NAFENOPIN

Details

Stereochemistry	RACEMIC
Molecular Formula	C20H22O3
Molecular Weight	310.3869
Optical Activity	( + / - )
Defined Stereocenters	0 / 1
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CC(C)(OC1=CC=C(C=C1)C2CCCC3=C2C=CC=C3)C(O)=O

InChI

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)

HIDE SMILES / InChI

Molecular Formula	C20H22O3
Molecular Weight	310.3869
Charge	0
Count

Stereochemistry	RACEMIC
Additional Stereochemistry	No
Defined Stereocenters	0 / 1
E/Z Centers	0
Optical Activity	( + / - )

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/5099889 | https://www.ncbi.nlm.nih.gov/pubmed/4577009 | https://www.ncbi.nlm.nih.gov/pubmed/2244926 | https://www.ncbi.nlm.nih.gov/pubmed/9950074

Nafenopin is a hypolipidemic drug. It is also a peroxisome proliferator. In rats and mice, nafenopin is a nongenotoxic hepatocarcinogen, which induces hepatic DNA synthesis and enzyme induction both in vivo and in hepatocyte cultures in vitro. Hepatic Ca2+ mobilization induced by nafenopin may play an important role in the mechanism by which nafenopin exerts its physiological as well as its tumour promotive activity upon chronic treatment with carcinogenic doses.

Approval Year

PubMed

Title	Date	PubMed
cDNA cloning, chromosomal mapping, and functional characterization of the human peroxisome proliferator activated receptor.	1993 Jun 1	7684926
Differential effect of peroxisome proliferators on rat glutathione S-transferase isoenzymes.	1996 Oct	8914623
Peroxisome proliferator nafenopin potentiated cytotoxicity and genotoxicity of cyclophosphamide in the liver and bone marrow cells.	1997 Jul 11	9251722
Mouse hepatocyte response to peroxisome proliferators: dependency on hepatic nonparenchymal cells and peroxisome proliferator activated receptor alpha (PPARalpha).	2001 Aug	11570693
Modulation by nutrients and drugs of liver acyl-CoAs analyzed by mass spectrometry.	2002 Jul	12091497
Follistatin overexpression in rodent liver tumors: a possible mechanism to overcome activin growth control.	2002 Sep	12203361
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.	2004 Apr 1	15093245
No increase of apoptosis in regressing mouse liver after withdrawal of growth stimuli or food restriction.	2005 May	15728705
Triglyceride accumulation by peroxisome proliferators in rat hepatocytes.	2007 Apr	17409492
Clofibrate treatment in pigs: effects on parameters critical with respect to peroxisome proliferator-induced hepatocarcinogenesis in rodents.	2007 Apr 16	17437637
The Role of NF-kappaB in PPARalpha-Mediated Hepatocarcinogenesis.	2008	19197377
PPAR Regulation of Inflammatory Signaling in CNS Diseases.	2008	18670616
The Role of PPARs in Cancer.	2008	18584037
Genomic profiling reveals an alternate mechanism for hepatic tumor promotion by perfluorooctanoic acid in rainbow trout.	2008 Aug	18709148
A human hepatocyte-bearing mouse: an animal model to predict drug metabolism and effectiveness in humans.	2009	19884982
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.	2009 Dec 22	19883121
PPARalpha: energy combustion, hypolipidemia, inflammation and cancer.	2010 Apr 16	20414453
Genomic models of short-term exposure accurately predict long-term chemical carcinogenicity and identify putative mechanisms of action.	2014	25058030

Patents

Sample Use Guides

In Vivo Use Guide

The repeated oral administration of nafenopin, a hypolipidaemic compound, at a dose of 100 mg/kg to male C57BL/6, DBA/2, Balb c and C3H mice caused an increase in the specific activity of liver cytosolic epoxide hydrolase, the activity of microsomal epoxide hydrolase was also increased in all except the C3H mice. In the range of 10-200 mg/kg nafenopin the induction of the two hydrolase activities was found to increase with increasing doses of the test compound.

Route of Administration: Oral

In Vitro Use Guide

Nafenopin (Ki 430 uM) was competitive inhibitor of rat peroxisomal palmitoyl-CoA formation suggesting that it binds at the active site and thus potentially functions as alternative substrate for the peroxisomal ligase.

Substance Class	Chemical Created by `admin` on `Fri Dec 15 14:59:27 UTC 2023` Edited by `admin` on `Fri Dec 15 14:59:27 UTC 2023`
Record UNII	093W78U96W
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

NAFENOPIN

Official Name

English

SU-13437

Code

English

PROPANOIC ACID, 2-METHYL-2-(4-(1,2,3,4-TETRAHYDRO-1-NAPHTHALENYL)PHENOXY)-

Common Name

English

NAFENOPIN [IARC]

Common Name

English

2-METHYL-2-(P-(1,2,3,4-TETRAHYDRO-1-NAPHTHYL)PHENOXY)PROPIONIC ACID

Common Name

English

nafenopin [INN]

Common Name

English

NAFENOPIN [USAN]

Common Name

English

Code System Code Type Description

MESH

D009255