ethanol 2-[benzyl(phenyl)amino]ethyl 5-(5,5-dimethyl-2-oxo-1,3,2λ5-dioxaphosphinan-2-yl)-2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3-carboxylate hydrochloride

• ChemBase ID: 154222
• Molecular Formular: C36H45ClN3O8P
• Molecular Mass: 714.184561
• Monoisotopic Mass: 713.26327973
• SMILES: CCO.CC1=C(C(C(=C(N1)C)P1(=O)OCC(CO1)(C)C)c1cccc(c1)[N+](=O)[O-])C(=O)OCCN(Cc1ccccc1)c1ccccc1.Cl
• Canonical SMILES: CC1=C(C(=O)OCCN(c2ccccc2)Cc2ccccc2)C(C(=C(N1)C)P1(=O)OCC(CO1)(C)C)c1cccc(c1)[N+](=O)[O-].CCO.Cl
• InChI: InChI=1S/C34H38N3O7P.C2H6O.ClH/c1-24-30(33(38)42-19-18-36(28-15-9-6-10-16-28)21-26-12-7-5-8-13-26)31(27-14-11-17-29(20-27)37(39)40)32(25(2)35-24)45(41)43-22-34(3,4)23-44-45;1-2-3;/h5-17,20,31,35H,18-19,21-23H2,1-4H3;3H,2H2,1H3;1H
• InChIKey: IKBJGZQVVVXCEQ-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: ethanol 2-[benzyl(phenyl)amino]ethyl 5-(5,5-dimethyl-2-oxo-1,3,2λ^5-dioxaphosphinan-2-yl)-2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3-carboxylate hydrochloride
• IUPAC Traditional name: efonidipine ethyl alcohol hydrochloride
• Synonyms: Efonidipine hydrochloride monoethanolate

Database IDs

• MDL Number: MFCD00875717
• PubChem SID: 162248361
• PubChem CID: 163838

CALCULATED PROPERTIES

• H Acceptors: 6
• H Donor: 1
• LogD (pH = 5.5): 5.434907
• LogD (pH = 7.4): 5.443263
• Log P: 5.4433703
• Molar Refractivity: 176.4043 cm^3
• Polarizability: 66.61665 Å^3
• Polar Surface Area: 122.92 Å^2
• Rotatable Bonds: 11
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: DMSO: >5 mg/mL; H2O: insoluble
• Apperance: pale yellow powder

Safety Information

• Storage Condition: desiccated
• German water hazard class: 1
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: 2-8°C

Product Information

• Purity: ≥98% (HPLC)
• Empirical Formula (Hill Notation): C34H38N3O7P · HCl · C2H5OH

DETAILS

Sigma Aldrich - E0159

Biochem/physiol Actions
Racemic efonidipine has both L-type and T-type calcium channel blocking activity. The R(-)-isomer appears to be very selective for T-type calcium channel. The S(+)-isomer inhibits the expressed Ca(V)1.2, Ca(V)1.3 and Ca(V)3.1 channel currents almost equally.1