Page last updated: 2024-12-11

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

Description Research Excerpts Clinical Trials Roles Classes Pathways Study Profile Bioassays Related Drugs Related Conditions Protein Interactions Research Growth Market Indicators

Description

You are describing **5-Iodo-2'-deoxyuridine (IdU)**, a synthetic nucleoside analog.

**Here's a breakdown of its structure and significance in research:**

**Structure:**

* **1-(2-deoxy-beta-ribofuranosyl)-5-iodo-2-pyrimidinone** is a rather complex chemical name.
* Let's break it down:
* **1-(2-deoxy-beta-ribofuranosyl):** This part refers to the sugar component, a modified deoxyribose molecule.
* **5-iodo-2-pyrimidinone:** This describes the nitrogenous base. It's a pyrimidine base (like cytosine or thymine) with an iodine atom attached at the 5th position.

**Importance in Research:**

IdU is a crucial tool in various research areas, primarily due to its unique properties:

* **Thymidine Analog:** IdU is an analog of thymidine, a base found in DNA. This means it can be incorporated into DNA during replication.
* **Radioactive Labeling:** The iodine atom in IdU can be made radioactive (e.g., 125I). This allows researchers to track the incorporation of IdU into DNA, providing insights into:
* **DNA Replication:** Monitoring the rate and timing of DNA synthesis.
* **Cell Proliferation:** Quantifying how rapidly cells are dividing.
* **DNA Damage Repair:** Studying the repair mechanisms involved in DNA damage.
* **Immunofluorescence Staining:** IdU can be used in immunofluorescence microscopy to visualize DNA replication.
* **Other Applications:**
* **Cancer Research:** Studying the growth and spread of cancer cells.
* **Neurobiology:** Understanding neuronal development and plasticity.

**Key Points:**

* **High Affinity for DNA Polymerases:** IdU is readily incorporated into DNA by DNA polymerases.
* **Toxicity:** IdU can be toxic in high doses, as its incorporation into DNA can disrupt normal DNA function.
* **Antiviral Activity:** IdU has antiviral activity against herpesviruses.

**In summary:**

IdU is a valuable tool in research due to its ability to mimic thymidine and its potential for radioactive labeling and immunofluorescence applications. It allows scientists to investigate various cellular processes related to DNA replication, cell division, and DNA damage repair.

ropidoxuridine: a prodrug of 5-iodo-2'-deoxyuridine and a radiosensitizing agent; RN given refers to erythro-(D)-isomer; structure given in first source [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Cross-References

ID SourceID
PubMed CID9840777
CHEMBL ID2103821
SCHEMBL ID8602575
MeSH IDM0133227

Synonyms (32)

Synonym
5-iodo-2-pyrimidinone-2'-deoxyribose
nsc-726188
ipdr
D08992
93265-81-7
ropidoxuridine (inn/usan)
ipd-r
CHEMBL2103821
3hx21a3sqf ,
ropidoxuridine [usan:inn]
1-(2-deoxy-beta-ribofuranosyl)-5-iodo-2-pyrimidinone
2(1h)-pyrimidinone, 1-(2-deoxy-beta-d-erythro-pentofuranosyl)-5-iodo-
ropidoxuridine
unii-3hx21a3sqf
5-iodo-2-pyrimidinone 2' deoxyribonucleoside
ropidoxuridine [usan]
1-(2-deoxy-.beta.-d-erythro-pentofuranosyl)-5-iodopyrimidin-2(1h)-one
ropidoxuridine [inn]
2(1h)-pyrimidinone, 1-(2-deoxy-.beta.-d-erythro-pentofuranosyl)-5-iodo-
SCHEMBL8602575
5-iodo-2-pyrimidinone-2-deoxyribose
DTXSID00239353
CS-0007768
HY-13742
1-((2r,4s,5r)-4-hydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)-5-iodopyrimidin-2(1h)-one
DB06485
Q27257237
D96122
MS-25135
A901121
1-[(2r,4s,5r)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-5-iodopyrimidin-2-one
AKOS040742573

Research Excerpts

Pharmacokinetics

ExcerptReferenceRelevance
"A toxicology and pharmacokinetic study of orally administered (po) IPdR (5-3iodo-2-pyrimidinone-2'deoxyribose, NSC-726188) was performed in Fischer-344 rats using a once daily (qd) x 28 days dosing schedule as proposed for an initial phase I clinical trial of IPdR as a radiosensitizer."( 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.
Burback, B; Hong, S; Johnson, JP; Kinsella, MT; Kinsella, TJ; Tosca, PJ, 2008
)
0.35
" These toxicology and pharmacokinetic data were used when considering the design of our initial phase I trial of po IPdR as a clinical radiosensitizer."( 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.
Burback, B; Hong, S; Johnson, JP; Kinsella, MT; Kinsella, TJ; Tosca, PJ, 2008
)
0.35

Dosage Studied

ExcerptRelevanceReference
" administered 5-iodo2-pyrimidinone-2'-deoxyribose (IPdR) given daily for 14 days as a prodrug for 5-iodo-2'-deoxyuridine (IUdR)-mediated tumor radiosensitization, we determined the systemic toxicities and the percentage IUdR-DNA incorporation in normal athymic mouse tissues and a human glioblastoma xenograft (U251) after this dosing schedule of IPdR."( 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.
Davis, TW; Kinsella, TJ; Kunugi, KA; Sands, H; Schupp, J; Vielhuber, KA, 2000
)
0.31
" For the IPdR systemic toxicity and toxicology study, twenty-four male or female ferrets were randomly assigned to four IPdR dosage groups receiving 0, 15, 150, and 1500 mg/kg/day by oral gavage x 14 days prior to sacrifice on study day 15."( 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.
Balis, F; Barnett, J; Berry, SE; Davis, TW; Hwang, HS; Kinsella, TJ; Sands, H; Schupp, JE; Warren, K, 2000
)
0.31
" The purpose of this study is to measure the effect of different drug dosing schedules on tumor radiosensitization and therapeutic index in human glioblastoma xenografts."( Schedule-dependent drug effects of oral 5-iodo-2-pyrimidinone-2'-deoxyribose as an in vivo radiosensitizer in U251 human glioblastoma xenografts.
Kinsella, TJ; Radivoyevitch, T; Schupp, JE; Seo, Y; Yan, T, 2005
)
0.33
"A toxicology and pharmacokinetic study of orally administered (po) IPdR (5-3iodo-2-pyrimidinone-2'deoxyribose, NSC-726188) was performed in Fischer-344 rats using a once daily (qd) x 28 days dosing schedule as proposed for an initial phase I clinical trial of IPdR as a radiosensitizer."( 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.
Burback, B; Hong, S; Johnson, JP; Kinsella, MT; Kinsella, TJ; Tosca, PJ, 2008
)
0.35
" Animals were monitored for clinical signs during and following treatment with full necropsy of one-half of each dosage group at day 29 and 57."( 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.
Burback, B; Hong, S; Johnson, JP; Kinsella, MT; Kinsella, TJ; Tosca, PJ, 2008
)
0.35
" Recently, a once-daily IPdR dosing up to 2000/mg/kg for 28 days in Fischer-344 rats showed reversible mild-to-moderate systemic toxicities without any severe or life-threatening toxicities."( IPdR: a novel oral radiosensitizer.
Berk, G; Cheng, YC; Kinsella, TJ; Saif, MW, 2007
)
0.34
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (16)

TimeframeStudies, This Drug (%)All Drugs %
pre-19901 (6.25)18.7374
1990's4 (25.00)18.2507
2000's7 (43.75)29.6817
2010's3 (18.75)24.3611
2020's1 (6.25)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 12.17

According to the monthly volume, diversity, and competition of internet searches for this compound, as well the volume and growth of publications, there is estimated to be weak demand-to-supply ratio for research on this compound.

MetricThis Compound (vs All)
Research Demand Index12.17 (24.57)
Research Supply Index2.94 (2.92)
Research Growth Index5.11 (4.65)
Search Engine Demand Index0.00 (26.88)
Search Engine Supply Index0.00 (0.95)

This Compound (12.17)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials2 (12.50%)5.53%
Reviews2 (12.50%)6.00%
Case Studies1 (6.25%)4.05%
Observational0 (0.00%)0.25%
Other11 (68.75%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]