7077. Pemetrexed

Nomenclature

CAS number: 137281-23-3
N-[4-[2-(2-Amino-4,7-dihydro-4-oxo-1H-pyrrolo[2,3-d]pyrimidin-5-yl)ethyl]benzoyl]-l-glutamic acid.
C20H21N5O6; mol wt 427.41.
C 56.20%, H 4.95%, N 16.39%, O 22.46%.

Description and references

Multitargeted antifolate; inhibits thymidylate synthase as well as other folate dependent enzymes. Prepn: E. C. Taylor et al., EP 432677; idem, US 5344932 (1991, 1994 both to Trustees Princeton Univ.); idem et al., J. Med. Chem. 35, 4450 (1992). Profile of enzyme inhibition: C. Shih et al., Adv. Enzyme Regul. 38, 135 (1998). HPLC determn in plasma: C. L. Hamilton, J. A. Kirkwood, J. Chromatogr. B 654, 297 (1994). Clinical pharmacokinetics in cancer patients: A. C. McDonald et al., Clin. Cancer Res. 4, 605 (1998). Clinical evaluation in colorectal carcinoma: W. John et al., Cancer 88, 1807 (2000); in pancreatic cancer: K. D. Miller et al., Ann. Oncol. 11, 101 (2000).

Chemical structure

Properties

Crystals from 50% methanol/methylene chloride.

Derivative

Sodium salt.

Nomenclature

CAS number: 150399-23-8
Pemetrexed disodium; LY-231514; Alimta (Lilly).
C20H19N5Na2O6; mol wt 471.37.
C 50.96%, H 4.06%, N 14.86%, Na 9.75%, O 20.37%.

Therapeutic Category

Antineoplastic.

Keywords

Antineoplastic; Antimetabolites; Folic Acid Analogs/Antagonists