Details
Stereochemistry | ACHIRAL |
Molecular Formula | C16H19ClN4O2S |
Molecular Weight | 366.866 |
Optical Activity | NONE |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
CC1=CC=CC(NC2=NC(SCC(=O)NCCO)=NC(Cl)=C2)=C1C
InChI
InChIKey=RZCKTPORLKUFGY-UHFFFAOYSA-N
InChI=1S/C16H19ClN4O2S/c1-10-4-3-5-12(11(10)2)19-14-8-13(17)20-16(21-14)24-9-15(23)18-6-7-22/h3-5,8,22H,6-7,9H2,1-2H3,(H,18,23)(H,19,20,21)
Molecular Formula | C16H19ClN4O2S |
Molecular Weight | 366.866 |
Charge | 0 |
Count |
|
Stereochemistry | ACHIRAL |
Additional Stereochemistry | No |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Optical Activity | NONE |
Pirinixil is an ethanolamine derivative of Wy-14,643 [4-chloro-6-(2,3-xylidino)-2-pyrimidinythio]acetic acid. It is the hypolipidemic agent of low toxicity. It has been reported to increase high density lipoprotein cholesterol levels in experimental animals. Pirinixil increased plasma cholesterol levels significantly without affecting plasma triglycerides. Pirinixil exerted a powerful antilipolytic activity against epinephrine, ACTH, nicotine and cold exposure. It is a potent inducer of liver peroxisones and of mitochondrial carmitine acetyltransferase. Pirinixil was developed treatment of hyperlipidemias and atherosclerosis. Pirinixil can increase generation of ROS, leading to DNA damage and p53 phosphorylation, which, in turn, induces the activation of Bax, release of cytochrome-c from mitochondria and activation of caspases, culminating in rat hepatoma FaO cell death.
Approval Year
PubMed
Title | Date | PubMed |
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Peroxisome proliferation in primary cultures of rat hepatocytes. | 1983 Jan |
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Effect of hypolipidemic peroxisome proliferators on unscheduled DNA synthesis in cultured hepatocytes and on mutagenesis in Salmonella. | 1984 Sep |
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Accelerated regression of carcinogen-induced preneoplastic hepatocyte foci by peroxisome proliferators, BR931, 4-chloro-6-(2,3-xylidino)-2-pyrimidinylthio (N-B-hydroxyethyl)acetamide, and di-(2-ethylhexyl)phthalate. | 1984 Sep |
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Effect of peroxisome proliferator carcinogens on unscheduled DNA synthesis in rat hepatocytes determined by autoradiography. | 1986 Dec |
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Suppression of choline-deficient diet-induced hepatocyte membrane lipid peroxidation in rats by the peroxisome proliferators 4-chloro-6-(2,3-xylidino)-2-pyrimidinylthio(N-beta-hydroxyethyl)- acetamide and di(2-ethylhexyl)phthalate. | 1986 Jul |
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N-imidazolylchroman-4-ones, N-imidazolyl-1-tetralones, and their alcohols as hypolipemic agents raising high-density lipoproteins. | 1986 Mar |
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Suppression of EGF binding in rat liver by the hypolipidemic peroxisome proliferators, 4-chloro-6-(2,3-xylidino)-2-pyrimidinylthio-(N-beta-hydroxyethyl)ac etamide and di(2-ethylhexyl)phthalate. | 1988 Jan |
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Lack of expression of glutathione-S-transferase P, gamma-glutamyl transpeptidase, and alpha-fetoprotein messenger RNAs in liver tumors induced by peroxisome proliferators. | 1988 Sep 1 |
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Differential induction and regulation of peroxisomal enzymes: predictive value of peroxisome proliferation in identifying certain nonmutagenic carcinogens. | 1989 Jan |
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Elevated levels of prostaglandin E2 in the liver of rats fed a choline deficient diet: possible involvement in liver tumor promotion. | 1989 Jul 15 |
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Effect of peroxisome proliferators on intrachromosomal and interchromosomal recombination in yeast. | 1990 Jan |
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Changes in expression of cellular oncogenes and endogenous retrovirus-like sequences during hepatocarcinogenesis induced by a peroxisome proliferator. | 1991 Nov |
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Loss of peroxisomal enzyme expression in preneoplastic and neoplastic lesions induced by peroxisome proliferators in rat livers. | 1992 Feb |
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Differential expression of hepatocyte growth factor, transforming growth factor-alpha and transforming growth factor-beta 1 messenger RNAs in two experimental models of liver cell proliferation. | 1992 Nov |
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Lack of mutations of the p53 tumor suppressor gene in hepatocellular carcinomas induced in rats by a peroxisome proliferator. | 1993 |
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Cyclosporine stimulates hepatocyte proliferation and accelerates development of hepatocellular carcinomas in rats. | 1993 Aug |
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Hepatocyte proliferation induced by a single dose of a peroxisome proliferator. | 1996 Mar |
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Hepatic hyperplasia and cancer in rats: metabolic alterations associated with cell growth. | 1997 Jul |
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Induction of cellular DNA synthesis in the pancreas and kidneys of rats by peroxisome proliferators, 9-cis retinoic acid, and 3,3',5-triiodo-L-thyronine. | 1997 Mar 1 |
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Hepatic hyperplasia and cancer in rats: alterations in copper metabolism. | 1999 Jun |
|
The peroxisome proliferator BR931 kills FaO cells by p53-dependent apoptosis. | 2004 Jun 4 |
Patents
Substance Class |
Chemical
Created
by
admin
on
Edited
Fri Dec 15 15:54:46 GMT 2023
by
admin
on
Fri Dec 15 15:54:46 GMT 2023
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Record UNII |
969LVT6GJ2
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Record Status |
Validated (UNII)
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Record Version |
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Official Name | English | ||
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Common Name | English |
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NCI_THESAURUS |
C29703
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68851
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100000081669
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C66424
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CHEMBL1908320
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DTXSID9020291
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C016908
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65089-17-0
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SUB09916MIG
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Related Record | Type | Details | ||
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ACTIVE MOIETY |