(2R,3R)-2,3-bis(benzoyloxy)butanedioic acid 3-ethyl 5-methyl (4R)-2-[(2-aminoethoxy)methyl]-4-(2-chlorophenyl)-6-methyl-1,4-dihydropyridine-3,5-dicarboxylate

• ChemBase ID: 160556
• Molecular Formular: C38H39ClN2O13
• Molecular Mass: 767.17486
• Monoisotopic Mass: 766.214067
• SMILES: N1C(=C([C@H](C(=C1COCCN)C(=O)OCC)c1ccccc1Cl)C(=O)OC)C.[C@H]([C@@H](OC(=O)c1ccccc1)C(=O)O)(OC(=O)c1ccccc1)C(=O)O
• Canonical SMILES: OC(=O)[C@@H]([C@H](C(=O)O)OC(=O)c1ccccc1)OC(=O)c1ccccc1.NCCOCC1=C(C(=O)OCC)[C@@H](C(=C(N1)C)C(=O)OC)c1ccccc1Cl
• InChI: InChI=1S/C20H25ClN2O5.C18H14O8/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;19-15(20)13(25-17(23)11-7-3-1-4-8-11)14(16(21)22)26-18(24)12-9-5-2-6-10-12/h5-8,17,23H,4,9-11,22H2,1-3H3;1-10,13-14H,(H,19,20)(H,21,22)/t17-;13-,14-/m11/s1
• InChIKey: HGESXLUHWHUOLN-YVGNGXOTSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2R,3R)-2,3-bis(benzoyloxy)butanedioic acid 3-ethyl 5-methyl (4R)-2-[(2-aminoethoxy)methyl]-4-(2-chlorophenyl)-6-methyl-1,4-dihydropyridine-3,5-dicarboxylate
• IUPAC Traditional name: (2R,3R)-2,3-bis(benzoyloxy)butanedioic acid; (R)-amlodipine
• Synonyms: (4R)-2-[(2-Aminoethoxy)methyl]-4-(2-chlorophenyl)-1,4-dihydro-6-methyl-3,5-pyridinedicarboxylic Acid 3-Ethyl 5-Methyl Ester Hemi-dibenzoyl-L-tartrate; (+)-Amlodipine Hemi-dibenzoyl-L-tartrate; (R)-(+)-Amlodipine Hemi-dibenzoyl-L-tartrate; d-Amlodipine Hemi-dibenzoyl-L-tartrate; (R)-Amlodipine Hemi-dibenzoyl-L-tartrate

Database IDs

• PubChem SID: 162254691
• PubChem CID: 71313379

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: 19
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: Methanol
• Apperance: Off-White Solid

DETAILS

Toronto Research Chemicals - A633505

(R)-Enantiomer of Amlodipine. 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)