Ibrolipim | CAS#133208-93-2 | activator

MedKoo Cat#: 584862 | Name: Ibrolipim

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Description:

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

Ibrolipim increases lipoprotein lipase activity with resulting elevation of high density lipoprotein cholesterol.

Chemical Structure

Ibrolipim

CAS#133208-93-2

Theoretical Analysis

MedKoo Cat#: 584862

Name: Ibrolipim

CAS#: 133208-93-2

Chemical Formula: C19H20BrN2O4P

Exact Mass: 450.0344

Molecular Weight: 451.26

Elemental Analysis: C, 50.57; H, 4.47; Br, 17.71; N, 6.21; O, 14.18; P, 6.86

Price and Availability

Size	Price	Availability
10mg	USD 250.00	2 Weeks
25mg	USD 450.00	2 Weeks
50mg	USD 750.00	2 Weeks

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Related CAS #

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Synonym

Ibrolipim; NO-1886; OPF 009

IUPAC/Chemical Name

Diethyl (4-((4-bromo-2-cyanophenyl)carbamoyl)benzyl)phosphonate

InChi Key

KPRTURMJVWXURQ-UHFFFAOYSA-N

InChi Code

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)

SMILES Code

O=C(C1=CC=C(C=C1)CP(OCC)(OCC)=O)NC2=CC=C(Br)C=C2C#N

Appearance

Solid powder

Purity

>97% (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

Shelf Life

>3 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).

HS Tariff Code

2934.99.9001

More Info

Product Data

Product Data

Instruction

View handling instruction

Biological target:

Ibrolipim (NO-1886) is an orally active lipoprotein lipase (LPL)-promoting agent. Ibrolipim decreases plasma triglycerides, increases high-density lipoprotein cholesterol levels.

In vitro activity:

Consistent with apoA-I, ibrolipim treatment also induced a significant increase of cholesterol efflux from foam cells to HDL in a dose- and time-dependent manner (Figure 1H and 1I). For directly measuring the cellular cholesterol content, ibrolipim-treated foam cells also showed a decrease compared with the control (HDL only, Table 3). Reference: Acta Pharmacol Sin. 2010 Oct;31(10):1343-9. https://pubmed.ncbi.nlm.nih.gov/20871621/

In vivo activity:

Immunohistochemistry analysis exhibited that Nox-4 was overexpressed in renal glomeruli, proximal tubules and distal convoluted tubules (brown staining) of the HSFD-fed minipigs compared to the CD-fed minipigs (Fig. 5). In contrast, these increases were obviously attenuated by Ibrolipim treatment (Fig. 4, Fig. 5 and Table 3). These results suggested that Ibrolipim effectively inhibited HSFD-stimulated Nox-4 activation and expression. Reference: Biomed Pharmacother. 2020 Sep;129:110321. https://pubmed.ncbi.nlm.nih.gov/32535382/

	Solvent	mg/mL	mM
Solubility
	DMF	25.0	55.40
	DMF:PBS (pH 7.2) (1:1)	0.5	1.11
	DMSO	80.0	177.28
	Ethanol	6.5	14.40

Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 451.26 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Concentration / Solvent Volume / Mass	1 mg	5 mg	10 mg
1 mM	1.15 mL	5.76 mL	11.51 mL
5 mM	0.23 mL	1.15 mL	2.3 mL
10 mM	0.12 mL	0.58 mL	1.15 mL
50 mM	0.02 mL	0.12 mL	0.23 mL

Formulation protocol:

1. Chen SG, Xiao J, Liu XH, Liu MM, Mo ZC, Yin K, Zhao GJ, Jiang J, Cui LB, Tan CZ, Yin WD, Tang CK. Ibrolipim increases ABCA1/G1 expression by the LXRα signaling pathway in THP-1 macrophage-derived foam cells. Acta Pharmacol Sin. 2010 Oct;31(10):1343-9. doi: 10.1038/aps.2010.166. Epub 2010 Sep 27. PMID: 20871621; PMCID: PMC4012897. 2. Nishimura M, Imai T, Morioka Y, Kuribayashi S, Kamataki T, Naito S. Effects of NO-1886 (Ibrolipim), a lipoprotein lipase-promoting agent, on gene induction of cytochrome P450s, carboxylesterases, and sulfotransferases in primary cultures of human hepatocytes. Drug Metab Pharmacokinet. 2004 Dec;19(6):422-9. doi: 10.2133/dmpk.19.422. PMID: 15681896. 3. Liu Y, Li H, Wang S, Yin W, Wang Z. Ibrolipim attenuates early-stage nephropathy in diet-induced diabetic minipigs: Focus on oxidative stress and fibrogenesis. Biomed Pharmacother. 2020 Sep;129:110321. doi: 10.1016/j.biopha.2020.110321. Epub 2020 Jun 12. PMID: 32535382. 4. Liu Y, Wang ZB, Yin WD, Li QK, Cai MB, Yu J, Li HG, Zhang C, Zu XH. Preventive effect of Ibrolipim on suppressing lipid accumulation and increasing lipoprotein lipase in the kidneys of diet-induced diabetic minipigs. Lipids Health Dis. 2011 Jul 16;10:117. doi: 10.1186/1476-511X-10-117. PMID: 21762526; PMCID: PMC3155903.

In vitro protocol:

In vivo protocol:

1. Liu Y, Li H, Wang S, Yin W, Wang Z. Ibrolipim attenuates early-stage nephropathy in diet-induced diabetic minipigs: Focus on oxidative stress and fibrogenesis. Biomed Pharmacother. 2020 Sep;129:110321. doi: 10.1016/j.biopha.2020.110321. Epub 2020 Jun 12. PMID: 32535382. 2. Liu Y, Wang ZB, Yin WD, Li QK, Cai MB, Yu J, Li HG, Zhang C, Zu XH. Preventive effect of Ibrolipim on suppressing lipid accumulation and increasing lipoprotein lipase in the kidneys of diet-induced diabetic minipigs. Lipids Health Dis. 2011 Jul 16;10:117. doi: 10.1186/1476-511X-10-117. PMID: 21762526; PMCID: PMC3155903.

1: Nishimura M, Imai T, Morioka Y, Kuribayashi S, Kamataki T, Naito S. Effects of NO-1886 (Ibrolipim), a lipoprotein lipase-promoting agent, on gene induction of cytochrome P450s, carboxylesterases, and sulfotransferases in primary cultures of human hepatocytes. Drug Metab Pharmacokinet. 2004 Dec;19(6):422-9. PubMed PMID: 15681896. 2: Kano S, Doi M. NO-1886 (ibrolipim), a lipoprotein lipase-promoting agent, accelerates the expression of UCP3 messenger RNA and ameliorates obesity in ovariectomized rats. Metabolism. 2006 Feb;55(2):151-8. PubMed PMID: 16423620. 3: Tsutsumi K, Inoue Y, Murase T. Effects of NO-1886, a lipoprotein lipase promoting agent, on homozygous and heterozygous Watanabe heritable hyperlipidaemic rabbits. Arzneimittelforschung. 2000 Feb;50(2):118-21. PubMed PMID: 10719613. 4: Liu Y, Wang ZB, Yin WD, Li QK, Cai MB, Yu J, Li HG, Zhang C, Zu XH. Preventive effect of Ibrolipim on suppressing lipid accumulation and increasing lipoprotein lipase in the kidneys of diet-induced diabetic minipigs. Lipids Health Dis. 2011 Jul 16;10:117. doi: 10.1186/1476-511X-10-117. PubMed PMID: 21762526; PubMed Central PMCID: PMC3155903. 5: Doi M, Kondo Y, Tsutsumi K. Lipoprotein lipase activator NO-1886 (ibrolipim) accelerates the mRNA expression of fatty acid oxidation-related enzymes in rat liver. Metabolism. 2003 Dec;52(12):1547-50. PubMed PMID: 14669153. 6: Zhang C, Yin W, Liao D, Huang L, Tang C, Tsutsumi K, Wang Z, Liu Y, Li Q, Hou H, Cai M, Xiao J. NO-1886 upregulates ATP binding cassette transporter A1 and inhibits diet-induced atherosclerosis in Chinese Bama minipigs. J Lipid Res. 2006 Sep;47(9):2055-63. Epub 2006 Jun 28. PubMed PMID: 16807312. 7: Wang ZB, Zeng HC, Wei HS, Yi GH, Yu J, Wang YT, Zhang YL, Yin WD. NO-1886 ameliorates glycogen metabolism in insulin-resistant HepG2 cells by GSK-3β signalling. J Pharm Pharmacol. 2012 Feb;64(2):293-301. doi: 10.1111/j.2042-7158.2011.01402.x. Epub 2011 Nov 21. PubMed PMID: 22221106. 8: Li Q, Yin W, Cai M, Liu Y, Hou H, Shen Q, Zhang C, Xiao J, Hu X, Wu Q, Funaki M, Nakaya Y. NO-1886 suppresses diet-induced insulin resistance and cholesterol accumulation through STAT5-dependent upregulation of IGF1 and CYP7A1. J Endocrinol. 2010 Jan;204(1):47-56. doi: 10.1677/JOE-09-0278. Epub 2009 Oct 8. PubMed PMID: 19815588. 9: Geldenhuys WJ, Aring D, Sadana P. A novel Lipoprotein lipase (LPL) agonist rescues the enzyme from inhibition by angiopoietin-like 4 (ANGPTL4). Bioorg Med Chem Lett. 2014 May 1;24(9):2163-7. doi: 10.1016/j.bmcl.2014.03.021. Epub 2014 Mar 18. PubMed PMID: 24703657. 10: Wu Q, Harada N, Nakamura A, Yoshida M, Mawatari K, Hattori A, Li Q, Shimohata T, Yinhua, Lian X, Nakano M, Hosaka T, Takahashi A, Nakaya Y. NO-1886, a lipoprotein lipase activator, attenuates contraction of rat intestinal ring preparations. J Med Invest. 2008 Feb;55(1-2):61-70. PubMed PMID: 18319547. 11: Yin W, Tsutsumi K, Yuan Z, Yang B. Effects of the lipoprotein lipase activator NO-1886 as a suppressor agent of atherosclerosis in aorta of mild diabetic rabbits. Arzneimittelforschung. 2002;52(8):610-4. PubMed PMID: 12236049. 12: Morioka Y, Nishimura M, Imai T, Suzuki S, Harada M, Satoh T, Naito S. Assessment of induction of cytochrome P450 by NO-1886 (ibrolipim), a lipoprotein lipase-promoting agent, in primary cultures of human hepatocytes and in female rat liver. Drug Metab Pharmacokinet. 2006 Feb;21(1):19-28. PubMed PMID: 16547390. 13: Yin W, Yuan Z, Tsutsumi K, Xie Y, Zhang Q, Wang Z, Fu G, Long G, Yang Y. A lipoprotein lipase-promoting agent, NO-1886, improves glucose and lipid metabolism in high fat, high sucrose-fed New Zealand white rabbits. Int J Exp Diabesity Res. 2003 Jan-Mar;4(1):27-34. PubMed PMID: 12745668; PubMed Central PMCID: PMC2480496. 14: Shimono K, Tsutsumi K, Yaguchi H, Omura M, Sasano H, Nishikawa T. Lipoprotein lipase promoting agent, NO-1886, modulates adrenal functions: species difference in effects of NO-1886 on steroidogenesis. Steroids. 1999 Jul;64(7):453-9. PubMed PMID: 10443901. 15: Cai M, Yin W, Li Q, Liao D, Tsutsumi K, Hou H, Liu Y, Zhang C, Li J, Wang Z, Xiao J. Effects of NO-1886 on inflammation-associated cytokines in high-fat/high-sucrose/high-cholesterol diet-fed miniature pigs. Eur J Pharmacol. 2006 Jul 1;540(1-3):139-46. Epub 2006 Apr 30. PubMed PMID: 16730700. 16: Kusunoki M, Tsutsumi K, Iwata K, Yin W, Nakamura T, Ogawa H, Nomura T, Mizutani K, Futenma A, Utsumi K, Miyata T. NO-1886 (ibrolipim), a lipoprotein lipase activator, increases the expression of uncoupling protein 3 in skeletal muscle and suppresses fat accumulation in high-fat diet-induced obesity in rats. Metabolism. 2005 Dec;54(12):1587-92. PubMed PMID: 16311090. 17: Kawamura I, Yamamoto N, Sakai F, Yamazaki H, Goto T. Effect of lipoprotein lipase activators bezafibrate and NO-1886, on B16 melanoma-induced cachexia in mice. Anticancer Res. 1999 Sep-Oct;19(5B):4099-103. PubMed PMID: 10628360. 18: Hagi A, Hirai I, Kohri H, Tsutsumi K. The novel compound NO-1886 activates lipoprotein lipase in primary cultured adipose and skeletal muscle cells. Biol Pharm Bull. 1997 Oct;20(10):1108-10. PubMed PMID: 9353574. 19: Morioka Y, Harada M, Imai T, Naito S. Pharmacokinetics and metabolism of NO-1886, a lipoprotein lipase-promoting agent, in cynomolgus monkey. Xenobiotica. 2003 Dec;33(12):1247-60. PubMed PMID: 14742146. 20: Niho N, Mutoh M, Takahashi M, Tsutsumi K, Sugimura T, Wakabayashi K. Concurrent suppression of hyperlipidemia and intestinal polyp formation by NO-1886, increasing lipoprotein lipase activity in Min mice. Proc Natl Acad Sci U S A. 2005 Feb 22;102(8):2970-4. Epub 2005 Feb 14. PubMed PMID: 15710887; PubMed Central PMCID: PMC549478.