1-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-5-iodo-1,2,3,4-tetrahydropyrimidine-2,4-dione

• ChemBase ID: 134
• Molecular Formular: C9H11IN2O5
• Molecular Mass: 354.09851
• Monoisotopic Mass: 353.97126946
• SMILES: Ic1cn([C@@H]2O[C@@H]([C@@H](O)C2)CO)c(=O)[nH]c1=O
• Canonical SMILES: OC[C@H]1O[C@H](C[C@@H]1O)n1cc(I)c(=O)[nH]c1=O
• InChI: 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
• InChIKey: XQFRJNBWHJMXHO-RRKCRQDMSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 1-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-5-iodo-1,2,3,4-tetrahydropyrimidine-2,4-dione
• IUPAC Traditional name: idoxuridine
• Brand Name: Spectanefran; Stoxil; Synmiol; Virudox; Antizona; Dendrid; Emanil; Heratil; Herpe-Gel; Herpes-Gel; Herpesil; Herpid; Herpidu; Herplex; Herplex Liquifilm; Idexur; Idoxene; Idu Oculos; Iducher; Idulea; Iduridin; Iduviran; Joddeoxiuridin; Kerecid; Ophthalmadine
• Synonyms: (+)-5-Iodo-2'-deoxyuridine; 1-(2-Deoxy-β-D-ribofuranosyl)-5-iodouracil; 2′-Deoxy-5-iodouridine; 5-IUdR; IdUrd; Idoxuridine; 5-Iodo-2′-deoxyuridine; Iodoxuridine; Iododeoxyridine; Idoxuridinum [INN-Latin]; Idoxuridina [INN-Spanish]; Idoxuridin; Idossuridina [DCIT]; IDU; 5IUDR; 5IDU; Allergan 201; Allergan 211; ID2; IDUR; IUDR; Idoxuridine; 5-Iodo-2'-deoxyuridine; (+)-5-碘-2'-脱氧尿苷

Database IDs

• CAS Number: 54-42-2
• EC Number: 200-207-8
• MDL Number: MFCD00134656
• Beilstein Number: 30397
• Merck Index: 144891
• PubChem SID: 46507573; 24896108; 160963597
• PubChem CID: 5905

CALCULATED PROPERTIES

JChem

• Acid pKa: 8.056083
• H Acceptors: 5
• H Donor: 3
• LogD (pH = 5.5): -0.5301102
• LogD (pH = 7.4): -0.6144564
• Log P: -0.5289186
• Molar Refractivity: 64.4039 cm^3
• Polarizability: 25.542524 Å^3
• Polar Surface Area: 99.1 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: -0.7
• LOG S: -1.18
• Solubility (Water): 2.34e+01 g/l

PROPERTIES

Physical Property

• Solubility: <0.01 g/100 mL
• Melting Point: 194 °C(lit.); ca 190°C dec.
• Optical Rotation: [α]20/D +29±2°, c = 1% in 1 M NaOH
• Hydrophobicity(logP): -0.5

Safety Information

• Storage Warning: Air & Light Sensitive
• RTECS: YU7700000
• European Hazard Symbols: Toxic (T); X; Harmful (Xn)
• German water hazard class: 3
• Risk Statements: 40-63; 45-46-61; 63-36/37/38-62-68
• Safety Statements: 26-36/37; 36/37; 53-45
• TSCA Listed: 是
• GHS Pictograms: GHS07; GHS08
• GHS Signal Word: Warning
• GHS Hazard statements: H315-H319-H335-H341-H361; H351-H361
• GHS Precautionary statements: P261-P281-P305 + P351 + P338; P281-P201-P202-P308+P313-P405-P501A
• Personal Protective Equipment: Eyeshields, Faceshields, Gloves, type P2 (EN 143) respirator cartridges
• Storage Temperature: 2-8°C

Product Information

• Purity: ≥98.0% (NT); ≥99% (HPLC); 98%
• Empirical Formula (Hill Notation): C9H11IN2O5

DETAILS

DrugBank - DB00249

• Drug Groups: approved
• Description: An analog of deoxyuridine that inhibits viral DNA synthesis. The drug is used as an antiviral agent. [PubChem]
• Indication: For use in keratoconjunctivitis and keratitis caused by herpes simplex virus.
• Pharmacology: In chemical structure idoxuridine closely approximates the configuration of thymidine, one of the four building blocks of DNA (the genetic material of the Herpes virus). As a result, idoxuridine is able to replace thymidine in the enzymatic step of viral replication or "growth". The consequent production of faulty DNA results in a pseudostructure which cannot infect or destroy tissue. In short, by pre-empting a vital building block in the genetic material of the Herpes simplex virus, Herplex-D topical solution destroys the infective and destructive capacity of the viral material. The virus infected cell may only be attacked during the period of active synthesis of DNA. This occurs early in the development of the Herpes simplex lesion, but at different times in different cells. Therefore, ideally, the affected area should remain saturated with the antiviral agent.
• Toxicity: Hypersensitivity or increased sensitivity of eyes to light. LD₅₀=3080 mg/kg (orally in mice).
• Affected Organisms: Herpes simplex virus
• Biotransformation: Idoxuridine is rapidly inactivated by deaminases or nucleotidases.
• Absorption: Systemic absorption is unlikely following ocular administration even when nasolacrimal secretions are swallowed, since vidarabine is rapidly deaminated in the gastrointestinal tract.
• References: Seth AK, Misra A, Umrigar D: Topical liposomal gel of idoxuridine for the treatment of herpes simplex: pharmaceutical and clinical implications. Pharm Dev Technol. 2004 Aug;9(3):277-89. [Pubmed] ; Otto SE: Radiopharmaceuticals (Strontium 89) and radiosensitizers (idoxuridine). J Intraven Nurs. 1998 Nov-Dec;21(6):335-7. [Pubmed] ; Fauth E, Zankl H: Comparison of spontaneous and idoxuridine-induced micronuclei by chromosome painting. Mutat Res. 1999 Apr 6;440(2):147-56. [Pubmed]
• External Links: Wikipedia; Drugs.com

Sigma Aldrich - I7125

包装
5, 25 g in glass bottle
Application
5-Iodo-2′-deoxyuridine (5-IUdR; IdUrd) is a pyrimidine analog (halogenated thymidine) that has antiviral activity agains vaccinia virus (orthopoxviruses). IdUrd is used as a radiosensitizer in human cancer studies.

Sigma Aldrich - 57830

Other Notes
An efficient inducing agent of oncornaviruses in mouse cells1; Potent inhibitor of thymidine kinase and thymidylate synthetase2; Incorporation into viral DNA3

REFERENCES

• Seth AK, Misra A, Umrigar D: Topical liposomal gel of idoxuridine for the treatment of herpes simplex: pharmaceutical and clinical implications. Pharm Dev Technol. 2004 Aug;9(3):277-89. Pubmed
• Otto SE: Radiopharmaceuticals (Strontium 89) and radiosensitizers (idoxuridine). J Intraven Nurs. 1998 Nov-Dec;21(6):335-7. Pubmed
• Fauth E, Zankl H: Comparison of spontaneous and idoxuridine-induced micronuclei by chromosome painting. Mutat Res. 1999 Apr 6;440(2):147-56. Pubmed