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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
Structure of PIRINIXIL

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)

HIDE SMILES / InChI

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

PubMed

TitleDatePubMed
Peroxisome proliferation in primary cultures of rat hepatocytes.
1983 Jan
Effect of hypolipidemic peroxisome proliferators on unscheduled DNA synthesis in cultured hepatocytes and on mutagenesis in Salmonella.
1984 Sep
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
Effect of peroxisome proliferator carcinogens on unscheduled DNA synthesis in rat hepatocytes determined by autoradiography.
1986 Dec
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
N-imidazolylchroman-4-ones, N-imidazolyl-1-tetralones, and their alcohols as hypolipemic agents raising high-density lipoproteins.
1986 Mar
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
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
Differential induction and regulation of peroxisomal enzymes: predictive value of peroxisome proliferation in identifying certain nonmutagenic carcinogens.
1989 Jan
Elevated levels of prostaglandin E2 in the liver of rats fed a choline deficient diet: possible involvement in liver tumor promotion.
1989 Jul 15
Effect of peroxisome proliferators on intrachromosomal and interchromosomal recombination in yeast.
1990 Jan
Changes in expression of cellular oncogenes and endogenous retrovirus-like sequences during hepatocarcinogenesis induced by a peroxisome proliferator.
1991 Nov
Loss of peroxisomal enzyme expression in preneoplastic and neoplastic lesions induced by peroxisome proliferators in rat livers.
1992 Feb
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
Lack of mutations of the p53 tumor suppressor gene in hepatocellular carcinomas induced in rats by a peroxisome proliferator.
1993
Cyclosporine stimulates hepatocyte proliferation and accelerates development of hepatocellular carcinomas in rats.
1993 Aug
Hepatocyte proliferation induced by a single dose of a peroxisome proliferator.
1996 Mar
Hepatic hyperplasia and cancer in rats: metabolic alterations associated with cell growth.
1997 Jul
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
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

Patents

Substance Class Chemical
Created
by admin
on Fri Dec 15 15:54:46 GMT 2023
Edited
by admin
on Fri Dec 15 15:54:46 GMT 2023
Record UNII
969LVT6GJ2
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
PIRINIXIL
INN  
INN  
Official Name English
pirinixil [INN]
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C29703
Created by admin on Fri Dec 15 15:54:46 GMT 2023 , Edited by admin on Fri Dec 15 15:54:46 GMT 2023
Code System Code Type Description
FDA UNII
969LVT6GJ2
Created by admin on Fri Dec 15 15:54:46 GMT 2023 , Edited by admin on Fri Dec 15 15:54:46 GMT 2023
PRIMARY
PUBCHEM
68851
Created by admin on Fri Dec 15 15:54:46 GMT 2023 , Edited by admin on Fri Dec 15 15:54:46 GMT 2023
PRIMARY
SMS_ID
100000081669
Created by admin on Fri Dec 15 15:54:46 GMT 2023 , Edited by admin on Fri Dec 15 15:54:46 GMT 2023
PRIMARY
NCI_THESAURUS
C66424
Created by admin on Fri Dec 15 15:54:46 GMT 2023 , Edited by admin on Fri Dec 15 15:54:46 GMT 2023
PRIMARY
ChEMBL
CHEMBL1908320
Created by admin on Fri Dec 15 15:54:46 GMT 2023 , Edited by admin on Fri Dec 15 15:54:46 GMT 2023
PRIMARY
EPA CompTox
DTXSID9020291
Created by admin on Fri Dec 15 15:54:46 GMT 2023 , Edited by admin on Fri Dec 15 15:54:46 GMT 2023
PRIMARY
INN
4515
Created by admin on Fri Dec 15 15:54:46 GMT 2023 , Edited by admin on Fri Dec 15 15:54:46 GMT 2023
PRIMARY
MESH
C016908
Created by admin on Fri Dec 15 15:54:46 GMT 2023 , Edited by admin on Fri Dec 15 15:54:46 GMT 2023
PRIMARY
CAS
65089-17-0
Created by admin on Fri Dec 15 15:54:46 GMT 2023 , Edited by admin on Fri Dec 15 15:54:46 GMT 2023
PRIMARY
EVMPD
SUB09916MIG
Created by admin on Fri Dec 15 15:54:46 GMT 2023 , Edited by admin on Fri Dec 15 15:54:46 GMT 2023
PRIMARY
Related Record Type Details
ACTIVE MOIETY