Nafenopin - CAS 3771-19-5
Catalog number:
3771-19-5
Category:
Inhibitor
Not Intended for Therapeutic Use. For research use only.
Molecular Formula:
C20H22O3
Molecular Weight:
310.39
COA:
Inquire
Targets:
Others
Description:
Nafenopin is a hypolipidemic agent, a peroxisome proliferator, on the activities of rat liver glutathione-requiring enzymes and catalase in comparison to the action of phenobarbital.
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Purity:
≥98%
Appearance:
Crystals.
Synonyms:
2-Methyl-2-[4-(1,2,3,4-tetrahydronaphthalen-1-yl)phenoxy]propanoic acid;
Solubility:
Soluble in DMSO
Storage:
Store at -20 °C
MSDS:
Inquire
Application:
A hypolipidemic agent
Quality Standard:
Enterprise standard
Shelf Life:
As supplied, 2 years from the QC date provided on the Certificate of Analysis, when stored properly.
Quantity:
Milligrams-Grams
InChIKey:
XJGBDJOMWKAZJS-UHFFFAOYSA-N
InChI:
1S/C20H22O3/c1-20(2,19(21)22)23-16-12-10-15(11-13-16)18-9-5-7-14-6-3-4-8-17(14)18/h3-4,6,8,10-13,18H,5,7,9H2,1-2H3,(H,21,22)
Canonical SMILES:
CC(C)(C(=O)O)OC1=CC=C(C=C1)C2CCCC3=CC=CC=C23
1.Bioactivation of carboxylic acid compounds by UDP-Glucuronosyltransferases to DNA-damaging intermediates: role of glycoxidation and oxidative stress in genotoxicity.
Sallustio BC1, Degraaf YC, Weekley JS, Burcham PC. Chem Res Toxicol. 2006 May;19(5):683-91.
Nonenzymatic modification of proteins by acyl glucuronides is well documented; however, little is known about their potential to damage DNA. We have previously reported that clofibric acid undergoes glucuronidation-dependent bioactivation to DNA-damaging species in cultured mouse hepatocytes. The aim of this study was to investigate the mechanisms underlying such DNA damage, and to screen chemically diverse carboxylic acid drugs for their DNA-damaging potential in glucuronidation proficient murine hepatocytes. Cells were incubated with each aglycone for 18 h, followed by assessment of compound cytotoxicity using the MTT assay and evaluation of DNA damage using the Comet assay. Relative cytotoxic potencies were ketoprofen > diclofenac, benoxaprofen, nafenopin >> gemfibrozil, probenecid > bezafibrate > clofibric acid. At a noncytotoxic (0.1 mM) concentration, only benoxaprofen, nafenopin, clofibric acid, and probenecid significantly increased Comet moments (P < 0.
2.Triglyceride accumulation by peroxisome proliferators in rat hepatocytes.
Kawano H1, Nagata T, Narahara M, Kanazawa M, Miyake M. Biol Pharm Bull. 2007 Apr;30(4):627-32.
Peroxisome proliferators (PxPs) induce peroxisomal beta-oxidation (Px-ox) in the liver of rodents and have a hypolipidemic function. To investigate hypolipidemic effect of PxPs, the relationship between TG fluctuation and Px-ox activity, as an indicator of the function of PxPs, was studied in primary cultured rat hepatocytes. Nafenopin (Nf) treatment of hepatocytes caused an increase in Px-ox activity in association with cellular TG accumulation in a time-dependent manner with a coefficient of r=0.918. This relationship between the activity and cellular TG were obtained using structurally diverse PxPs with a correlation coefficient of r=0.747. Treatment of the hypolipidemic drug, but non-PxP Pravastatin, decreased TG in the medium, but did not have the effects on cellular TG and Px-ox activity. The total amount of TG and diacylglycerol acyltransferase activity, the last enzyme in the TG de novo synthesis pathway, were not affected by Nf treatment.
3.Evidence that the capacity of nongenotoxic carcinogens to induce oxidative stress is subject to marked variability.
Henderson CJ1, Cameron AR1, Chatham L1, Stanley LA1, Wolf CR2. Toxicol Sci. 2015 May;145(1):138-48. doi: 10.1093/toxsci/kfv039. Epub 2015 Feb 17.
Many drugs and environmental chemicals which are not directly mutagenic have the capacity to increase the incidence of tumors in the liver and other tissues. For this reason, such compounds are known as nongenotoxic carcinogens. The mechanisms underlying their effects remain unclear; however, their capacity to induce oxidative stress is considered to be a critical step in the carcinogenic process, although the evidence that this is actually the case remains equivocal and sparse. We have exploited a novel heme oxygenase-1 reporter mouse to evaluate the capacity of nongenotoxic carcinogens with different mechanisms of action to induce oxidative stress in the liver in vivo. When these compounds were administered at doses reported to cause liver tumors, marked differences in activation of the reporter were observed. 1,4-Dichlorobenzene and nafenopin were strong inducers of oxidative stress, whereas phenobarbital, piperonyl butoxide, cyproterone acetate, and WY14,643 were, at best, only very weak inducers.
4.Regulation of CYP4A expression by bezafibrate in primary culture of rat and human hepatocytes: interspecies difference and influence of N-acetylcysteine.
Alvergnas M1, Richert L, Blanchard N, Abadie C, Heyd B, Mantion G, Gallemann D, Martin H. Toxicol In Vitro. 2009 Oct;23(7):1259-67. doi: 10.1016/j.tiv.2009.07.027. Epub 2009 Jul 30.
The effects of fibrates on cytochrome P450 4A (CYP4A) expression have not been clearly evaluated in human hepatocytes, human being reported as a non-responsive species. We have evaluated the effects of clofibrate, bezafibrate (BEZA), WY-14643, nafenopin and ciprofibrate at the concentration of 250 microM on CYP4A expression in primary cultures of rat and human hepatocytes. BEZA greatly induced mRNA expression in both species. Eight out of 10 human cultures responded to BEZA 250 microM. CYP4A-dependent activity was increased in rat, but not in human hepatocytes. The antioxidant N-acetylcysteine (Nac) enhanced the inducing effect of BEZA on mRNA expression, this potentialization being higher in human compared to rat hepatocytes. By contrast, Nac decreased the inducing effect of BEZA on CYP4A-dependent activity in rat and had either no effect or decreased the activity in BEZA-treated human hepatocytes. In conclusion, the cellular environment appears as an important parameter to take into account when studying CYP4A induction and could partly explain interspecies differences in the complex regulation of CYP4A expression.
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CAS 3771-19-5 Nafenopin

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