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

• ChemBase ID: 160557
• Molecular Formular: C40H43ClN2O13
• Molecular Mass: 795.22802
• Monoisotopic Mass: 794.24536713
• SMILES: N1C(=C([C@@H](C(=C1COCCN)C(=O)OCC)c1ccccc1Cl)C(=O)OC)C.[C@@H]([C@H](OC(=O)c1ccc(cc1)C)C(=O)O)(OC(=O)c1ccc(cc1)C)C(=O)O
• Canonical SMILES: Cc1ccc(cc1)C(=O)O[C@@H]([C@@H](C(=O)O)OC(=O)c1ccc(cc1)C)C(=O)O.NCCOCC1=C(C(=O)OCC)[C@H](C(=C(N1)C)C(=O)OC)c1ccccc1Cl
• InChI: InChI=1S/C20H25ClN2O5.C20H18O8/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;1-11-3-7-13(8-4-11)19(25)27-15(17(21)22)16(18(23)24)28-20(26)14-9-5-12(2)6-10-14/h5-8,17,23H,4,9-11,22H2,1-3H3;3-10,15-16H,1-2H3,(H,21,22)(H,23,24)/t17-;15-,16-/m00/s1
• InChIKey: DGMFRGMUDAJQAA-CJSNSBGFSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S,3S)-2,3-bis(4-methylbenzoyloxy)butanedioic acid 3-ethyl 5-methyl (4S)-2-[(2-aminoethoxy)methyl]-4-(2-chlorophenyl)-6-methyl-1,4-dihydropyridine-3,5-dicarboxylate
• IUPAC Traditional name: (2S,3S)-2,3-bis(4-methylbenzoyloxy)butanedioic acid 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 Di-p-Tolyoyl-D-tartrate; (-)-Amlodipine Di-p-Tolyoyl-D-tartrate; (S)-(+)-Amlodipine Di-p-Tolyoyl-D-tartrate; (S)-Amlodipine Di-p-Toluoyl-D-tartrate

Database IDs

• CAS Number: 1215226-53-1
• PubChem SID: 162254692
• PubChem CID: 71313380

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: White Solid

DETAILS

Toronto Research Chemicals - A633506

(S)-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)