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

• ChemBase编号: 134
• 分子式: C9H11IN2O5
• 平均质量: 354.09851
• 单一同位素质量: 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

名称和登记号

名称

• IUPAC标准名: 1-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-5-iodo-1,2,3,4-tetrahydropyrimidine-2,4-dione
• IUPAC传统名: idoxuridine
• 商标名: 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
• 别名: (+)-5-碘-2'-脱氧尿苷; (+)-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

登记号

• CAS号: 54-42-2
• EC号: 200-207-8
• MDL号: MFCD00134656
• Beilstein号: 30397
• 默克索引号: 144891
• PubChem SID: 24896108; 46507573; 160963597
• PubChem CID: 5905

理论计算性质

JChem

• Acid pKa: 8.056083
• 质子受体: 5
• 质子供体: 3
• LogD (pH = 5.5): -0.5301102
• LogD (pH = 7.4): -0.6144564
• Log P: -0.5289186
• 摩尔折射率: 64.4039 cm^3
• 极化性: 25.542524 Å^3
• 极化表面积: 99.1 Å^2
• 可自由旋转的化学键: 2
• 里宾斯基五规则: true

ALOGPS 2.1

• Log P: -0.7
• LOG S: -1.18
• 溶解度: 2.34e+01 g/l

分子性质

理化性质

• 溶解度: <0.01 g/100 mL
• 熔点: 194 °C(lit.); ca 190°C dec.
• 比旋光度: [α]20/D +29±2°, c = 1% in 1 M NaOH
• 疏水性(logP): -0.5

安全信息

• 保存注意事项: Air & Light Sensitive
• RTECS编号: YU7700000
• 欧盟危险性物质标志: 有毒(Toxic) (T); X; 有害性(Harmful) (Xn)
• 德国WGK号: 3
• 危险公开号: 40-63; 45-46-61; 63-36/37/38-62-68
• 安全公开号: 26-36/37; 36/37; 53-45
• TSCA收录: 是
• GHS危险品标识: GHS07; GHS08
• GHS警示词: Warning
• GHS危险声明: H315-H319-H335-H341-H361; H351-H361
• GHS警示性声明: P261-P281-P305 + P351 + P338; P281-P201-P202-P308+P313-P405-P501A
• 个人保护装置: Eyeshields, Faceshields, Gloves, type P2 (EN 143) respirator cartridges
• 保存温度: 2-8°C

产品相关信息

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

详细说明

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

参考文献

• 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