2,6-dimethyl-3,5-bis(2/'-propoxyethoxycarbonyl)-4-(2/'/'-difluoromethoxyphenyl)-1,4-dihydropyridine


CAS No. : 118790-71-9

2,6-dimethyl-3,5-bis(2/
Product Details
For research use only. Not Intended for Therapeutic Use!
Cat No:M029332
Synonyms:2,6-dimethyl-3,5-bis(2/'-propoxyethoxycarbonyl)-4-(2/'/'-difluoromethoxyphenyl)-1,4-dihydropyridine
Molecular Formula:C26H35F2NO7
Molecular Weight:511.563
Target:Calcium Channel Antagonist
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Appearance:Solid powder
Purity: > 98%
Cat No:M029332
Cas No:118790-71-9
Product-Name:2,6-dimethyl-3,5-bis(2/'-propoxyethoxycarbonyl)-4-(2/'/'-difluoromethoxyphenyl)-1,4-dihydropyridine
IUPAC Name:bis(2-propoxyethyl) 4-[2-(difluoromethoxy)phenyl]-2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate
InChI:InChI=1S/C26H35F2NO7/c1-5-11-32-13-15-34-24(30)21-17(3)29-18(4)22(25(31)35-16-14-33-12-6-2)23(21)19-9-7-8-10-20(19)36-26(27)28/h7-10,23,26,29H,5-6,11-16H2,1-4H3
InChIKey:ASCWBYZMMHUZMQ-UHFFFAOYSA-N
SMILES:CCCOCCOC(=O)C1=C(NC(=C(C1C2=CC=CC=C2OC(F)F)C(=O)OCCOCCC)C)C
Cerebrocrast, also known as IOS-11212, is a calcium channel antagonist potentially for the treatment of cerebral vasospasm and cognition disorder. As Cerebrocrast decreased glucose levels in normal and streptozotocin (STZ)-induced diabetic rats, it also promoted glucose uptake by the brain, intensified insulin action and formation de novo of insulin receptors. Cerebrocrast did not alter current kinetics in either investigated channel, and the inhibition of calcium current was partly reversible or irreversible. As Cerebrocrast inhibited L- and T-type calcium channels, it can prevent vasoconstriction of kidney arterioles and aldosterone secretion that have significant roles in the development of hypertension and diabetic nephropathy.

1: Leonova E, Sokolovska J, Boucher JL, Isajevs S, Rostoka E, Baumane L, Sjakste T, Sjakste N. New 1,4-Dihydropyridines Down-regulate Nitric Oxide in Animals with Streptozotocin-induced Diabetes Mellitus and Protect Deoxyribonucleic Acid against Peroxynitrite Action. Basic Clin Pharmacol Toxicol. 2016 Jul;119(1):19-31. doi: 10.1111/bcpt.12542. Epub 2016 Jan 25. PubMed PMID: 26663724.
2: Garaliene V, Barsys V, Giedraitis S, Benetis R, Krauze A. The role of external Ca²⁺ in the action of Ca²⁺-channel agonists and antagonists on isolated human thoracic arteries. J Physiol Pharmacol. 2014 Feb;65(1):35-1. PubMed PMID: 24622828.
3: Rumaks J, Pupure J, Svirskis S, Isajevs S, Duburs G, Kalvinsh I, Klusa V. Search for stroke-protecting agents in endothelin-1-induced ischemic stroke model in rats. Medicina (Kaunas). 2012;48(10):525-31. PubMed PMID: 23324249.
4: Garaliene V, Barsys V, Jakuška P, Benetis R. Action of calcium antagonists and agonists on isolated human thoracic arteries used for coronary artery bypass grafting. Pharmacol Rep. 2012;64(3):733-8. PubMed PMID: 22814026.
5: Garaliene V, Barsys V, Jakuska P, Krauze A, Duburs G. Effects of calcium antagonists and agonists on isolated human v. saphena magna used for coronary artery bypass grafting and guinea pig/'s papillary muscle. Arzneimittelforschung. 2011;61(7):386-92. doi: 10.1055/s-0031-1296216. PubMed PMID: 21899206.
6: Lovaković T, Poljak-Blazi M, Duburs G, Cipak A, Cindrić M, Vigante B, Bisenieks E, Jaganjac M, Mrakovcić L, Dedić A, Zarković N. Growth modulation of human cells in vitro by mild oxidative stress and 1,4-dihydropyridine derivative antioxidants. Coll Antropol. 2011 Mar;35(1):137-41. PubMed PMID: 21661362.
7: Drígelová M, Tarabová B, Duburs G, Lacinová L. The dihydropyridine analogue cerebrocrast blocks both T-type and L-type calcium currents. Can J Physiol Pharmacol. 2009 Nov;87(11):923-32. doi: 10.1139/y09-086. PubMed PMID: 19935900.
8: Briede J, Stivrina M, Stoldere D, Vigante B, Duburs G. Effect of cerebrocrast on body and organ weights, food and water intake, and urine output of normal rats. Cell Biochem Funct. 2008 Dec;26(8):908-15. doi: 10.1002/cbf.1525. PubMed PMID: 19039818.
9: Pupure J, Isajevs S, Gordjushina V, Taivans I, Rumaks J, Svirskis S, Kratovska A, Dzirkale Z, Pilipenko J, Duburs G, Klusa V. Distinct influence of atypical 1,4-dihydropyridine compounds in azidothymidine-induced neuro- and cardiotoxicity in mice ex vivo. Basic Clin Pharmacol Toxicol. 2008 Nov;103(5):401-6. doi: 10.1111/j.1742-7843.2008.00221.x. Epub 2008 Sep 17. PubMed PMID: 18801031.
10: Fernandes MA, Pereira SP, Jurado AS, Custódio JB, Santos MS, Moreno AJ, Duburs G, Vicente JA. Comparative effects of three 1,4-dihydropyridine derivatives [OSI-1210, OSI-1211 (etaftoron), and OSI-3802] on rat liver mitochondrial bioenergetics and on the physical properties of membrane lipid bilayers: relevance to the length of the alkoxyl chain in positions 3 and 5 of the DHP ring. Chem Biol Interact. 2008 Jun 17;173(3):195-204. doi: 10.1016/j.cbi.2008.03.001. Epub 2008 Mar 15. PubMed PMID: 18452904.
11: Briede J, Stivrina M, Vigante B, Stoldere D, Duburs G. Acute effect of antidiabetic 1,4-dihydropyridine compound cerebrocrast on cardiac function and glucose metabolism in the isolated, perfused normal rat heart. Cell Biochem Funct. 2008 Mar-Apr;26(2):238-45. PubMed PMID: 17990288.
12: Klusa V, Klimaviciusa L, Duburs G, Poikans J, Zharkovsky A. Anti-neurotoxic effects of tauropyrone, a taurine analogue. Adv Exp Med Biol. 2006;583:499-508. PubMed PMID: 17153637.
13: Briede J, Stivrina M, Stoldere Dz, Vigante B, Duburs G. Effect of cerebrocrast, a new long-acting compound on blood glucose and insulin levels in rats when administered before and after STZ-induced diabetes mellitus. Cell Biochem Funct. 2007 Nov-Dec;25(6):673-80. PubMed PMID: 16986170.
14: Vaitkuviene A, Ulinskaite A, Meskys R, Duburs G, Klusa V, Liutkevicius E. Study of the interaction of 1,4-dihydropyridine derivatives with glucocorticoid hormone receptors from the rat liver. Pharmacol Rep. 2006 Jul-Aug;58(4):551-8. PubMed PMID: 16963802.
15: Klimaviciusa L, Klusa V, Duburs G, Kaasik A, Kalda A, Zharkovsky A. Distinct effects of atypical 1,4-dihydropyridines on 1-methyl-4-phenylpyridinium-induced toxicity. Cell Biochem Funct. 2007 Jan-Feb;25(1):15-21. PubMed PMID: 16927412.
16: Briede J, Duburs G. Protective effect of cerebrocrast on rat brain ischaemia induced by occlusion of both common carotid arteries. Cell Biochem Funct. 2007 Mar-Apr;25(2):203-10. PubMed PMID: 16444767.
17: Fernandes MA, Santos MS, Vicente JA, Moreno AJ, Velena A, Duburs G, Oliveira CR. Effects of 1,4-dihydropyridine derivatives (cerebrocrast, gammapyrone, glutapyrone, and diethone) on mitochondrial bioenergetics and oxidative stress: a comparative study. Mitochondrion. 2003 Aug;3(1):47-59. PubMed PMID: 16120344.
18: Fernandes MA, Jurado AS, Videira RA, Santos MS, Moreno AJ, Velena A, Duburs G, Oliveira CR, Vicente JA. Cerebrocrast promotes the cotransport of H+ and Cl- in rat liver mitochondria. Mitochondrion. 2005 Oct;5(5):341-51. PubMed PMID: 16099223.
19: Briede J, Stivriņa M, Stoldere D, Bisenieks E, Uldriķis J, Poikāns J, Makarova N, Duburs G. Effect of new and known 1,4-dihydropyridine derivatives on blood glucose levels in normal and streptozotocin-induced diabetic rats. Cell Biochem Funct. 2004 Jul-Aug;22(4):219-24. PubMed PMID: 15248181.
20: Klegeris A, Liutkevicius E, Mikalauskiene G, Duburs G, McGeer PL, Klusa V. Anti-inflammatory effects of cerebrocrast in a model of rat paw edema and on mononuclear THP-1 cells. Eur J Pharmacol. 2002 Apr 26;441(3):203-8. PubMed PMID: 12063093.
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