MedKoo Cat#: 122485 | Name: 5-Iodo-2'-deoxyuridine
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Description:

WARNING: This product is for research use only, not for human or veterinary use.

5-Iodo-2'-deoxyuridine is a nucleoside analog that inhibits the replication of viruses and other DNA-containing organisms.

Chemical Structure

5-Iodo-2'-deoxyuridine
5-Iodo-2'-deoxyuridine
CAS#54-42-2

Theoretical Analysis

MedKoo Cat#: 122485

Name: 5-Iodo-2'-deoxyuridine

CAS#: 54-42-2

Chemical Formula: C9H11IN2O5

Exact Mass: 353.9713

Molecular Weight: 354.10

Elemental Analysis: C, 30.53; H, 3.13; I, 35.84; N, 7.91; O, 22.59

Price and Availability

Size Price Availability Quantity
5g USD 250.00 2 Weeks
10g USD 450.00 2 Weeks
25g USD 750.00 2 Weeks
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Related CAS #
No Data
Synonym
idoxuridine; 5-Iodo-2'-deoxyuridine; 54-42-2; 5-Iododeoxyuridine; Idoxuridin
IUPAC/Chemical Name
1-(2-Deoxy-beta-D-ribofuranosyl)-5-iodouracil
InChi Key
XQFRJNBWHJMXHO-RRKCRQDMSA-N
InChi Code
InChI=1S/C9H11IN2O5/c10-4-2-12(9(16)11-8(4)15)7-1-5(14)6(3-13)17-7/h2,5-7,13-14H,1,3H2,(H,11,15,16)/t5-,6+,7+/m0/s1
SMILES Code
O=C(N1)N([C@H]2C[C@@H]([C@@H](CO)O2)O)C=C(I)C1=O
Appearance
To be determined
Purity
>98% (or refer to the Certificate of Analysis)
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.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
To be determined
Shelf Life
>2 years if stored properly
Drug Formulation
To be determined
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.9001
More Info

Preparing Stock Solutions

The following data is based on the product molecular weight 354.10 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
1: Kori S, Khandagale D, Sanghvi YS, Serrano JL, Lozano P, Kapdi AR. Suzuki- Miyaura Coupling, Heck Alkenylation, and Amidation of DMTr-Protected 5-Iodo-2'-Deoxyuridine via Palladium-catalyzed Reactions. Curr Protoc. 2022 Jul;2(7):e502. doi: 10.1002/cpz1.502. PMID: 35895086. 2: Prusoff WH, Chen MS, Fischer PH, Lin TS, Shiau GT, Schinazi RF, Walker J. Antiviral iodinated pyrimidine deoxyribonucleosides: 5-iodo-2'-deoxyuridine; 5-iodo-2'-deoxycytidine; 5-iodo-5'-amino-2',5'-dideoxyuridine. Pharmacol Ther. 1979;7(1):1-34. doi: 10.1016/0163-7258(79)90023-8. PMID: 392550. 3: Rösler TW, Matusch A, Librizzi D, Arias-Carrión O, Freundlieb N, Hoeffken H, Oertel WH, Depboylu C, Höglinger GU. Diesterified derivatives of 5-iodo-2'-deoxyuridine as cerebral tumor tracers. PLoS One. 2014 Jul 16;9(7):e102397. doi: 10.1371/journal.pone.0102397. PMID: 25028935; PMCID: PMC4100890. 4: Devine RD, Behbehani GK. Use of the Pyrimidine Analog, 5-Iodo-2'-Deoxyuridine (IdU) with Cell Cycle Markers to establish Cell Cycle Phases in a Mass Cytometry Platform. J Vis Exp. 2021 Oct 22;(176). doi: 10.3791/60556. PMID: 34747407. 5: Kassis AI, Adelstein SJ. 5-[125]iodo-2'-deoxyuridine in the radiotherapy of solid CNS tumors in rats. Acta Oncol. 1996;35(7):935-9. doi: 10.3109/02841869609104048. PMID: 9004774. 6: Schuerman G, Van Hecke K, Van Meervelt L. Exploration of the influence of 5-iodo-2'-deoxyuridine incorporation on the structure of d[CACG(IDU)G]. Acta Crystallogr D Biol Crystallogr. 2003 Aug;59(Pt 8):1525-8. doi: 10.1107/s0907444903012381. Epub 2003 Jul 23. PMID: 12876373. 7: BUI NM, GILLET R, DUMONT P. AN IMPROVED SYNTHESIS OF 5-IODO-2'-DEOXYURIDINE-I-131 AND 5-IODOURACIL-I-131. Int J Appl Radiat Isot. 1965 May;16:337-9. doi: 10.1016/0020-708x(65)90061-x. PMID: 14313715. 8: Ghosh MK, Mitra AK. Brain parenchymal metabolism of 5-iodo-2'-deoxyuridine and 5'-ester prodrugs. Pharm Res. 1992 Aug;9(8):1048-52. doi: 10.1023/a:1015858512407. PMID: 1409376. 9: Narurkar MM, Mitra AK. Prodrugs of 5-iodo-2'-deoxyuridine for enhanced ocular transport. Pharm Res. 1989 Oct;6(10):887-91. doi: 10.1023/a:1015968724007. PMID: 2608631. 10: Klecker RW Jr, Jenkins JF, Kinsella TJ, Fine RL, Strong JM, Collins JM. Clinical pharmacology of 5-iodo-2'-deoxyuridine and 5-iodouracil and endogenous pyrimidine modulation. Clin Pharmacol Ther. 1985 Jul;38(1):45-51. doi: 10.1038/clpt.1985.132. PMID: 4006375. 11: Foulon CF, Zhang YZ, Adelstein SJ, Kassis AI. Instantaneous preparation of radiolabeled 5-iodo-2'-deoxyuridine. Appl Radiat Isot. 1995 Oct;46(10):1039-46. doi: 10.1016/0969-8043(95)00214-x. PMID: 7496371. 12: CALABRESI P. CURRENT STATUS OF CLINICAL INVESTIGATIONS WITH 6-AZAURIDINE, 5-IODO-2'-DEOXYURIDINE, AND RELATED DERIVATIVES. Cancer Res. 1963 Sep;23:1260-7. PMID: 14073547. 13: Khalili P, Naimi E, Knaus EE, Wiebe LI. Pharmacokinetics and metabolism of the novel synthetic C-nucleoside, 1-(2-deoxy-beta-D- ribofuranosyl)-2,4-difluoro-5-iodobenzene: a potential mimic of 5-iodo-2'-deoxyuridine. Biopharm Drug Dispos. 2002 Apr;23(3):105-13. doi: 10.1002/bdd.301. PMID: 12173545. 14: Marcialis MA, Biondi E, Atzeni A, Schivo ML, Uccheddu P, Loddo B. 5-Iodo-2-deoxyuridine resistance of vaccinia viruses in cells endowed with thymidine kinase activity. Experientia. 1973 Jun 15;29(6):733-4. doi: 10.1007/BF01944806. PMID: 4268858. 15: 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. PMID: 10778979. 16: Kelsey DK, Kern ER, Overall JC Jr, Glasgow LA. Effect of cytosine arabinoside and 5-iodo-2'-deoxyuridine on a cytomegalovirus infection in newborn mice. Antimicrob Agents Chemother. 1976 Mar;9(3):458-64. doi: 10.1128/AAC.9.3.458. PMID: 176935; PMCID: PMC429552.