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Eniluracil

Eniluracil structure

Eniluracil 

structure
  • CAS No:

    59989-18-3

  • Formula:

    C6H4N2O2

  • Chemical Name:

    Eniluracil

  • Synonyms:

    2,4(1H,3H)-Pyrimidinedione,5-ethynyl-;5-Ethynyl-2,4(1H,3H)-pyrimidinedione;5-Ethynyluracil;Eniluracil;776C85;NSC 687296

Description

Eniluracil is a 9,11,15-octadecatrienoic acid.|Eniluracil, which was previously under development by GlaxoSmithKline (GSK), is being developed by Adherex to enhance the therapeutic value and effectiveness of 5-fluorouracil (5-FU), one of the world’s most widely-used oncology agents. 5-FU is widely used in the U.S. and is often first or second line therapy for a variety of cancers including colorectal, breast, gastric, head and neck, ovarian and basal cell cancer of the skin. Eniluracil could improve 5-FU by increasing its effectiveness, reducing its side effects and/or making it orally available. Eniluracil has received Orphan Drug status from the FDA for the treatment of hepatocellular cancer in combination with fluoropyrimidines (including 5-FU).|Eniluracil is an orally-active fluoropyrimidine analogue. Eniluracil inhibits dihydropyrimidine dehydrogenase, the rate-limiting enzyme that catabolizes and inactivates 5-fluorouracil (5-FU) in the liver. Co-administration of ethynyluracil permits the oral administration of 5-FU.

Eniluracil Basic Attributes

136.11

136.11

2E2W0W5XIU

687296

DTXSID10208696

C1773

Characteristics

58.2 Ų

1.527

>220 °C (decomp) @ Solvent: Ethanol

7.44±0.10

Drug Information

For the treatment of cancer in combination with 5-fluorouracil.

Eniluracil is an orally active dihydropyrimidine dehydrogenase (DPD) inhibitor, designed to enhance activity of chemotaxic agents. It is under investigation by Adherex, under license from GlaxoSmithKline, for the treatment of cancer in combination with 5-fluorouracil (5-FU).

Compounds or agents that combine with an enzyme in such a manner as to prevent the normal substrate-enzyme combination and the catalytic reaction. (See all compounds classified as Enzyme Inhibitors.)

Normally, 5-FU is rapidly broken down in the body by an enzyme known as dihydropyrimidine dehydrogenase (DPD). Eniluracil irreversibly inhibits DPD, thereby substantially slowing the breakdown of 5-FU and prolonging exposure of the tumor cells to the drug.

5-ethynyluracil

Eniluracil Use and Manufacturing

Potent inactivator of Dihydropyrimidine dehydrogenase (DPD).

Computed Properties

Molecular Weight:136.11
XLogP3:-0.7
Hydrogen Bond Donor Count:2
Hydrogen Bond Acceptor Count:2
Rotatable Bond Count:1
Exact Mass:136.027277375
Monoisotopic Mass:136.027277375
Topological Polar Surface Area:58.2
Heavy Atom Count:10
Complexity:269
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

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