Details
| Stereochemistry | ACHIRAL |
| Molecular Formula | C19H20BrN2O4P |
| Molecular Weight | 451.251 |
| Optical Activity | NONE |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
CCOP(=O)(CC1=CC=C(C=C1)C(=O)NC2=C(C=C(Br)C=C2)C#N)OCC
InChI
InChIKey=KPRTURMJVWXURQ-UHFFFAOYSA-N
InChI=1S/C19H20BrN2O4P/c1-3-25-27(24,26-4-2)13-14-5-7-15(8-6-14)19(23)22-18-10-9-17(20)11-16(18)12-21/h5-11H,3-4,13H2,1-2H3,(H,22,23)
| Molecular Formula | C19H20BrN2O4P |
| Molecular Weight | 451.251 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ACHIRAL |
| Additional Stereochemistry | No |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Optical Activity | NONE |
DescriptionCurator's Comment: description was created based on several sources, including
https://www.ncbi.nlm.nih.gov/pubmed/12847564
Curator's Comment: description was created based on several sources, including
https://www.ncbi.nlm.nih.gov/pubmed/12847564
Lipoprotein lipase (LPL) is a rate-limiting enzyme that hydrolyzes circulating triglyceride-rich lipoproteins such as very low-density lipoproteins and chylomicrons. Otsuka Pharmaceutical Factory, Inc. synthesized the LPL activator NO-1886 (ibrolipim, [4-(4-bromo-2-cyano-phenylcarbamoyl)-benzyl]-phosphonic acid diethyl ester, CAS 133208-93-2). NO-1886 increased LPL mRNA and LPL activity in adipose tissue, myocardium and skeletal muscle, resulting in an elevation of postheparin plasma LPL activity and LPL mass. It was discovered, that this agent has a potentially beneficial for the treatment of hypertriglyceridemia, hypo-HDL cholesterolemia, and protection from atherosclerosis. In addition, this agent may be used in the treatment of obesity and obesity-linked health problems in postmenopausal women.
Originator
Approval Year
PubMed
| Title | Date | PubMed |
|---|---|---|
| Effect of lipoprotein lipase activators bezafibrate and NO-1886, on B16 melanoma-induced cachexia in mice. | 1999 Sep-Oct |
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| [Lipid-lowering drugs]. | 2001 Dec |
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| Effects of the lipoprotein lipase activator NO-1886 as a suppressor agent of atherosclerosis in aorta of mild diabetic rabbits. | 2002 |
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| A lipoprotein lipase activator, NO-1886 prevents impaired endothelium-dependent relaxation of aorta caused by exercise in aged rats. | 2002 Jul |
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| Correlation between lipid and glycogen contents in liver and insulin resistance in high-fat-fed rats treated with the lipoprotein lipase activator NO-1886. | 2002 Jun |
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| Phosphonate O-deethylation of [4-(4-bromo-2-cyano-phenylcarbamoyl) benzyl]-phosphonic acid diethyl ester, a lipoprotein lipase-promoting agent, catalyzed by cytochrome P450 2C8 and 3A4 in human liver microsomes. | 2002 Mar |
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| Pharmacokinetics and metabolism of NO-1886, a lipoprotein lipase-promoting agent, in cynomolgus monkey. | 2003 Dec |
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| Lipoprotein lipase activator NO-1886 (ibrolipim) accelerates the mRNA expression of fatty acid oxidation-related enzymes in rat liver. | 2003 Dec |
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| A lipoprotein lipase-promoting agent, NO-1886, improves glucose and lipid metabolism in high fat, high sucrose-fed New Zealand white rabbits. | 2003 Jan-Mar |
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| Lipoprotein lipase and atherosclerosis. | 2003 Mar |
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| Lipoprotein lipase activator NO-1886. | 2003 Summer |
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| Lipoprotein lipase activator NO-1886 improves fatty liver caused by high-fat feeding in streptozotocin-induced diabetic rats. | 2004 Feb |
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| NO-1886 inhibits size of adipocytes, suppresses plasma levels of tumor necrosis factor-alpha and free fatty acids, improves glucose metabolism in high-fat/high-sucrose-fed miniature pigs. | 2004 Mar |
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| Concomitant suppression of hyperlipidemia and intestinal polyp formation by increasing lipoprotein lipase activity in Apc-deficient mice. | 2006 Apr |
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| Uncoupling proteins, dietary fat and the metabolic syndrome. | 2006 Sep 12 |
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| Lipoprotein lipase activator ameliorates the severity of dietary steatohepatitis. | 2007 Apr 27 |
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| NO-1886, a lipoprotein lipase activator, attenuates vascular smooth muscle contraction in rat aorta. | 2007 Jan 12 |
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| NO-1886, a lipoprotein lipase activator, attenuates contraction of rat intestinal ring preparations. | 2008 Feb |
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| Evaluation of induction potency of new drug candidates on CYP1A2 and CYP3A4 using real-time one-step RT-PCR in primary cultures of cryopreserved human hepatocytes. | 2009 |
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| Pharmacological approaches to modifying HDL: more basic science to understand HDL metabolism is necessary. Editorial to: "NO-1886 up-regulates Niemann-Pick C1 protein (NPC1) expression through liver X receptor alpha signaling pathway in THP-1 macrophage-derived foam cells" by Xin Ma et al. | 2009 Jun |
|
| NO-1886 up-regulates Niemann-Pick C1 protein (NPC1) expression through liver X receptor alpha signaling pathway in THP-1 macrophage-derived foam cells. | 2009 Jun |
|
| NO-1886 suppresses diet-induced insulin resistance and cholesterol accumulation through STAT5-dependent upregulation of IGF1 and CYP7A1. | 2010 Jan |
|
| Ibrolipim increases ABCA1/G1 expression by the LXRα signaling pathway in THP-1 macrophage-derived foam cells. | 2010 Oct |
Patents
Sample Use Guides
for rats: 100 mg/kg. The animals were fed the high-fat chow for 8 weeks
Route of Administration:
Oral
NO-1886 (ibrolipim) stimulated glucose consumption, glycogen synthesis and free fatty acids (FFA) absorption in insulin-resistant HepG2 cells. Maximum stimulation effects were observed with 10 µm NO-1886 for 24 h. Compared with the dimethyl sulfoxide-treated group, 2.5 µm NO-1886 or higher could induce the mRNA expression of lipoprotein lipase. Meanwhile, NO-1886 increased the protein content of P-GSK-3βser(9) and decreased the protein level of GSK-3β in insulin-resistant HepG2 cells, but NO-1886 didn't change the protein levels of PI3-Kp85 and Akt2.
| Substance Class |
Chemical
Created
by
admin
on
Edited
Fri Dec 15 16:37:25 GMT 2023
by
admin
on
Fri Dec 15 16:37:25 GMT 2023
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| Record UNII |
07H1561618
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| Record Status |
Validated (UNII)
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| Record Version |
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C29703
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8255
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IBROLIPIM
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07H1561618
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CHEMBL34234
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C75256
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300000034136
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131601
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DTXSID20157989
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133208-93-2
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NN-01
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| Related Record | Type | Details | ||
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TARGET -> ACTIVATOR |
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ACTIVE MOIETY |
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