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54-42-2 molecular structure
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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 and InChIs

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

Cite this record

CBID:134 http://www.chembase.cn/molecule-134.html

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NAMES AND DATABASE IDS

NAMES AND DATABASE IDS

Names Database IDs
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
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
Spectanefran
Stoxil
Synmiol
Virudox
Synonyms
Iodoxuridine
Iododeoxyridine
Idoxuridinum [INN-Latin]
Idoxuridina [INN-Spanish]
Idoxuridin
Idossuridina [DCIT]
IDU
5IUDR
5IDU
Allergan 201
Allergan 211
ID2
IDUR
IUDR
1-(2-Deoxy-β-D-ribofuranosyl)-5-iodouracil
2′-Deoxy-5-iodouridine
5-IUdR
IdUrd
Idoxuridine
5-Iodo-2′-deoxyuridine
5-Iodo-2'-deoxyuridine
(+)-5-Iodo-2'-deoxyuridine
Idoxuridine
(+)-5-碘-2'-脱氧尿苷
CAS Number
54-42-2
EC Number
200-207-8
MDL Number
MFCD00134656
Beilstein Number
30397
Merck Index
144891
PubChem SID
24896108
160963597
46507573
PubChem CID
5905

CALCULATED PROPERTIES

CALCULATED PROPERTIES

JChem ALOGPS 2.1
Acid pKa 8.056083  H Acceptors
H Donor LogD (pH = 5.5) -0.5301102 
LogD (pH = 7.4) -0.6144564  Log P -0.5289186 
Molar Refractivity 64.4039 cm3 Polarizability 25.542524 Å3
Polar Surface Area 99.1 Å2 Rotatable Bonds
Lipinski's Rule of Five true 
Log P -0.7  LOG S -1.18 
Solubility (Water) 2.34e+01 g/l 

PROPERTIES

PROPERTIES

Physical Property Safety Information Product Information Bioassay(PubChem)
Solubility
<0.01 g/100 mL expand Show data source
Melting Point
194 °C(lit.) expand Show data source
ca 190°C dec. expand Show data source
Optical Rotation
[α]20/D +29±2°, c = 1% in 1 M NaOH expand Show data source
Hydrophobicity(logP)
-0.5 expand Show data source
Storage Warning
Air & Light Sensitive expand Show data source
RTECS
YU7700000 expand Show data source
European Hazard Symbols
Toxic Toxic (T) expand Show data source
X expand Show data source
Harmful Harmful (Xn) expand Show data source
MSDS Link
Download expand Show data source
German water hazard class
3 expand Show data source
Risk Statements
40-63 expand Show data source
45-46-61 expand Show data source
63-36/37/38-62-68 expand Show data source
Safety Statements
26-36/37 expand Show data source
36/37 expand Show data source
53-45 expand Show data source
TSCA Listed
expand Show data source
GHS Pictograms
GHS07 expand Show data source
GHS08 expand Show data source
GHS Signal Word
Warning expand Show data source
GHS Hazard statements
H315-H319-H335-H341-H361 expand Show data source
H351-H361 expand Show data source
GHS Precautionary statements
P261-P281-P305 + P351 + P338 expand Show data source
P281-P201-P202-P308+P313-P405-P501A expand Show data source
Personal Protective Equipment
Eyeshields, Faceshields, Gloves, type P2 (EN 143) respirator cartridges expand Show data source
Storage Temperature
2-8°C expand Show data source
Purity
≥98.0% (NT) expand Show data source
≥99% (HPLC) expand Show data source
98% expand Show data source
Empirical Formula (Hill Notation)
C9H11IN2O5 expand Show data source

DETAILS

DETAILS

DrugBank DrugBank Sigma Aldrich Sigma Aldrich
DrugBank - DB00249 external link
Item Information
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 external link
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 external link
Other Notes
An efficient inducing agent of oncornaviruses in mouse cells1; Potent inhibitor of thymidine kinase and thymidylate synthetase2; Incorporation into viral DNA3

REFERENCES

REFERENCES

From Suppliers Google Scholar IconGoogle Scholar PubMed iconPubMed Google Books IconGoogle Books
  • • 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
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PATENTS

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