Gemfibrozil

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Structural formula
Structural formula of gemfibrozil
General
Non-proprietary name Gemfibrozil
other names
  • 5- (2,5-dimethylphenoxy) -2,2-dimethylpentanoic acid ( IUPAC )
  • Gemfibrozilum ( Latin )
Molecular formula C 15 H 22 O 3
Brief description

white to almost white, waxy, crystalline powder

External identifiers / databases
CAS number 25812-30-0
EC number 247-280-2
ECHA InfoCard 100,042,968
PubChem 3463
ChemSpider 3345
DrugBank DB01241
Wikidata Q384295
Drug information
ATC code

C10 AB04

Drug class

Fibrates (lipid lowering agents)

properties
Molar mass 250.34 g · mol -1
Physical state

firmly

Melting point

61-63 ° C

boiling point

158-159 ° C (2.66 Pa )

pK s value

4.7

solubility

practically insoluble in water, very easily soluble in dichloromethane , easily soluble in ethanol and in methanol

safety instructions
Please note the exemption from the labeling requirement for drugs, medical devices, cosmetics, food and animal feed
GHS labeling of hazardous substances
07 - Warning

Caution

H and P phrases H: 302
P: no P-phrases
Toxicological data

1414 mg kg −1 ( LD 50 ,  rat ,  oral )

As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Gemfibrozil is an oral lipid-lowering drug (used to lower high blood lipids ). It belongs to the drug class of fibrates . Gemfibrozil was patented as a lipid lowering agent in 1969 by Parke-Davis (now Pfizer ) and is available under the trade name Gevilon and as a generic .

Mechanism of action

The drug is a ligand of the peroxisome proliferator-activated receptor of subtype α (PPAR α ), a receptor that is involved in the metabolism of carbohydrates and fats and also in the formation of adipose tissue . The increase in the synthesis of lipoprotein lipase also increases the breakdown of triglycerides .

Therapeutic effect

Gemfibrozil

  • reduces the level of triglycerides (by 20-40%)
  • reduces the level of VLDL
  • moderately reduces the level of LDL (by 10–20%)
  • moderately increases the level of HDL (by 5–20%).

Side effects and toxic effects

Common side effects are dizziness, headache, gastrointestinal discomfort, skin eczema and fatigue. An increase in transaminases, muscle problems, gallstone formation and hair loss can also occur, as with other fibrates.

In animal experiments there were indications of carcinogenicity at abnormal doses .

Indications

Contraindications

Gemfibrozil should only be used with caution in the presence of increased liver enzymes , advanced renal insufficiency and biliary tract disease . It is only permitted during pregnancy if there is a vital indication. There is a risk of hypoglycaemia when taken with repaglinide . When taken with statins, the common metabolic pathway via cytochrome P450 increases the risk of rhabdomyolysis .

Interactions

Individual evidence

  1. ↑ a b c data sheet GEMFIBROZIL CRS 06/27/2013 (PDF) at EDQM , accessed on August 29, 2017.
  2. ↑ a b c d Entry on Gemfibrozil. In: Römpp Online . Georg Thieme Verlag, accessed on July 10, 2019.
  3. ↑ a b Gemfibrozil data sheet at Sigma-Aldrich , accessed on April 3, 2011 ( PDF ).
  4. ↑ Thomas Karow, Ruth Lang-Roth: General and special pharmacology and toxicology . P. 654.
  5. ↑ Red List online, accessed on February 1, 2014.
  6. ↑ Richard Daikeler, idols Use, Sylke Waibel: diabetes. Evidence-based diagnosis and therapy. 10th edition. Kitteltaschenbuch, Sinsheim 2015, ISBN 978-3-00-050903-2 , p. 149.
  7. ↑ rxlist.com: Lopid ( Memento from June 12, 2008 in the Internet Archive ).
  8. ↑ Red List Online Gemfibrozol, accessed February 1, 2014.