
• 德国WGK号: 3
• 危险公开号: 22
• 安全公开号: 36
• TSCA收录: false
• GHS危险品标识: GHS07
• GHS警示词: Warning
• GHS危险声明: H302
• 个人保护装置: dust mask type N95 (US), Eyeshields, Gloves

药理学性质

• 生物活性机理: Increases activity of Peroxisome proliferator-activated receptor-alpha (PPAR-alpha)

产品相关信息

• 成盐信息: Free Base
• 适用性: suitable for 1694 per US EPA
• 应用领域: Antihyperlipidaemic drug

详细说明

DrugBank - DB01241

• Drug Groups: approved
• Description: A lipid-regulating agent that lowers elevated serum lipids primarily by decreasing serum triglycerides with a variable reduction in total cholesterol. These decreases occur primarily in the VLDL fraction and less frequently in the LDL fraction. Gemfibrozil increases HDL subfractions HDL2 and HDL3 as well as apolipoproteins A-I and A-II. Its mechanism of action has not been definitely established. [PubChem]
• Indication: For treatment of adult patients with very high elevations of serum triglyceride levels (types IV and V hyperlipidemia) who are at risk of developing pancreatitis (inflammation of the pancreas) and who do not respond adequately to a strict diet.
• Pharmacology: Gemfibrozil, a fibric acid antilipemic agent similar to clofibrate, is used to treat hyperlipoproteinemia and as a second-line therapy for type IIb hypercholesterolemia. It acts to reduce triglyceride levels, reduce VLDL levels, reduce LDL levels (moderately), and increase HDL levels (moderately).
• Toxicity: Oral, mouse: LD₅₀ = 3162 mg/kg. Symptoms of overdose include abdominal cramps, diarrhea, joint and muscle pain, nausea, and vomiting.
• Affected Organisms: Humans and other mammals
• Biotransformation: Hepatic. Gemfibrozil mainly undergoes oxidation of a ring methyl group to successively form a hydroxymethyl and a carboxyl metabolite.
• Absorption: Well absorbed from gastrointestinal tract (within 1-2 hours).
• Half Life: 1.5 hours
• Protein Binding: 95%
• Elimination: Approximately seventy percent of the administered human dose is excreted in the urine, mostly as the glucuronide conjugate, with less than 2% excreted as unchanged gemfibrozil.
• External Links: Wikipedia; RxList; PDRhealth; Drugs.com

Selleck Chemicals - S1729

Research Area: Cardiovascular Disease
Biological Activity:
Gemfibrozil (Lopid) is an oral drug used to lower lipid levels. It belongs to a group of drugs known as fibrates. Increases activity of Peroxisome proliferator-activated receptor-alpha (PPARα) ’transcription factor ligand’ , a receptor that is involved in metabolism of carbohydrates and fats, as well as adipose tissue differentiation. This increase in the synthesis of lipoprotein lipase thereby increases the clearance of triglycerides. [1]

Sigma Aldrich - G9518

Biochem/physiol Actions
Selectively increases Apolipoprotein A-I levels.
Other Notes
Tandem Mass Spectrometry data independently generated by Scripps Center for Metabolomics is available to view or download in PDF. G9518.pdf Tested metabolites are featured on Scripps Center for Metabolomics METLIN Metabolite Database. To learn more, visit sigma.com/metlin.

Toronto Research Chemicals - G305750

A serum lipid regulating agent used as an antihyperlipoproteinemic.

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