| Identification | Back Directory | [Name]
EFONIDIPINE | [CAS]
111011-63-3 | [Synonyms]
EFONIDIPINE
Efonidipine(NZ-105)
EFONIDIPINE FREE BASE
2-(N-benzylanilino)ethyl 5-(5,5-dimethyl-2-oxo-1,3,2λ5-dioxaphosphinan-2-yl)-2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3-carboxylate
2-(N-benzylanilino)ethyl 5-(5,5-dimethyl-2-oxo-1,3,2λ5-dioxaphosphinan-2-yl)-2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3-carboxylate
5,5-Dimethyl-2-[[1,4-dihydro-2,6-dimethyl-4-(3-nitrophenyl)-5-[[2-[phenyl(phenylmethyl)amino]ethoxy]carbonyl]pyridin]-3-yl]-1,3,2-dioxaphosphorinane 2-oxide
5-(5,5-Dimethyl-2-oxo-1,3,2-dioxaphosphorinan-2-yl)-1,4-dihydro-2,6-dimethyl-4-(3-nitrophenyl)-3-pyridinecarboxylic acid 2-[phenyl(phenylmethyl)amino]ethyl ester
3-Pyridinecarboxylic acid, 5-(5,5-dimethyl-2-oxido-1,3,2-dioxaphosphorinan-2-yl)-1,4-dihydro-2,6-dimethyl-4-(3-nitrophenyl)-, 2-[phenyl(phenylmethyl)amino]ethyl ester | [Molecular Formula]
C34H38N3O7P | [MDL Number]
MFCD00865899 | [MOL File]
111011-63-3.mol | [Molecular Weight]
631.66 |
| Chemical Properties | Back Directory | [Melting point ]
169-170℃ | [Boiling point ]
746.9±60.0 °C(Predicted) | [density ]
1.30±0.1 g/cm3(Predicted) | [storage temp. ]
Store at -20°C | [solubility ]
DMF:30.0(Max Conc. mg/mL);47.49(Max Conc. mM)
Ethanol:40.0(Max Conc. mg/mL);63.32(Max Conc. mM) | [form ]
A crystalline solid | [pka]
4.03±0.50(Predicted) | [color ]
Off-white to light yellow |
| Hazard Information | Back Directory | [Uses]
Efonidipine(NZ-105) is a dual T-type and L-type calcium channel blocker (CCB).
IC50 value:
Target: calcium channel blocker
in vitro: Efonidipine and nifedipine, but not other examined CCBs, also increased the N(6), 2'-O-dibutyryladenosine 3',5'-cyclic monophosphate (dbcAMP)-induced StAR mRNA, which reflects the action of adrenocorticotropic hormone, and efonidipine and R(-)-efonidipine enhanced the dbcAMP-induced DHEA-S production in NCI-H295R adrenocortical carcinoma cells [1]. I(Ca(T)) was blocked mainly by a tonic manner by nifedipine, by a use-dependent manner by mibefradil, and by a combination of both manners by efonidipine. IC50s of these Ca2+ channel antagonists to I(Ca(T)) and L-type Ca2+ channel current (I(Ca(L))) were 1.2 micromol/l and 0.14 nmol/l for nifedipine; 0.87 and 1.4 micromol/l for mibefradil, and 0.35 micromol/l and 1.8 nmol/l for efonidipine, respectively [4].
in vivo: Twenty hypertensive patients on chronic hemodialysis were given efonidipine 20-60 mg twice daily and amlodipine 2.5-7.5 mg once daily for 12 weeks each in a random crossover manner. The average blood pressure was comparable between the efonidipine and amlodipine periods (151 + or - 15/77 + or - 8 versus 153 + or - 15/76 + or - 8 mmHg). The pulse rate did not change significantly during the administration periods [2]. In the UM-X7.1 group, EFO treatment significantly attenuated the decrease of LVEF without affecting blood pressure compared with the vehicle group. EFO treatment decreased heart rate (by approximately 10%) in both groups [3]. | [Definition]
ChEBI: 2-[benzyl(phenyl)amino]ethyl 5-(5,5-dimethyl-2-oxido-1,3,2-dioxaphosphinan-2-yl)-2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3-carboxylate is a carboxylic ester resulting from the formal condensation of the carboxy group of 5-(5,5-dimethyl-2-oxido-1,3,2-dioxaphosphinan-2-yl)-2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3-carboxylic acid with the hydroxy group of 2-[benzyl(phenyl)amino]ethanol. It is a C-nitro compound, a carboxylic ester, a tertiary amino compound and a dihydropyridine. | [References]
[1] Ikeda K, et al. Efonidipine, a Ca(2+)-channel blocker, enhances the production of dehydroepiandrosterone sulfate in NCI-H295R human adrenocortical carcinoma cells. Tohoku J Exp Med. 2011;224(4):263-71. DOI:10.1620/tjem.224.263
[2] Nakano N, et al. Effects of efonidipine, an L- and T-type calcium channel blocker, on the renin-angiotensin-aldosterone system in chronic hemodialysis patients. Int Heart J. 2010 May;51(3):188-92. DOI:10.1536/ihj.51.188
[3] Suzuki S, et al. Beneficial effects of the dual L- and T-type Ca2+ channel blocker efonidipine on cardiomyopathic hamsters. Circ J. 2007 Dec;71(12):1970-6. DOI:10.1253/circj.71.1970
[4] Lee TS, et al. Actions of mibefradil, efonidipine and nifedipine block of recombinant T- and L-type Ca channels with distinct inhibitory mechanisms. Pharmacology. 2006;78(1):11-20. DOI:10.1159/000094900 |
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LETOPHARM LIMITED
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www.letopharm.com |
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