disodium (2S)-2-{[4-(2-{2-amino-4-oxo-3H,4H,7H-pyrrolo[2,3-d]pyrimidin-5-yl}ethyl)phenyl]formamido}pentanedioate heptahydrate

• ChemBase ID: 179706
• Molecular Formular: C20H33N5Na2O13
• Molecular Mass: 597.48126
• Monoisotopic Mass: 597.1870247
• SMILES: c12nc([nH]c(=O)c1c(c[nH]2)CCc1ccc(C(=O)N[C@H](C(=O)[O-])CCC(=O)[O-])cc1)N.[Na+].[Na+].O.O.O.O.O.O.O
• Canonical SMILES: [O-]C(=O)CC[C@@H](C(=O)[O-])NC(=O)c1ccc(cc1)CCc1c[nH]c2c1c(=O)[nH]c(n2)N.O.O.O.O.O.O.O.[Na+].[Na+]
• InChI: InChI=1S/C20H21N5O6.2Na.7H2O/c21-20-24-16-15(18(29)25-20)12(9-22-16)6-3-10-1-4-11(5-2-10)17(28)23-13(19(30)31)7-8-14(26)27;;;;;;;;;/h1-2,4-5,9,13H,3,6-8H2,(H,23,28)(H,26,27)(H,30,31)(H4,21,22,24,25,29);;;7*1H2/q;2*+1;;;;;;;/p-2/t13-;;;;;;;;;/m0........./s1
• InChIKey: QJVSMHJWAOSBMD-MYXYZBIASA-L

NAMES AND DATABASE IDS

Names

• IUPAC name: disodium (2S)-2-{[4-(2-{2-amino-4-oxo-3H,4H,7H-pyrrolo[2,3-d]pyrimidin-5-yl}ethyl)phenyl]formamido}pentanedioate heptahydrate
• IUPAC Traditional name: disodium (2S)-2-{[4-(2-{2-amino-4-oxo-3H,4H,7H-pyrrolo[2,3-d]pyrimidin-5-yl}ethyl)phenyl]formamido}pentanedioate heptahydrate
• Synonyms: Alimta; Pemetrexed Disodium Heptahydrate

Database IDs

• CAS Number: 357166-29-1
• PubChem SID: 164235616
• PubChem CID: 23725084

CALCULATED PROPERTIES

• Acid pKa: 3.0041838
• H Acceptors: 8
• H Donor: 4
• LogD (pH = 5.5): -2.7648282
• LogD (pH = 7.4): -5.6923404
• Log P: -0.029441621
• Molar Refractivity: 131.5572 cm^3
• Polarizability: 39.994446 Å^3
• Polar Surface Area: 192.63 Å^2
• Rotatable Bonds: 9
• Lipinski's Rule of Five: false

PROPERTIES

Pharmacology Properties

• Mechanism of Action: Thymidylate synthase inhibitor

Product Information

• Salt Data: 2 Na+, 7 H2O
• Application(s): Antineoplastic agent

REFERENCES

• Taylor, E.C. et al., J. Med. Chem., 1992, 35, 4450-4454, (synth, pmr, pharmacol)
• Miwa, T. et al., J.O.C., 1993, 58, 1696-1701, (synth, ir, pmr)
• Eur. Pat., 1994, Eli Lilly, 589 720; CA, 121, 83363m, (synth)
• Hamilton, C.L. et al., J. Chromatogr., B: Biomed. Appl., 1994, 654, 297-303, (hplc)
• Rinaldi, D.A. et al., J. Clin. Oncol., 1995, 13, 2842-2850, (clin trial)
• Shih, C. et al., Cancer Res., 1997, 57, 1116-1123, (pharmacol)
• Woodland, J.M. et al., Drug Metab. Dispos., 1997, 25, 693-700, (hplc, metab)
• Calvert, A.H. et al., Br. J. Cancer, 1998, 78, 35-40, (rev)
• Graul, A. et al., Drugs of the Future, 1998, 23, 498-507, (rev)
• Taylor, E.C. et al., Tet. Lett., 1999, 40, 4023-4026, (synth)