3-ethyl 5-methyl (4S)-2-[(2-aminoethoxy)methyl]-4-(2-chlorophenyl)-6-methyl-1,4-dihydropyridine-3,5-dicarboxylate

• ChemBase ID: 160551
• Molecular Formular: C20H25ClN2O5
• Molecular Mass: 408.8759
• Monoisotopic Mass: 408.14519959
• SMILES: N1C(=C([C@@H](C(=C1COCCN)C(=O)OCC)c1ccccc1Cl)C(=O)OC)C
• Canonical SMILES: NCCOCC1=C(C(=O)OCC)[C@H](C(=C(N1)C)C(=O)OC)c1ccccc1Cl
• InChI: InChI=1S/C20H25ClN2O5/c1-4-28-20(25)18-15(11-27-10-9-22)23-12(2)16(19(24)26-3)17(18)13-7-5-6-8-14(13)21/h5-8,17,23H,4,9-11,22H2,1-3H3/t17-/m0/s1
• InChIKey: HTIQEAQVCYTUBX-KRWDZBQOSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 3-ethyl 5-methyl (4S)-2-[(2-aminoethoxy)methyl]-4-(2-chlorophenyl)-6-methyl-1,4-dihydropyridine-3,5-dicarboxylate
• IUPAC Traditional name: amlodipine besylate
• Synonyms: (4S)-2-[(2-Aminoethoxy)methyl]-4-(2-chlorophenyl)-1,4-dihydro-6-methyl-3,5-pyridinedicarboxylic Acid 3-Ethyl 5-Methyl Ester; (-)-Amlodipine; (R)-(-)-Amlodipine; Levamlodipine; Levoamlodipine; Lodien; l-Amlodipine; (S)-Amlodipine

Database IDs

• CAS Number: 103129-82-4
• PubChem SID: 162254686
• PubChem CID: 9822750

CALCULATED PROPERTIES

• H Acceptors: 5
• H Donor: 2
• LogD (pH = 5.5): -1.366646
• LogD (pH = 7.4): -0.37164375
• Log P: 1.6355954
• Molar Refractivity: 108.6381 cm^3
• Polarizability: 41.695133 Å^3
• Polar Surface Area: 99.88 Å^2
• Rotatable Bonds: 10
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Chloroform; Methanol
• Apperance: White to Off-White Solid
• Melting Point: 102-104°C

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - A633491

(S)-Enantiomer of Amlodipine (A633495). A dihydropyridine calcium channel blocker; activity resides mainly in the (-)-isomer.

REFERENCES

• Arrowsmith, J.E., et al.: J. Med. Chem., 29, 1696 (1986)
• Burges, R.A., et al.: J. Cardiovasc. Pharmacol., 9, 110 (1986)
• Haria, M., et al.: Drugs, 50, 560 (1986)