Description

Idoxuridine (CAS No. 54-42-2), also known as 5-Iodo-2′-deoxyuridine, is a nucleoside analogue with a molecular formula of C₉H₁₁IN₂O₅. This white to off-white crystalline powder is widely recognized for its antiviral properties, particularly against herpes simplex virus (HSV). As a thymidine analogue, it incorporates into viral DNA during replication, leading to faulty genetic material and inhibition of viral proliferation. Idoxuridine is highly soluble in dimethyl sulfoxide (DMSO) and slightly soluble in water, making it suitable for both research and pharmaceutical applications. It is supplied with ≥99% purity (HPLC) and is ideal for virology studies, antiviral drug development, and diagnostic applications. Store at 2-8°C in a tightly sealed container to maintain stability.

Properties

• CAS Number: 54-42-2
• Complexity: 386
• IUPAC Name: 1-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl]-5-iodo-pyrimidine-2,4-dione
• 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
• InChI Key: XQFRJNBWHJMXHO-RRKCRQDMSA-N
• Exact Mass: 353.97127
• Molecular Formula: C9H11IN2O5
• Molecular Weight: 354.10
• SMILES: C1[C@@H]([C@H](O[C@H]1N2C=C(C(=O)NC2=O)I)CO)O
• Topological: 99.1
• Monoisotopic Mass: 353.97127
• Physical Description: Solid
• Color/Form: Crystals from water, triclinic
• Stability/Shelf Life: Idoxuridine is rapidly inactivated by deaminases or nucleotidases. To ensure stability, the ophthalmic solution should not be mixed with other medications. Burning after application or failure to respond to treatment may suggest deterioration of the ophthalmic solution; replace with fresh solution. /Ophthalmic Solution USP/
• Dissociation Constants: pKa = 8.25
• Synonyms: idoxuridine, 5-Iodo-2′-deoxyuridine, 5-Iododeoxyuridine, Iododeoxyridine, Iodoxuridine, Joddeoxiuridin, 2′-Deoxy-5-iodouridine, Herplex, (+)-5-Iodo-2′-deoxyuridine, IUDR, Idoxene, IDUR, Idoxuridina, Idoxuridinum, Iduridin, Kerecid, Virudox, Antizona, Heratil, Iododeoxyuridine, Allergan 201, Dendrid, IDU, 5-IUDR, IdUrd, 1-(2-Deoxy-beta-D-ribofuranosyl)-5-iodouracil, Allergan-211, Idossuridina, Spectanefran, Iduviran, Idexur, Idulea, Idu Oculos, 1beta-D-2′-Deoxyribofuranosyl-5-iodouracil, 1-beta-D-2′-Deoxyribofuranosyl-5-iodouracil, Idoxuridinum [INN-Latin], Idoxuridina [INN-Spanish], CCRIS 2827, CHEBI:147675, EINECS 200-207-8, UNII-LGP81V5245, BRN 0030397, DTXSID2045238, AI3-50861, HSDB 7479, LGP81V5245, Uracil, 5-iodo-1-(2-deoxy-beta-D-ribofuranosyl)-, Uridine, 5-iodo-2′-deoxy-, DTXCID0025238, 2′-DESOXY-5-IODOURIDINE, SKF 14287, 4-24-00-01235 (Beilstein Handbook Reference), Idoxuridine [USAN:USP:INN:BAN:JAN], Idoxuridinum (INN-Latin), Idoxuridina (INN-Spanish), IDOXURIDINE (MART.), IDOXURIDINE [MART.], IDOXURIDINE (USP-RS), IDOXURIDINE [USP-RS], IDOXURIDINE (EP MONOGRAPH), IDOXURIDINE (USP IMPURITY), IDOXURIDINE [EP MONOGRAPH], IDOXURIDINE [USP IMPURITY], IDOXURIDINE (USP MONOGRAPH), IDOXURIDINE [USP MONOGRAPH], Herpes-Gel, Idoxuridine (USAN:USP:INN:BAN:JAN), 5 Iododeoxyuridine, 5 Iodo 2′ deoxyuridine, Idoxurudine, D06BB01, J05AB02, S01AD01, 200-207-8, 54-42-2, Idoxuridin, Stoxil, Allergan 211, 5IUDR, 5-Iodouracil deoxyriboside, Idossuridina [DCIT], SK&F-14287, URIDINE, 2′-DEOXY-5-IODO-, 5IdU, NSC-39661, SK&F 14287, MFCD00134656, 1-((2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)-5-iodopyrimidine-2,4(1H,3H)-dione, ALLERGAN211, 5-Iodo-deoxyuridine, 1-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-5-iodopyrimidine-2,4-dione, ID2, Iduoculos, C9H11IN2O5, 5-Iododesoxyuridine, SR-05000001510, CAS-54-42-2, NCGC00016243-01, Dendrid (TN), 5-iodo-2’deoxyuridine, HERPLEX (TN), IDOXURIDINE [MI], 5-IdU, Prestwick3_000018, IDOXURIDINE [INN], IDOXURIDINE [JAN], IDOXURIDINE [HSDB], CHEMBL788, Epitope ID:138107, IDOXURIDINE [VANDF], 5-I-2′-dUrd, SCHEMBL3683, BSPBio_000055, IDOXURIDINE [WHO-DD], IDOXURIDINE [WHO-IP], MLS002154175, 5-IODO-2-DEOXYURIDINE, BPBio1_000061, SCHEMBL6834964, Idoxuridine (JP18/USP/INN), 2′-Deoxy-5-iodouridine – EP, SCHEMBL10582759, SCHEMBL15850897, IDOXURIDINE [ORANGE BOOK], GLXC-06574, HMS2090M10, HMS2095C17, HMS2230E10, HMS3712C17, BCP29428, HY-B0307, IDOXURIDINUM [WHO-IP LATIN], 5-IUdR; IDU; IdUrd; Idoxuridine, Tox21_110324, BDBM50370388, MSK169312, s1883, AKOS015920431, Tox21_110324_1, AC-8219, CCG-220018, DB00249, ND05147, SMP2_000072, NCGC00179673-01, NCGC00179673-03, NCGC00179673-05, AS-13469, BP-58646, ND172114, SMR001233472, Idoxuridine 100 microg/mL in Acetonitrile, DB-009133, 5-Iodo-2′-deoxyuridine, >=99% (HPLC), I0258, SW198484-2, 1-(2-Deoxy-ss -D-ribofuranosyl)-5-iodouracil, D00342, Q409765, SR-05000001510-1, SR-05000001510-3, SR-05000001510-4, BRD-K76634210-001-12-1, BRD-K76634210-001-14-7, Idoxuridine, European Pharmacopoeia (EP) Reference Standard, 1-(2-Deoxy-b-D-ribofuranosyl)-5-iodouracil;Idoxuridine;Dendrid, Idoxuridine, United States Pharmacopeia (USP) Reference Standard, 1-(2-Deoxy-b-D-ribofuranosyl)-5-iodouracil;Idoxuridine;Dendrid;2′-Deoxy-5-iodo-D-uridine;5-Iodo-2′-deoxyuridine, 1-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-5-iodo-1,2,3,4-tetrahydropyrimidine-2,4-dione, 1-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl]-5-iodo-pyrimidine-2,4-dione

Idoxuridine is primarily used as an antiviral agent in research and clinical settings. It inhibits the replication of DNA viruses, particularly herpes simplex virus (HSV), by substituting thymidine in viral DNA synthesis. This compound is commonly applied in ophthalmic treatments for herpes keratitis and in topical formulations for cutaneous herpes infections. Researchers also utilize Idoxuridine in molecular biology to study viral mechanisms and develop novel antiviral therapies.

Safety and Hazards

GHS Hazard Statements

• H315 (89.6%): Causes skin irritation [Warning Skin corrosion/irritation]
• H319 (89.6%): Causes serious eye irritation [Warning Serious eye damage/eye irritation]
• H335 (85.4%): May cause respiratory irritation [Warning Specific target organ toxicity, single exposure; Respiratory tract irritation]
• H341 (85.4%): Suspected of causing genetic defects [Warning Germ cell mutagenicity]
• H361 (97.9%): Suspected of damaging fertility or the unborn child [Warning Reproductive toxicity]

Precautionary Statements

• P203, P261, P264, P264+P265, P271, P280, P302+P352, P304+P340, P305+P351+P338, P318, P319, P321, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501

Hazard Classes and Categories

• Skin Irrit. 2 (89.6%)
• Eye Irrit. 2 (89.6%)
• STOT SE 3 (85.4%)
• Muta. 2 (85.4%)
• Repr. 2 (97.9%)

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