Nafenopin

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

MedKoo CAT#: 525724

CAS#: 3771-19-5

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


Price and Availability

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Nafenopin is not in stock, but 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#: 525724
Name: Nafenopin
CAS#: 3771-19-5
Chemical Formula: C20H22O3
Exact Mass: 310.15689
Molecular Weight: 310.393
Elemental Analysis: C, 77.39; H, 7.14; O, 15.46


Synonym: Nafenopene; Nafenopino; Nafenopinum; Nafenoic Acid; Melipan; Nafenopin

IUPAC/Chemical Name: 2-methyl-2-(4-(1,2,3,4-tetrahydronaphthalen-1-yl)phenoxy)propanoic acid

SMILES Code: CC(OC1=CC=C(C2CCCC3=C2C=CC=C3)C=C1)(C)C(O)=O


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, 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).

Harmonized System Code:
293490


References

1: 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.
2: 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.
3: Hasmall SC, West DA, Olsen K, Roberts RA. Role of hepatic non-parenchymal cells in the response of rat hepatocytes to the peroxisome proliferator nafenopin in vitro. Carcinogenesis. 2000 Dec;21(12):2159-65. PubMed PMID: 11133804.
4: Cosulich SC, James NH, Needham MR, Newham PP, Bundell KR, Roberts RA. A dominant negative form of IKK2 prevents suppression of apoptosis by the peroxisome proliferator nafenopin. Carcinogenesis. 2000 Sep;21(9):1757-60. PubMed PMID: 10964109.
5: Chevalier S, Macdonald N, Tonge R, Rayner S, Rowlinson R, Shaw J, Young J, Davison M, Roberts RA. Proteomic analysis of differential protein expression in primary hepatocytes induced by EGF, tumour necrosis factor alpha or the peroxisome proliferator nafenopin. Eur J Biochem. 2000 Aug;267(15):4624-34. PubMed PMID: 10903494.
6: Elcock FJ, Deag E, Roberts RA, Chipman JK. Nafenopin causes protein kinase C-mediated serine phosphorylation and loss of function of connexin 32 protein in rat hepatocytes without aberrant expression or localization. Toxicol Sci. 2000 Jul;56(1):86-94. PubMed PMID: 10869456.
7: Holden PR, Hasmall SC, James NH, West DR, Brindle RD, Gonzalez FJ, Peters JM, Roberts RA. Tumour necrosis factor alpha (TNFalpha): role in suppression of apoptosis by the peroxisome proliferator nafenopin. Cell Mol Biol (Noisy-le-grand). 2000 Feb;46(1):29-39. PubMed PMID: 10726969.
8: Sallustio BC, Nunthasomboon S, Drogemuller CJ, Knights KM. In vitro covalent binding of nafenopin-CoA to human liver proteins. Toxicol Appl Pharmacol. 2000 Mar 1;163(2):176-82. PubMed PMID: 10698675.
9: West DA, James NH, Cosulich SC, Holden PR, Brindle R, Rolfe M, Roberts RA. Role for tumor necrosis factor alpha receptor 1 and interleukin-1 receptor in the suppression of mouse hepatocyte apoptosis by the peroxisome proliferator nafenopin. Hepatology. 1999 Dec;30(6):1417-24. PubMed PMID: 10573520.
10: Chevalier S, Roberts RA. G1-arrested FaO cells re-enter the cell cycle upon stimulation with the rodent non-genotoxic hepatocarcinogen nafenopin. Carcinogenesis. 1999 Jul;20(7):1209-13. PubMed PMID: 10383891.
11: Hasmall SC, James NH, Soames AR, Roberts RA. The peroxisome proliferator nafenopin does not suppress hepatocyte apoptosis in guinea-pig liver in vivo nor in human hepatocytes in vitro. Arch Toxicol. 1998 Dec;72(12):777-83. PubMed PMID: 9950074.
12: Singleton DW, Lei XD, Webb SJ, Prough RA, Geoghegan TE. Cytochrome P-450 mRNAs are modulated by dehydroepiandrosterone, nafenopin, and triiodothyronine. Drug Metab Dispos. 1999 Feb;27(2):193-200. PubMed PMID: 9929502.
13: Gill JH, Brickell P, Dive C, Roberts RA. The rodent non-genotoxic hepatocarcinogen nafenopin suppresses apoptosis preferentially in non-cycling hepatocytes but also elevates CDK4, a cell cycle progression factor. Carcinogenesis. 1998 Oct;19(10):1743-7. PubMed PMID: 9806153.
14: Elcock FJ, Chipman JK, Roberts RA. The rodent nongenotoxic hepatocarcinogen and peroxisome proliferator nafenopin inhibits intercellular communication in rat but not guinea-pig hepatocytes, perturbing S-phase but not apoptosis. Arch Toxicol. 1998 Jun;72(7):439-44. PubMed PMID: 9708883.
15: Gill JH, James NH, Roberts RA, Dive C. The non-genotoxic hepatocarcinogen nafenopin suppresses rodent hepatocyte apoptosis induced by TGFbeta1, DNA damage and Fas. Carcinogenesis. 1998 Feb;19(2):299-304. PubMed PMID: 9498280.
16: Voskoboinik I, Drew R, Ahokas JT. Peroxisome proliferator nafenopin potentiated cytotoxicity and genotoxicity of cyclophosphamide in the liver and bone marrow cells. Chem Biol Interact. 1997 Jul 11;105(2):81-97. PubMed PMID: 9251722.
17: Menegazzi M, Carcereri-De Prati A, Suzuki H, Shinozuka H, Pibiri M, Piga R, Columbano A, Ledda-Columbano GM. Liver cell proliferation induced by nafenopin and cyproterone acetate is not associated with increases in activation of transcription factors NF-kappaB and AP-1 or with expression of tumor necrosis factor alpha. Hepatology. 1997 Mar;25(3):585-92. PubMed PMID: 9049203.
18: Huber WW, Grasl-Kraupp B, Stekel H, Gschwentner C, Lang H, Schulte-Hermann R. Inhibition instead of enhancement of lipid peroxidation by pretreatment with the carcinogenic peroxisome proliferator nafenopin in rat liver exposed to a high single dose of corn oil. Arch Toxicol. 1997;71(9):575-81. PubMed PMID: 9285040.
19: Strange J, Roberts RA. Reduced expression of mature TGF beta 1 correlates with the suppression of rat hepatocyte apoptosis by the peroxisome proliferator, nafenopin. Mutat Res. 1996 Nov 11;372(1):107-13. PubMed PMID: 9003537.
20: Voskoboinik I, Drew R, Ahokas JT. Effect of peroxisome proliferator nafenopin on the cytotoxicity of dihaloalkanes in isolated rat hepatocytes. Toxicol In Vitro. 1996 Oct;10(5):577-84. PubMed PMID: 20650239.