59989-18-3

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 NO: 59989-18-3
• Molecular Formula: C₆H₄N₂O₂
• Molecular Weight: 136.10816
• Product Categories: PYRIMIDINE;Bases & Related Reagents;Intermediates & Fine Chemicals;Nucleotides;Pharmaceuticals
• Mol File: 59989-18-3.mol

Chemical Properties

• Melting Point: 320° (dec)
• Appearance: /
• Density: 1.527
• Refractive Index: 1.589
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• Solubility: Soluble in DMSO
• PKA: 7.44±0.10(Predicted)
• 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.
• Merck: 14,3584
• CAS DataBase Reference: 2,4(1H,3H)-Pyrimidinedione, 5-ethynyl- (9CI)(CAS DataBase Reference)
• NIST Chemistry Reference: 2,4(1H,3H)-Pyrimidinedione, 5-ethynyl- (9CI)(59989-18-3)
• EPA Substance Registry System: 2,4(1H,3H)-Pyrimidinedione, 5-ethynyl- (9CI)(59989-18-3)

Safety Data

• Hazardous Substances Data: 59989-18-3(Hazardous Substances Data)

Usage

Description

2,4(1H,3H)-Pyrimidinedione, 5-ethynyl(9CI), also known as Eniluracil, is an organic compound with the molecular formula C6H4N2O2. It is a potent inactivator of Dihydropyrimidine dehydrogenase (DPD), an enzyme involved in the degradation of pyrimidine-based chemotherapeutic drugs such as 5-fluorouracil (5-FU). Eniluracil is characterized by its ability to form an irreversible bond with DPD, thereby increasing the effectiveness and duration of 5-FU in the body.

Uses

Used in Pharmaceutical Industry:
2,4(1H,3H)-Pyrimidinedione, 5-ethynyl(9CI) is used as an enzyme inhibitor for the enhancement of chemotherapeutic drug efficacy. It is particularly effective in combination with 5-fluorouracil (5-FU), a widely used anticancer drug. By inactivating DPD, Eniluracil prolongs the circulating concentrations of 5-FU, allowing for a more sustained and effective treatment of various types of cancer.
Used in Anticancer Applications:
Eniluracil is employed as a potent inactivator of Dihydropyrimidine dehydrogenase (DPD), which plays a crucial role in the metabolism of pyrimidine-based chemotherapeutic drugs. By inhibiting DPD, Eniluracil increases the availability and effectiveness of 5-FU, leading to improved treatment outcomes for patients with various types of cancer, including colorectal, breast, head and neck, and esophageal cancers.
Used in Drug Development and Research:
2,4(1H,3H)-Pyrimidinedione, 5-ethynyl(9CI) serves as a valuable compound in the development and research of new anticancer drugs and drug delivery systems. Its unique mechanism of action as an irreversible DPD inhibitor makes it an interesting candidate for further investigation and potential incorporation into novel therapeutic strategies for cancer treatment.

References

1) Porter?et al. (1992),?Mechanism-based Inactivation of Dihydropyrimidine Dehydrogenase by 5-Ethynyluracil; J. Biol. Chem.,?267?5236 2) Baccalnari?et al. (1993),?5-Ethynyluracil (776C85): a potent modulator of the pharmacokinetics and antitumor efficacy of 5-fluorouracil; Proc. Natl. Acad. Sci. USA,?90?11064 3) Schilsky and Kindler (2000)?Eniluracil: an irreversible inhibitor of dihydropyrimidine dehydrogenase; Expert Opin. Investig. Drugs,?9?1635

InChI:InChI=1/C6H4N2O2/c1-2-4-3-7-6(10)8-5(4)9/h1,3H,(H2,7,8,9,10)