CAS 25812-30-0|Jezil|5-(2,5-dimethylphenoxy)-2,2-dimethylpentanoic acid|Fibratol|Gemfibromax|Gemfibrozil|gemfibrozil|Lipur|Genlip|Lipozid|Lopid|Hipolixan|Cholespid|Novo-Gemfibrozil|Fibrocit|Gen-Fibr...

General Information

Structure

Molecular Formula

C₁₅H₂₂O₃

Molecular Mass

250.33338

Exact Mass

250.15689456

Charge

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

Calculated Properties

JChem

LogD (pH = 7.4)

1.51

LogD (pH = 5.5)

3.27

Log P

4.39

Rotatable Bonds

H Donor

H Acceptors

Lipinski's Rule of Five

true

Acid pKa

4.42

Polar Surface Area

46.53

Polarizability

28.89

Molar Refractivity

71.82

LOG S

-3.31

Data Source

Names and Identifiers

Brand Name

JezilFibratolGemfibromaxLipurGenlipLipozidLopidHipolixanCholespidNovo-GemfibrozilFibrocitGen-FibroGemlipidNu-GemfibrozilDecrelipGemfibrilApo-GemfibrozilBolutolGevilon

IUPAC name

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

Synonyms

GemfibrozilJezilGen-FibroGemcorLopidGemfibrozil2,2-Dimethyl-5-(2,5-dimethylphenoxy)pentanoic acid5-(2,5-Dimethylphenoxy)-2,2-dimethylpentanoic acid5-(2,5-Dimethylphenoxy)-2,2-dimethylpentanoic AcidLipozidDecrelipGenlipCI-72,2-Dimethyl-5-(2,5-xylyloxy)valeric AcidGevilonEmfibOrganolipidHipolixanLipur2,2-Dimethyl-5-(2,5-xylyloxy)valeric acidgemfibrozil2,2-Dimethyl-5-(2,5-dimethylphenoxy)valeriansaeureGemfibrozil2,2-Dimethyl-5-(2,5-xylyloxy)valeriansaeure

IUPAC Traditional name

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

API Name

Gemfibrozil

International Nonproprietary Name (INN)

gemfibrozilumgemfibrozilGemfibrozilo

Names and Identifiers

Registration numbers

Properties

Product Information

Salt Data

Free Base

Suitability

suitable for 1694 per US EPA

Certificate of Analysis

Download link

Application(s)

Antihyperlipidaemic drug

Pharmacology Properties

Mechanism of Action

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

Properties

Related Proteins

Molecular Spectra

No Data Available

Click here to submit data

Molecule Details

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.

Molecule Details

References

PubChem Literature

From Data Sources

• 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)

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

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

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

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

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

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

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

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

• 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

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

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

• 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)

References

Bioactivity

PubChem BioAssay

Bioactivity

Names and Identifiers

Brand Name

JezilFibratolGemfibromaxLipurGenlipLipozidLopidHipolixanCholespidNovo-GemfibrozilFibrocitGen-FibroGemlipidNu-GemfibrozilDecrelipGemfibrilApo-GemfibrozilBolutolGevilon

IUPAC name

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

Synonyms

IUPAC Traditional name

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

API Name

Gemfibrozil

International Nonproprietary Name (INN)

gemfibrozilumgemfibrozilGemfibrozilo

Molecule Details

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.

References

PubChem Literature