sodium 2-[1-({[(1S)-1-{3-[(E)-2-(7-chloroquinolin-2-yl)ethenyl]phenyl}-3-[2-(2-hydroxypropan-2-yl)phenyl]propyl]sulfanyl}methyl)cyclopropyl]acetate

• ChemBase ID: 174783
• Molecular Formular: C35H35ClNNaO3S
• Molecular Mass: 608.16507
• Monoisotopic Mass: 607.19238695
• SMILES: c1cc(cc2c1ccc(n2)/C=C/c1cccc(c1)[C@H](CCc1c(cccc1)C(C)(C)O)SCC1(CC(=O)[O-])CC1)Cl.[Na+]
• Canonical SMILES: [O-]C(=O)CC1(CS[C@H](c2cccc(c2)/C=C/c2ccc3c(n2)cc(cc3)Cl)CCc2ccccc2C(O)(C)C)CC1.[Na+]
• InChI: InChI=1S/C35H36ClNO3S.Na/c1-34(2,40)30-9-4-3-7-25(30)13-17-32(41-23-35(18-19-35)22-33(38)39)27-8-5-6-24(20-27)10-15-29-16-12-26-11-14-28(36)21-31(26)37-29;/h3-12,14-16,20-21,32,40H,13,17-19,22-23H2,1-2H3,(H,38,39);/q;+1/p-1/b15-10+;/t32-;/m0./s1
• InChIKey: LBFBRXGCXUHRJY-YBGTYPRZSA-M

NAMES AND DATABASE IDS

Names

• IUPAC name: sodium 2-[1-({[(1S)-1-{3-[(E)-2-(7-chloroquinolin-2-yl)ethenyl]phenyl}-3-[2-(2-hydroxypropan-2-yl)phenyl]propyl]sulfanyl}methyl)cyclopropyl]acetate
• IUPAC Traditional name: sodium 2-[1-({[(1S)-1-{3-[(E)-2-(7-chloroquinolin-2-yl)ethenyl]phenyl}-3-[2-(2-hydroxypropan-2-yl)phenyl]propyl]sulfanyl}methyl)cyclopropyl]acetate
• Synonyms: 1-[[[(1S)-1-[3-[(1E)-2-(7-Chloro-2-quinolinyl)ethenyl]phenyl]-3-[2-(1-hydroxy-1-methylethyl)phenyl]propyl]thio]methyl]cyclopropaneacetic Acid Sodium Salt; L 768232; ent-Montelukast Sodium Salt

Database IDs

• CAS Number: 190078-45-6
• PubChem SID: 164230693
• PubChem CID: 46782396

CALCULATED PROPERTIES

• Acid pKa: 4.400609
• H Acceptors: 4
• H Donor: 1
• LogD (pH = 5.5): 7.5461497
• LogD (pH = 7.4): 5.7954516
• Log P: 8.493533
• Molar Refractivity: 180.341 cm^3
• Polarizability: 66.98581 Å^3
• Polar Surface Area: 73.25 Å^2
• Rotatable Bonds: 12
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: Chloroform; Methanol
• Apperance: Pale Yellow Solid
• Melting Point: 112-115°C

Safety Information

• Storage Condition: Refrigerator, Under Inert Atmosphere

DETAILS

Toronto Research Chemicals - M567995

The S-enantiomer of Montelukast. Results indicate that there is no apparent bioinversion of Montelukast to its S-enantiomer in humans.

REFERENCES

• Cheng, H., et al.: Pharm. Res., 11, 824 (1994)
• Amin, R., et al.: J. Pharm. Biomed. Anal., 13, 155 (1994)
• Jones, T., et al.: Can. J. Physiol. Pharmacol., 73, 191 (1994)
• Labelle, M., et al.: Bioorg. Med. Chem. Lett., 5, 283 (1994)