Nafenopin

    WARNING: This product is for research use only, not for human or veterinary use.

MedKoo CAT#: 551050

CAS#: 3771-19-5

Description: Nafenopin is a peroxisome proliferator that is used to promote liver tumors. It has been used as an antihyperlipoproteinemic agent.


Price and Availability

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Nafenopin is not in stock, may be available through custom synthesis. For cost-effective reason, minimum 1 gram order is requested. The product will be characterized by NMR, HPLC and MS analysis. Purity (HPLC) is usually >98%. CoA, QC data, MSDS will be provided when product is successfully made. The estimated lead time is 2-3 months. Please send email to sales@medkoo.com to inquire quote.


Chemical Structure

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Theoretical Analysis

MedKoo Cat#: 551050
Name: Nafenopin
CAS#: 3771-19-5
Chemical Formula: C20H22O3
Exact Mass: 310.16
Molecular Weight: 310.39
Elemental Analysis: C, 77.39; H, 7.14; O, 15.46


Synonym: Nafenopin

IUPAC/Chemical Name: 2-methyl-2-(4-(1,2,3,4-tetrahydronaphthalen-1-yl)phenoxy)propanoic acid; 2-Methyl-2-(4-(1,2,3,4-tetrahydro-1-naphthyl)phenoxy)propanoic acid; 2-Methyl-2-(p-(1,2,3,4-tetrahydro-1-naphthyl)phenoxy)propionic acid; alpha-Methyl-alpha-(p-1,2,3,4-tetrahydronaphth-1-ylphenoxy)propionic acid; BRN 2005820; C 13437 SU

InChi Key: XJGBDJOMWKAZJS-UHFFFAOYSA-N

InChi Code: 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)

SMILES Code: C1(c2c(CCC1)cccc2)c1ccc(cc1)OC(C(=O)O)(C)C


Technical Data

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

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).

Harmonized System Code:
293490


References

1: Henderson CJ, Cameron AR, Chatham L, Stanley LA, Wolf CR. Evidence that the capacity of nongenotoxic carcinogens to induce oxidative stress is subject to marked variability. Toxicol Sci. 2015 May;145(1):138-48. doi: 10.1093/toxsci/kfv039. Epub 2015 Feb 17. PubMed PMID: 25690736; PubMed Central PMCID: PMC4833039.

2: Wahlang B, Falkner KC, Clair HB, Al-Eryani L, Prough RA, States JC, Coslo DM, Omiecinski CJ, Cave MC. Human receptor activation by aroclor 1260, a polychlorinated biphenyl mixture. Toxicol Sci. 2014 Aug 1;140(2):283-97. doi: 10.1093/toxsci/kfu083. Epub 2014 May 8. PubMed PMID: 24812009; PubMed Central PMCID: PMC4176050.

3: Mogilenko DA, Dizhe EB, Shavva VS, Lapikov IA, Orlov SV, Perevozchikov AP. Role of the nuclear receptors HNF4 alpha, PPAR alpha, and LXRs in the TNF alpha-mediated inhibition of human apolipoprotein A-I gene expression in HepG2 cells. Biochemistry. 2009 Dec 22;48(50):11950-60. doi: 10.1021/bi9015742. PubMed PMID: 19883121.

4: Alvergnas M, Richert L, Blanchard N, Abadie C, Heyd B, Mantion G, Gallemann D, Martin H. Regulation of CYP4A expression by bezafibrate in primary culture of rat and human hepatocytes: interspecies difference and influence of N-acetylcysteine. Toxicol In Vitro. 2009 Oct;23(7):1259-67. doi: 10.1016/j.tiv.2009.07.027. Epub 2009 Jul 30. PubMed PMID: 19647067.

5: Tamasi V, Miller KK, Ripp SL, Vila E, Geoghagen TE, Prough RA. Modulation of receptor phosphorylation contributes to activation of peroxisome proliferator activated receptor alpha by dehydroepiandrosterone and other peroxisome proliferators. Mol Pharmacol. 2008 Mar;73(3):968-76. Epub 2007 Dec 13. PubMed PMID: 18079279; PubMed Central PMCID: PMC2423814.

6: Kawano H, Nagata T, Narahara M, Kanazawa M, Miyake M. Triglyceride accumulation by peroxisome proliferators in rat hepatocytes. Biol Pharm Bull. 2007 Apr;30(4):627-32. PubMed PMID: 17409492.

7: Hadzimehmedović A, Balić A, Balić D. [Adolescents and knowledge of sexually transmitted diseases in Tuzla Canton]. Med Arh. 2006;60(5):304-7. Bosnian. PubMed PMID: 16944733.

8: Sallustio BC, Degraaf YC, Weekley JS, Burcham PC. Bioactivation of carboxylic acid compounds by UDP-Glucuronosyltransferases to DNA-damaging intermediates: role of glycoxidation and oxidative stress in genotoxicity. Chem Res Toxicol. 2006 May;19(5):683-91. PubMed PMID: 16696571.

9: Bursch W, Wastl U, Hufnagl K, Schulte-Hermann R. No increase of apoptosis in regressing mouse liver after withdrawal of growth stimuli or food restriction. Toxicol Sci. 2005 May;85(1):507-14. Epub 2005 Feb 23. PubMed PMID: 15728705.

10: Bursch W, Grasl-Kraupp B, Wastl U, Hufnagl K, Chabicovsky M, Taper H, Schulte-Hermann R. Role of apoptosis for mouse liver growth regulation and tumor promotion: comparative analysis of mice with high (C3H/He) and low (C57Bl/6J) cancer susceptibility. Toxicol Lett. 2004 Apr 1;149(1-3):25-35. Review. PubMed PMID: 15093245.

11: Gardner OS, Dewar BJ, Earp HS, Samet JM, Graves LM. Dependence of peroxisome proliferator-activated receptor ligand-induced mitogen-activated protein kinase signaling on epidermal growth factor receptor transactivation. J Biol Chem. 2003 Nov 21;278(47):46261-9. Epub 2003 Sep 9. PubMed PMID: 12966092.

12: Ripp SL, Falkner KC, Pendleton ML, Tamasi V, Prough RA. Regulation of CYP2C11 by dehydroepiandrosterone and peroxisome proliferators: identification of the negative regulatory region of the gene. Mol Pharmacol. 2003 Jul;64(1):113-22. PubMed PMID: 12815167.

13: Gu S, Ripp SL, Prough RA, Geoghegan TE. Dehydroepiandrosterone affects the expression of multiple genes in rat liver including 11 beta-hydroxysteroid dehydrogenase type 1: a cDNA array analysis. Mol Pharmacol. 2003 Mar;63(3):722-31. PubMed PMID: 12606783.

14: Coddou C, Loyola G, Boyer JL, Bronfman M, Huidobro-Toro JP. The hypolipidemic drug metabolites nafenopin-CoA and ciprofibroyl-CoA are competitive P2Y1 receptor antagonists. FEBS Lett. 2003 Feb 11;536(1-3):145-50. PubMed PMID: 12586354.

15: Roberts RA, Chevalier S, Hasmall SC, James NH, Cosulich SC, Macdonald N. PPAR alpha and the regulation of cell division and apoptosis. Toxicology. 2002 Dec 27;181-182:167-70. Review. PubMed PMID: 12505304.

16: Rossmanith W, Chabicovsky M, Grasl-Kraupp B, Peter B, Schausberger E, Schulte-Hermann R. Follistatin overexpression in rodent liver tumors: a possible mechanism to overcome activin growth control. Mol Carcinog. 2002 Sep;35(1):1-5. PubMed PMID: 12203361.

17: Hasmall S, Orphanides G, James N, Pennie W, Hedley K, Soames A, Kimber I, Roberts R. Downregulation of lactoferrin by PPARalpha ligands: role in perturbation of hepatocyte proliferation and apoptosis. Toxicol Sci. 2002 Aug;68(2):304-13. PubMed PMID: 12151626.

18: Kalderon B, Sheena V, Shachrur S, Hertz R, Bar-Tana J. Modulation by nutrients and drugs of liver acyl-CoAs analyzed by mass spectrometry. J Lipid Res. 2002 Jul;43(7):1125-32. PubMed PMID: 12091497.

19: Drogemuller CJ, Nunthasomboon S, Knights KM. Nafenopin-, ciprofibroyl-, and palmitoyl-CoA conjugation in vitro: kinetic and molecular characterization of marmoset liver microsomes and expressed MLCL1. Arch Biochem Biophys. 2001 Dec 1;396(1):56-64. PubMed PMID: 11716462.

20: Yang Q, Xie Y, Eriksson AM, Nelson BD, DePierre JW. Further evidence for the involvement of inhibition of cell proliferation and development in thymic and splenic atrophy induced by the peroxisome proliferator perfluoroctanoic acid in mice. Biochem Pharmacol. 2001 Oct 15;62(8):1133-40. PubMed PMID: 11597582.