disodium (2R)-2-{[4-(2-{2-amino-4-oxo-1H,4H,7H-pyrrolo[2,3-d]pyrimidin-5-yl}ethyl)phenyl]formamido}pentanedioate

• ChemBase ID: 176254
• Molecular Formular: C20H19N5Na2O6
• Molecular Mass: 471.3743
• Monoisotopic Mass: 471.11307192
• SMILES: c1(nc(=O)c2c([nH]1)[nH]cc2CCc1ccc(cc1)C(=O)N[C@H](CCC(=O)[O-])C(=O)[O-])N.[Na+].[Na+]
• Canonical SMILES: [O-]C(=O)CC[C@H](C(=O)[O-])NC(=O)c1ccc(cc1)CCc1c[nH]c2c1c(=O)nc([nH]2)N.[Na+].[Na+]
• InChI: InChI=1S/C20H21N5O6.2Na/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);;/q;2*+1/p-2/t13-;;/m1../s1
• InChIKey: NYDXNILOWQXUOF-FFXKMJQXSA-L

NAMES AND DATABASE IDS

Names

• IUPAC name: disodium (2R)-2-{[4-(2-{2-amino-4-oxo-1H,4H,7H-pyrrolo[2,3-d]pyrimidin-5-yl}ethyl)phenyl]formamido}pentanedioate
• IUPAC Traditional name: disodium (2R)-2-{[4-(2-{2-amino-4-oxo-1H,7H-pyrrolo[2,3-d]pyrimidin-5-yl}ethyl)phenyl]formamido}pentanedioate
• Synonyms: N-[4-[2-(2-Amino-4,7-dihydro-4-oxo-3H-pyrrolo[2,3-d]pyrimidin-5-yl)ethyl]benzoyl]-L-glutamic Acid Sodium Salt; N-[4-[(2-Amino-4,7-dihydro-4-oxo-1H-pyrrolo[2,3-d]pyrimidin-5-yl)ethyl]benzoyl]-L-glutamic Acid Disodium; Alimta; LY 231514; LY 231514 Disodium; Pemetrexed Sodium; Rolazar; Tifolar; Pemetrexed Disodium; D-Pemetrexed Hydrate; N-[4-[2-(2-Amino-4,7-dihydro-4-oxo-3H-pyrrolo[2,3-d]pyrimidin-5-yl)ethyl]benzoyl]-D-glutamic Acid Hydrate

Database IDs

• CAS Number: 150399-23-8
• PubChem SID: 164232164
• PubChem CID: 125891

CALCULATED PROPERTIES

• Acid pKa: 3.3411286
• H Acceptors: 9
• H Donor: 4
• LogD (pH = 5.5): -2.0354757
• LogD (pH = 7.4): -5.0479527
• Log P: 1.4881234
• Molar Refractivity: 131.1238 cm^3
• Polarizability: 40.18901 Å^3
• Polar Surface Area: 192.63 Å^2
• Rotatable Bonds: 9
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO; Methanol; Water
• Apperance: Off-White Solid
• Melting Point: 176-178°C (dec.); 254-258°C (dec.)

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - P219490

Pemetrexed (P219500) isomer impurity.

Toronto Research Chemicals - P219500

Multitargeted antifolate; inhibits thymidylate synthase as well as other folate dependent enzymes. Antineoplastic.

REFERENCES

• McDonald, A.C., et al.: Clin. Cancer Res., 4, 605 (1998)
• John, W., et al.: Cancer, 88, 1807 (1998)
• Miller, K.D., et al.: Ann. Oncol., 11, 101 (1998)
• McDonald, A.C., et al.: Clin. Cancer Res., 4, 605 (1998)
• John, W., et al.: Cancer, 88, 1807 (1998)
• Miller, K.D., et al.: Ann. Oncol., 11, 101 (1998)