3584. Eniluracil

Nomenclature

CAS number: 59989-18-3
5-Ethynyl-2,4(1H,3H)-pyrimidinedione; 5-ethynyluracil; 5-EU; 776C85.
C6H4N2O2; mol wt 136.11.
C 52.95%, H 2.96%, N 20.58%, O 23.51%.

Description and references

Irreversible inhibitor of dihydropyrimidine dehydrogenase, the rate-determining enzyme in catabolism of 5-fluorouracil, q.v. Prepn: J. Perman et al., Tetrahedron Lett. 1976, 2427; P. J. Barr et al., Nucleic Acids Res. 3, 2845 (1976). Large scale synthesis: N. G. Kundu, S. A. Schmitz, J. Heterocycl. Chem. 19, 463 (1982). Crystal structure determn: M. Sacchetti et al., J. Pharm. Sci. 90, 1049 (2001). Mechanism-based inactivation of dihydropyrimidine dehydrogenase: D. J. T. Porter et al., J. Biol. Chem. 267, 5236 (1992). Prolongs plasma concentration of 5-fluorouracil: D. P. Baccanari et al., Proc. Natl. Acad. Sci. USA 90, 11064 (1993). Clinical safety and efficacy: R. A. Humerickhouse et al., Clin. Cancer Res. 5, 291 (1999). Clinical study with 5-fluorouracil in advanced pancreatic cancer: M. L. Rothenberg et al., Ann. Oncol. 13, 1576 (2002); in metastatic/advanced colorectal cancer: R. L. Schilsky et al., J. Clin. Oncol. 20, 1519 (2002). Review of clinical development: J. A. Hohneker, Oncology 12, 52-56 (1998).

Chemical structure

Properties

Cream colored solid from methanol-water, mp 320° (dec). d 1.527. uv max (methanol): 284, 225 nm (ε 9450, 10330).

Therapeutic Category

Antineoplastic adjunct (chemomodulator).

Keywords

Antineoplastic Adjunct; Chemomodulator