Eniluracil
Basic information
- CAS
59989-18-3- Standard SMILES
C#Cc1c[nH]c(=O)[nH]c1=O- InChIKey
JOZGNYDSEBIJDH-UHFFFAOYSA-N- Molecular formula
- C6H4N2O2
- Average molar mass
- 136.11 g/mol
- Monoisotopic mass
- 136.02727738
Overview
Eniluracil is a pyrimidone.
Names & identifiers
- Preferred name
- Eniluracil
- IUPAC
- 5-ethynyl-1H-pyrimidine-2,4-dione
- English name
- 2,4(1H,3H)-Pyrimidinedione, 5-ethynyl- (9CI)
- Molecular formula
- C6H4N2O2
- Molecular weight
- 136.11
Names & synonyms
Eniluracil59989-18-35-ETHYNYLURACIL776C85ethynyluracilEniluracilo5-ethynyl-1,2,3,4-tetrahydropyrimidine-2,4-dione2E2W0W5XIU2,4(1H,3H)-Pyrimidinedione, 5-ethynyl-DTXSID10208696776-C-85NSC687296
Show more names
GW-776GW776C85PCS-6422ADH-300004NSC 687296BW-776-C855-Ethynyluracil>13C,15N2]-Eniluracil
5-Ethynyl-2,4(1H,3H)-pyrimidinedioneeniluracilum5-Fluorouracil EnhancerRefChem:590847DTXCID60131187PCS6422GW776PCS 6422
Database identifiers
- CAS
59989-18-3- PubChem CID
- 43157
- DTXSID
DTXSID10208696- ChEMBL
CHEMBL355200- ChEBI
CHEBI:177783- UNII
- 2E2W0W5XIU
- Nikkaji
- J574.717A
Properties
Computed structural properties
- XLogP
- -0.7
- Topological polar surface area
- 58.2 Ų
- Hydrogen bond donors
- 2
- Hydrogen bond acceptors
- 2
- Rotatable bonds
- 1
- Heavy atoms
- 10
- Formal charge
- 0
- Complexity
- 269
Experimental & physicochemical properties
DrugsPharmaceuticals -> Listed in ZINC15
Physicochemical properties
- Melting point
- 320 ° · 320° (dec)
- Density
- 1.527 · 1.527
- storage temp.
- 2 · under inert gas (nitrogen or Argon) at 2-8°C
- solubility
- Soluble in DMSO
- form
- solid
- pka
- 7.44 · 7.44±0.10(Predicted)
- color
- Yellow
- λmax
- 284 nm · 284nm(MeOH)(lit.)
- Merck
- 14 · 14,3584
- Stability
- 1 year · Stable for 1 year from date of purchase as supplied. Solutions in DMSO may be stored at -20°C for up to 3 months.
- FDA UNII
- 2 E2W0W5XIU · 2E2W0W5XIU
- Symbol(GHS)
- 7 · GHS07
- Signal word
- Warning
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
Safety data
- hs_code
- 2933.59.9500
- Signal word
- Warning
- Symbol(GHS)
- GHS07
- Hazard statements
- H302-H315-H319-H335
- Precautionary statements
- P261-P305+P351+P338
Chemistry & industry
Pharmacology
Pharmacodynamics
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).
Mechanism of Action
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.
MeSH Pharmacological ClassificationCompounds or agents that combine with an enzyme in such a manner as to prevent the normal substrate-enzyme combination and the catalytic reaction.
Applications
DescriptionEniluracil (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.
UsesPotent inactivator of Dihydropyrimidine dehydrogenase (DPD).
Additional notes
DefinitionChEBI: Eniluracil is a pyrimidone.
Related reactions
12 records
Compound notes
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