QuickView for Gemfibrozil (compound)

Summary
General Info

PubChem

PubChem Compound 3463

Name:	Gemfibrozil
PubChem Compound ID:	3463
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.
Molecular formula:	C₁₅H₂₂O₃
Molecular weight:	250.333 g/mol
Synonyms:	Lifibron; Taborcil; Gemfibrozil (JAN/USP); Elmogan; Renabrazin; Synbrozil; AIDS-121781; Gozid; Gemfibrozil [USAN:BAN:INN]; Lipizyl. show more » Lifibron; Taborcil; Gemfibrozil (JAN/USP); Elmogan; Renabrazin; Synbrozil; AIDS-121781; Gozid; Gemfibrozil [USAN:BAN:INN]; Lipizyl; Lanaterom; DivK1c_000138; CHEBI:5296; Apo-Gemfibrozil; Gem-S; GEM; Lipur; 2,2-Dimethyl-5-(2,5-xylyloxy)valeriansaeure; Gemd; Bolutol; Gemfibrozil; NCGC00016794-01; Lopid (TN); Prestwick0_000214; Low-Lip; KBioGR_000964; Progemzal; MLS000028421; Fibrocit; 5-(2,5-Dimethylphenoxy)-2,2-dimethylpentanoic acid; KBio1_000138; 25812-30-0; KBioSS_001305; Innogen; Innogem; 2,2-Dimethyl-5-(2,5-xylyloxy)valeric acid; GFZ; Prestwick_637; Fetinor; Tentroc; Lopid; Gemnpid; Gemlipid; Reducel; BRN 1881200; Micolip; Spectrum_000825; Gemfibril; Prestwick1_000214; Cholespid; NCGC00022722-03; Clearol; Trialmin; Regulip; Normolip; Spectrum4_000562; CI 719; Spectrum3_000440; Spectrum2_001097; SPBio_001174; Litarek; Ipolipid; Gevilon; KBio3_001280; nchembio790-comp22; SPBio_002148; Jezil; 2,2-Dimethyl-5-(2,5-dimethylphenoxy)valeriansaeure; Gemfibrozilo [INN-Spanish]; AIDS121781; Brozil; Lipira; EINECS 247-280-2; Polyxit; KBio2_003873; Gemfibrozilum [INN-Latin]; NINDS_000138; WL-Gemfibrozil; Ausgem; Pilder; Gevilon Uno; Hipolixan; Sinelip; KBio2_001305; Lipazil; D00334; Decrelip; CI-719; CAS-25812-30-0; TEVA-A; Lipigem; Lipozid; SMR000058393; CCRIS 318; Pentanoic acid, 5-(2,5-dimethylphenoxy)-2,2-dimethyl-; Hidil; Fibratol; Gemfibromax; KBio2_006441; Valeric acid, 2,2-dimethyl-5-(2,5-xylyloxy)- show less «

DrugBank

Identification

Name:	Gemfibrozil
Name (isomeric):	DB01241
Drug Type:	small molecule
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.
Brand:	Decrelip, Novo-Gemfibrozil, Lopid, Fibratol, Gemlipid, Genlip, Jezil, Lipur, Apo-Gemfibrozil, Cholespid, Gemfibril, Gen-Fibro, Lipozid, Gemfibromax, Bolutol, Fibrocit, Gevilon, Hipolixan, Nu-Gemfibrozil
Category:	Fribic Acid Derivatives, Antilipemic Agents
CAS number:	25812-30-0

Pharmacology

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).
Mechanism of Action:	Gemfibrozil increases the activity of extrahepatic lipoprotein lipase (LL), thereby increasing lipoprotein triglyceride lipolysis. It does so by activating 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 differentia... show more » Gemfibrozil increases the activity of extrahepatic lipoprotein lipase (LL), thereby increasing lipoprotein triglyceride lipolysis. It does so by activating 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. Chylomicrons are degraded, VLDLs are converted to LDLs, and LDLs are converted to HDL. This is accompanied by a slight increase in secretion of lipids into the bile and ultimately the intestine. Gemfibrozil also inhibits the synthesis and increases the clearance of apolipoprotein B, a carrier molecule for VLDL. show less «
Absorption:	Well absorbed from gastrointestinal tract (within 1-2 hours).
Protein binding:	95%
Biotransformation:	Hepatic. Gemfibrozil mainly undergoes oxidation of a ring methyl group to successively form a hydroxymethyl and a carboxyl metabolite.
Route of 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.
Half Life:	1.5 hours
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

Interactions

Food interaction:

Take 30 minutes before meals.

Drug interaction:

Dicumarol	Gemfibrozil may increase the anticoagulant effect of dicumarol.
Cerivastatin	Increased risk of myopathy/rhabdomyolysis
Trimipramine	The strong CYP2C19 inhibitor, Gemfibrozil, may decrease the metabolism and clearance of Trimipramine, a CYP2C19 substrate. Consider alternate therapy or monitor for changes in therapeutic and adverse effects of Trimipramine if Gemfibrozil is initiated, discontinued or dose changed.
Tolbutamide	Gemfibrozil, a strong CYP2C9 inhibitor, may decrease the metabolism and clearance of Tolbutamide, a CYP2C9 substrate. Consider alternate therapy or monitor for changes in Tolbutamide therapeutic and adverse effects if Gemfibrozil is initiated, discontinued or dose changed.
Repaglinide	Gemfibrozil may increase the effect and toxicity of repaglinide.

Dicumarol	Gemfibrozil may increase the anticoagulant effect of dicumarol.
Cerivastatin	Increased risk of myopathy/rhabdomyolysis
Trimipramine	The strong CYP2C19 inhibitor, Gemfibrozil, may decrease the metabolism and clearance of Trimipramine, a CYP2C19 substrate. Consider alternate therapy or monitor for changes in therapeutic and adverse effects of Trimipramine if Gemfibrozil is initiated, discontinued or dose changed.
Tolbutamide	Gemfibrozil, a strong CYP2C9 inhibitor, may decrease the metabolism and clearance of Tolbutamide, a CYP2C9 substrate. Consider alternate therapy or monitor for changes in Tolbutamide therapeutic and adverse effects if Gemfibrozil is initiated, discontinued or dose changed.
Repaglinide	Gemfibrozil may increase the effect and toxicity of repaglinide.
Torasemide	Gemfibrozil, a strong CYP2C9 inhibitor, may increase the serum concentration of Torasemide, a CYP2C9 substrate, by decreasing Torasemide metabolism and clearance. Consider alternate therapy or monitor for changes in the therapeutic and adverse effects of Torasemide if Gemfibrozil is initiated, discontinued or dose changed.
Rosiglitazone	Increases the effect and toxicity of rosiglitazone/pioglitazone
Tacrine	The metabolism of Tacrine, a CYP1A2 substrate, may be reduced by Gemfibrozil, a CYP1A2 inhibitors. Monitor the efficacy and toxicity of Tacrine if Gemfibrozil is initiated, discontinued or if the dose is changed.
Ursodeoxycholic acid	The fibric acid derivative decreases the effect of ursodiol
Voriconazole	Gemfibrozil, a strong CYP2C9 inhibitor, may increase the serum concentration of voriconazole by decreasing its metabolism. Monitor for changes in the therapeutic and adverse effects of voriconazole if gemfibrozil is initiated, discontinued or dose changed.
Tamoxifen	Gemfibrozil may reduce clearance rate of Tamoxifen. Monitor for changes in therapeutic/adverse effects of Tamoxifen if Gemfibrozil is initiated, discontinued or dose changed.
Simvastatin	Increased risk of myopathy/rhabdomyolysis
Warfarin	Gemfibrozil, a strong CYP2C9 inhibitor, may decrease the metabolism of warfarin. Consider alternate therapy or monitor for changes in the therapeutic and adverse effects of warfarin if gemfibrozil is initiated, discontinued or dose changed.
Lovastatin	Increased risk of myopathy/rhabdomyolysis
Anisindione	Gemfibrozil may increase the anticoagulant effect of anisindione.
Bexarotene	Gemfibrozil may increase the serum concentration of bexarotene. This combination should be avoided.
Acenocoumarol	Gemfibrozil may increase the anticoagulant effect of acenocoumarol.
Tizanidine	Gemfibrozil may decrease the metabolism and clearance of Tizanidine. Consider alternate therapy or use caution during co-administration.
Pioglitazone	Gemfibrozil may increase the effect and toxicity of pioglitazone.
Zafirlukast	Gemfibrozil, a strong CYP2C9 inhibitor, may decrease the metabolism and clearance of zafirlukast. Consider alternate therapy or monitor for changes in zafirlukast therapeutic and adverse effects if gemfibrozil is initiated, discontinued or dose changed.
Fluvastatin	Increased risk of myopathy/rhabdomyolysis
Atorvastatin	Increased risk of myopathy/rhabdomyolysis
Glimepiride	Gemfibrozil increases the effect and toxicity of rosiglitazone/pioglitazone
Pravastatin	Increased risk of myopathy/rhabdomyolysis
Carisoprodol	Strong CYP2C19 inhibitors such as gemfibrozil may decrease the metabolism of CYP2C19 substrates such as carisoprodol. Consider an alternative for one of the interacting drugs in order to avoid toxicity of the substrate. Some combinations are specifically contraindicated by manufacturers. Suggested dosage adjustments are also offered by some manufacturers. Please review applicable package inserts. Monitor for increased effects of the CYP substrate if a CYP inhibitor is initiated/dose increased, and decreased effects if a CYP inhibitor is discontinued/dose decreased.
Rosuvastatin	Gemfibrozil may increase the therapeutic and toxic effects of rosuvastatin. Consider alternate therapy or monitor for changes in the therapeutic and adverse effects of rosuvastatin if gemfibrozil is initiated, discontinued or dose changed.
Tretinoin	The strong CYP2C8 inhibitor, Gemfibrozil, may decrease the metabolism and clearance of oral Tretinoin. Consider alternate therapy or monitor for changes in Tretinoin effectiveness and adverse/toxic effects if Gemfibrozil is initiated, discontinued to dose changed.
Trimethoprim	The strong CYP2C9 inhibitor, Gemfibrozil, may decrease the metabolism and clearance of Trimethoprim, a CYP2C9 substrate. Consider alternate therapy or monitor for changes in therapeutic and adverse effects of Trimethoprim if Gemfibrozil is initiated, discontinued or dose changed.

show less «

Targets

Peroxisome proliferator-activated receptor alpha

Enzymes

Transporters

Solute carrier organic anion transporter family member 1B1