2,4(1H,3H)-Pyrimidinedione, 5-ethynyl- (9CI)
2,4(1H,3H)-Pyrimidinedione, 5-ethynyl- (9CI) Basic information
- Product Name:
- 2,4(1H,3H)-Pyrimidinedione, 5-ethynyl- (9CI)
- Synonyms:
-
- 5-ethynyluracil
- 5-Ethynyl-2,4(1H,3H)-pyriMidinedione
- NSC 687296
- GW776C85
- ADH-300004
- GW-776
- 5-EthynylpyriMidine-2,4(1H,3H)-dione
- 5-Ethynyl-1H-pyrimidine-2,4-dione
- CAS:
- 59989-18-3
- MF:
- C6H4N2O2
- MW:
- 136.11
- Product Categories:
-
- Nucleotides
- Pharmaceuticals
- PYRIMIDINE
- Bases & Related Reagents
- Intermediates & Fine Chemicals
- Mol File:
- 59989-18-3.mol
2,4(1H,3H)-Pyrimidinedione, 5-ethynyl- (9CI) Chemical Properties
- Melting point:
- 320° (dec)
- Density
- 1.527
- storage temp.
- under inert gas (nitrogen or Argon) at 2-8°C
- solubility
- Soluble in DMSO
- form
- solid
- pka
- 7.44±0.10(Predicted)
- color
- Yellow
- λmax
- 284nm(MeOH)(lit.)
- Merck
- 14,3584
- Stability:
- Stable for 1 year from date of purchase as supplied. Solutions in DMSO may be stored at -20°C for up to 3 months.
2,4(1H,3H)-Pyrimidinedione, 5-ethynyl- (9CI) Usage And Synthesis
Description
Eniluracil (59989-18-3) is an irreversible dihydropyrimidine dehydrogenase (DPD) inhibitor.1-3? DPD is involved in the degradation of pyrimidine-based chemotherapeutic drugs such as 5-fluorouracil (5-FU).? Eniluracil has been used along with 5-FU to prolong circulating concentrations of the drug.
Uses
Potent inactivator of Dihydropyrimidine dehydrogenase (DPD).
Definition
ChEBI: Eniluracil is a pyrimidone.
in vivo
Eniluracil (5-Ethynyluracil) (1 mg/kg; i.p.; single daily for 3 days) exhibits neither toxicity nor intrinsic antitumor activity, and greatly improves FUra (5-fluorouracil) therapy in rats[1].
| Animal Model: | Female Fischer 344/HSD rats (6 to 7-week-old; 150-200 g)[1]. |
| Dosage: | 1 mg/kg |
| Administration: | Intraperitoneal injection; single daily for 3 days (l h before FUra (5-fluorouracil) and for an additional 2 days after FUra therapy) |
| Result: | Produced complete tumor regression that was sustained for at least 90 days posttherapy when combined with 3.5 mg/kg FUra, however, 35 mg/kg FUra alone produced partial responses in 75% of the treated animals ( the tumors regrew in all of these animals). |
References
[1] D J PORTER. Mechanism-based inactivation of dihydropyrimidine dehydrogenase by 5-ethynyluracil.[J]. The Journal of Biological Chemistry, 1992, 267 8: 5236-5242.
[2] D P BACCANARI. 5-Ethynyluracil (776C85): a potent modulator of the pharmacokinetics and antitumor efficacy of 5-fluorouracil.[J]. Proceedings of the National Academy of Sciences of the United States of America, 1993, 90 23: 11064-11068. DOI:10.1073/pnas.90.23.11064
[3] R L SCHILSKY H L K. Eniluracil: an irreversible inhibitor of dihydropyrimidine dehydrogenase.[J]. Expert opinion on investigational drugs, 2000, 9 7: 1635-1649. DOI:10.1517/13543784.9.7.1635
2,4(1H,3H)-Pyrimidinedione, 5-ethynyl- (9CI)Supplier
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