Idoxuridine

Base Information

• Chemical Name: Idoxuridine
• CAS No.: 54-42-2
• Deprecated CAS: 1336-77-2,888-04-0,1556847-71-2,888-04-0
• Molecular Formula: C9H11IN2O5
• Molecular Weight: 354.101
• Hs Code.: 29389090
• European Community (EC) Number: 200-207-8
• UNII: LGP81V5245
• DSSTox Substance ID: DTXSID2045238
• Nikkaji Number: J4.490C
• Wikipedia: Idoxuridine
• Wikidata: Q409765
• NCI Thesaurus Code: C563
• RXCUI: 5653
• Metabolomics Workbench ID: 42650
• ChEMBL ID: CHEMBL788
• Mol file: 54-42-2.mol

Synonyms:123I-Labeled Idoxuridine;125I-Labeled Idoxuridine;131I-Labeled Idoxuridine;3H-Labeled Idoxuridine;5 Iodo 2' deoxyuridine;5 Iododeoxyuridine;5-Iodo-2'-deoxyuridine;5-Iododeoxyuridine;Allergan 211;Herplex Liquifilm;Idoxuridine;Idoxuridine, 123I Labeled;Idoxuridine, 123I-Labeled;Idoxuridine, 125I Labeled;Idoxuridine, 125I-Labeled;Idoxuridine, 131I Labeled;Idoxuridine, 131I-Labeled;Idoxuridine, 3H Labeled;Idoxuridine, 3H-Labeled;Idoxuridine, Radical Ion (+1);Idoxuridine, Radical Ion (1-);Iododeoxyuridine;IUdR;Kerecide;Liquifilm, Herplex;NSC 39661;NSC-39661;NSC39661;Oftan IDU;Oftan-IDU;OftanIDU;SK and F-14287;Stoxil

Chemical Property of Idoxuridine

Chemical Property:

• Appearance/Colour: crystalline solid
• Melting Point: 194 °C(lit.)
• Refractive Index: 30 ° (C=1, 1mol/L NaOH)
• PKA: 8.25(at 25℃)
• PSA: 104.55000
• Density: 2.148 g/cm³
• LogP: -1.21810
• Storage Temp.: 2-8°C
• Sensitive.: Air & Light Sensitive
• Solubility.: DMSO (Slightly, Sonicated), Methanol (Slightly, Heated, Sonicated), Water (Sligh
• Water Solubility.: 1.6 g/L (20 ºC)
• XLogP3: -1
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 2
• Exact Mass: 353.97127
• Heavy Atom Count: 17
• Complexity: 386

Purity/Quality:

99% ^*data from raw suppliers

Idoxuridine ^*data from reagent suppliers

Safty Information:

• Pictogram(s): T,Xn
• Hazard Codes: T,Xn
• Statements: 45-46-61-40-68-62-36/37/38-63
• Safety Statements: 53-45-36-22-36/37-26

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1C(C(OC1N2C=C(C(=O)NC2=O)I)CO)O
• Isomeric SMILES: C1[C@@H]([C@H](O[C@H]1N2C=C(C(=O)NC2=O)I)CO)O
• Recent ClinicalTrials: Combination Chemotherapy Plus Biological Therapy in Treating Patients With Acute Myelogenous Leukemia
• Description: 5-Iodo-2'-deoxyuridine is a nucleoside analog that inhibits the replication of viruses and other DNA-containing organisms. 2'-Deoxy-5-iodouridine also has inhibitory properties on cell nuclei, which may be due to its ability to bind with DNA and prevent the synthesis of RNA or protein.
• Uses: Idoxuridine is an antiviral agent effective against herpes-simplex infections; in ophthalmie eyedrops, ointments, and solutions. 5-Iodo-2'-deoxyuridine is antitumor nucleoside enantiomer thymidine kinase used as potential antiviral agents. Antiviral;Nucleic acid synthesis inhibitors A cytotoxic analog of thymidine, antiviral
• Indications: Idoxuridine (Herplex) is a water-soluble iodinated derivative of deoxyuridine that inhibits several DNA viruses including HSV, VZV, vaccinia, and polyoma virus. The triphosphorylated metabolite of idoxuridine inhibits both viral and cellular DNA synthesis and is also incorporated into DNA. Such modified DNA is susceptible to strand breakage and causes aberrant viral protein synthesis. Because of its significant host cytotoxicity, idoxuridine cannot be used to treat systemic viral infections. The development of resistance to this drug is common.
• Therapeutic Function: Antiviral (ophthalmic)
• Clinical Use: The only FDA-approved use of idoxuridine is in the treatment of herpes simplex infections of the eyelid, conjunctiva conjunctiva, and cornea. It is most effective against surface infections because it has little ability to penetrate the tissues of the eye. intravenous idoxuridine was designated an orphan drug for the treatment of soft tissue sarcoma.

Technology Process of Idoxuridine

There total 16 articles about Idoxuridine which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 100.0%

2'-deoxyuridine (951-78-0,63844-76-8) → 5-Iodo-2'-deoxyuridine (54-42-2,162239-35-2)

Guidance literature:

With iodine; silver nitrate; In methanol; at 40 ℃; for 3h;

DOI:10.1016/j.bmc.2017.03.045 DOI:10.1016/j.bmcl.2018.04.058

Reference yield: 90.0%

3',5'-O-diacetyl-5-iodo-2'-deoxyuridine (1956-30-5) → 5-Iodo-2'-deoxyuridine (54-42-2,162239-35-2)

Guidance literature:

With sodium methylate; In methanol; for 1h; Ambient temperature;

DOI:10.1021/jo00303a033

Reference yield:

2'-deoxyuridine (951-78-0,63844-76-8) + 5-iodouracil (696-07-1) → 5-Iodo-2'-deoxyuridine (54-42-2,162239-35-2) + uracil (66-22-8,144104-68-7,18324-22-6,27072-01-1,2920-92-5,51953-19-6)

Guidance literature:

With thymidine phosphorylase from Escherichia coli (E_.C_. 2.4.2.4) immobilized on Sepabeads EC-EP; In aq. phosphate buffer; at 20 ℃; for 3h; pH=7.5; Reagent/catalyst; Enzymatic reaction;

DOI:10.1016/j.molcatb.2013.05.007

upstream raw materials:

2'-deoxyuridine

3',5'-O-diacetyl-5-iodo-2'-deoxyuridine

5-trimethylstannyl-2'-deoxyuridine

5-iodouracil

Downstream raw materials:

5-iodo-2,3'-anhydro-5'-O-benzoyl-2'-deoxyuridine

5-(1-propynyl)-2'-deoxyuridine

3-(β-D-2-deoxyribofuranosyl)-6-methylfuro[2,3-d]pyrimidin-2-one

5-(4-benzoylthio-1-butynyl)-2'-deoxyuridine

Refernces

• 1、 Kaspar, Felix,Giessmann, Robert T.,Neubauer, Peter,Wagner, Anke,Gimpel, Matthias. "Thermodynamic Reaction Control of Nucleoside Phosphorolysis". supporting information. p. 867 - 876. Retrieved 2020/01/24.
• 2、 Makurat, Samanta,Spisz, Paulina,Kozak, Witold,Rak, Janusz,Zdrowowicz, Magdalena. "5-iodo-4-thio-2′-deoxyuridine as a sensitizer of X-ray induced cancer cell killing". . . Retrieved 2019/05/10.