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Home > Encyclopedia > 1-(2-Deoxy-2-fluoro-β-D-arabinofuranosyl)-2,4(1H,3H)-pyrimidinedione

1-(2-Deoxy-2-fluoro-β-D-arabinofuranosyl)-2,4(1H,3H)-pyrimidinedione

1-(2-Deoxy-2-fluoro-β-D-arabinofuranosyl)-2,4(1H,3H)-pyrimidinedione structure

1-(2-Deoxy-2-fluoro-β-D-arabinofuranosyl)-2,4(1H,3H)-pyrimidinedione 

structure
  • CAS No:

    69123-94-0

  • Formula:

    C9H11FN2O5

  • Chemical Name:

    1-(2-Deoxy-2-fluoro-β-D-arabinofuranosyl)-2,4(1H,3H)-pyrimidinedione

  • Synonyms:

    2,4(1H,3H)-Pyrimidinedione,1-(2-deoxy-2-fluoro-β-D-arabinofuranosyl)-;1-(2-Deoxy-2-fluoro-β-D-arabinofuranosyl)-2,4(1H,3H)-pyrimidinedione;NUK-7;1190089-69-0

  • Categories:

    Biochemical Engineering  >  Saccharides

Description

Colourless solid


2'-fluoro-5-ethylarabinosyluracil (FAU) has been used in trials studying the treatment of Small Intestine Lymphoma, Stage IV Mantle Cell Lymphoma, Waldenström Macroglobulinemia, Splenic Marginal Zone Lymphoma, and Recurrent Mantle Cell Lymphoma, among others.|2'-F-ara-deoxyuridine is a deoxyuridine prodrug with potential antineoplastic activity. Upon cellular uptake, 2'-F-ara-deoxyuridine (FAU) is phosphorylated by thymidine kinase to FAU monophosphate and subsequently methylated in the 5'-position by thymidylate synthase (TS) to its activated form, 1-(2-deoxy-2-fluoro-beta-D-arabinofuranosyl) 5-methyluracil monophosphate (FMAUMP). FMAUMP is incorporated into DNA leading to an inhibition of DNA synthesis and so cell growth. The catalytic activity of TS is critical to activation of FAU and subsequent incorporation into DNA. FAU may be beneficial in the case of tumors with high TS activity that are resistant to TS inhibitors.

1-(2-Deoxy-2-fluoro-β-D-arabinofuranosyl)-2,4(1H,3H)-pyrimidinedione Basic Attributes

246.19

246.19

K7386OMP29

DTXSID20219192

C80036

2934999090

Characteristics

99.1

-1.31

Colourless solid

1.6±0.1 g/cm3

161-162 °C @ Solvent: Chloroform, Methanol

1.608

Drug Information

Agents used in the prophylaxis or therapy of VIRUS DISEASES. Some of the ways they may act include preventing viral replication by inhibiting viral DNA polymerase; binding to specific cell-surface receptors and inhibiting viral penetration or uncoating; inhibiting viral protein synthesis; or blocking late stages of virus assembly. (See all compounds classified as Antiviral Agents.)|Endogenous or exogenous substances which inhibit the normal growth of human and animal cells or micro-organisms, as distinguished from those affecting plant growth (= PLANT GROWTH REGULATORS). (See all compounds classified as Growth Inhibitors.)

2'-fluoro-5-ethyl-1-beta-D-ara U

Computed Properties

Molecular Weight:246.19
XLogP3:-1
Hydrogen Bond Donor Count:3
Hydrogen Bond Acceptor Count:6
Rotatable Bond Count:2
Exact Mass:246.06519962
Monoisotopic Mass:246.06519962
Topological Polar Surface Area:99.1
Heavy Atom Count:17
Complexity:374
Defined Atom Stereocenter Count:4
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

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