NAV

Ropidoxuridine

This drug entry is a stub and has not been fully annotated. It is scheduled to be annotated soon.

Identification

Generic Name
Ropidoxuridine
DrugBank Accession Number
DB06485
Background

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 brain tumor.

Type
Small Molecule
Groups
Investigational
Structure
3D
Similar Structures
Weight
Average: 338.101
Monoisotopic: 337.97635
Chemical Formula
C9H11IN2O4
Synonyms
  • 1-(2-DEOXY-.BETA.-D-ERYTHRO-PENTOFURANOSYL)-5-IODOPYRIMIDIN-2(1H)-ONE
  • 2(1H)-PYRIMIDINONE, 1-(2-DEOXY-.BETA.-D-ERYTHRO-PENTOFURANOSYL)-5-IODO-
  • 5-iodo-2-pyrimidinone-2'-deoxyribose
  • Ropidoxuridine
External IDs
  • IPD-R
  • IPDR
  • NSC-726188
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Pharmacology

Indication

Investigated for use/treatment in cancer/tumors (unspecified).

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Contraindications & Blackbox Warnings
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Pharmacodynamics

Not Available

Mechanism of action
Not Available
Absorption

Not Available

Volume of distribution

Not Available

Protein binding

Not Available

Metabolism
Not Available
Route of elimination

Not Available

Half-life

Not Available

Clearance

Not Available

Adverse Effects
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Toxicity

Not Available

Pathways
Not Available
Pharmacogenomic Effects/ADRs Browse all" title="About SNP Mediated Effects/ADRs" id="snp-actions-info" class="drug-info-popup" href="javascript:void(0);">
Not Available

Interactions

Drug Interactions Learn More" title="About Drug Interactions" id="structured-interactions-info" class="drug-info-popup" href="javascript:void(0);">
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
Not Available
Food Interactions
Not Available

Categories

Drug Categories
Chemical TaxonomyProvided by Classyfire
Description
This compound belongs to the class of organic compounds known as pyrimidine 2'-deoxyribonucleosides. These are compounds consisting of a pyrimidine linked to a ribose which lacks a hydroxyl group at position 2.
Kingdom
Organic compounds
Super Class
Nucleosides, nucleotides, and analogues
Class
Pyrimidine nucleosides
Sub Class
Pyrimidine 2'-deoxyribonucleosides
Direct Parent
Pyrimidine 2'-deoxyribonucleosides
Alternative Parents
Pyrimidones / Halopyrimidines / Hydropyrimidines / Aryl iodides / Tetrahydrofurans / Heteroaromatic compounds / Secondary alcohols / Oxacyclic compounds / Azacyclic compounds / Primary alcohols
show 5 more
Substituents
Alcohol / Aromatic heteromonocyclic compound / Aryl halide / Aryl iodide / Azacycle / Halopyrimidine / Heteroaromatic compound / Hydrocarbon derivative / Hydropyrimidine / Organic nitrogen compound
show 15 more
Molecular Framework
Aromatic heteromonocyclic compounds
External Descriptors
Not Available
Affected organisms
Not Available

Chemical Identifiers

UNII
3HX21A3SQF
CAS number
93265-81-7
InChI Key
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
IUPAC Name
1-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-5-iodo-1,2-dihydropyrimidin-2-one
SMILES
OC[C@H]1O[C@H](C[C@@H]1O)N1C=C(I)C=NC1=O

References

General References
Not Available
ChemSpider
8016494
ChEMBL
CHEMBL2103821
ZINC
ZINC000006091380

Clinical Trials

Clinical Trials Learn More" title="About Clinical Trials" id="clinical-trials-info" class="drug-info-popup" href="javascript:void(0);">
PhaseStatusPurposeConditionsCount
1Active Not RecruitingTreatmentAdvanced Bile Duct Carcinoma / Stage II Esophageal Cancer AJCC v7 / Stage II Pancreatic Cancer AJCC v6 and v7 / Stage IIA Esophageal Cancer AJCC v7 / Stage IIA Pancreatic Cancer AJCC v6 and v7 / Stage IIB Esophageal Cancer AJCC v7 / Stage IIB Pancreatic Cancer AJCC v6 and v7 / Stage III Colon Cancer AJCC v7 / Stage III Esophageal Cancer AJCC v7 / Stage III Gastric Cancer AJCC v7 / Stage III Liver Cancer / Stage III Pancreatic Cancer AJCC v6 and v7 / Stage III Rectal Cancer AJCC v7 / Stage III Small Intestinal Cancer AJCC v7 / Stage IIIA Colon Cancer AJCC v7 / Stage IIIA Esophageal Cancer AJCC v7 / Stage IIIA Gastric Cancer AJCC v7 / Stage IIIA Rectal Cancer AJCC v7 / Stage IIIA Small Intestinal Cancer AJCC v7 / Stage IIIB Colon Cancer AJCC v7 / Stage IIIB Esophageal Cancer AJCC v7 / Stage IIIB Gastric Cancer AJCC v7 / Stage IIIB Rectal Cancer AJCC v7 / Stage IIIB Small Intestinal Cancer AJCC v7 / Stage IIIC Colon Cancer AJCC v7 / Stage IIIC Esophageal Cancer AJCC v7 / Stage IIIC Gastric Cancer AJCC v7 / Stage IIIC Rectal Cancer AJCC v7 / Stage IV Colon Cancer AJCC v7 / Stage IV Esophageal Cancer AJCC v7 / Stage IV Gastric Cancer AJCC v7 / Stage IV Liver Cancer / Stage IV Pancreatic Cancer AJCC v6 and v7 / Stage IV Rectal Cancer AJCC v7 / Stage IV Small Intestinal Cancer AJCC v7 / Stage IVA Colon Cancer AJCC v7 / Stage IVA Liver Cancer / Stage IVA Rectal Cancer AJCC v7 / Stage IVB Colon Cancer AJCC v7 / Stage IVB Liver Cancer / Stage IVB Rectal Cancer AJCC v71
1Active Not RecruitingTreatmentBrain Metastases / Hematopoietic and Lymphoid System Neoplasm / Malignant Solid Neoplasms1
1CompletedTreatmentLymphoma / Neoplasm1
1TerminatedTreatmentLocally Advanced Rectal Carcinoma / Rectal Adenocarcinoma / Stage II Rectal Cancer AJCC v8 / Stage III Rectal Cancer AJCC v81

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage Forms
Not Available
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
Not Available
Predicted Properties
PropertyValueSource
Water Solubility3.13 mg/mLALOGPS
logP-0.63ALOGPS
logP-0.32Chemaxon
logS-2ALOGPS
pKa (Strongest Acidic)13.89Chemaxon
pKa (Strongest Basic)-3Chemaxon
Physiological Charge0Chemaxon
Hydrogen Acceptor Count5Chemaxon
Hydrogen Donor Count2Chemaxon
Polar Surface Area82.36 Å2Chemaxon
Rotatable Bond Count2Chemaxon
Refractivity63.51 m3·mol-1Chemaxon
Polarizability25.32 Å3Chemaxon
Number of Rings2Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterYesChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleNoChemaxon
Predicted ADMET Features
Not Available

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSsplash10-0036-9053000000-2f793ec3be5384e8449a
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-0079-2159000000-abcc1e9654bf8ae09747
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-000j-0179000000-5cb8281cea9c2af9a2ca
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-00di-6290000000-4051824393f4c224b9c1
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-00di-2290000000-484d60b11a53711bbc61
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-0096-9784000000-af6b5a9050e6c032ab46
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-002f-9880000000-d5462d20abb1cf98f003
Predicted 1H NMR Spectrum1D NMRNot Applicable
Predicted 13C NMR Spectrum1D NMRNot Applicable
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-160.5516
predicted
DeepCCS 1.0 (2019)
[M+H]+162.94717
predicted
DeepCCS 1.0 (2019)
[M+Na]+168.8597
predicted
DeepCCS 1.0 (2019)

Drug created at March 19, 2008 16:34 / Updated at July 18, 2023 22:56