WARNING: This product is for research use only, not for human or veterinary use.
Hodoodo CAT#: H317967
CAS#: 25812-30-0
Description: Gemfibrozil is a peroxisome proliferator receptor alpha agonist. The mechanism of action of gemfibrozil is as a Peroxisome Proliferator-activated Receptor alpha Agonist. The chemical classification of gemfibrozil is PPAR alpha. Gemfibrozil is a lipid-regulating agent that lowers elevated serum lipids primarily by decreasing serum triglycerides with a variable reduction in total cholesterol.
Hodoodo Cat#: H317967
Name: Gemfibrozil
CAS#: 25812-30-0
Chemical Formula: C15H22O3
Exact Mass: 250.16
Molecular Weight: 250.338
Elemental Analysis: C, 71.97; H, 8.86; O, 19.17
Synonym: Gemfibrozil; Lopid; 5-(2,5-Dimethylphenoxy)-2,2-dimethylpentanoic acid; Jezil; Lipur; Terry White Chemists Gemfibrozil; Trialmin; United Drug Brand of Gemfibrozil; Warner Lambert Brand of Gemfibrozil; Warner-Lambert Brand of Gemfibrozil; Pilder; PMS Gemfibrozil; PMS-Gemfibrozil; Quimifar Brand of Gemfibrozil; SBPA Gemfibrozil;
IUPAC/Chemical Name: 5-(2,5-dimethylphenoxy)-2,2-dimethylpentanoic acid
InChi Key: HEMJJKBWTPKOJG-UHFFFAOYSA-N
InChi Code: 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)
SMILES Code: CC1=CC(=C(C=C1)C)OCCCC(C)(C)C(=O)O
Appearance: Solid powder
Purity: >98% (or refer to the Certificate of Analysis)
Shipping Condition: Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition: Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility: Soluble in DMSO, not in water
Shelf Life: >2 years if stored properly
Drug Formulation: This drug may be formulated in DMSO
Stock Solution Storage: 0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code: 2934.99.9001
More Info:
| Biological target: | Gemfibrozil is an activator of PPAR-α, used as a lipid-lowering drug; Gemfibrozil is also a nonselective inhibitor of several P450 isoforms, with Ki values for CYP2C9, 2C19, 2C8, and 1A2 of 5.8, 24, 69, and 82 μM, respectively. |
| In vitro activity: | The level of cellular TG (triglycerides) was detected and was observed to be decreased by 43.8% at 50 µM GEM (gemfibrozil) compared with cells treated with 1 mM OA only (Fig. 2C). To further confirm the lipid changes in the cellular model, TLC analysis was performed. TLC results suggested that there was a decrease in TG levels in cells treated with 50 µM GEM compared with those treated with OA only (Fig. 2D). Taken together, GEM may lower the lipid accumulation in an in vitro model of NAFLD. The optimal concentration is 50 µM. Reference: Exp Ther Med. 2019 Feb;17(2):1282-1289. https://pubmed.ncbi.nlm.nih.gov/30680004/ |
| In vivo activity: | Finally, this study found that animals in the gemfibrozil treatment group showed significant improvement in locomotive activity (Fig. 1J), and in the frequency of supported rearing (Fig. 1L) and grooming (Fig. 1M), indicating a functional improvement in activities mediated by the striatum. In addition, treatment with gemfibrozil significantly improved motor coordination as measured by rotarod (Fig. 1K). Together, these results suggest that gemfibrozil protects the nigrostriatum and improves locomotor activities in the MPTP mouse model of PD. Reference: J Neurosci. 2021 Mar 10;41(10):2287-2300. https://pubmed.ncbi.nlm.nih.gov/33514677/ |
| Solvent | Max Conc. mg/mL | Max Conc. mM | |
|---|---|---|---|
| Solubility | |||
| DMF | 30.0 | 119.84 | |
| DMSO | 55.3 | 221.03 | |
| Ethanol | 40.0 | 159.78 | |
| Ethanol:PBS (pH 7.2) (1:1) | 0.5 | 2.00 |
The following data is based on the product molecular weight 250.34 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.
| Concentration / Solvent Volume / Mass | 1 mg | 5 mg | 10 mg |
|---|---|---|---|
| 1 mM | 1.15 mL | 5.76 mL | 11.51 mL |
| 5 mM | 0.23 mL | 1.15 mL | 2.3 mL |
| 10 mM | 0.12 mL | 0.58 mL | 1.15 mL |
| 50 mM | 0.02 mL | 0.12 mL | 0.23 mL |
| Formulation protocol: | 1. Zhang X, Wang S, Hu L, Wang J, Liu Y, Shi P. Gemfibrozil reduces lipid accumulation in SMMC-7721 cells via the involvement of PPARα and SREBP1. Exp Ther Med. 2019 Feb;17(2):1282-1289. doi: 10.3892/etm.2018.7046. Epub 2018 Dec 5. PMID: 30680004; PMCID: PMC6327679. 2. Pahan K, Jana M, Liu X, Taylor BS, Wood C, Fischer SM. Gemfibrozil, a lipid-lowering drug, inhibits the induction of nitric-oxide synthase in human astrocytes. J Biol Chem. 2002 Nov 29;277(48):45984-91. doi: 10.1074/jbc.M200250200. Epub 2002 Sep 18. PMID: 12244038; PMCID: PMC2045648. 3. Gottschalk CG, Jana M, Roy A, Patel DR, Pahan K. Gemfibrozil Protects Dopaminergic Neurons in a Mouse Model of Parkinson's Disease via PPARα-Dependent Astrocytic GDNF Pathway. J Neurosci. 2021 Mar 10;41(10):2287-2300. doi: 10.1523/JNEUROSCI.3018-19.2021. Epub 2021 Jan 29. PMID: 33514677; PMCID: PMC8018777. 4. Shields CA, Poudel B, McPherson KC, Brown AK, Ekperikpe US, Browning E, Sutton L, Cornelius DC, Williams JM. Treatment With Gemfibrozil Prevents the Progression of Chronic Kidney Disease in Obese Dahl Salt-Sensitive Rats. Front Physiol. 2020 Sep 18;11:566403. doi: 10.3389/fphys.2020.566403. PMID: 33071820; PMCID: PMC7533555. |
| In vitro protocol: | 1. Zhang X, Wang S, Hu L, Wang J, Liu Y, Shi P. Gemfibrozil reduces lipid accumulation in SMMC-7721 cells via the involvement of PPARα and SREBP1. Exp Ther Med. 2019 Feb;17(2):1282-1289. doi: 10.3892/etm.2018.7046. Epub 2018 Dec 5. PMID: 30680004; PMCID: PMC6327679. 2. Pahan K, Jana M, Liu X, Taylor BS, Wood C, Fischer SM. Gemfibrozil, a lipid-lowering drug, inhibits the induction of nitric-oxide synthase in human astrocytes. J Biol Chem. 2002 Nov 29;277(48):45984-91. doi: 10.1074/jbc.M200250200. Epub 2002 Sep 18. PMID: 12244038; PMCID: PMC2045648. |
| In vivo protocol: | 1. Gottschalk CG, Jana M, Roy A, Patel DR, Pahan K. Gemfibrozil Protects Dopaminergic Neurons in a Mouse Model of Parkinson's Disease via PPARα-Dependent Astrocytic GDNF Pathway. J Neurosci. 2021 Mar 10;41(10):2287-2300. doi: 10.1523/JNEUROSCI.3018-19.2021. Epub 2021 Jan 29. PMID: 33514677; PMCID: PMC8018777. 2. Shields CA, Poudel B, McPherson KC, Brown AK, Ekperikpe US, Browning E, Sutton L, Cornelius DC, Williams JM. Treatment With Gemfibrozil Prevents the Progression of Chronic Kidney Disease in Obese Dahl Salt-Sensitive Rats. Front Physiol. 2020 Sep 18;11:566403. doi: 10.3389/fphys.2020.566403. PMID: 33071820; PMCID: PMC7533555. |
1: Kjeldal H, Zhou NA, Wissenbach DK, von Bergen M, Gough HL, Nielsen JL.
Genomic, Proteomic, and Metabolite Characterization of Gemfibrozil-Degrading
Organism Bacillus sp. GeD10. Environ Sci Technol. 2016 Jan 19;50(2):744-55. doi:
10.1021/acs.est.5b05003. Epub 2015 Dec 31. PubMed PMID: 26683816.
2: Henriques JF, Almeida AR, Andrade T, Koba O, Golovko O, Soares AM, Oliveira M,
Domingues I. Effects of the lipid regulator drug gemfibrozil: A toxicological and
behavioral perspective. Aquat Toxicol. 2016 Jan;170:355-64. doi:
10.1016/j.aquatox.2015.09.017. Epub 2015 Oct 3. PubMed PMID: 26482382.
3: Kose D, Tarakci N, Celik ZE, Vatansev H, Cimbek EA, Ugras S, Sen Y, Caliskan
U, Koksal Y. Effects of Prednisolone, L-Asparaginase, Gemfibrozil, and
Combinations of These Elements on Mice Lipid Profile, Liver, and Pancreas. J
Pediatr Hematol Oncol. 2016 Jan;38(1):e42-9. doi: 10.1097/MPH.0000000000000484.
PubMed PMID: 26599986.
4: Bussière-Côté S, Omlin T, de Càssia Pinheiro E, Weber JM. Gemfibrozil disrupts
the metabolism of circulating lipids in bobwhite quails. Comp Biochem Physiol C
Toxicol Pharmacol. 2016 Jan;179:137-43. doi: 10.1016/j.cbpc.2015.09.011. Epub
2015 Sep 30. PubMed PMID: 26432161.
5: Yang SJ, Kim BJ, Mo L, Han HK. Alteration of the intravenous and oral
pharmacokinetics of valsartan via the concurrent use of gemfibrozil in rats.
Biopharm Drug Dispos. 2015 Dec 10. doi: 10.1002/bdd.2001. [Epub ahead of print]
PubMed PMID: 26663350.
6: Al-Habsi AA, Massarsky A, Moon TW. Exposure to gemfibrozil and atorvastatin
affects cholesterol metabolism and steroid production in zebrafish (Danio rerio).
Comp Biochem Physiol B Biochem Mol Biol. 2015 Nov 25. pii: S1096-4959(15)00209-2.
doi: 10.1016/j.cbpb.2015.11.009. [Epub ahead of print] PubMed PMID: 26627126.
7: Kimoto E, Li R, Scialis RJ, Lai Y, Varma MV. Hepatic Disposition of
Gemfibrozil and Its Major Metabolite Gemfibrozil 1-O-β-Glucuronide. Mol Pharm.
2015 Nov 2;12(11):3943-52. doi: 10.1021/acs.molpharmaceut.5b00411. Epub 2015 Sep
30. PubMed PMID: 26378985.
8: Usyskin A, Bukhanovsky N, Borisover M. Interactions of triclosan, gemfibrozil
and galaxolide with biosolid-amended soils: Effects of the level and nature of
soil organic matter. Chemosphere. 2015 Nov;138:272-80. doi:
10.1016/j.chemosphere.2015.05.095. Epub 2015 Jun 16. PubMed PMID: 26091868.
9: Martín-Navarro JA, Petkov-Stoyanov V, Gutiérrez-Sánchez MJ, Pedraza-Cezón L.
Acute renal failure secondary to interstitial acute nephritis and Fanconi
syndrome for metamizole and gemfibrozil. Nefrologia. 2015 Aug 5. pii:
S0211-6995(15)00107-1. doi: 10.1016/j.nefro.2015.06.022. [Epub ahead of print]
English, Spanish. PubMed PMID: 26306948.
10: Takagi M, Sakamoto M, Itoh T, Fujiwara R. Underlying mechanism of drug-drug
interaction between pioglitazone and gemfibrozil: Gemfibrozil acyl-glucuronide is
a mechanism-based inhibitor of CYP2C8. Drug Metab Pharmacokinet. 2015
Aug;30(4):288-94. doi: 10.1016/j.dmpk.2015.05.001. Epub 2015 May 16. PubMed PMID:
26195223.
11: Varma MV, Lin J, Bi YA, Kimoto E, Rodrigues AD. Quantitative Rationalization
of Gemfibrozil Drug Interactions: Consideration of Transporters-Enzyme Interplay
and the Role of Circulating Metabolite Gemfibrozil 1-O-β-Glucuronide. Drug Metab
Dispos. 2015 Jul;43(7):1108-18. doi: 10.1124/dmd.115.064303. Epub 2015 May 4.
PubMed PMID: 25941268.
12: Sharina IG, Sobolevsky M, Papakyriakou A, Rukoyatkina N, Spyroulias GA,
Gambaryan S, Martin E. The fibrate gemfibrozil is a NO- and haem-independent
activator of soluble guanylyl cyclase: in vitro studies. Br J Pharmacol. 2015
May;172(9):2316-29. doi: 10.1111/bph.13055. Epub 2015 Feb 10. PubMed PMID:
25536881; PubMed Central PMCID: PMC4403096.
13: Singh AP, Singh R, Krishan P. Ameliorative role of gemfibrozil against
partial abdominal aortic constriction-induced cardiac hypertrophy in rats.
Cardiol Young. 2015 Apr;25(4):725-30. doi: 10.1017/S104795111400081X. Epub 2014
Jun 6. PubMed PMID: 24905340.
14: Cámara-Lemarroy CR, Guzman-DE LA Garza FJ, Cordero-Perez P, Ibarra-Hernandez
JM, Muñoz-Espinosa LE, Fernandez-Garza NE. Gemfibrozil attenuates the
inflammatory response and protects rats from abdominal sepsis. Exp Ther Med. 2015
Mar;9(3):1018-1022. Epub 2015 Jan 19. PubMed PMID: 25667670; PubMed Central
PMCID: PMC4316892.
15: Abdolmohammad-Zadeh H, Talleb Z. Magnetic solid phase extraction of
gemfibrozil from human serum and pharmaceutical wastewater samples utilizing a
β-cyclodextrin grafted graphene oxide-magnetite nano-hybrid. Talanta. 2015
Mar;134:387-93. doi: 10.1016/j.talanta.2014.11.054. Epub 2014 Dec 2. PubMed PMID:
25618684.
16: Abtahi-Naeini B, Sadeghiyan H, Adibi N, Shokrollahi MR, Pourazizi M. Bullous
dermatosis of childhood induced by gemfibrozil. J Res Med Sci. 2015
Feb;20(2):207-8. PubMed PMID: 25983779; PubMed Central PMCID: PMC4400721.
17: Rai H, Dhaneshwar SS. Amide-linked Ethanolamine Conjugate of Gemfibrozil as a
Profound HDL Enhancer: Design, Synthesis, Pharmacological Screening and Docking
Study. Curr Drug Discov Technol. 2015;12(3):155-69. PubMed PMID: 26285608.
18: Gutierrez-Macias T, Nacheva PM. Clofibric acid and gemfibrozil removal in
membrane bioreactors. Water Sci Technol. 2015;71(8):1143-50. doi:
10.2166/wst.2015.079. PubMed PMID: 25909723.
19: Siavash M, Amini M. Vitamin C may have similar beneficial effects to
Gemfibrozil on serum high-density lipoprotein-cholesterol in type 2 diabetic
patients. J Res Pharm Pract. 2014 Jul;3(3):77-82. doi: 10.4103/2279-042X.141075.
PubMed PMID: 25328896; PubMed Central PMCID: PMC4199195.
20: Krkosek WH, Peldszus S, Huck PM, Gagnon GA. Formation kinetics of gemfibrozil
chlorination reaction products: analysis and application. Water Environ Res. 2014
Jul;86(7):654-62. PubMed PMID: 25112033.
