Ropidoxuridine

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Also known as: 93265-81-7, Ipdr, 5-iodo-2-pyrimidinone-2'-deoxyribose, Ipd-r, 3hx21a3sqf, 1-(2-deoxy-beta-ribofuranosyl)-5-iodo-2-pyrimidinone

Molecular Formula

C₉H₁₁IN₂O₄

Molecular Weight

338.10 g/mol

InChI Key

XIJXHOVKJAXCGJ-XLPZGREQSA-N

FDA UNII

3HX21A3SQF

Ropidoxuridine is an orally available 5-substituted 2-pyrimidinone-2'-deoxyribonucleoside analogue and prodrug of 5-iododeoxyuridine (IUdR), an iodinated analogue of deoxyuridine, with radiosensitizing activity. Upon oral administration, ropidoxuridine (IPdR) is efficiently converted to idoxuridine (IUdR) by a hepatic aldehyde oxidase. In turn, IUdR is incorporated into DNA during replication, thereby sensitizing cells to ionizing radiation by increasing DNA strand breaks. Compared to IUdR, ropidoxuridine is associated with a lower toxicity profile and improved anti-tumor activity.

1 2D Structure

Ropidoxuridine

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

1-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-5-iodopyrimidin-2-one

2.1.2 InChI

InChI=1S/C9H11IN2O4/c10-5-2-11-9(15)12(3-5)8-1-6(14)7(4-13)16-8/h2-3,6-8,13-14H,1,4H2/t6-,7+,8+/m0/s1

2.1.3 InChI Key

XIJXHOVKJAXCGJ-XLPZGREQSA-N

2.1.4 Canonical SMILES

C1C(C(OC1N2C=C(C=NC2=O)I)CO)O

2.1.5 Isomeric SMILES

C1[C@@H]([C@H](O[C@H]1N2C=C(C=NC2=O)I)CO)O

2.2 Other Identifiers

2.2.1 UNII

3HX21A3SQF

2.3 Synonyms

2.3.1 MeSH Synonyms

1. 1-(2-deoxy-beta-ribofuranosyl)-5-iodo-2-pyrimidinone

2. 5-iodo-2-pyrimidinone 2' Deoxyribonucleoside

3. 5-iodo-2-pyrimidinone-2'-deoxyribose

4. Ipdr

2.3.2 Depositor-Supplied Synonyms

1. 93265-81-7

2. Ipdr

3. 5-iodo-2-pyrimidinone-2'-deoxyribose

4. Ipd-r

5. 3hx21a3sqf

6. 1-(2-deoxy-beta-ribofuranosyl)-5-iodo-2-pyrimidinone

7. Nsc-726188

8. 2(1h)-pyrimidinone, 1-(2-deoxy-beta-d-erythro-pentofuranosyl)-5-iodo-

9. 1-((2r,4s,5r)-4-hydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)-5-iodopyrimidin-2(1h)-one

10. Ropidoxuridine [usan]

11. Unii-3hx21a3sqf

12. Ropidoxuridine (inn/usan)

13. Ropidoxuridine [usan:inn]

14. 5-iodo-2-pyrimidinone 2' Deoxyribonucleoside

15. Ropidoxuridine [inn]

16. Schembl8602575

17. Chembl2103821

18. Dtxsid00239353

19. Zinc6091380

20. 5-iodo-2-pyrimidinone-2-deoxyribose

21. Db06485

22. 1-[(2r,4s,5r)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-5-iodopyrimidin-2-one

23. Hy-13742

24. Cs-0007768

25. D08992

26. D96122

27. 265i817

28. A901121

29. Q27257237

30. 5-iodo-1-(2-deoxy-beta-d-ribofuranosyl)pyrimidin-2(1h)-one

31. 1-(2-deoxy-.beta.-d-erythro-pentofuranosyl)-5-iodopyrimidin-2(1h)-one

32. 2(1h)-pyrimidinone, 1-(2-deoxy-.beta.-d-erythro-pentofuranosyl)-5-iodo-

2.4 Create Date

2006-10-25

3 Chemical and Physical Properties

Molecular Formula	C₉H₁₁IN₂O₄
Molecular Weight	338.10 g/mol
XLogP3	-0.5
Hydrogen Bond Donor Count	2
Hydrogen Bond Acceptor Count	4
Rotatable Bond Count	2
Exact Mass	337.97635 g/mol
Monoisotopic Mass	337.97635 g/mol
Topological Polar Surface Area	82.4 Å²
Heavy Atom Count	16
Formal Charge	0
Complexity	357
Isotope Atom Count	0
Defined Atom Stereocenter Count	3
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	1