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Fialuridine

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ACTIVE PHARMA INGREDIENTS

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1 API Suppliers
1 USDMF

Synopsis

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Chemistry

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Also known as: 69123-98-4, Fiau, Fluoroiodoarauridine, 1-(2-deoxy-2-fluoro-b-d-arabinofuranosyl)-5-iodouracil, 53t7in77lc, 1-(2'fluoro-2'-deoxyarabinofuranosyl)-5-iodouracil

Molecular Formula

C₉H₁₀FIN₂O₅

Molecular Weight

372.09 g/mol

InChI Key

IPVFGAYTKQKGBM-BYPJNBLXSA-N

FDA UNII

53T7IN77LC

Fialuridine is a nucleoside analog of uridine with activity against hepatitis B virus and herpes viruses. Fialuridine inhibits viral DNA polymerase and viral replication.

1 2D Structure

Fialuridine

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

1-[(2R,3S,4R,5R)-3-fluoro-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-5-iodopyrimidine-2,4-dione

2.1.2 InChI

InChI=1S/C9H10FIN2O5/c10-5-6(15)4(2-14)18-8(5)13-1-3(11)7(16)12-9(13)17/h1,4-6,8,14-15H,2H2,(H,12,16,17)/t4-,5+,6-,8-/m1/s1

2.1.3 InChI Key

IPVFGAYTKQKGBM-BYPJNBLXSA-N

2.1.4 Canonical SMILES

C1=C(C(=O)NC(=O)N1C2C(C(C(O2)CO)O)F)I

2.1.5 Isomeric SMILES

C1=C(C(=O)NC(=O)N1[C@H]2[C@H]([C@@H]([C@H](O2)CO)O)F)I

2.2 Other Identifiers

2.2.1 UNII

53T7IN77LC

2.3 Synonyms

2.3.1 MeSH Synonyms

1. 1-(2'fluoro-2'-deoxyarabinofuranosyl)-5-iodouracil

2. 1-(2-deoxy-2-fluoro-beta-d-arabinofuranosyl)-5-iodo-2,4(1h,3h)-pyrimidinedione

3. 1-(2-deoxy-2-fluoro-beta-d-arabinofuranosyl)-5-iodo-unracil

4. 123i-fiau

5. 2'-fluoro-5-iodoarauracil

6. Fiau

2.3.2 Depositor-Supplied Synonyms

1. 69123-98-4

2. Fiau

3. Fluoroiodoarauridine

4. 1-(2-deoxy-2-fluoro-b-d-arabinofuranosyl)-5-iodouracil

5. 53t7in77lc

6. 1-(2'fluoro-2'-deoxyarabinofuranosyl)-5-iodouracil

7. 1-[(2r,3s,4r,5r)-3-fluoro-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-5-iodopyrimidine-2,4-dione

8. Nsc-678514

9. 1-((2r,3s,4r,5r)-3-fluoro-4-hydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)-5-iodopyrimidine-2,4(1h,3h)-dione

10. Drg-0098

11. 1-(2-deoxy-2-fluoro-beta-d-arabinofuranosyl)-5-iodouracil

12. Fialuridine [usan:inn]

13. Unii-53t7in77lc

14. Mfcd00866922

15. 2'-fluoro-5-iodo-1-beta-d-arabinofuranosyluracil

16. Uracil, 1-(2-deoxy-2-fluoro-beta-d-arabinofuranosyl)-5-iodo-

17. Fialuridine [mi]

18. 2'-fluoro-5-iodouracil

19. Fialuridine [inn]

20. 5-iodo-2-fluoroarauracil

21. Fialuridine (usan/inn)

22. Fialuridine [usan]

23. Schembl3189

24. 1-(2-deoxy-2-fluoro-beta-d-arabinofuranosyl)-5-iodo-2,4(1h,3h)-pyrimidinedione

25. 2,4(1h,3h)-pyrimidinedione, 1-(2-deoxy-2-fluoro-beta-d-arabinofuranosyl)-5-iodo-

26. Fialuridine [mart.]

27. 1-(2-deoxy-2-fluoro-.beta.-d-arabinofuranosyl)-5-iodouracil

28. Chembl271475

29. Fialuridine, >=98% (hplc)

30. Dtxsid701028030

31. Zinc4216113

32. Bdbm50367488

33. Akos015856198

34. Akos016009483

35. Db15427

36. Nsc 678514

37. 1-[(2r,3s,4r,5r)-3-fluoro-4-hydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl]-5-iodo-pyrimidine-2,4-dione

38. Ac-32361

39. As-69583

40. Hy-118122

41. Cs-0065233

42. D04181

43. F12931

44. 691f984

45. A848801

46. J-700174

47. J-700352

48. Q5446286

49. 1-(2-deoxy-2-fluoro--d-arabinofuranosyl)-5-iodouracil

50. 1-(2'-deoxy-2'-fluoro-.beta.-d-arabinofuranosyl)-5-iodouracil

51. 1-(2'-deoxy-2'-fluoro-b-d-arabinofuranosyl)-5-iodouracil

52. 2,4(1h,3h)-pyrimidinedione, 1-(2-deoxy-2-fluoro-.beta.-d-arabinofuranosyl)-5-iodo-

53. 1-((2s,3r,4s,5s)-3-fluoro-4-hydroxy-5-(hydroxymethyl)-tetrahydrofuran-2-yl)-5-iodopyrimidine-2,4(1h,3h)-dione

54. 1-[(2r,3s,4r,5r)-3-fluoro-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-5-iodo-1,2,3,4-tetrahydropyrimidine-2,4-dione

2.4 Create Date

2005-08-01

3 Chemical and Physical Properties

Molecular Formula	C₉H₁₀FIN₂O₅
Molecular Weight	372.09 g/mol
XLogP3	-0.9
Hydrogen Bond Donor Count	3
Hydrogen Bond Acceptor Count	6
Rotatable Bond Count	2
Exact Mass	371.96185 g/mol
Monoisotopic Mass	371.96185 g/mol
Topological Polar Surface Area	99.1 Å²
Heavy Atom Count	18
Formal Charge	0
Complexity	418
Isotope Atom Count	0
Defined Atom Stereocenter Count	4
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	1

4 Pharmacology and Biochemistry

4.1 MeSH Pharmacological Classification

Antiviral Agents

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.)

Nucleic Acid Synthesis Inhibitors

Compounds that inhibit cell production of DNA or RNA. (See all compounds classified as Nucleic Acid Synthesis Inhibitors.)

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