Ropidoxuridine

Catalog No: 20595

CAS Number: 93265-81-7

Purity: 98% Min.

Ropidoxuridine is a novel, orally available, thymidine analogue and prodrug for IUdR, which demonstrated a survival advantage in Phase II studies in anaplastic astrocytoma, a type of glioma. Preclinical studies have also demonstrated that Ropidoxuridine has dose responsive and synergistic effects when combined with radiation in human glioblastoma models. Ropidoxuridine has also shown reduced toxicity, with better tissue incorporation and improved anti-tumor activity when compared to IUdR in nonclinical models. Ropidoxuridine was in clinical trials in patients with colorectal, gastric, and pancreatic cancer, and other solid tumors.

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Chemical Information

Name	Ropidoxuridine
Iupac Chemical Name	1-((2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)-5-iodopyrimidin-2(1H)-one
Synonyms	IPdR; D08992; Ropidoxuridine; 5-Iodo-2-pyrimidinone-2-deoxyribose.
Molecular Formula	C9H11IN2O4
Molecular Weight	338.10
Smile	O=C1N=CC(I)=CN1[C@@H]2O[C@H](CO)[C@@H](O)C2
InChiKey	XIJXHOVKJAXCGJ-XLPZGREQSA-N
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
CAS Number	93265-81-7
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Formulation	Solid powder
Purity	98% Min.
Storage	Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility	Soluble in DMSO
Handling
Shipping Condition	Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
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Targets
Mechanism
Cell study
Animal study
Clinical study

1: Kummar S, Anderson L, Hill K, Majerova E, Allen D, Horneffer Y, Ivy SP, Rubinstein L, Harris P, Doroshow JH, Collins JM. First-in-human phase 0 trial of oral 5-iodo-2-pyrimidinone-2'-deoxyribose in patients with advanced malignancies. Clin Cancer Res. 2013 Apr 1;19(7):1852-7. doi: 10.1158/1078-0432.CCR-12-3118. Epub 2013 Feb 12. PubMed PMID: 23403637; PubMed Central PMCID: PMC3658146.

2: Bihina Bella MA, Eloff JH, Olivier MS. A fraud management system architecture for next-generation networks. Forensic Sci Int. 2009 Mar 10;185(1-3):51-8. doi: 10.1016/j.forsciint.2008.12.013. Epub 2009 Jan 24. PubMed PMID: 19168299.

3: Bose ME, Littrell JC, Patzer AD, Kraft AJ, Metallo JA, Fan J, Henrickson KJ. The Influenza Primer Design Resource: a new tool for translating influenza sequence data into effective diagnostics. Influenza Other Respir Viruses. 2008 Jan;2(1):23-31. doi: 10.1111/j.1750-2659.2007.00031.x. PubMed PMID: 19453490.

4: Kinsella TJ, Kinsella MT, Seo Y, Berk G. 5-iodo-2-pyrimidinone-2'-deoxyribose-mediated cytotoxicity and radiosensitization in U87 human glioblastoma xenografts. Int J Radiat Oncol Biol Phys. 2007 Nov 15;69(4):1254-61. PubMed PMID: 17967315; PubMed Central PMCID: PMC2128756.

5: Saif MW, Berk G, Cheng YC, Kinsella TJ. IPdR: a novel oral radiosensitizer. Expert Opin Investig Drugs. 2007 Sep;16(9):1415-24. Review. PubMed PMID: 17714027.

6: Kinsella TJ, Kinsella MT, Hong S, Johnson JP, Burback B, Tosca PJ. Toxicology and pharmacokinetic study of orally administered 5-iodo-2-pyrimidinone-2'deoxyribose (IPdR) x 28 days in Fischer-344 rats: impact on the initial clinical phase I trial design of IPdR-mediated radiosensitization. Cancer Chemother Pharmacol. 2008 Feb;61(2):323-34. Epub 2007 Jun 12. PubMed PMID: 17562042.

7: Seo Y, Yan T, Schupp JE, Radivoyevitch T, Kinsella TJ. Schedule-dependent drug effects of oral 5-iodo-2-pyrimidinone-2'-deoxyribose as an in vivo radiosensitizer in U251 human glioblastoma xenografts. Clin Cancer Res. 2005 Oct 15;11(20):7499-507. PubMed PMID: 16243824.

8: Seo Y, Yan T, Schupp JE, Colussi V, Taylor KL, Kinsella TJ. Differential radiosensitization in DNA mismatch repair-proficient and -deficient human colon cancer xenografts with 5-iodo-2-pyrimidinone-2'-deoxyribose. Clin Cancer Res. 2004 Nov 15;10(22):7520-8. PubMed PMID: 15569982.

9: Kinsella TJ, Schupp JE, Davis TW, Berry SE, Hwang HS, Warren K, Balis F, Barnett J, Sands H. Preclinical study of the systemic toxicity and pharmacokinetics of 5-iodo-2-deoxypyrimidinone-2'-deoxyribose as a radiosensitizing prodrug in two, non-rodent animal species: implications for phase I study design. Clin Cancer Res. 2000 Sep;6(9):3670-9. PubMed PMID: 10999760.

10: Kinsella TJ, Vielhuber KA, Kunugi KA, Schupp J, Davis TW, Sands H. Preclinical toxicity and efficacy study of a 14-day schedule of oral 5-iodo-2-pyrimidinone-2'-deoxyribose as a prodrug for 5-iodo-2'-deoxyuridine radiosensitization in U251 human glioblastoma xenografts. Clin Cancer Res. 2000 Apr;6(4):1468-75. PubMed PMID: 10778979.

11: Kinsella TJ, Kunugi KA, Vielhuber KA, Potter DM, Fitzsimmons ME, Collins JM. Preclinical evaluation of 5-iodo-2-pyrimidinone-2'-deoxyribose as a prodrug for 5-iodo-2'-deoxyuridine-mediated radiosensitization in mouse and human tissues. Clin Cancer Res. 1998 Jan;4(1):99-109. PubMed PMID: 9516958.

12: Kinsella TJ, Kunugi KA, Vielhuber KA, McCulloch W, Liu SH, Cheng YC. An in vivo comparison of oral 5-iodo-2'-deoxyuridine and 5-iodo-2-pyrimidinone-2'-deoxyribose toxicity, pharmacokinetics, and DNA incorporation in athymic mouse tissues and the human colon cancer xenograft, HCT-116. Cancer Res. 1994 May 15;54(10):2695-700. PubMed PMID: 8168099.

13: Chang CN, Doong SL, Cheng YC. Conversion of 5-iodo-2-pyrimidinone-2'-deoxyribose to 5-iodo-deoxyuridine by aldehyde oxidase. Implication in hepatotropic drug design. Biochem Pharmacol. 1992 May 28;43(10):2269-73. PubMed PMID: 1599512.

14: Lewandowski GA, Cheng YC. Mechanism and mode of action of 5-iodo-2-pyrimidinone 2'-deoxyribonucleoside, a potent anti-herpes simplex virus compound, in herpes simplex virus-infected cells. Mol Pharmacol. 1991 Jan;39(1):27-33. PubMed PMID: 1846219.

15: Efange SM, Alessi EM, Shih HC, Cheng YC, Bardos TJ. Synthesis and biological activities of 2-pyrimidinone nucleosides. 2. 5-Halo-2-pyrimidinone 2'-deoxyribonucleosides. J Med Chem. 1985 Jul;28(7):904-10. PubMed PMID: 2989522.

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Ropidoxuridine

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