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Also known as: 5-iodo-2'-deoxyuridine, 54-42-2, 5-iododeoxyuridine, Idoxuridin, Iododeoxyridine, Iodoxuridine

Molecular Formula

C₉H₁₁IN₂O₅

Molecular Weight

354.10 g/mol

InChI Key

XQFRJNBWHJMXHO-RRKCRQDMSA-N

FDA UNII

LGP81V5245

An analog of DEOXYURIDINE that inhibits viral DNA synthesis. The drug is used as an antiviral agent.

Idoxuridine is a Nucleoside Analog Antiviral.

1 2D Structure

Idoxuridine

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

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

2.1.2 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

2.1.3 InChI Key

XQFRJNBWHJMXHO-RRKCRQDMSA-N

2.1.4 Canonical SMILES

C1C(C(OC1N2C=C(C(=O)NC2=O)I)CO)O

2.1.5 Isomeric SMILES

C1[C@@H]([C@H](O[C@H]1N2C=C(C(=O)NC2=O)I)CO)O

2.2 Other Identifiers

2.2.1 UNII

LGP81V5245

2.3 Synonyms

2.3.1 MeSH Synonyms

1. 123i-labeled Idoxuridine

2. 125i-labeled Idoxuridine

3. 131i-labeled Idoxuridine

4. 3h-labeled Idoxuridine

5. 5 Iodo 2' Deoxyuridine

6. 5 Iododeoxyuridine

7. 5-iodo-2'-deoxyuridine

8. 5-iododeoxyuridine

9. Allergan 211

10. Herplex Liquifilm

11. Idoxuridine, 123i Labeled

12. Idoxuridine, 123i-labeled

13. Idoxuridine, 125i Labeled

14. Idoxuridine, 125i-labeled

15. Idoxuridine, 131i Labeled

16. Idoxuridine, 131i-labeled

17. Idoxuridine, 3h Labeled

18. Idoxuridine, 3h-labeled

19. Idoxuridine, Radical Ion (+1)

20. Idoxuridine, Radical Ion (1-)

21. Iododeoxyuridine

22. Iudr

23. Kerecide

24. Liquifilm, Herplex

25. Nsc 39661

26. Nsc-39661

27. Nsc39661

28. Oftan Idu

29. Oftan-idu

30. Oftanidu

31. Sk And F-14287

32. Stoxil

2.3.2 Depositor-Supplied Synonyms

1. 5-iodo-2'-deoxyuridine

2. 54-42-2

3. 5-iododeoxyuridine

4. Idoxuridin

5. Iododeoxyridine

6. Iodoxuridine

7. Joddeoxiuridin

8. 2'-deoxy-5-iodouridine

9. Herplex

10. Stoxil

11. Allergan 211

12. Iudr

13. (+)-5-iodo-2'-deoxyuridine

14. 5iudr

15. Idur

16. Idoxuridinum

17. Virudox

18. Dendrid

19. 5-iudr

20. Idu

21. Idoxuridina

22. Allergan 201

23. 5-iodouracil Deoxyriboside

24. Idossuridina [dcit]

25. Idoxene

26. Iduridin

27. Kerecid

28. 1-(2-deoxy-beta-d-ribofuranosyl)-5-iodouracil

29. Iododeoxyuridine

30. Sk&f-14287

31. Allergan-211

32. 5idu

33. 1beta-d-2'-deoxyribofuranosyl-5-iodouracil

34. Nsc-39661

35. 1-beta-d-2'-deoxyribofuranosyl-5-iodouracil

36. Sk&f 14287

37. Uridine, 2'-deoxy-5-iodo-

38. Chebi:147675

39. Nsc 39661

40. (+)-5-iodo-2-deoxyuridine

41. 1-((2r,4s,5r)-4-hydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)-5-iodopyrimidine-2,4(1h,3h)-dione

42. Antizona

43. Heratil

44. Lgp81v5245

45. Skf 14287

46. Id2

47. Iduoculos

48. Idurd

49. Mfcd00134656

50. 1-[(2r,4s,5r)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-5-iodopyrimidine-2,4-dione

51. Dsstox_cid_25238

52. Dsstox_rid_80769

53. Dsstox_gsid_45238

54. Idoxuridinum [inn-latin]

55. Idoxuridina [inn-spanish]

56. Idossuridina

57. 5-iododesoxyuridine

58. 5-iodo-deoxyuridine

59. Ccris 2827

60. Sr-05000001510

61. Einecs 200-207-8

62. Brn 0030397

63. Unii-lgp81v5245

64. Ai3-50861

65. Hsdb 7479

66. Cas-54-42-2

67. Ncgc00016243-01

68. Dendrid (tn)

69. Uracil, 5-iodo-1-(2-deoxy-beta-d-ribofuranosyl)-

70. Idoxuridine [usan:usp:inn:ban:jan]

71. 5-iodo-2'deoxyuridine

72. Herplex (tn)

73. Idoxuridine [mi]

74. Prestwick3_000018

75. Idoxuridine [inn]

76. Idoxuridine [jan]

77. Idoxuridine [hsdb]

78. Chembl788

79. Epitope Id:138107

80. Idoxuridine [vandf]

81. 5-i-2'-durd

82. Schembl3683

83. 5-iodo-2 Inverted Exclamation Marka-deoxyuridine

84. Idoxuridine [mart.]

85. Bspbio_000055

86. Idoxuridine [usp-rs]

87. Idoxuridine [who-dd]

88. Idoxuridine [who-ip]

89. 4-24-00-01235 (beilstein Handbook Reference)

90. Mls002154175

91. 5-iodo-2-deoxyuridine

92. Bpbio1_000061

93. Idoxuridine (jp17/usp/inn)

94. Dtxsid2045238

95. Schembl15850897

96. 2'-desoxy-5-iodouridine

97. Idoxuridine [orange Book]

98. Hms2090m10

99. Hms2095c17

100. Hms2230e10

101. Hms3712c17

102. Idoxuridine [ep Monograph]

103. Idoxuridine [usp Impurity]

104. Idoxuridine [usp Monograph]

105. Bcp29428

106. Hy-b0307

107. Idoxuridinum [who-ip Latin]

108. Zinc3834173

109. 5-iudr; Idu; Idurd; Idoxuridine

110. Tox21_110324

111. Bdbm50370388

112. S1883

113. Akos015920431

114. Tox21_110324_1

115. (+)-5-iodo-2'-deoxyuridine, 98%

116. Ac-8219

117. Ccg-220018

118. Db00249

119. Smp2_000072

120. Ncgc00179673-01

121. Ncgc00179673-03

122. Ncgc00179673-05

123. As-13469

124. Smr001233472

125. Idoxuridine 100 Microg/ml In Acetonitrile

126. Db-009133

127. 5-iodo-2'-deoxyuridine, >=99% (hplc)

128. I0258

129. Sw198484-2

130. 1-(2-deoxy-ss -d-ribofuranosyl)-5-iodouracil

131. D00342

132. 134i656

133. Q409765

134. J-009907

135. J-700180

136. Sr-05000001510-1

137. Sr-05000001510-3

138. Sr-05000001510-4

139. Brd-k76634210-001-14-7

140. Idoxuridine, European Pharmacopoeia (ep) Reference Standard

141. Idoxuridine, United States Pharmacopeia (usp) Reference Standard

142. 1-[(2r,4s,5r)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-5-iodo-1,2,3,4-tetrahydropyrimidine-2,4-dione

143. 1-[(2r,4s,5r)-4-hydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl]-5-iodo-pyrimidine-2,4-dione

2.4 Create Date

2005-06-24

3 Chemical and Physical Properties

Molecular Formula	C₉H₁₁IN₂O₅
Molecular Weight	354.10 g/mol
XLogP3	-1
Hydrogen Bond Donor Count	3
Hydrogen Bond Acceptor Count	5
Rotatable Bond Count	2
Exact Mass	353.97127 g/mol
Monoisotopic Mass	353.97127 g/mol
Topological Polar Surface Area	99.1 Å²
Heavy Atom Count	17
Formal Charge	0
Complexity	386
Isotope Atom Count	0
Defined Atom Stereocenter Count	3
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	1

4 Drug and Medication Information

4.1 Drug Information

1 of 4
Drug Name	Dendrid
PubMed Health	Idoxuridine (Into the eye)
Drug Classes	Antiviral
Drug Label	Dendrid (idoxuridine) is an antiviral chemotherapeutic agent prepared in a sterile buffered isotonic solution. The active ingredient is represented by the chemical structure:Established name:IdoxuridineChemical name:Uridine, 2-deoxy-5-iodo-Each...
Active Ingredient	Idoxuridine
Dosage Form	Solution/drops
Route	Ophthalmic
Strength	0.1%
Market Status	Prescription
Company	Alcon

2 of 4
Drug Name	Herplex
Active Ingredient	Idoxuridine
Dosage Form	Solution/drops
Route	Ophthalmic
Strength	0.1%
Market Status	Prescription
Company	Allergan

3 of 4
Drug Name	Dendrid
PubMed Health	Idoxuridine (Into the eye)
Drug Classes	Antiviral
Drug Label	Dendrid (idoxuridine) is an antiviral chemotherapeutic agent prepared in a sterile buffered isotonic solution. The active ingredient is represented by the chemical structure:Established name:IdoxuridineChemical name:Uridine, 2-deoxy-5-iodo-Each...
Active Ingredient	Idoxuridine
Dosage Form	Solution/drops
Route	Ophthalmic
Strength	0.1%
Market Status	Prescription
Company	Alcon

4 of 4
Drug Name	Herplex
Active Ingredient	Idoxuridine
Dosage Form	Solution/drops
Route	Ophthalmic
Strength	0.1%
Market Status	Prescription
Company	Allergan

4.2 Therapeutic Uses

Antiviral

O'Neil, M.J. (ed.). The Merck Index - An Encyclopedia of Chemicals, Drugs, and Biologicals. 13th Edition, Whitehouse Station, NJ: Merck and Co., Inc., 2001., p. 878

Idoxuridine is indicated in the treatment of keratitis caused by herpes simplex virus (HSV). /Included in US product label/

Thomson/Micromedex. Drug Information for the Health Care Professional. Volume 1, Greenwood Village, CO. 2006.

Idoxuridine is indicated in the treatment of keratitis caused by vaccinia virus. /Not included in US product label/

Thomson/Micromedex. Drug Information for the Health Care Professional. Volume 1, Greenwood Village, CO. 2006.

Idoxuridine is used in the treatment of keratoconjunctivitis caused by herpes simplex virus (HSV). /Not included in US product label/

Thomson/Micromedex. Drug Information for the Health Care Professional. Volume 1, Greenwood Village, CO. 2006.

Idoxuridine has no effect on accumulated scarring, vascularization, or progressive loss of vision that may result from the infection. It also has no effect on corneal inflammation that may follow HSV keratitis when the virus is absent, nor on adenoviral keratoconjunctivitis. /Not included in US product label/

Thomson/Micromedex. Drug Information for the Health Care Professional. Volume 1, Greenwood Village, CO. 2006.

4.3 Drug Warning

Patients sensitive to iodine or iodine-containing preparations may be sensitive to this medication also.

Thomson/Micromedex. Drug Information for the Health Care Professional. Volume 1, Greenwood Village, CO. 2006.

The following side/adverse effects have been selected on the basis of their potential clinical significance: Incidence less frequent /include/ Hypersensitivity (itching, redness, swelling, pain, or other sign of irritation not present before therapy), or increased sensitivity of eyes to light; Incidence rare: Corneal clouding (blurring, dimming, or haziness of vision).

Thomson/Micromedex. Drug Information for the Health Care Professional. Volume 1, Greenwood Village, CO. 2006.

FDA Pregnancy Risk Category: C /RISK CANNOT BE RULED OUT. Adequate, well controlled human studies are lacking, and animal studies have shown risk to the fetus or are lacking as well. There is a chance of fetal harm if the drug is given during pregnancy; but the potential benefits may outweigh the potential risk./

Briggs, G.G, R.K. Freeman, S.J. Yaffe. A Reference Guide to Fetal and Neonatal Risk. Drugs in Pregnancy and Lactation. 4th ed. Baltimore, MD: Williams & Wilkins 1994., p. 435

The ... toxicity of topical applications of 30% idoxuridine in dimethyl sulfoxide, dimethyl sulfoxide alone, or saline in 96 recurrent and 39 first episodes of genital herpes simplex virus (HSV) infection were compared. ...Complications in patients given idoxuridine in dimethyl sulfoxide included local burning, generalized contact dermatitis, and vulvar carcinoma in situ. Thirty percent idoxuridine in dimethyl sulfoxide has no effect on clinical manifestations of genital HSV infection and may be hazardous.

PMID:7047788 Silvestri DL et al; JAMA 248 (8): 953-9 (1982)

4.4 Drug Indication

For use in keratoconjunctivitis and keratitis caused by herpes simplex virus.

5 Pharmacology and Biochemistry

5.1 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.

5.2 MeSH Pharmacological Classification

Antiviral Agents

Agents used in the prophylaxis or therapy of VIRUS DISEASES. Some of the ways they may act include preventing viral replication by inhibiting viral DNA polymerase; binding to specific cell-surface receptors and inhibiting viral penetration or uncoating; inhibiting viral protein synthesis; or blocking late stages of virus assembly. (See all compounds classified as Antiviral Agents.)

Nucleic Acid Synthesis Inhibitors

Compounds that inhibit cell production of DNA or RNA. (See all compounds classified as Nucleic Acid Synthesis Inhibitors.)

5.3 FDA Pharmacological Classification

5.3.1 Active Moiety

IDOXURIDINE

5.3.2 FDA UNII

LGP81V5245

5.3.3 Pharmacological Classes

Established Pharmacologic Class [EPC] - Nucleoside Analog Antiviral

5.4 ATC Code

D - Dermatologicals

D06 - Antibiotics and chemotherapeutics for dermatological use

D06B - Chemotherapeutics for topical use

D06BB - Antivirals

D06BB01 - Idoxuridine

J - Antiinfectives for systemic use

J05 - Antivirals for systemic use

J05A - Direct acting antivirals

J05AB - Nucleosides and nucleotides excl. reverse transcriptase inhibitors

J05AB02 - Idoxuridine

S - Sensory organs

S01 - Ophthalmologicals

S01A - Antiinfectives

S01AD - Antivirals

S01AD01 - Idoxuridine

5.5 Absorption, Distribution and Excretion

Absorption

Systemic absorption is unlikely following ocular administration even when nasolacrimal secretions are swallowed, since vidarabine is rapidly deaminated in the gastrointestinal tract.

Idoxuridine penetrates the cornea poorly and therefore is ineffective in the treatment of iritis or deep stromal infections.

Thomson/Micromedex. Drug Information for the Health Care Professional. Volume 1, Greenwood Village, CO. 2006.

Idoxuridine crosses the placenta. Studies in humans have not been done.

Thomson/Micromedex. Drug Information for the Health Care Professional. Volume 1, Greenwood Village, CO. 2006.

It is not known whether idoxuridine is distributed into breast milk. However, problems in humans have not been documented.

Thomson/Micromedex. Drug Information for the Health Care Professional. Volume 1, Greenwood Village, CO. 2006.

A reproducible microbiologic assay of microgram quantities of idoxuridine (IDU) in serum, urine, or cerebrospinal fluid is presented. The antiviral assay is not interfered with by type-specific antibody or interferon. During slow intravenous infusions of idox-uridine (4 mg/min) in patients with suspected diagnoses of Herpesvirus hominis encephalitis, the rate of inactivation and/or removal of drug exceeded its administration. During several rapid infusions of idoxuridine (50 mg/min) significant quantities of the drug were found in serum, urine, and cerebrospinal fluid. Idoxuridine is not significantly bound to serum proteins and is not deiodinated in fresh serum or urine in vitro to inactive products (iodouracil, uracil, iodide). It is rapidly excreted into the urine. Inactivation of IDU occurs in tissues. This antiviral assay of IDU in body fluids should be applicable to other viruses and potential antiviral agents.

PMID:4331799 Full text: https://www.ncbi.nlm.nih.gov/pmc/articles/PMC332927 Lerner A et al; J Clin Invest 51 (1): 45-9 (1972)

5.6 Metabolism/Metabolites

Idoxuridine is rapidly inactivated by deaminases or nucleotidases.

Thomson/Micromedex. Drug Information for the Health Care Professional. Volume 1, Greenwood Village, CO. 2006.

5.7 Mechanism of Action

Idoxuridine acts as an antiviral agent by inhibiting viral replication by substituting itself for thymidine in viral DNA. This in turn inhibits thymidylate phosphorylase and viral DNA polymerases from properly functioning. The effect of Idoxuridine results in the inability of the virus to reproduce or to infect/destroy tissue.

Idoxuridine, which closely resembles thymidine, inhibits thymidylic phosphorylase and specific DNA polymerases, which are necessary for the incorporation of thymidine into viral DNA. Idoxuridine is incorporated in place of thymidine into viral DNA, resulting in faulty DNA and the inability to infect or destroy tissue or to reproduce. Idoxuridine is incorporated into mammalian DNA as well.

Thomson/Micromedex. Drug Information for the Health Care Professional. Volume 1, Greenwood Village, CO. 2006.

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