CAS 25812-30-0|Cholespid|Lopid|Bolutol|Novo-Gemfibrozil|Decrelip|Gemfibril|Gemlipid|Hipolixan|Jezil|Fibratol|Gemfibrozil|Gevilon|Lipozid|Gen-Fibro|Fibrocit|5-(2,5-dimethylphenoxy)-2,2-dimethylpentan...

基本信息

化学结构

分子式

C₁₅H₂₂O₃

分子量

250.33338

精确质量

250.15689456

电荷

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

Canonic Smiles

Cc1ccc(c(c1)OCCCC(C(=O)O)(C)C)C

Isomeric Smiles

O(CCCC(C)(C)C(=O)O)c1c(ccc(c1)C)C

计算属性

JChem

LogD (pH = 7.4)

1.51

LogD (pH = 5.5)

3.27

Log P

4.39

可自由旋转的化学键

质子供体

质子受体

里宾斯基五规则

true

Acid pKa

4.42

极化表面积

46.53

极化性

28.89

摩尔折射率

71.82

LOG S

-3.31

数据来源

名称和标识

商标名

CholespidLopidBolutolNovo-GemfibrozilDecrelipGemfibrilGemlipidHipolixanJezilFibratolGevilonLipozidGen-FibroFibrocitGenlipGemfibromaxNu-GemfibrozilApo-GemfibrozilLipur

别名

GemfibrozilJezilGemcorGen-FibroLopidGemfibrozil2,2-Dimethyl-5-(2,5-dimethylphenoxy)pentanoic acid5-(2,5-Dimethylphenoxy)-2,2-dimethylpentanoic acidCI-7LipozidGenlipDecrelip5-(2,5-Dimethylphenoxy)-2,2-dimethylpentanoic Acid2,2-Dimethyl-5-(2,5-xylyloxy)valeric AcidGevilonLipurOrganolipidEmfibHipolixangemfibrozil2,2-Dimethyl-5-(2,5-dimethylphenoxy)valeriansaeure2,2-Dimethyl-5-(2,5-xylyloxy)valeric acidGemfibrozil2,2-Dimethyl-5-(2,5-xylyloxy)valeriansaeure

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

API名称

Gemfibrozil

国际非专利药品(INN)

Gemfibrozilogemfibrozilgemfibrozilum

名称和标识

数据登录号

CAS号

25812-30-0

PubChem SID

465082641609645732489537711533483

PubChem CID

MDL号

EC号

DrugBank ID

专利号

EP1629835EP1997489US2005080087US2007253934US2008221161WO2005073221US2004073037US2006154975WO2005011677EP1746099US2008004251EP1714648US2007243233WO2007103149

LINCS数据库

LSM-2227

BRENDA数据库

1.13.12.51.1.1.1461.1.1.213.1.2.202.4.1.173.1.2.2

MetaboLights数据库

MTBLS3886MTBLS2633MTBLS2349MTBLS2384MTBLS2096MTBLS136MTBLS2267MTBLS1455

Drug Central Database

BindingDB数据库

BRENDA Ligand数据库

维基百科标题

PDB数据库

ACToR数据库

CHEMBL

BKMS React数据库

SureChEMBL数据库

SABIO-RK数据库

CompTox数据库

CHEBI ID

UniProt数据库

KEGG DRUG Database

Beilstein号

NURSA Database

数据登录号

化合物性质

产品相关信息

Free Base

suitable for 1694 per US EPA

下载链接

Antihyperlipidaemic drug

药理学性质

Increases activity of Peroxisome proliferator-activated receptor-alpha (PPAR-alpha)

化合物性质

分子相关蛋白质

分子图谱

暂无数据

点击上传数据

描述信息

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]

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]

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.

TRC

G305750

A serum lipid regulating agent used as an antihyperlipoproteinemic.

描述信息

参考文献

PubChem文献

数据源提供

• www.bentham.org/prc/samples/prc1-1/Higashi.pdf

• Kissebach, A.H., et al.: Atherosclerosis, 24, 199 (1976)

• Rubins, H.B., et al.: N. Engl. J. Med., 341, 410 (1999)

• Lewis, J.E., et al.: Pract. Cardiol., 9, 99 (1976)

• Todd, P.A. et al., Drugs, 1988, 36, 314, (rev)

• Alegret, M. et al., Br. J. Pharmacol., 1995, 114, 1351, (pharmacol)

• Martindale, The Extra Pharmacopoeia, 32nd edn., Pharmaceutical Press, 1999, 1273

• U.S. Pat., 1979, 4 126 637; CA, 90, 121021z, (synth)

• Peroxisomes: Biology and Importance in Toxicology and Medicine, (Eds. Gibson, G. et al), Taylor and Francis, 1993, (tox)

• Barter, P.J., J. Drug Eval. Cardiovasc. Med., 2002, 1, 13-39, (rev)

• U.S. Pat., 1973, 3 707 566; CA, 78, 58105q, (synth)

• Glueck, C., Am. J. Cardiol., 1983, 52, 31, (rev)

• Creger, P.L. et al., Proc. R. Soc. Med., (Suppl. 2), 1976, 69, 1, (pharmacol, metab, tox)

• Zimetbaum, P. et al., J. Clin. Pharmacol., 1991, 31, 25, (pharmacol, rev)

• Spencer, C.M. et al., Drugs, 1996, 51, 982, (rev, pharmacol)

• Abraham, D.J. et al., J. Med. Chem., 1984, 27, 967, (synth, props)

• Negwer, M., Organic-Chemical Drugs and their Synonyms, 7th edn., Akademie-Verlag, 1994, 4802, (synonyms)

• Lewis, R.J., Sax's Dangerous Properties of Industrial Materials, 8th edn., Van Nostrand Reinhold, 1992, GCK300

参考文献

生物活性

PubChem BioAssay

生物活性

名称和标识

商标名

CholespidLopidBolutolNovo-GemfibrozilDecrelipGemfibrilGemlipidHipolixanJezilFibratolGevilonLipozidGen-FibroFibrocitGenlipGemfibromaxNu-GemfibrozilApo-GemfibrozilLipur

别名

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

API名称

Gemfibrozil

国际非专利药品(INN)

Gemfibrozilogemfibrozilgemfibrozilum

描述信息

Selleck Chemicals

S1729

DrugBank

DB01241

Drug Groups

approved

Description

Indication

Pharmacology

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]

Sigma Aldrich

G9518

TRC

G305750

A serum lipid regulating agent used as an antihyperlipoproteinemic.

参考文献

PubChem文献