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MedKoo Cat#: 551050 | Name: Nafenopin

Description:

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

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

Chemical Structure

Nafenopin
Nafenopin
CAS#3771-19-5

Theoretical Analysis

MedKoo Cat#: 551050

Name: Nafenopin

CAS#: 3771-19-5

Chemical Formula: C20H22O3

Exact Mass: 310.1600

Molecular Weight: 310.39

Elemental Analysis: C, 77.39; H, 7.14; O, 15.46

Price and Availability

This product is currently not in stock but may be available through custom synthesis. To ensure cost efficiency, the minimum order quantity is 1 gram. The estimated lead time is 2 to 4 months, with pricing dependent on the complexity of the synthesis (typically high for intricate chemistries). Quotes for quantities below 1 gram will not be provided. To request a quote, please click the button below. Note: If this product becomes available in stock in the future, pricing will be listed accordingly.
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Related CAS #
No Data
Synonym
Nafenopin; BRN 2005820; C 13437 SU
IUPAC/Chemical Name
2-methyl-2-(4-(1,2,3,4-tetrahydronaphthalen-1-yl)phenoxy)propanoic acid
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
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).
HS Tariff Code
2934.99.9001
More Info

Preparing Stock Solutions

The following data is based on the product molecular weight 310.39 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.

Recalculate based on batch purity %
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
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.

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